Novel malyngamide structural analogs: synthesis and biological evaluation
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Med Chem Res (2013) 22:4581–4591 DOI 10.1007/s00044-013-0466-y
ORIGINAL RESEARCH
Novel malyngamide structural analogs: synthesis and biological evaluation G. Venkateswar Reddy • T. Vijaya Kumar • B. Siva K. Suresh Babu • P. V. Srinivas • Irum Sehar • A. K. Saxena • J. Madhusudana Rao
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Received: 13 July 2012 / Accepted: 1 January 2013 / Published online: 13 January 2013 Ó Springer Science+Business Media New York 2013
Abstract In the course of our search for new anticancer agents, a series of novel malyngamide derivatives were synthesized by sharpless asymmetric epoxidation, followed by Julia-Kocinski olefination reactions as key reaction sequence. Anticancer activities of all these derivatives were screened against IMR-32, SF-295, SKNSH, HeLa, Colon502713, SW-620, and Hop-62 cell lines for the first time. Keywords Malyngamides Plants of Piperaceae family Anticancer activity Hybrid amides Sharpless asymmetric epoxidation Julia olefination
Introduction Marine organisms have been proven to be valuable resources for discovery of structurally unique and biologically important natural products. Apart from human medicines, the research involving marine natural products in the last three decades has also generated significant discoveries that are now utilized routinely as pharmacological tools with unique cellular targets. Some of them have become G. V. Reddy T. V. Kumar B. Siva K. S. Babu (&) P. V. Srinivas J. M. Rao Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500607, India e-mail: [email protected] I. Sehar A. K. Saxena Pharmacology Division, CSIR-Indian Institute of Integrative Medicine (IIM), Canal Road, Jammu 180001, India Present Address: P. V. Srinivas Process, Research and Development Center, Biocon Limited, Bangalore 560100, India
indispensable tools in biochemical research and played vital roles in the recent advancements of life sciences. Malyngamides (Suntornchaswej et al., 2007; Li et al., 2007): are a class of fatty acid amides, are the secondary metabolites isolated from the marine cyanobacterium Lyngbya majuscule, and constitute an interesting group of marine natural products, for which a wide variety of biological activities have been described, including anti-inflammatory, anti-feedant activity, cytotoxicity to marine animals, anti-leukemic, and anti-tumor activity, antifungal, anti-HIV, and most often antineoplastic activities (Wylie and Paul, 1988). Most of these malyngamides possessing a fatty acid side chain containing a 4E double bond and a 7S stereogenic center which is connected via an amide linkage to a heavily oxygenated six membered ring or a heterocycle and/or with a functional unit of a vinylic chloride. A close observation at the structures of all these amides (or) in most of the malyngamides clearly suggests that acid portion (left hand part of malyngamides) of the molecule always remains the same; however, the amines keep changing (Fig. 1). In a similar fashion, plants of the Piperaceae family are a well-known so
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