Abstract
Chromene and coumarin scaffolds are known for their potential antimicrobial activity. Herein, we have synthesized hybrid compounds containing both, substituted 4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-ones, 3a–o have been synthesized from substituted (E)-1-(7-Hydroxy-4-methyl-8-coumarinyl)-3-phenyl-2-propen-1-ones, 2a–o in good yield using the microwave-assisted Vilsmeier–Haack reaction. All the synthesized compounds were tested in vitro for their antimicrobial activity. The compounds 3e, 3f and 3g were found to be potent against tested fungal and bacterial strains.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Ashok D, Sudershan K, Khalilullah M (2012) Microwave assisted synthesis of [5-chloro-3-methyl-7-aryl-7H-furo[3,2-g]chromen-2-yl](phenyl)methanones and their antibacterial activity. Indian J Heterocycl Chem 21(4):301–304
Ashwood VA, Buckingham RE, Cassidy F, Evans JM, Faruk EA, Hamilton TC, Nash DJ, Stemp G, Willcocks K (1986) Synthesis and antihypertensive activity of 4-(cyclic amido)-2H-1-benzopyrans. J Med Chem 29:2194–2201
Benson HJ (1990) Microbiological applications, 5th edn. W. C. Brown Publications, Boston
Cassidy F, Evans JM, Hadley MS, Haladij AH, Leach PE, Stemp (1992) Synthesis and antihypertensive activity of 3-[(substituted-carbonyl)amino]-2H-1-benzopyrans. Med Chem 35:1623–1627
El-Agrody AM, El-Hakim MH, AbdEl-latif MS, Fakery AH, El Sayeed ESM, El-Ghareeb KA (2000) Synthesis of pyrano[2,3-d]pyrimidine and pyrano[3,2-e][1,2,4]triazolo[2,3-c]pyrimidine derivatives with promising antibacterial activity. Acta Pharm 50:111–120
Jung K, Park YJ, Ryu JS (2008) Scandium(III) triflate-catalyzed coumarin synthesis. Synth Commun 38(1):4395–4406
Khan MSY, Sharma P (1993) Synthesis of new α-pyranochalcones and related cyclization products. Indian J Chem 32B:374–376
Kusanur R, Manjunath G, Kulkarni MV (2004) Synthesis and biological activities of some substituted 4-{4-(1,5-diphenyl-1Hpyrazol- 3-yl) phenoxymethyl}coumarins. Indian J Heterocycl Chem 13:201–204
Martinez AG, Marco LJ (1997) Friedlander reaction on 2-amino-3-cyano-4H-pyrans: synthesis of derivatives of 4H-pyran [2,3-b] quinoline, new tacrine analogues. Bioorg Med Chem Lett 24:3165–3170
Mohr SJ, Chirigos MA, Fuhrman FS, Pryor JW (1975) Pyran copolymer as an effective adjuvant to chemotherapy against a murine leukemia and solid tumor. Cancer Res 35:3750–3754
Mulwad VV, Shirodkhar JM (2002) Synthesis and biological activity of some new thiazolidinones and azetidinones of 6-amino coumarin. Indian J Heterocycl Chem 11:192–194
Musiliyu AM, Veera LDB, Lekan ML, John C, Andre S, Ahkinyala A (2011) Cytotoxic activity of new acetoxycoumarin derivatives in cancer cell lines. Anticancer Res 31:2017–2022
Nofal ZM, El-Zahar MI, Abd El-Karim SS (2005) Synthesis and chemoprophylactic effect of novel coumarin derivatives. Egypt J Chem 48(5):587–604
Ohira T, Yatagai MJ (1993) Extractives of Abies mariesii masters. II. The efficient extraction of maltol using supercritical fluid, and its antifungal and plant growth regulation effects. Jpn Wood Res Soc 39(2):237–242
Patil AD, Freyer AJ, Eggleston DS, Haltiwanger RC, Bean MF, Taylor PB, Caranfa MJ, Breen AL, Bartus HR, Johnson RK, Hertzberg RP, Westley JW (1993) The Inophyllums, novel inhibitors of HIV-1 reverse-transcriptase isolated from the Malaysian tree, Calophyllum inophyllumlinn. J Med Chem 36:4131–4138
Rimbault CG, Narbel PM (1985) American Patent 4.665.202. Chem abstr 104:50730
Rochfort SJ, Metzger R, Hobbs L, Capon R (1996) New chromenols from a southern Australian tunicate, Aplidium solidum. Aust J Chem 49:1217–1219
Song SQ, Zhou LG, Li D, Tang D, Li JQ, Jiang WB (2004) Antifungal activity of five plants from Xinjiang. Nat Prod Res Dev 16:157–159
Zamocka J, Misikova E, Durinda J (1992) Preparation, properties, and effects of 5-hydroxy or 5-methoxy-4-oxo-4H-pyran-2 -ylmethyl 2-alkoxycarbanilates. Cesk-Farm (Ceska a Slovenska Farmacie). 41:170–172
Acknowledgments
The authors are thankful to The Head, Department of Chemistry, Osmania University, Hyderabad for providing Laboratory facilities and one of the authors B. Vijaya Lakshmi, thankful to CSIR, New Delhi, India for financial support in the form of CSIR-SRF. We also thankful to The Director, CFRD, Osmania University, Hyderabad for providing elemental and spectral analysis facilities.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Ashok, D., Vijaya Lakshmi, B., Ravi, S. et al. Microwave-assisted synthesis of substituted 4-chloro-8-methyl-2-phenyl-1,5-dioxa-2H-phenanthren-6-ones and their antimicrobial activity. Med Chem Res 24, 1487–1495 (2015). https://doi.org/10.1007/s00044-014-1204-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-014-1204-9