SYNTHESIS OF SOME NOVEL BENZOPYRANES DERIVATIVES AND EVALUATION THEIR BIOLOGICAL ACTIVITY
Benzopyran (chromene) is one of the privileged medicinal pharmacophore, which appears as an important structural component in natural
compounds and generated great attention because of their interesting biological activity. The derivatives of benzopyran moiety can be capable of
interacting with a variety of cellular targets which leads to their wide ranging biological activities such as antitumor, antihepatotoxic, antioxidant, antiinflammatory,
diuretic, anticoagulant, antispasmolytic, estrogenic, antiviral, antifungal, antimicrobial, anti-helminthic, hypothermal, vasodilatory,
anti-HIV, antitubercular, herbicidal, anticonvulsant and analgesic activity. In the present study the synthesis of substituted benzopyran derivatives
have been reported as one-pot reaction by reaction of 2-chlororesorcinol with malononitrile in the presence and aldehydes or ketones. The produced
products were led to react with formamide to produce pyrimidochromene. Aminochromene-2-carbonitrile was converted into the corresponding
imidate, which in turn converted upon treatment withhydrazine or ammonia to the corresponding amidine. The produced amidines were cyclized into
the pyrimidochromene derivatives. The synthesized compounds have been characterized by TLC, Elemental analysis, IR and 1H-NMR Spectroscopy.
Some of the synthesized compounds in this work were chosen and screened in vitro for their antimicrobial and anti-fungal activity against some
strains of bacteria and fungi. The antibacterial and anti-fungal activities of synthesized compounds were compared with antibacterial and anti-fungal
activity of the standard antibiotics Chloramphenicol and Sertaconazol. The most of the tested compounds revealed antibacterial and antifungal
properties. This review is summarized to know about the different pharmacological activities of chromene nucleus with the extended knowledge
about its antimicrobial and antifungal activity.
Keywords: 2-Chlororesorcinol, Pyrimidochromene, Amidines, antimicrobial and antifungal activity.
1. Behrami A, Vaso K, Krasniqi I. Antibacterial activityof coumarine derivatives synthesized from hydroxyl-4-2H--Benzopyran-2-one, The comparison with standard drug. J Int Environ Appl Sci 2010;5:247.
2. Aytemir MD, Hider RC, Erol DD, Ozalp M, Ekizoglu M. Synthesis of new antimicrobial agents; Amide derivatives of pyranones and pyridinones. Turk J Chem 2003;27(4):445-52.
3. Aziz B, Kozata V, Sevdie G, Islam K, Skender D, Idreiz V. Synthesis, characterisation and antibacterial activity of some [8-Amino-4, 7 dihydroxy-chromen-2-one], [N-(3-Cyano-4-ethoxy-2-oxo-2H-chromen-7-yl) - formamide] Derivatives. The comparison with standard drug. Res J Pharm Biol Chem Sci 2012;3(2):876.
4. Kulkarni MV, Kulkarni GM, Lin CH, Sun CM. Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents. Curr Med Chem 2006;13(23):2795-818.
5. Emmanuel-Giota AA, Fylaktakidou KC, Hadjipavlou Litina DJ, Litinas KE, Nicolaides DN. Synthesis and biological evaluation of several 3-(coumarin-4-yl) tetrahydroisoxazole and 3-(coumarin-4-yl) dihydropyrazole derivatives. J Heterocycl Chem 2001;38:717-22.
6. Afsaneh Z, Roghieh M, Maliheh S, Sussan KA, Saeed E, Alireza F. 2-Amino-4-(nitroalkyl)-4H-chromene-3-carbonitriles as new cytotoxic agents. Iran J Pharm Res 2013;12(4):679-85.
7. Schweizer E E, Meeder-Nycz O. In: Chromenes, Chromanes, Chromones. Ellis G P, editor. New York, NY: Wiley-Interscience; 1977. pp. 11â€“139.
8. Curini M, Cravotto G, Epifano F, Giannone G Chemistry and biological activity of natural and synthetic prenyloxycoumarins. Curr Med Chem 2006;13:199-222.
9. Ren Q, Woon YS, Zhiyun DU, Kun Z, Jian W. Expeditious assembly of a 2-amino-4H-chromene skeleton by using an enantioselective Mannich intramolecular ring cyclization-tautomerization cascade sequence. Chem Eur J 2011;17(28):7781-5.
10. Abd-El-Aziz AS, El Agrody AM, Bedair AH, Corkery TC, Ata A. Synthesis of hydroxyquinoline derivatives, amino-hydroxychromene, aminocoumarin and their antibacterial activities. Heterocyclic 2004;63(8):1793-812.
11. Borges F, Roleira F, Milhazes N, Santana L, Uriarte E. Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity. Curr Med Chem 2005;12:887-916.
12. Chimenti F, Bizzarri B, Bolasco A, Secci D, Chimenti P, Carradori S. Synthesis and in vitro selective anti-Helicobacter pylori activity of N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides. Eur J Med Chem 2006;41(2):208-12.
13. Khan KM, Saify ZS, Khan MZ, Zia U, Choudhary MI, Attaur R. Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity. J Enzyme Inhib Med Chem 2004;19(4):373-9.
14. Yu D, Suzuki M, Xie L, Morris-Natschke SL, Lee KH. Recent progress
Asian J Pharm Clin Res, Vol 8, Issue 4, 2015, 7-12
in the development of coumarin derivatives as potent anti-HIV agents. Med Res Rev 2003;23:322-45.
15. Deb ML, Bhuyah PJ. Uncatalysed knoevenagel condensation in aqueous medium at room temperature. Tetrahedron Lett 2005;46:6453-6.
16. Wang, X., Zeng, Z., Shi, D., Wei, X., Zong, Z., 2004b. One-step synthesis of 2-amino-3-cyano-4-aryl-1,4,5,6-tetrahydropyrano[3,2- c]quinolin-5-one derivatives using KF-Al2O3 as catalyst. Synth. Commun. 34, 3021â€“3027.
17. DerivativesMahfouz NM, Moharam M. Synthesis, characterization and in vitro antifungal evaluation of some dithiocarbamic acid. Pharm Pharmacol Commun 1999;5(5):315-22.
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