A Convergent Approach for the Synthesis of New Pyrazolyl Bipyridinyl Substituted Coumarin Derivatives as Antimicrobials

Bhila, Varun G.; Chovatiya, Yogita L.; Patel, Chirag V.; Giri, Rakesh R.; Brahmbhatt, Dinkar I.

doi:10.18052/www.scipress.com/ILCPA.40.1

ILCPA > Volume 40 > A Convergent Approach for the Synthesis of New...

< Back to Volume

A Convergent Approach for the Synthesis of New Pyrazolyl Bipyridinyl Substituted Coumarin Derivatives as Antimicrobials

Full Text PDF

Abstract:

Some new 3-[3-(1-phenyl-3-aryl-1H-pyrazol-4-yl) acryloyl] coumarins 3a-f were synthesized (coumarin chalcones) by the condensation of various 3-acetyl coumarins 1 and appropriate 1-phenyl-3-aryl-1H-pyrazole-4-carbaldehyde 2. These coumarin chalcones 3a-f were then employed for the synthesis of pyrazolyl bipyridinyl substituted coumarins 7a-f, 8a-f, and 9a-f under Krohnke’s reaction condition. The characterization of all the synthesized compounds was carried out by elemental analysis, IR, ¹H-NMR, ¹³C-NMR, DEPT-135 and mass spectral analysis. In addition to that, in vitro antimicrobial competency of the title compounds was assessed against selected pathogens. Compounds 3b, 3e, 7b, 8b, 8c and 9b exhibited excellent antimicrobial activity and said to be the most proficient members of the series.

Info:

Periodical:

International Letters of Chemistry, Physics and Astronomy (Volume 40)

Pages:

1-16

DOI:

https://doi.org/10.18052/www.scipress.com/ILCPA.40.1

Citation:

V. G. Bhila et al., "A Convergent Approach for the Synthesis of New Pyrazolyl Bipyridinyl Substituted Coumarin Derivatives as Antimicrobials", International Letters of Chemistry, Physics and Astronomy, Vol. 40, pp. 1-16, 2015

Online since:

October 2014

Authors:

Varun G. Bhila, Yogita L. Chovatiya, Chirag V. Patel, Rakesh R. Giri, Dinkar I. Brahmbhatt

Keywords:

Antimicrobial Activity, Bipyridine, Coumarin, Kröhnke’s Reaction, Pyrazole

Export:

RIS, BibTeX, Text

Distribution:

Open Access

This work is licensed under a
Creative Commons Attribution 4.0 International License

References:

Neu, H.C. The Crisis in Antiboitic Resistance. Science, 1992, 257(5073), 1064-1072.

Opar, A. Bad Bugs Needs more Drugs. Nat. Rev. Drug Discovery, 2007, 6(12), 943-944.

Anderson, A. C; Schiffer, C; Pollastri, M and Peet, N.P. The challenge of developing robust drugs to overcome resistance. Drug Discovery Today, 2011, 16(17-18), 755-761.

Todd, B. Beyond MRSA: VISA and VRSA: what will ward off these pathogens in health care facilities? Am. J. Nurs., 2006, 106(4), 28-30.

Moffett, R.B. Central nervous system depressants VII. Pyridyl coumarins. J. Med. Chem., 1964, 7, 446-449.

Garazd, Y. L; Kornienko, E. M; Maloshtan; L. N; Garazd, M. M; Khilya, V.P. Modified coumarins. 17. Synthesis and anticoagulant activity of 3, 4-cycloannelated coumarin D- glycopyranosides. Chem. Nat. Prod., 2005, 41, 508-512.

Sreenivasulu, B; Sundaramurthy, V; Subba Rao, N.V. Search for physiologically active compounds. Part XXIII. Synthesis of 3-(3-pyridyl) and 3-(3-pyridyl)-4-methyl coumarins. Proc. Indian. Acad. Sci. A, 1974, 79, 41-48.

Moffett, R. B. Pyridylcoumarins. U. S. Patent, 3, 201, 406, (1965).

Matos, M. J; Vilar, Gonzalez-Franco, R. M; Uriarte, E; Santana, L; Friedman, C; Tatonetti, N. P; Viña, D and Fontenla, J.A. Novel (coumarin-3-yl)carbamates as selective MAO-B inhibitors: Synthesis, in vitro and in vivo assays, theoretical evaluation of ADME properties and docking study. Eur. J. Med. Chem., 2013, 63, 151-161.

Lad, H. B; Giri, R. R and Brahmbhatt, D.I. An efficient synthesis of some new 3- bipyridinyl substituted coumarins as potent antimicrobial agents. Chin. Chem. Lett., 2013, 24, 227-229.

Bhila, V. G; Patel, C. V; Brahmbhatt, D.I. One pot synthesis of some novel coumarins containing 5-(substituted-2-hydroxybenzoyl) pyridine as a new class of antimicrobial and antituberculosis agents. Med. Chem . Res., 2013, 22(9), 4338-4346.

Shimizu, T; Nozawa, T; Hatano, M. Magnetic circular dichroism studies of pyridine- heme complexes in aqueous media. Bioinorg. Chem., 1976, 6(2), 119-131.

Jia, J; Hubberstey, P; Champness, N. R and Schröder, M. In: Molecular Networks (Struct Bond); Mir Wais Hosseini, Ed.; Springer: Verlag Berlin Heidelberg, 2009; Vol. 132, pp.135-161.

Fraser, C. L and Smith, A.P. Metal complexes with polymeric ligands: Chelation and metalloinitiation approaches to metal tris(bipyridine) containing materials. J. Polym. Sci., Part A: Polym. Chem., 2000, 38(S1), 4704-4716.

Mongin, F; Trécourt, F; Gervais, B; Mongin, O; Quéguiner, G. First Synthesis of Caerulomycin B. A New Synthesis of Caerulomycin C. J. Org. Chem., 2002, 67, 3272-3276.

El-Kemary, M; Organero, J. A; Douhal, A. Fast Relaxation Dynamics of the Cardiotonic Drug Milrinone in Water Solutions. J. Med. Chem., 2006, 49(11), 3086-3091.

Patel, M. N; Dosi, P. A; Bhatt, B.S. Square planar palladium (II) complexes of bipyridines: synthesis, characterization and biological studies. J. Coord. Chem., 2012, 65(21), 3833-3844.

Patel, M. N; Parmar, P. A; Gandhi, D.S. DNA interactions and cytotoxic studies of cis- platin analogues of substituted 2, 2-bipyridines, Spectrochim. Acta., 2012, 97C, 54-59.

Dai, H; Yu, H; Liu, J; Li, Y; Qin, X; Zhang, X; Qin, Z; Wang, T; Fang, J. Synthesis and bioactivities of novel trifluoromethylated pyrazole oxime ether derivatives containing a pyridyl moiety. Arkivoc., 2009(vii), 126-142.

Johns, B. A; Gudmundsson, K. A; Allen, S.H. Pyrazolo[1, 5-a]pyridine antiherpetics: Effects of the C3 substituent on antiviral activity. Bioorg. Med. Chem. Lett., 2007, 17(10), 2858-2862.

Robertson, D. W; Krushinski, J. H; Pollock, G. D; Haye, J.S. Imidazole-pyridine bioisosterism: comparison of the inotropic activities of pyridine- and imidazole- substituted 6-phenyldihydropyridazinone cardiotonics. J. Med. Chem., 1988, 31, 461-465.

Thomas, K. D; Adhikari, A. V; Shetty, N.S. Design, synthesis and antimicrobial activities of some new quinoline derivatives carrying 1, 2, 3-triazole moiety. Eur. J. Med. Chem., 2010, 45(9), 3803-3810.

Krohnke, F. The specific synthesis of pyridines and oligopyridines, Synthesis, 1976, 1, 1-24.

NCCLS (National Committee for Clinical Laboratory Standards), Performance Standards for Antimicrobial Susceptibility Testing: Twelfth Informational Supplement. 2002, 1-56238-454-6, M100-S12 (M7).

Biscler, A. Ueber die entstehung einiger substituirter indole. Chem Ber., 1892, 25, 2860-2879.

Kira, M. A; Abdel-Raeman, M. O; Gadalla, K.Z. The vilsmeier-haack reaction - III Cyclization of hydrazones to pyrazoles. Tetrahedron. Lett., 1969, 10(2), 109-110.

Basnet, A.; Thapa, P.; Karki, R.; Na, Y.; Jhang, Y.; Jeong, B. S.; Jeong, T. C.; Lee, C. S.; Lee, E. S. 2, 4, 6-Trisubstituted pyridines: synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship. Bioorg. Med. Chem., 2007, 15(13), 4351-4359. ( Received 28 September 2014; accepted 08 October 2014 ).

Show More Hide

Cited By:

This article has no citations.