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Novel malyngamide structural analogs: synthesis and biological evaluation

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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, Colon-502713, SW-620, and Hop-62 cell lines for the first time.

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References

  • Baudin JB, Hareau G, Julia SA, Ruel O (1991) A direct synthesis of olefins by reaction of carbonyl compounds with lithio derivatives of 2-[alkyl- or (2′-alkenyl)- or benzyl-sulfonyl]-benzothiazoles. Tetrahedron Lett 32:1175

    Article  CAS  Google Scholar 

  • Blakemore PR, Cole WJ, Kocienski PJ, Morley A (1998) A stereoselective synthesis of trans-1,2-disubstituted alkenes based on the condensation of aldehydes with metallated 1-phenyl-1h-tetrazol-5-yl sulfones. Synlett 26–28

  • Blanchette MA, Choy W, Davis JT, Essenfeld AP, Masumune S, Roush WR, Sakai T (1984) Horner–Wadsworth–Emmons reaction: use of lithium chloride and an amine for base-sensitive compounds. Tetrahedron Lett 25:2183

    Article  CAS  Google Scholar 

  • Bouz S, Simmons R, Cossy J (2004) Regioselective Cross-metathesis reaction induced by steric hindrince. Org Lett 6:3465 and references cited therein

    Google Scholar 

  • Corey EJ, Venkateswarlu A (1972) Protection of hydroxyl groups as tert-butyldimethylsilyl derivatives. J Am Chem Soc 94:6190

    Article  CAS  Google Scholar 

  • Corey EJ, Niwa H, Knolle J (1978) Total synthesis of (S)-12-hydroxy-5,8,14-cis-10-trans-eicosatetraenoic acid (Samuelsson’s HETE). J Am Chem Soc 100:1942

    Article  CAS  Google Scholar 

  • Finan JM, Kishi Y (1982) Reductive ring openings of allyl-alcohol epoxides. Tetrahedron Lett 23:2719

    Article  CAS  Google Scholar 

  • Frigerio M, Santagostino M (1994) A mild oxidizing reagent for alcohols and 1,2-diols: o-iodoxybenzoic acid (IBX) in DMSO. Tetrahedron Lett 35:8019

    CAS  Google Scholar 

  • Gao Y, Hanson RM, Klunder JM, Ko SY, Masamune H, Sharpless KB (1987) J Am Chem Soc 109:5765

    Article  CAS  Google Scholar 

  • Hanawa H, Hashimoto T, Maruoka K (2003) Bis((s)-binapthoxy)(isopropoxy)titanium) oxide a μ-oxo-type chiral Lewis acid: application to catalytic asymmetric allylation of aldehydes. J Am Chem Soc 125:1708

    Article  PubMed  CAS  Google Scholar 

  • Ireland RE, Norbeck DW (1985) Application of the Swern oxidaion to the manipulation of higly reactive carbonyl compounds. J Org Chem 50:2198

    Article  CAS  Google Scholar 

  • Kocienski PJ, Bell, PR, Blakemore PR (2000) 1-tert-Butyl-1H-tetrazol-5-yl sulfones in the modified Julia olefination. Synlett 365

  • Li Y, Feng JP, Wang WH, Chen J, Cao XP (2007) Total synthesis and correct absolute configuration of malyngamide U. J Org Chem 72:2344

    Article  PubMed  CAS  Google Scholar 

  • Mitsunobu O, Yamada M (1967) Preparation of esters of carboxylic and phosphoric acid via quaternary phosphonium salts. Bull Chem Soc Jpn 40:2380

    Article  CAS  Google Scholar 

  • Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Langley J, Cronise P, Vaigro-Wolff A, Gray-Goodrich M, Campbell H, Mayo J, Boyd M (1991) Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines. J Natl Cancer Inst 83:757

    Article  PubMed  CAS  Google Scholar 

  • Parmar VS, Jain SC, Bisht KS, Jain R, Taneja P, Jha A, Tyagi OD, Prasad AK, Wengel J, Olsen CE, Boll PM (1997) Phytochemistry of the genus Piper. Phytochemistry 46:597

    Article  CAS  Google Scholar 

  • Reddy GV, Kumar RSC, Babu KS, Rao JM (2009) Stereoselective syntheses of 11-α-methoxycurvularin and 11-β-methoxycurvularin. Tetrahedron Lett 50:4117

    Article  Google Scholar 

  • Shailesh DS, Reddy GV, Kumar RSC, Yadav PA, Babu KS (2011) Concise approach to alkenamide skeleton: total synthesis of guineensine. J Asian Nat Prod Res 13:128

    Article  Google Scholar 

  • Skehan P, Storeng R, Scudiero D, Monks A, Mohan JM, Vistica D, Warren JT, Bokesch H, Kenney S, Boyd MR (1990) New colorimetric cytotoxic assay for anticancer drug. J Nat Cancer Inst 82:1107

    Article  PubMed  CAS  Google Scholar 

  • Smith ABIII, Kim D (2004) Multicomponent linchpin coupling of silyl dithianes employing an N-Ts aziridine as the second electrophile synthesis of (−)-indolizidine 223AB. Org Lett 6:1493

    Article  PubMed  CAS  Google Scholar 

  • Srinivas PV, Tiwari AK, Sarma VUM, Anuradha V, Haribabu T, Rao DK, Khan IA, Rao JM (2006) HPLC assisted chemobiological standardization of α-glucosidase-I enzyme inhibitory constituents from Piper longum Linn—an Indian medicinal plant. J Ethnopharmacol 108:445

    Article  Google Scholar 

  • Suntornchaswej S, Suwanborirux K, Koga K, Isobe M (2007) Malyngamide X: the first (7R)-lyngbic acid that connects to a new tripeptide backbone from the thai sea hare Bursatella leachii. Chem Asian J 2:114

    Article  Google Scholar 

  • Wohlrab A, Lamer R, VanNieuwenhze SV (2007) Total synthesis of plusbacin A3: a despeptide antibiotic active agent vancomycin-resistant bacteria. J Am Chem Soc 129:4175

    Article  PubMed  CAS  Google Scholar 

  • Wylie CR, Paul VJ (1988) Feeding preferences of the surgeonfish Zebrasoma flavescens in relation to chemical defences of tropical algae. Mar Ecol Prog Ser 45:23

    Article  CAS  Google Scholar 

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Acknowledgments

The authors gratefully acknowledge the keen interest of Dr. J. S. Yadav, Director, IICT, Hyderabad, India in the present work. GV thanks UGC for financial support.

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Author notes

  1. P. V. Srinivas

    Present address: Process, Research and Development Center, Biocon Limited, Bangalore, 560100, India

Authors and Affiliations

  1. Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500607, India

    G. Venkateswar Reddy, T. Vijaya Kumar, B. Siva, K. Suresh Babu, P. V. Srinivas & J. Madhusudana Rao

  2. Pharmacology Division, CSIR-Indian Institute of Integrative Medicine (IIM), Canal Road, Jammu, 180001, India

    Irum Sehar & A. K. Saxena

Authors
  1. G. Venkateswar Reddy
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  2. T. Vijaya Kumar
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  3. B. Siva
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  4. K. Suresh Babu
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  5. P. V. Srinivas
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  6. Irum Sehar
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  8. J. Madhusudana Rao
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Correspondence to K. Suresh Babu.

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Reddy, G.V., Kumar, T.V., Siva, B. et al. Novel malyngamide structural analogs: synthesis and biological evaluation. Med Chem Res 22, 4581–4591 (2013). https://doi.org/10.1007/s00044-013-0466-y

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  • DOI: https://doi.org/10.1007/s00044-013-0466-y

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