Section A Section A Synthesis and Biological Evaluation of Some Nitrogen Containing Heterocycles Chapter 1 Nitrogen Containing Heterocycles − A Brief Review Chapter 2 Synthesis and Biological Evaluation of Some Pyrazole Derivatives Chapter 3 Synthesis of Some Novel Imidazobenzothiazoles (IBTs) as Inhibitors of Apoptosis Chapter 4 Synthesis and Evaluation of Some Polyhydroquinolines as Antioxidants and Antimicrobial Agents Chapter 5 Synthesis and Biological Evaluation of Some Thiazolylhydrazinomethylideneferrocenes as Antimicrobial Agents
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Synthesis and Biological Evaluation of Some Nitrogen
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Section A
Section A
Synthesis and Biological Evaluation of Some Nitrogen Containing Heterocycles
Chapter 1 Nitrogen Containing Heterocycles − A Brief Review Chapter 2 Synthesis and Biological Evaluation of Some Pyrazole Derivatives Chapter 3 Synthesis of Some Novel Imidazobenzothiazoles (IBTs) as Inhibitors of Apoptosis Chapter 4 Synthesis and Evaluation of Some Polyhydroquinolines as Antioxidants and Antimicrobial Agents Chapter 5 Synthesis and Biological Evaluation of Some Thiazolylhydrazinomethylideneferrocenes as Antimicrobial Agents
Chapter 1
Nitrogen Containing Heterocycles − A Brief Review
Brief review on nitrogen containing heterocycles
CHAPTER 1. Nitrogen Containing Heterocycles − A Brief Review
1.1. Spotlight on heterocyclic compounds The chemistry of heterocycles is one of the most complex but equally
important branch of organic chemistry, constituting one of the largest areas of
research for more than a century. It is equally interesting for its theoretical
implications, for the diversity of its synthetic procedures as well as continually
contributing to the development of society from a biological and industrial point of
view to understand the life processes and to improve the quality of life.1
Heterocyclic compounds are the cyclic organic substances which contain in
the ring system at least one atom other than carbon. Presumably, any atom which can
form two covalent bonds is capable of forming a heterocyclic compound. However,
with few exceptions like mercury or iodine, all the known heterocyclic compounds
involve an element from group IVB, VB or VIB of the periodic table. The most
important “heteroatoms” undoubtedly are nitrogen, oxygen and sulfur. It seems likely
that more than a third of the known organic compounds are heterocyclic. Many
alkaloids, vitamins, antibiotics as well as many synthetic medicines and dyestuffs are
heterocyclic, and so are many other substances such as nucleic acids which are
fundamental to any life process on planet earth. Simple fact that the heterocycles are
able to get involved in an extraordinarily wide range of reaction types which are, in
general, not feasible with carbocycles explains the reason as to why nature utilizes
heterocycles at such a scale.2 Depending on the pH of the medium, they may behave
as acids or bases, forming anions or cations. Some interact readily with electrophilic
reagents, others with nucleophiles, yet others with both. Some are easily oxidized, but
resist reduction, while others can readily be hydrogenated but are stable toward the
action of oxidizing agents. Certain amphoteric heterocyclic systems simultaneously
demonstrate all of the above-mentioned properties. The presence of different
heteroatoms makes tautomerism ubiquitous in the heterocyclic series. One of the
striking structural features inherent to heterocycles, which continues to be exploited to
great advantage by the drug industry, lies in their ability to manifest substituents
around a core scaffold in defined three dimensional representations.2 Moreover, these
1
Chapter 1
heterocycles are more flexible and better able to respond to many demands of
biochemical systems which could otherwise not be fulfilled by the carbocycles.
Just like carbocyclic derivatives, heterocycles may too be classified as
saturated, unsaturated, or aromatic. The constantly accelerating rate of research and
development in heterocyclic chemistry suggests that enormous number of heterocyclic
systems are well known and this number is still increasing rapidly.
1.2. Nitrogen containing heterocycles: A general introduction Nitrogen containing heterocycles are perhaps by far the most explored
heterocyclic compounds because of their occurrence in a myriad of natural products
and biologically active compounds. For this reason, synthetic chemists continue to be
interested in the construction and functionalization of these heterocycles. The most
common examples of naturally occurring N-heterocycles which otherwise too are of
fundamental importance to life are haemoglobin and chlorophyll (Figure 1.1).
Figure 1.1.
Human Blood Haemoglobin Plant Chlorophyll
Haemoglobin helps in oxygen transportation within body while chlorophyll
helps in light harvesting that is further used for making ATP and NADPH. A common
feature in haemoglobin and chlorophyll is that both contain porphyrin system in which
four pyrrole rings are interconnected through alternate single-double bonds on
periphery and connected with Fe2+ (haemoglobin) and Mg2+ (chlorophyll) in the
centre through nitrogen atoms. β-Lactam antibiotics such as penicillins (1) and
Pyrazoline bisphosphonate esters 71 synthesized by Nugent et al.84 have
proved to be better anti-inflammatory agents which are capable of inhibiting both
chronic arthritis and inflammation in animals. Kaplancıklı et al.85 synthesized some
novel triazolo-pyrazoline derivatives (72) exhibiting different levels of activities as
compared to reference drug fluoxetine and none changed motor coordination of
animals when assayed in the Rota-Rod test. A series of 1,3,5-trisubstituted pyrazolines
(73) synthesized by Acharya et.al.86 exhibited strong antimalarial activity against
chloroquine resistant strain of Plasmodium falciparum. Some novel pyrazoline
derivatives (74) mimicing bacterial siderophores were synthesized by Stirrett et al.87
NNR
R1
S
69a R = Cl;
69b R = Br; 69c R = Cl;
69d R = Br; 69e R = Cl;
N(CH2)3CH3
CH3
NCH2CH3
CH2CH3
N(CH2)2CH3
(CH2)2CH3
R1 =
R1 =
R1 =
HNN
OHt-Bu
HOt-Bu
t-Bu
70
HN N
O
RP
PO
O
(C2H5O)2
(C2H5O)2
a R = Hb R = 3-F
71
NN
OSN
NN
NH2
HO
R1
R2
S
72
NNHO
O
N
R5
R4
R2
R3
R1
73
N N
R1 R
SNH
H
R2
R3
R4
O
S
R5
R6
H
74
13
Chapter 1
which showed promising antibacterial activity against iron-scarcity adapted
Mycobacterium tuberculosis and Yersinia pestis.
1.4.2. Synthetic procedures A few recent methods used for the synthesis of pyrazoline derivatives are
summarized below:
1.4.2.1. Zinc-catalyzed regioselective synthesis of aryl-substituted pyrazolines
Alex et al.88 demonstrated an elegant zinc-catalyzed novel regioselective
synthesis of aryl-substituted pyrazolines 77. Substituted phenylhydrazines 75 have
been shown to react with 3-butynol in the presence of a catalytic amount of zinc
triflate to give pyrazoline derivatives 77 in excellent yields (Scheme 1.9). A plausible
mechanism for this reaction is believed to involve two steps as shown in Scheme 1.9,
first hydrohydrazination of 3-butynol forming corresponding intermediate
arylhydrazone 76 followed by an unusual nucleophilic substitution of the hydroxy
group yielding pyrazoline 77.
NHH2N
R
OH+
5 mol% Zn(OTf)2,
THF, 24 h, 1000C
N
R
N
+ H2O
NH
R
N
OH
75 77
76
Zn catalyst
Scheme 1.9.
1.4.2.2. Synthesis of 1,3,5-triaryl-2-pyrazolines in aqueous medium under ultrasound irradiation Li et al.89 reported an efficient and green practical procedure for the synthesis
of 1,3,5-triaryl-2-pyrazolines 78 by ultrasound irradiation of an aqueous solution of
14
Brief review on nitrogen containing heterocycles
chalcones and phenylhydrazine hydrochloride containing sodium acetate and acetic
acid as depicted in Scheme 1.10.
))))
N
N
Ar1
Ar2NHNH2. HCl
Ar2Ar1
O
+CH3COONaCH3COOH/H2O/
78
Scheme 1.10.
1.4.2.3. Synthesis of 5-hydroxy N-acylpyrazolines from 2-alkyn-1-ones
Waldo et al.90 recently synthesized a number of novel 5-hydroxy N-
acylpyrazolines 80 in moderate to excellent yield by reacting corresponding 2-alkyn-
1-ones 79 with acetylhydrazine in toluene at 80 °C (Scheme 1.11).
Ar
O
R
NN
R
Ar
HO
Me O
2 eq. H2N NHAc
toluene, 80 0C, 6h
79 80
R = Ar, alkyl, vinyl
Scheme 1.11.
1.4.2.4. 2-Pyrazolines formation by domino reaction of 2-acylaziridines with the Huisgen zwitterions
Huisgen zwitterions 82 generated in situ by the redox coupling of
triphenylphosphine and dialkyl azodicarboxylates 81 on domino reaction91 with 2-
acylaziridines 83 have been reported to yield 2-pyrazolines 84 quantitatively by
refluxing in toluene (Scheme 1.12).
RO2CN
NCO2R
+
HN
ArAr'
O
toluene, N2reflux, 2h N N
Ar'
NHCO2R
Ar
RO2C
+PPh3
RO2CN
NCO2R
PPh3
82
81
83 84
Scheme 1.12.
15
Chapter 1
1.4.2.5. Gold(I)-catalyzed formation of 3-pyrazolines through cycloaddition of diaziridine to alkynes
Capretto et al.92 reported the first gold(I)-catalyzed cycloaddition of diaziridine
86 on to alkynes 85 giving high yields of 3-pyrazolines 87 (Scheme 1.13).
H
R
+
NNPhCbz
NN
R
Cbz
Ph
10 mol% Ph3PAuNTf2Touene, 18h, 70
0C
R = alkyl, aryl85 86 87
Scheme 1.13.
)
A A,B A,X
chemical shift values of carbon atoms C-3 (154-156 ppm), C-4 (42-44 ppm) and C-5
1.4.3. Spectral characteristics Although a large number of pyrazolines have been synthesized and
characterized, general trends or guidelines for 1H NMR spectral assignments for the
pyrazoline class have still not emerged contrary to the pyrazole class. It has been
undoubtedly reported that 1,3,5-trisubstituted-2-pyrazolines display three doublets of
doublets, a typical pattern of ABX type system due to three protons, two at position-4
and one at postion-5, and the coupling constants (
were found to be quite sensitive to the
nature of the substituent on the
nitrogen atom.
Jgem, Jcis and Jtrans ) of these protons
93 1H NMR spectra of
1,3,5-trisubstituted-2-pyrazolines (88
synthesized by Andotra et al.94
displayed first doublet of doublet,
centred at δ ≅3.26 which was assigned to H (J ≅18.0 Hz and J ≅5.0 Hz trans);
signal due to HB appeared as doublet of doublet at around δ ≅3.86 while the third
doublet of doublet due to third proton of pyrazoline appeared centred at δ ≅5.4
attributed to HX (JX,A 5.0 Hz trans, JX,B 11.0 Hz cis). The non-equivalence of C4-HA
and C4-HB might be due to the chiral centre at C5, which makes the protons
diastereotopic. Presumably, the appearance of HA at a higher field than the
diastereotopic proton HB might be attributed to the fact that HA being cis to C5-Ar may
be lying in the shielding zone of the benzene ring. In the 13C NMR spectra of 88, the
N N
Ac
HX
ORROHB HA
Ar
12
3
4 5
R = CH3, CH2CH3
Ar = Ph, p-anisyl, etc.
88
16
Brief review on nitrogen containing heterocycles
(56-58 ppm) supports the 2-pyrazoline structure determined by 1H NMR
spectroscopic measurements.95
1.5. Thiazoles Thiazole or 1,3-thiazole is a member of azole heterocycle class featuring both
a nitrogen and sulfur atom at 1,3-positions within five-membered aromatic ring.
Thiazole is not as reactive as thiophene toward electrophilic substitution reaction and
its reactivity would parallel the deactivated benzenoid compound, m-dinitrobenzene.
This is because of the presence of the “pyridine-like” electronegative nitrogen which
not only withdraws electron density from the ring but under the acidic conditions of
many electrophilic reactions, the nitrogen is protonated becoming less prone to further
attack by a positively charged electrophile.
1.5.1. Biological properties of thiazoles Thiazole ring system is a useful structural motif that has found extensive
applications in drug development, e.g. for the treatment of inflammation,96- 98
HIV,132 etc. Riluzole133 (102) is the only FDA approved drug bearing benzothiazole
moiety for symptomatic amyotrophic lateral sclerosis (ALS) treatment which prevents
further degeneration of motor neurons by targeting glutamate tranporters. A novel
N
S
N
R6R5
R1
R2
R3
R4
104
N
SNH2
O
F
F
F
102S
NS N N
N
R
103
18
Brief review on nitrogen containing heterocycles
scaffold (103) consisting of 2-mercaptobenzthiazole and 1,2,3-triazole was recently
synthesized by Shafi et al.134 following click chemistry approach possessing
significant anti-inflammatory activity. Imidazobenzothiazoles (IBTs) 104 are well
known inhibitors of apoptosis and exhaustive work135- 138 has been done on these
compounds. These aromatic IBTs (104) have shown better anti-apoptotic activity
compared to well known standard drug piffithrin-α (PFT-α) following p-53
independent pathway.
1.5.2. Synthetic procedures Some latest methods as well as the most celebrated classic Hantzsch method
used for the synthesis of thiazole and benzothiazole derivatives are summarized
below:
1.5.2.1. Hantzsch thiazole synthesis It is the chemical reaction139 between α-haloketones (105) and thiamides (106)
to form substituted thiazoles (107) as shown in Scheme 1.14.
OR1
R2X
HNH
R3S+
N S
R3
R1 R2
105 106
X = Cl, Br
107
Scheme 1.14.
1.5.2.2. Synthesis from N,N-diformylaminomethyl aryl ketones N,N-Diformylaminomethyl aryl ketones (108)140 on treatment with phosphorus
pentasulfide and triethylamine in chloroform have been reported to yield 5-
arylthiazoles (109) in good yield as shown in Scheme 1.15.
Scheme 1.15.
1.5.2.3. Synthesis from 1H-1-(1′-alkynyl)-5-methyl-1,2,3-benziodoxathiole 3,3-dioxides
ArS
NNCHOAr
CHOO
2 eq. P2S5, 2 eq. NEt3CHCl3, 60 0C, 45-60 min.
108 109
19
Chapter 1
Ishiwata and Togo141 synthesized 2,4-disubstituted thiazoles 112 by reacting
1H-1-(1′-alkynyl)-5-methyl-1,2,3-benziodoxathiole 3,3-dioxides (111) with
thioamides 110 in the presence of potassium carbonate (Scheme 1.16). The advantage
claimed for this reaction is that the coproduct, potassium 2-iodo-5-
methylbenzenesulfonate (113) formed in this reaction can be separated just by
filtration and is used to regenerate reactant 111.
IOS
OO
R'R
S
NH2+
N
S
R'
R2.3 eq. K2CO3
THF, r.t. or 45 0C5h - o.n
+I
SO3 K
112110 111 113
1.2 eq.R = Ar, Me, NH2R' = Ph, Bu, C6H13
IOS
OO
OH Ac-O-OH, conc. H2SO4
AcOH, 10 -> 25 0C, [17h]TsOH.H2O, MeCN,
reflux, [20h]
C CHR'
114
115
Scheme 1.16.
1.5.2.4. Aqueous phase synthesis under supramolecular catalysis Narender et al.142 reported one pot synthesis of 2-amino-4-alkyl/arylthiazole-
5-carboxylates (117) by α-halogenation of β-ketoesters (116) with N-
bromosuccinimide (NBS), followed by cyclization with thiourea in the presence of β-
cyclodextrin in water at 50 °C (Scheme 1.18).
R OR'
O O
H2N NH2
S
+
S
NR
H2NOR'
O1.2 eq. NBS
1eq. β-cyclodextrinH2O/acetone (20:1)
50 0C, 1.2-1.5 h116 117
1.2 eq.R = alkyl or arylR' = alkyl
Scheme 1.17.
1.5.2.5. Synthesis from α-amido-β-ketoesters α-Amido-β-ketoesters143 118 formed by the double acylation of protected
glycine on reaction with Lawesson’s reagent (119) provide 2,5-disubstituted thiazoles
120 as depicted in Scheme 1.18.
20
Brief review on nitrogen containing heterocycles
O
Scheme 1.18.
1.5.2.6. Synthesis by domino alkylation-cyclization Castagnolo et al.144 recently reported a fast, high yielding synthesis of 2-
aminothiazoles 123 by domino alkylation-cyclization reaction of propargyl bromides
(121) with thioureas (122) under microwave irradiation as shown in Scheme 1.19.
a fast, high yielding synthesis of 2-
aminothiazoles 123 by domino alkylation-cyclization reaction of propargyl bromides
(121) with thioureas (122) under microwave irradiation as shown in Scheme 1.19.
S
N
S
NRNHR'Br
R S NHR'
NH2
+1 eq. K2CO3
DMF, MW (300W)130 0C, 2-5 min. R = Ar, H, COPh
R' = H, alkyl, allyl121 122 123
Scheme 1.19.
1.5.2.7. Benzothiazole synthesis by cyclization of thioformanilides Bose at al.145 reported the high yielding synthesis of various benzothiazoles
(125) by the intramolecular cyclization of thioformanilides (124) using DDQ (Scheme
1.20).
Scheme 1.20.
1.5.2.8. Solvent-free microwave-assisted synthesis of 2-substituted benzothiazoles Seizas et al.146 found Lawesson’s reagent as an efficient promoter in the
solvent-free microwave-assisted synthesis of 2-substituted benzothiazoles (127) from
carboxylic acids (126) and 2-aminothiophenol as depicted in Scheme 1.21.
Scheme 1.21.
R NH
O
CO2Bn
O R'
PO
S
S PO THF, reflux, 14h+
S
N
R R'
CO2BnO R, R' = alkyl, aryl120118 119
N
S
NH
Ar
SR
1.1 eq. DDQCH2Cl2, r.t. 20 min.
ArR
124 125
H2N
HSR COOH
N
S+
0.35 eq. Lawesson's reagentMW (300 W), 190 0C, open vessel
neat, 0.5-4 min.
R
R = alkyl, aryl or hetaryl
127126
21
Chapter 1
1.5.3. Spectral characteristics 1,3-Thiazole possesses three protons, HA, HB, HC at 2, 4 and
5-position respectively where HA appears at δ 8.68, HB at δ 7.83 and
HC at δ 7.19 having coupling constants 0.0 Hz (JAB), 1.9 Hz (JAC)
and 3.2 Hz (JBC) indicating that the electron density is maximum at position-5 of
thiazole. It has been revealed100 that 2,4-disubstituted-1,3-thiazoles display a
downfield shift for C5-H which appears at about δ 7.7 in 1H-NMR spectra in this case. 13C-NMR spectra of thiazoles display C-2, C-4 and C-5 signals in the region δ 165-
170, δ 145-150 and δ 100-105, respectively when recorded in DMSO-d6
S
N
HA
HB
HC
12
34
5
/CDCl3
mixture
MR
while the corresponding carbon signal (C-2) in 13C NMR is displayed at δ 166.4 when
-
azanaphthalene, 1-benzazine and benzo[b]pyridine. Quinoline and its derivatives,
.
Benzothiazole possesses a characteristic C2-H proton which
appears at δ 8.97 in 1H NMR spectrum and carbon signal (C-2) in 13C NMR is displayed at δ 153.8. NH2 group of 2-
aminobenzothiazole appears as a broad exchangeable singlet at δ 5.85 in 1H N
2
34
5
1S
NH
67
recorded in CDCl . 3
1.6. Quinolines Quinoline is a bicyclic heteroaromatic compound in which a pyridine ring is
fused with a benzene ring. It is also known by several other names such as 1
whether natural or synthetic ones, are classified and placed under the alkaloids class.
1.6.1. Biological properties of quinolines Quinolines are considered to be valuable building blocks in pharmaceuticals
and are known for exhibiting various pharmacological activities such as
display a characteristic singlet near at δ 4.5 corresponding to C4-
H.
1NR4
R4
R1
R2R3
2
345
8
164
6
7
28
Brief review on nitrogen containing heterocycles
29
1.7. References
Padwa, A.; Pearson, W. H. (Ed.) The Chemistry of Heterocyclic Compounds: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Vol. 59; John Wiley & Sons, Inc., New York, 2000; ISBN 0-471-38726-6.
Advan. Biol. Res. 2011, 5 (3), 120-144.
J.; Truglio, J. J.; Boyne, M. E.; Novichenok, P.; Zhang, X.; Stratton, C. F.; Li, H. J.; Kaur, T.; Amin, A.; Johnson, F.; Stayden, R. A.; Kisker, C.; Tonge, P. J. ACS Chem. Biol. 2006, 1, 43-53.
Bioorg. , 4075–4082.
Ragavan, R. V.; Vijaykumar, V.; Kumari, N. S. Eur. J. Med. Chem. 2010, 45, 1173-1180.
6
9 l-Din A.; Hassan, A. A. Eur. J. Med. Chem.
1 Eur. J. Med. Chem.
1 bbagh, O.; Baraka, M. M.; Ibrahim, S. M.; Pannecouque, C.; Andrei, G.;
1
. . 2008, 43, 2627-2630.
vellino, E.; Di Marzo, V.; Corelli, F. J. Med. Chem.
1 ad, A. J.; Berdini, V.; Boulstridge, J. A.; Carr, M. G.; Cross,
, .; Smith, D. M.; Squires, M. S.; Trewartha, G.; Walker, M. T.;
1
2 Dua, R.; Shrivastava, S.; Sonwane, S. K.; Srivastava, S. K.
3 Sultivan, T.
4 Liu, X. H.; Cui, P.; Song, B. A.; Bhadury, P. S.; Zhu, H. L.; Wang, S. F. Med. Chem. 2008, 16
5
Magedov, I. V.; Manpadi, M.; Van slambrouck, S.; Steelant, W. F. A.; Rozhkova, E.; Przheval’skii, N. M.; Rogelj, S.; Kornienko, A. J. Med. Chem. 2007, 50, 5183–5192.
7 Rovnyak, G. C.; Millonig, R. C.; Schwartz, J.; Shu, V. J. Med. Chem. 1982, 25, 1482–1488
8 Selvam, C.; Jachak, S. M.; Thilagavathi, R.; Chakraborti, A. K. Bioorg. Med. Chem. Lett. 2005, 15, 1793-1797.
Abdel-Aziz, M.; Abuo-Rahma, G. E2009, 44, 3480-3487. 0 Ozdemir, Z.; Kandilici, B.; Gumusel, B.; Calis, U.; Bilgin, A.
2007, 42, 373-379. 1 El-Sa
Snoeck, R.; Balzarini, J.; Rashad, A. A. Eur. J. Med. Chem. 2009, 44, 3746-3753. 2 Demirayak, S.; Karaburum, A. S.; Beis, R. Eur. J. Med. Chem. 2004, 39, 1089-
Med. Chem14 Silvestri, R.; Cascio, M. G.; La Regina, G.; Piscitelli, F.; Lavecchia, A.; Brizzi, A.;
Pasquini, S.; Botta, M.; No2008, 51, 1560-1576.
5 Wyatt, P. G.; WoodheD. M.; Davis, D. J.; Devine, L. A.; Early, T. R.; Feltell, R. E.; Lewis, E. J.; McMenamin, R. L.; Navarro, E. F.; O’Brien, M. A.; O’Reilly, M.; Reule, M.; SaxtyG.; Seavers, L. C. AWoolford, A. J. A. J. Med. Chem. 2008, 51, 4986-4999.
Chapter 1
30
ko,
ford, N. D. P. Bioorg. Med. Chem. Lett. 2009, 19, 222-225.
19 O 2005077934, 2005; Chem.
20
21
23 ,
, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S.
. 1997, 40, 1347-1365.
25
27 -
28
29
30 4, 85-93.
S.; Casti,
ss, M. Lett. 2008, 18,
33 own, S. C.; Hall, A.; Giblin, G. M. P.; Lorthioir, O.; Blunt, R.; Lewell, X. Q.;
16 Sidique, S.; Ardecky, R.; Su, Y.; Narisawa, S.; Brown, B.; Millán, J. L.; SergienE.; Cos
17 Rehse, K.; Kotthaus, J.; Kadembashi, L. Arch. Pharm. Chem. Life Sci. 2009, 342, 27-33.
18 Li, Y.; Zhang, H.; Liu, J.; Yang, X.; Liu, Z. J. Agric. Food Chem. 2006, 54, 3636-3640.
Toru, K.; Masayuki, M.; Kenichi, N.; Akihiro, H. WAbstr. 2005, 143, 229846.
Lahm, G. P.; Selby, T. P.; freudenberger, J. H.; Stevenson, T. M.; Myres, B. J.; Seburyamo, G.; Smith, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem Lett. 2005, 15, 4898-4906.
Meazza, G.; Bettarini, F.; La Porta, P.; Piccardi, P.; Signorini, E.; Portoso, D.; Fornara, L. Pest Manag. Sci. 2004, 60, 1178-1188.
22 Osterloh, I. H. The discovery and development of Viagra (sildenafil citerate) in Sildenafil; Dunzendorfer, U.; Ed., Birkhaeuser Verlag: Basel, 2004, 1-13.
Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; DocterS.; Granto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; RogierA.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.;Isakson, P C. J. Med. Chem
24 Kameyama, T.; Nabeshima, T. Neuropharmacology 1978, 17, 249-356.
Yoshida, N.; Nabeshima, T.; Yamaguchi, K. Neurosciences 1979, 5, 54. 26 Anderson, W. P. Non family herbicides. In: Weed Science: Principles and
Application, 3rd ed., West Publishing, St. Paul, MN, 1996, 253.
Caboni, P.; Sammelson, P. E.; Casida, J. E. J. Agric. Food Chem. 2003, 51, 70557061.
Brent J.; McMartin, K.; Phillips S.; Aaron C.; Kulig, K. N. Eng. J. Med. 2001, 344, 424-429.
Velez, L. I.; Shepherd, G.; Lee, Y. C.; Keyes, D. C. J. Med. Toxicol. 2007, 3, 125-128.
Roberto, S. Expert opinion on drug discovery 2009, 31 Ruiu, S.; Pinna G. A.; Marchese, G.; Mussinu, J. M.; Saba, P.; Tambaro,
P.; Vargiu, R.; Pani, L. J. Pharmaco. Exp. Ther. 2003, 306, 363-370. 32 Purandare, A. V.; Chen, Z.; Huynh, T.; Pang, S.; Geng, J.; Vaccaro, W.; Po
A.; Oconnell, J.; Nowak, K.; Jayaraman, L. Bioorg. Med. Chem.4438-4441.
McKeWilson, R. J.; Brown, S. H.; Chowdhury, A.; Coleman, T.; Watson, S. P.; Chessel, I. P.; Pipe, A.; Clayton, N.; Goldsmith, P. Bioorg. Med. Chem. Lett. 2006, 16, 4767-4771.
Brief review on nitrogen containing heterocycles
31
rg. Med. Chem. 2008, 16, 10165-10171.
. S.; Miao, J. Y.
36 Marin, C.;
37 u, M. S.; Liekens, S.; Kasiotis, K. M.; Haroutounian, S. A. Bioorg.
38 ,
, 961-965.
40 araka, A. M. Eur. J. Med Chem.
41 . Med. Chem. 2003, 336, 111-118.
ci.
44
45 Zhang, L. Org. Lett. 2000, 2, 3107-3109.
Babu,
47 .; Khan, T. A.; Ila, H.; Junjappa, H. J. Org. Chem. 2005, 70,
49 Shea, P. D.; Webster, R. A.; Reamer, R. A.; Tillyer, R. D.;
50 Y. K. J. Org. Chem. 2008, 73, 4698-4701.
, M.
g Z. Tetrahedron
53
16. 55 M.; Kobayashi, K.; Mori, A. Org. Lett. 2005, 7, 4487-4489.
34 Zhang, J. H.; Fan, C. D.; Zhao, B. X.; Shin, D. S.; Dong, W. L.; Xie, Y .S.; Mio, J.Y. Bio
Sanchez-Moréno, M.; Sanz, A. M.; Goméz-Contreras, F.; Navarro, P.;Ramirez-Macias, i.; Rosales, M. J.; Olmo, F.; Garcia-Aranda, I.; Campayo, L.; Cano, C.; Arrebola, F.; Yunta, M. J. R. J. Med. Chem. 2011, 54, 970-979.
ChristadouloMed. Chem. 2010, 18, 4338-4350.
Thaher, B. A.; Arnsmann, M.; Totzke, Ehlert, J. E.; Kubbutat, M. H. G.; SchachteleC.; Zimmermann, M. O.; Koch, P.; Boeckler, F. M.; Laufer, S. A. J. Med. Chem. 2012, 55
39 Bekhit, A. A.; Abdel-Azeim, T. Bioorg. Med. Chem. 2004, 12, 1935-1945.
Bekhit, A. A.; Fahmy, H. T. Y. Rostom, A. F.; B2003, 38, 27-36.
Bekhit, A. A.; Fahmy, H. T. Y. Arch. Pharm. Pharm42 Bekhit, A. A.; Ashour, H. M. A.; Guemei, A. Arch. Pharm. Chem. Life Sci. 2005,
338, 167-174. 43 Bekhit, A. A.; Abdel-Rahman, H. M.; Guemei, A. A. Arch. Pharm. Chem. Life S
2006, 339, 81-87.
Bekhit, A. A.; Ashour, H. M. A.; Bekhit, A. El-Din A.; Abdel-Rahman, H. M.; Bekhit, S. A. J. Enzyme Inhib. Med. Chem. 2009, 24, 296-309.
Wang, X.-J.; Tan, J.;46 Singh, S. K.; Reddy, M. S.; Shivaramakrishna, S.; Kavhita, D.; Vasudev, R.;
J. M.; Sivalakshmidevi, A.; Rao, Y. K. Tetrahedron Lett. 2004, 45, 7679-7682.
Perunchalathan, S10030-10035.
48 Nielsen, J.; Persson, T. Org. Lett. 2006, 8, 3219-3222.
Gosselin, F. O’Grabowski, E. J. J. Synlett 2006, 19, 3267-3270.
Lee, Y. T.; Chung,51 Rosa, F. A.; Machado, P.; Vargas, P. S.; Bonacorso, H. G.; Zanatta, N.; Martins
A. P. Synlett 2008, 11, 1673-1678. 52 Liu, H. L.; Jiang, H. F.; Zhang, M.; Yao, W. J.; Zhu, Q. H.; Tan
66 Elguero, J. Pyrazoles and Their Benzo derivatives Comprehensive Heterocyclic s, Oxford, 1984,
68 . Chem. 1973, 51, 2315-2322.
. Abstr. 1981,
71 Sobhia, H. R.; Yaminib, Y.; Esrafili, A.; Adiba, M. J. Pharm. Biomed. Anal. 2008,
Gill, C. H. Bioorg.
08, 18, 918-922.
ble, M. Chem. Biol. Drug Des.
77 , 4021-4026.
56 Schofield K.; Grimmett, M. R.; Keene, B. T. R. HeteroaCompounds: The Azoles, Cambridge University Press, Cambridge, 1976, 25
Batterham, T. J. NMR Spectra of Simple Heteroc165.
58 Habraken, C. L.; Moore, J. A. J. Org. Chem. 1965, 30,1892-1896.
Ritschi, F.; Dorn, H. J. Prakt. Chem60 Bouchet, P. Coquelet, C.; Elguero, J. Bull. Soc. Chim. Fr. 1977, 171; Chem. Abstr
1977, 87, 13513k. 61 Fabra, F.; Fos, E.; Vilarraba, J. Tetrahedron Lett. 1979, 3179-3180. 62 Pawan Kumar, Ph.D. Thesis 2010, Kurukshetra University, Kurukshetra. 63 Elguero, J.; Jacquier, R. J. Chim. Phys. 1966, 63, 1242; Chem Abstr. 1967, 66
80662t.
Heinisch, G.; Holzer, W. Heterocycles 1988, 27, 2443-2457. 65 Burton, R. E.; Finar, I. L. J. Chem. Soc. (B), 1970, 1692-1694.
Chemistry, edited by Katritzky, A. R.; Resse, C. W. Pergamon Pres167.
67 Finar, I .L.; Rackham, D. M. J. Chem. Soc. (B) 1968, 211-214.
Butler, R. N. Can. J69 Khan, M. A.; Pinto, A. A . A, Montasch Chem. 1980, 111, 883; Chem
94, 65539t. 70 Singh, S. P.; Sehgal, S.; Tarar, L. S. Indian J. Chem. 1989, 28B, 27.
45, 316-320. 72 Joshi, R. S.; Mandhane, P. G.; Diwakar, S. D.; Dabhade, S. K.;
Med. Chem. Lett. 2010, 20, 3721-3725. 73 Khode, S.; Maddi, V.; Aragade, P.; Palkar, M.; Ronad, P. K.; Mamledesai, S.;
Thippeswamy, A. H.; Satyanarayana, D. Eur. J. Med. Chem. 2009, 44, 1682-1688. 74 Amir, M.; Kumar, H.; Khan, S. A. Bioorg. Med. Chem. Lett. 2075 Sivakumar, P. M.; Ganesan, S.; Veluchamy, P.; Do
2010, 76, 407-411. 76 Palaskar, E.; Aytemir, M.; Uzbay, I. T.; Erol, D. Eur. J. Med. Chem. 2001, 36, 539-
543.
Adhikari, N.; Maiti, M. K.; Jha, T. Bioorg. Med. Chem. Lett. 2010, 2078 Hayat, F.; Salahuddin, A.; Umar, S.; Azam, A. Eur. J. Med. Chem. 2010, 45, 4669-
4675.
Brief review on nitrogen containing heterocycles
33
.
81 .; Drabu, S.; Kumar, R. Gupta, H. Recent Patents on Anti-
82 , M.; Azam, A. Bioorg. Med. Chem. 2005, 13, 2213-2220.
84 t, R. A.; Murphy, M.; Schlachter, S. T.; Dunn, C. J.; Smith, R. J.; Staite, N. .
apna,
, T.; Quadri, L. E.
88
90
91 -G. Org. Lett. 2008, 10, 13-16.
.
94
.
m, V.;
99 ć, A.; Soković, M. Bioorg. Med.
10 . K.; Nath, G.; Tilak, R.; Singh, S. K. Eur. J. Med. Chem. 2010, 45, 651-
79 Havrylyuk, D.; Kovach, N.; Zimenkovsky, B.; Vasylenko, O.; Lesyk, R. Arch. Pharm. Chem. life Sci. 2011, 344, 514-522.
80 Zhao, P. L.; Wang, F.; Zhang, M. Z.; Liu, Z. M.; Huang, W.; Yang, G. F. J. AgricFood Chem. 2008, 56, 10767-10773.
Kumar, S.; Bawa, SInfective Drug Discovery 2009, 4, 154-163.
Abid83 Jeong, T. -S.; Kim, K. S.; Kim, J. -R.; Cho, K. -H.; Lee, S.; Lee, W. S. Bioorg. Med.
Chem. Lett. 2004, 14, 2719-2723.
NugenD.; Galinef, L. A.; Shields, S. K.; Aspar, D. G.; Richard, K. A.; Rohloff, N. A. JMed. Chem. 1993, 36, 134-139.
85 Kaplancıklı, Z. A.; Özdemir, A.; Turan-Zitouni, G.; Altıntop, M. D.; Can, Ö. D. Eur. J. Med. Chem. 2010, 45, 4383-4387.
86 Acharya, B. N.; Saraswat, D.; Tiwari, M.; Srivastava, A. K.; Ghoarpade, R.; BS.; Kauhik, M. P. Eur. J. Med. Chem. 2010, 45, 430-438.
87 Stirrett, K. L.; Ferreras, J. A.; Jayaprakash, V.; Sinha, B. N.; RenN. Bioorg. Med. Chem. Lett. 2008, 18, 2612-2618.
Alex, K.; Tillack, A.; Schwarz, N.; Beller, M. Org. Lett. 2008, 10, 2377-2379. 89 Li, J. -T.; Zhang, X. -H.; Lin, Z. -P. Beilstein J. Org. Chem. 2007, 3, No. 13, 1-4.
Waldo, J. P.; Mehta, S.; Larock, R. C. J. Org. Chem. 2008, 73, 6666-6670.
Cui, S. -L.; Wang, J.; Wang, Y. 92 Capretto, D. A.; Brouwer, C.; Poor, C. B.; He, C. Org. Lett. 2011, 13, 5842-584593 Katritzky, A. R.; Pozharskii, A. F. “Handbook of Heterocyclic Chemistry”, Second
Edition, Elsevier Science Ltd., Oxford, 2000.
Andotra, C. S.; Khajuria, J.; Singh, G. B.; Singh, S. J. Indian Chem. Soc. 1993, 70, 266-267.
95 Levai, A.; Jeko, J. Arkivoc 2005, x, 199-205. 96 Kouatly, O.; Geronikaki, A.; Kamoutsis, C.; Hadjipavlou-Litina, D.; Eleftheriou, P
Eur. J. Med. Chem. 2009, 44, 1198-1204. 97 Giri, R. S.; Thakar, H. M.; Giordano, T.; Williams, J.; Rogers, D.; Sudersana
Vasu, K. K. Eur. J. Med. Chem. 2009, 44, 2184-2189. 98 Sharma, R. N.; Xavier, F. P.; Vasu, K. K.; Chaturvedi, S. C.; Pancholi, S. S. J
101 Karegoudar, P.; Karthikeyan, M. S.; Prasad, D. J.; Mahalinga, M.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2008, 43
102 Bakris, G. L.; Bank, A. J.; Kass, D. A.; Neutal, J. M.; Preston, R. A.; Oparil, S. Am. J. Hypertens. 2004, 17, 23S-30S.
103 Kurtz, T. W.; Gardner, D. G. Hypertension 1998, 32, 380-386. 4 Kitas, E.; mohr, P.; Kuhn, B.; Hebeisen, P.; We
Benz, J.; Joseph, C.; Huber, W.; Sanchez, R. A.; Paehler, A.; Benardeau, A.; Gubler, M.; Schott, B.; Tozzo
105 Dang, Q.; Liu, Y.; Cashion, D. K.; Kasibhatla, S. R.; Jiang, T.; Taplin, F.; JacinthoJ. D.van Poelje, P. D.; Potter, S. C.; Erion, M. D. J. Med. Chem. 2011, 54, 153-165.
106 P.; Montes, J. M.; 3),
, B.; Gandhi, S.;
;
110
111
2012, doi:
112 eoplastic Agents, Gower,
113 .
l. 4, p. 95-97.
117 R. Chem. Pharm. Bull. (Tokyo) 1979, 27, 1-11.
. . Conf. - Pests Dis. 1992, 1, 427-434.
proved efficacy. U. S. Patent 6043262, March 28, 2000.
Fagialini, A.; Coñas, F.; Gallhofer, B.; Larmo, I.; Levy,Papageorgiou, G. Zin, K. M.; Rossi, A. Expert. Opin. Pharmacother. 2010, 11(12199-2220.
107 Shiradkar, M. R.; Akula, K. C.; Dasari, V.; Baru, V.; ChiningiriKaur, R. Bioorg. Med. Chem. 2007, 15, 2601-2610.
108 Masilamoni, G. J.; Bogenpohl, J. W.; Alagille, D.; Delevich, K.; Tamagnan, G.Votaw, J. R.; Wichmann, T.; Smith, Y. Brain 2011, 134, 2057-2073.
109 Wagner, S. J.; Skripchenko, A.; Salata, J.; O'Sullivan, A. M.; Cardo, L. J. Transfusion 2008, 48(7), 1363-1367.
Turan-Zitouni, G.; Ozdemir, A.; Kaplancikli, Z. A.; Altintop, M. D.; Temel, H. E.; Ciftçi, G. A. J. Enzyme Inhib. Med. Chem. 10.3109/14756366.2011.153355.
Milne, G.W.A. in: Ashgate (Ed.), Handbook of AntinLondon, UK 2000.
de Souza, M. V. N.; de Almeida, M. V. Quím. Nova 2003, 26, 366-372114 Lednicer, D.; Mitscher, L. A.; George, G. I. In: Organic Chemistry of Drug
Synthesis, Wiley, New York, 1990, Vo115 Rehman, M. Z.; Anwar, C. J.; Ahmad, S. Bull. Korean Chem. Soc. 2005, 26, 1771-
1775. 116 Knadler, M. P.; Bergstrom, R. F.; Callaghan, J. T.; Rubin, A. Drug Metab. Dispos.
1986, 14, 175-182.
Suzuki, N.; Tanaka, Y.; Dohmori,118 O΄Reilly, P.; Kobayashi, S.; Yamane, S.; Phillips, W.; Raymond, P. Castanho, B
Proc. Br. Crop Prot119 Hayakawa, N.; Baba, M.; Suwa, N.; Yamagishi, K. Thifluzamide with im
Brief review on nitrogen containing heterocycles
35
n
dgerton, J. R.; Yaktis, J. J.; Camnpell, W. C.; Cuckler, A. C. J. Am. Chem.
122 rker, D. P.; Willardsen, J. A.; Gao, Z. -H.; Davis, T.; Ostanin,
123
2019.
.; J. J. S.; Norman, M. H. Bioorg.
125 .; Florio, M. A.; Di Mola, A.; Rosato, A.;
126 . Int. J. Antimicrob. Agents 1994, 4, 303-308. 127
128
8,
129
131 .; Al-Masoudi, N. A.; Lodo, R.; La Colla, P. Acta Pharm.
nts. US
134 m, M. M.; Mulakayala, N.; Mulakayala, C.; Vaneja, G.; Kalle, A. M.;
135
et,
137 umen, A.; Dono, R.; Lingor, P.; Planchamp, V.; Lamballe, F.; Bahr, M.; Kraus, J. L.; Maina, F. J. Med. Chem. 2006, 49, 3645-3652.
120 Achgill, R. K.; Matsuura, N.; Tabuchi, F. Synthesis of tricyclazole. EuropeoPatent 0213814A2, March 11,1987.
121 Brown, H. Dk.; Matzuk, A. R.; Ilveus, I. R.; Peterson, L. H.; Harris, S. A.; Sarett, L. H.; ESoc. 1961, 83, 1764-1765.
Bursavich, M. G.; PaK.; Robinson, R.; Peterson, A.; Cibora, D. M.; Zhu, J. -F.; Richards, B. Bioorg. Med. Chem. Lett. 2010, 20, 1677-1679.
van Tilburg, E. W.; van der Klein, P. A. M.; de Groote, M.; Beukers, M. W.; IJzerman, A. P. Bioorg. Med. Chem. Lett. 2001, 11, 2017-
124 Xi, N.; Bo, Y.; Doherty, E. M.; Fotsch, C.; Gavva, N. R.; Han, N.; Hungate, R. WKlionsky, L.; Liu, Q.; Tamir, R.; Xu, S.; Treanar,Med. Chem. Lett. 2005, 15, 5211-5217.
Franchini, C.; Muraglia, M.; Corbo, FMatucci, R.; Nesi, M.; van Bambeke, F.; Vitalic, C. Arch. Pharm. (Weinheim) 2009, 342, 605-613.
Budjáková, H.; Mucková, M
Sawhney, S, N.; Bansal, O. P. Indian J. Chem. 1977, 15B, 121-124..
Moreno-Díaz, H.; Villalobos-Molina, R.; Ortiz-Andrade, R.; Díaz-Coutiño, D.; Medina-Franco, J. L.; Webster, S. P.; binnie, M.; Estrada-Soto, S.; Ibarra-Barajas, M.; León-Rivera, I.; Návarrete-Vazquez, G. Bioorg. Med. Chem. Lett. 2008, 12871-2877.
Al-Soud, Y. A.; Al-Sa’doni, H. H.; Saeed, B.; Jaber, I. H.; Beni-Khalid, M. O.; Al Masoudi, N. A.; Abdul-Kadir, T.; colla, P. L.; Busonera, B.; Sahna, T.; Loddo, R. ARKIVOC 2008, XV, 225-238.
130 Amnerkar, N. D.; Busari, K. P. J. Enzyme Inhib. Med. Chem. 2011, 26, 22-28.
Akhtar, T.; Hameed, S2008, 58, 135-149.
132 Wang, T.; Kadow, J. F.; Meanwell, N. A. Benzothiazole antiviral agePatent 7087610B2, August 8, 2006.
133 Carlesi, C.; Pasquali, L.; Pizza, S.; Lo Gerfo, A.; Caldarazzo loco, E.; Alessi, R.; Fornai, F.; Siciliano, G. Archives italiennes de biologie 2011, 149, 151-167.
Shafi, S.; AlaPallu, R.; Alam, M. S. Eur. J. Med. Chem. 2012, 49, 324-333.
Barchéchath, S. D.; Tawatao, R. I.; Corr, M.; Carson, D. A.; Cottam, H. B. J. Med.Chem. 2005, 48, 6409-6422.
136 Pietrancosta, N.; Maina, F.; Dono, R.; Moumen, A.; Garino, C.; Laras, Y.; BurlS.; Quélvér, G.; Kraus, J. L. Bioorg. Med. Chem. Lett. 2005, 15, 1561-1564.
Pietrancosta, N.; Mo
Chapter 1
36
Chem. 2011, 19, 1649-1657.
140
142
144
145
d. Chem. 2011,
148 . N.; Smyth, W. F. International
2, 120, 343-352.
155
9,
157
011,
B.;
159 Eur. J. Med. Chem.
138 Christodoulou, M. S.; Colombo, F.; Passarella, D.; Ieronimo, G.; Zuco, V.; DeCesare, M.; Zunino, F. Bioorg. Med.
139 Hantzsch, A.; Weber, J. H. Chem. Ber. 1887, 20(2), 3118-3132.
Sheldrake, P. W.; Matteucci, M.; McDonald, E. Synlett 2006, 460-462. 141 Ishiwata, Y.; Togo, H. Synlett 2008, 2637-2641.
Narender, M.; Reddy, M. S.; Kumar, V. P.; Sriniwas, B.; Sridhar, R.; Nageswar, Y. V. D.; Rao, K. R. Synthesis 2007, 3469-3472.
143 Sanz-Cervera, J. F.; Blasco, R.; Piera, J.; Cynamon, M.; Ibáñez, I.; Murguía, M.; Fustero, S. J. Org. Chem. 2009, 74, 8988-8996.
Castagnolo, D.; Pagano, M.; Bernardini, M.; Botta, M. Synlett 2009, 2093-2096.
Bose, D. S.; Idrees, M.; Srikanth, B. Synthesis 2007, 819-823. 146 Seijas, J. A.; Vázquez-Tato, m. P.; Carballido-Reboredo, M. R.; Crecente-Campo,
J.; Romar-López, L. Synlett 2007, 313-316. 147 Mungra, D. C.; Patel, M. P.; Rajani, D. P.; Patel, R. G. Eur. J. Me
46, 4192-4200.
O’Donnell, F.; Smyth, T. J. P.; Ramachandran, VJournal of Antimicrobial Agents 2010, 35, 30-38.
149 Sun, X. -Y.; Wei, C. -X.; Chai, K. -Y.; Piao, H. -R. Quan, Z. -S. Arch. Pharm. Chem. Life Sci. 2008, 341, 288-293.
150 Chen, Y. -L.; Chen, I-L.; Lu, C. -M.; Tzeng, C. -C.; Tsao, L. T.; Wang, J. -P. Bioorg. Med. Chem. 2004, 12, 387-392.
151 Lee, C. H.; Lee, H. -S. J. Korean Soc. Appl. Biol. Chem. 2011, 54, 118-123. 152 Suzuki, J.; Nishikibe, M. Nihon Yakurigaku Zasshi (Japan) 200153 Sankaran, M.; Kumarasamy, C.; Chokkalingam, U.; Mohan, P. S. Bioorg. Med.
Chem. Lett. 2010, 20, 7147-7151. 154 Solomon, V. R.; Lee, H. Current Medicinal Chemistry 2011, 18, 1488-1508.
Ahmed, N.; brahmbhatt, K. G.; Sabde, S.; Mitra, D.; Singh, I. P.; Bhutani, K. K. Bioorg. Med. Chem. Lett. 2010, 18, 2872-2879.
156 Chen, S.; Chen, R.; He, M. Pang, R. Tan, Z.; Yang, M. Bioorg. Med. Chem. 20017, 1948-1956.
Loiseau, P. M.; Gupta, S.; Verma, A.; Srivastva, S.; Puri, S. K.; Sliman, F.; Normand-Bayle, M.; Desmaele, D. Antimicrobial Agents and Chemotherapy 255, 1777-1780.
158 Vieira, N. C.; Herrenknecht, C.; Vacus, J.; Fournet, A.; Bories, C.; Figadère, Espindola, L. S.; Loiseau, P. M. Biomedicine & Pharmacotherapy 2008, 62, 684-689.
Nayyar, A.; Patel, S. R.; Shaikh, M.; Coutinho, E.; Jain, R. 2009, 44, 2017-2029.
Brief review on nitrogen containing heterocycles
37
607.
162 hiller, T. M.; Powers, J. H.; Angulo, F. J. Clin. Infect. Dis. 2007,
163
nderson, P. S.; Pitzenberger, S. M.; Varga, S. L. J. Am. Chem.
164
165
166 ; Battina, S. K.; Rana, S.; Takemoto, D. J.; Chiang, P. K.;
167 , M.; Dadrass, O. G. Bioorg.
168
169
170 ; Noaman, E.; Heiba, H. I.; El-Hossary, E. M.
171 ed, M. M. Eur. J. Med. Chem. 2009, 44, 4211-
-
1853.
d, S. A.
2011, 46, 201-207.
179
180 Sandelier, M. J.; DeShang, P. Org. Lett. 2007, 9, 3209-3212.
160 Yang, C. -L.; Tseng, C. -H.; Chen, Y. -L.; Lu, C. -M.; Kao, C. -L.; Wu, M. -H.; Tzeng, C. -C. Eur. J. Med. Chem. 2010, 45, 602-
161 Foley, M.; Tilley, L. Pharmacol. Ther. 1998, 79, 55-87.
Nelson, J. M.; C44, 977-980.
Witherup, K. H.; Ransom, R. W.; Graham, A. C.; Bernard, A. M.; Salvatore, M. J.; Lumma, W. C.; ASoc. 1995, 117, 6682-6685.
Dansyz, W.; Parsons, C. G. Pharmacol. Rev. 1998, 50(4), 597-664.
Merck Index, 11th Edition, 3710.
Shi, A.; Nguyen, T. A.Hua, D. H. Bioorg. Med. Chem. Lett. 2008, 18, 3364-3368.