Abstract
A novel series of hitherto unknown 3-(4-aryl-5H-indeno[1,2-b]pyridin-2-yl)coumarin derivatives 3a–r have been synthesized by the reaction of 3-coumarinyl methyl pyridinium salts 1a-c with appropriate 2-arylidene-1-indanones 2a–f under Krohnke’s reaction condition so as to investigate their in vitro antimicrobial activity. Structures of the target compounds 3a–r were characterized by their spectral and elemental analyses. Among the series, compound 3l displayed an encouraging antibacterial activity profile as compared to the reference drug ampicillin against tested bacterial strains.
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Cooper K, Fray MJ, Cross PE, Richardson K (1989) Eur Pat Appl EP 299727 A1 19890118
El-Rayyes N, AI-Qatami S, Edun M (1987) Heterocycles. 14. Synthesis of 5H-Indeno pyrimidines. J Chem Eng Data 32:481–483
Evdokimov NM, Slambrouck SV, Heffeter P, Tu L, Calve BL, Theys DL, Hooten CJ, Uglinskii PY, Rogelj S, Kiss R, Steelant WFA, Berger W, Yang JJ, Bologa CG, Kornienko A, Magedov IV (2011) Structural simplification of bioactive natural products with multicomponent synthesis. 3. Fused uracil-containing heterocycles as novel topoisomerase-targeting agents. J Med Chem 54:2012–2021
Garazd YL, Kornienko EM, Maloshtan LN, Garazd MM, Khilya VP (2005) Modified Coumarins. 17. Synthesis and Anticoagulant Activity of 3,4-Cycloannelated Coumarin D-Glycopyranosides. Chem Nat Prod 41:508–512
Hage SE, Lajoie B, Feuillolay C, Roques C, Baziard G (2011) Synthesis, antibacterial and antifungal activities of bifonazole derivatives. Arch. Pharm. Chem. Life Sci. 11:402–410
Heintzelman GR, Averill KM, Dodd JH (2002) PCT Int Appl WO2002085894 A1 20021031
Heintzelman GR, Averill KM, Dodd JH, Demarest KT, Tang Y, Jackson PF (2004) Pat Appl Publ US 2004082578(A1):20040429
Hwu JR, Singha R, Hong SC, Chang YH, Das AR, Vliegen I, Clercq ED, Neyts (2008) Synthesis of new benzimidazole–coumarin conjugates as anti-hepatitis C virus agents. Antiviral Res 77:157–162
Kayser O, Kolodziej HZ (1999) Antibacterial activity of simple coumarins: structural requirements for biological activity. Naturforsch 54c:169–174
Koelsch CF (1950) Bromination of 3-acetocoumarin. J Am Chem Soc 72:2993–2995
Kontogiorgis CA, Hadjipavlou-Litina DJ (2005) Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem 48:6400–6408
Krohnke F (1976) The specific synthesis of pyridines and oligopyridines. Synthesis 1:1–24
Kunstmann R, Fischer G (1984) Molecular analysis of hexahydro-1H-indeno[1,2-b]pyridines: potential antidepressants. J Med Chem 27:1312–1316
Miri R, Javidnia K, Hemmateenejad B, Azarpira A, Mirghofran Z (2004) Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives. Bioorg Med Chem 12:2529–2536
Moffett RB (1964a) Central nervous system depressants. VII.1 pyridyl coumarins. J Med Chem 7:446
Moffett RB (1964b) USP. 3,156,697
Murray RD, Mendez J, Brown SA (1982) In The Natural Coumarins: Occurrence, Chemistry and Biochemistry, John Wiley: New York, NY
Rao TVP, Rao VR (1986) Studies on coumarin derivatives. Part I. Synthesis of some substituted thiazolyl- and benzoxazinylcoumarins. Indian J Chem 25B:413–415
Rappa G, Shyam K, Lorico A, Fodstad O, Sartorelli AC (2000) Structure-activity studies of novobiocin analogs as modulators of the cytotoxicity of etoposide (VP-16). Oncol Res 12:113–127
Rothenberg G, Downie AP, Raston CL, Scott JL (2001) Understanding Solid/Solid Organic Reactions. J Am Chem Soc 123:8701–8708
Safak C, Simsek R, Altas Y, Boydag S, Erol K (1997) 2-methyl-3-acetyl-4-aryl-5-oxo-1,4-dihydro-5H-indeno[1,2-b]pyridine derivatives studies and their calcium antagonistic activities. Boll Chim Farm 136:665–669
Sharma RC, Parashar RK (1988) Synthesis and microbicidal activity of N-(2-substituted) phenyl ureas and their metal complexes. J Inorg Biochem 32:163–169
Sreenivasulu B, Sundaramurthy V, Subba Rao NV (1974) Search for physiologically active compounds. Part XXIII. Synthesis of 3-(3-pyridyl) and 3-(3-pyridyl)-4-methyl coumarins. Proc Ind Acad Sci Sect A 79:41–48
Suzuki M, Nakagawa-Goto K, Nakamura S, Tokuda H, Morris-Natschke SL, Kozuka M, Nishino H, Lee KH (2006) Cancer preventive agents. Part 5. Anti-tumor-promoting effects of coumarins and related compounds on Epstein-Barr virus activation and two-stage mouse skin carcinogenesis. Pharm Biol 44:178–182
Thaisrivongs MN, Janakiraman KT, Chong PK, Tomich LA, Dolack SR, Turner JW, Strohbach JC, Lynn MM, Horng RR, Hinshaw KD (1996) Structure-based design of novel HIV protease inhibitors: sulfonamide-containing 4-hydroxycoumarins and 4-hydroxy-2-pyrones as potent non-peptidic inhibitors. J Med Chem 39:2400–2419
Vigante B, Ozols J, Sileniece G, Kimenis A, Duburs G (1989) USSR SU 794006 A119810107
Yang EB, Zhao YN, Zhang K, Mack P (1999) Daphnetin, one of coumarin derivatives, is a protein kinase inhibitor. Biochem Biophys Res Commun 260:682–685
Zhang J, Shabrawy ARO, Shanawany MA, Schiff PL, Slatkin DJ (1987) New Azafluorene Alkaloids from Oxandra xylopioides. J Nat Prod 50:800–806
Acknowledgments
The authors CVP, VGB, NHP, and AAP are grateful to UGC, New Delhi for providing financial assistance in the form of research fellowship in science for meritorious students. The authors are also thankful to the Head of the Department of Chemistry, Sardar Patel University, for providing research facilities.
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Brahmbhatt, D.I., Patel, C.V., Bhila, V.G. et al. An efficient synthesis and antimicrobial screening of new hybrid molecules containing coumarin and indenopyridine moiety. Med Chem Res 24, 1596–1604 (2015). https://doi.org/10.1007/s00044-014-1228-1
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DOI: https://doi.org/10.1007/s00044-014-1228-1