Naresh K et al., PharmaScient, Volume 1, Issue 1, 2012; 1-4. www.pharmascient.com 1 Evaluation of Anti-Bacterial and Anti-Fungal of Novel Thiophene Derivatives Madhukar. A, Anjali shah M, Sandeep Kumar C, Swetha M, Bharath Kumar B, Naresh K* Department of Pharmaceutical Chemistry, St.Mary’s College of Pharmacy, Secunderabad. A.P. – INDIA. *[email protected]ABSTRACT Thiophene nucleus has been established as the potential entity in the largely growing chemical world of heterocyclic compounds possessing promising pharmacological characteristics. The similar compounds synthesized through different routes bear variable magnitudes of biological activities. In the same way compounds with azitidinone moiety possess a varied number of biological activities. In view of this it is worthwhile to prepare different thiophene derivatives that bear an azitidinone moiety at C-2. Different 2-amino thiophene-3-carboxylic acid ethyl esters were prepared by using Gewald’s reaction. 2-amino thiophene 3-caboxy hydrazides were prepared by condensing Phenyl hydrazine with 2-amino thiophene-3-carboxylic acid ethyl esters. From 2-amino thiophene 3-caboxy hydrazides different Schiff’s bases were prepared by reacting with various aromatic aldehydes (viz. Benzaldehyde, Cinnamaldehyde, Para amino Dimethyl Benzaldehyde, Indole-3- caboxaldehyde). Finally the Schiff’s bases thus obtained were treated with chloroacetylchloride in presence of tri- ethyl amine to afford the title compounds. The title compounds were subjected to evaluate for their anti- bacterial and anti-fungal activities. Key words: Thiophene, azitidinone, anti-bacterial activity and anti-fungal activity. INTRODUCTION Thiophene nucleus is a biologically important heterocyclic moiety and attracting attention in chemistry research due to its diverse range of biological activities. An intensive literature review on thiophene, azitidinone and their derivatives revealed that they were found to possesses different biological activities such as antibacterial 1 , mycolytic 1 antimicrobial activity 2,3 , anti-mitotic 4 , antidepressant activity 5 . Azetidinone derivatives which contain β-lactam ring in their structure show potent anti-cunvulsant 6 , atni-tubercular 7 , anti- inflammatory and anti-tumor activities. 8 In view of the biological importance and the past research on the thiophene, azitidinone and their derivatives; it is worthwhile to synthesize some novel azatidinone incorporated thiophene derivatives. The synthesis of title compounds was achieved by a systematic approach is outlined in the Scheme-I. MATERIALS AND METHODS Melting points of all the compounds were determined in open capillaries using Toshniwal and Cintex melting point apparatus and are uncorrected. IR spectra of the compounds were recorded on SCHIMADZU FT-IR Spectrophotometer by using KBr discs. Progress of the each reaction in the present investigation was monitored by TLC using E-Merck 0.25mm silica gel plates. EXPERIMENTAL METHODS Synthesis of 2-amino-4,5-sustituted thiophene-3- carboxylate (Ib&Ic): An equimolar mixture of sulphur (0.1moles), ethyl cyano acetate (0.1mole) and ketone (cyclohexanone for I and buta-2-one for II), (0.1mole), were taken in a conical flask containing 10 to 15mL of ethanol. The mixture was stirred for 5minutes and morpholine (0.1mole) was slowly added with stirring for 15minutes. This was irradiated at 180W for four minutes and it was cooled to room temperature and kept in refrigerator
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Naresh K et al., PharmaScient, Volume 1, Issue 1, 2012; 1-4.
www.pharmascient.com 1
Evaluation of Anti-Bacterial and Anti-Fungal of Novel Thiophene Derivatives
Madhukar. A, Anjali shah M, Sandeep Kumar C, Swetha M, Bharath Kumar B, Naresh K* Department of Pharmaceutical Chemistry, St.Mary’s College of Pharmacy, Secunderabad. A.P. – INDIA. *[email protected]
ABSTRACT
Thiophene nucleus has been established as the potential entity in the largely growing chemical world of
heterocyclic compounds possessing promising pharmacological characteristics. The similar compounds
synthesized through different routes bear variable magnitudes of biological activities. In the same way
compounds with azitidinone moiety possess a varied number of biological activities. In view of this it is
worthwhile to prepare different thiophene derivatives that bear an azitidinone moiety at C-2. Different 2-amino
thiophene-3-carboxylic acid ethyl esters were prepared by using Gewald’s reaction. 2-amino thiophene 3-caboxy
hydrazides were prepared by condensing Phenyl hydrazine with 2-amino thiophene-3-carboxylic acid ethyl
esters. From 2-amino thiophene 3-caboxy hydrazides different Schiff’s bases were prepared by reacting with
various aromatic aldehydes (viz. Benzaldehyde, Cinnamaldehyde, Para amino Dimethyl Benzaldehyde, Indole-3-
caboxaldehyde). Finally the Schiff’s bases thus obtained were treated with chloroacetylchloride in presence of tri-
ethyl amine to afford the title compounds. The title compounds were subjected to evaluate for their anti-
bacterial and anti-fungal activities.
Key words: Thiophene, azitidinone, anti-bacterial activity and anti-fungal activity.
INTRODUCTION
Thiophene nucleus is a biologically important
heterocyclic moiety and attracting attention in
chemistry research due to its diverse range of
biological activities. An intensive literature review
on thiophene, azitidinone and their derivatives
revealed that they were found to possesses different