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Synthesis, Characterization and Antimicrobial Activity of Some Schiff Bases of 2-amino-4-(4-chlorophenyl)–n-(3-furan-2-ylmethyl carboxamido) thiophenes


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1 Department of Pharmaceutical Chemistry, PES College of Pharmacy, Bangalore-50, Karnataka, India
     

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2-amino-4-(4-chlorophenyl)-N-(3-furan-2-ylmethyl carboxamido) thiophenes was synthesized using versatile Gewald reaction .First step is preparation of furfuryl cyanoacetamide which was carried out by condensation of furfuryl amine and ethyl cyano acetate which was then reacted with p-chloro acetophenone, sulphur, diethyl amine to give 2-amino-4-(4- chlorophenyl)-N-(3-furan-2-yl methyl carboxamido) thiophene (SM-4) later the compound was treated with twelve different substituted aryl aldehydes to yield twelve new Schiff bases(SM 4a-4l). The compounds were characterized IR, 1H NMR and mass spectral data and screened for antimicrobial activity.

Keywords

Synthesis, Thiophenes, Schiff Bases, Spectral Analysis, Antimicrobial Activity
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  • Ajay DP, Parendu DR, Franklin PX, Harish P,Vasudevan S, Kamala KV. Tetra substituted thiophenes as anti-inflammatory agents: Exploitation of analogue-based drug design. Bioorg Med Chem Lettr 2005; 13:6685-92.
  • Bhattacharjee S et al. Synthesis, Characterization and CNS depressant activity of some schiff bases of 2-amino-4-(4- chlorophenyl) thiophene-3 carboxamide. Asian J of Res Chem. 2011; 4(10):1562-65.
  • Pinto E,Queiroz M.J, Vale-Silva L, Oliveira J, Begouin A, Antifungal activity of synthetic di(hetero) arylamines based on the benzo[b]thiophene moiety. Bioorg Med Chem 2008;16:8172– 8177.
  • Srinivas R,Sarvanan J,Mohan S, Synthesis of 2-substitutedamino- 3(N-o-tolylcarboxamido)-4,5-dimethyl thiophenes as analgesic and anti-inflammatory agents. Indian J Hetero Chem.1998;8:59-62.
  • Kristina S, Marijeta K, Ivo P, Grace K. Synthesis, photochemical synthesis, DNA binding and antitumour evaluation of novel cyano-amidino-substituted derivatives of naptha-furans, napthathiophenes, thieno benzofurans,benzo-dithiophenes and their acyclic precursors. Eur J Med Chem.2006; 41:1-15.
  • Lina Li,Lei Chang, Stephane P.R, Francois L, Marc L, Rene B, Yuqing Wu. Synthesis and evaluation of benzo[b]thiophene derivatives as inhibitors of alkaline phosphatise. Bioorg. Med. Chem. 2009; 3:7290-7300.
  • Isloor AM, Kalluraya B, Pai KS. Synthesis, characterization and biological activities of some new benzo[b]thiophene derivatives. Eur J Med Chem 2010;45:825–30.
  • Bhandari S, Bothara K, Raut M, Patil A, Sarkate A, Mokale V. Design, synthesis and evaluation of anti-inflammatory, analgesic and ulcerogenicity studies of novel substituted phenacyl-1,3,4- oxadiazole-2-thiol and Schiff bases of diclofenac acid as non ulcerogenic derivatives, Bioorg Med Chem 2008;16:1822–1831.
  • Chinnasamy R. P.; Sundararajan R.; Govindaraj S.; Synthesis, characterization and anticonvulsant activity of novel schiff base Of isatin derivatives. Int Jour Pharm Sci 2010; 2:177-181.
  • Bhattacharjee S, Sarvanan J, Mohan S,Arora M. Synthesis, Charaterization and CNS depressant activity of some schiff bases of 2-amino-4-(4-chlorophenyl) thiophene-3 carboxamide. Asian J of Res Chem.2011;4(10):1562-65.
  • Barry A L, Antimicrobial susceptibility test, principle and practices (Illus lea and fehinger, Philedepephia USA) 1976, pp 93-108.

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  • Synthesis, Characterization and Antimicrobial Activity of Some Schiff Bases of 2-amino-4-(4-chlorophenyl)–n-(3-furan-2-ylmethyl carboxamido) thiophenes

Abstract Views: 318  |  PDF Views: 5

Authors

Monica Arora
Department of Pharmaceutical Chemistry, PES College of Pharmacy, Bangalore-50, Karnataka, India
J. Saravanan
Department of Pharmaceutical Chemistry, PES College of Pharmacy, Bangalore-50, Karnataka, India
S. Mohan
Department of Pharmaceutical Chemistry, PES College of Pharmacy, Bangalore-50, Karnataka, India
Shivaji Bhattacharjee
Department of Pharmaceutical Chemistry, PES College of Pharmacy, Bangalore-50, Karnataka, India

Abstract


2-amino-4-(4-chlorophenyl)-N-(3-furan-2-ylmethyl carboxamido) thiophenes was synthesized using versatile Gewald reaction .First step is preparation of furfuryl cyanoacetamide which was carried out by condensation of furfuryl amine and ethyl cyano acetate which was then reacted with p-chloro acetophenone, sulphur, diethyl amine to give 2-amino-4-(4- chlorophenyl)-N-(3-furan-2-yl methyl carboxamido) thiophene (SM-4) later the compound was treated with twelve different substituted aryl aldehydes to yield twelve new Schiff bases(SM 4a-4l). The compounds were characterized IR, 1H NMR and mass spectral data and screened for antimicrobial activity.

Keywords


Synthesis, Thiophenes, Schiff Bases, Spectral Analysis, Antimicrobial Activity

References