An efficient one-pot approach for the regio- and diastereoselective synthesis of trans-dihydrofuran derivatives: cytotoxicity and DNA-binding studies

Organic and Biomolecular Chemistry - Tập 15 Số 32 - Trang 6837-6853
Yellaiah Tangella1,2,3,4,5, Kesari Lakshmi Manasa6,7,3,4,5, V. Laxma Nayak8,3,4,5, Manda Sathish8,3,4,5, B. Sridhar8,9,10,4, Abdullah Alarifi11,12,13,14,15, Narayana Nagesh16,3,4, Ahmed Kamal2,11,3,4,5
1Academy of Scientific and Innovative Research
2Academy of Scientific and Innovative Research, CSIR-Indian Institute of Chemical Technology, Hyderabad, India
3Hyderabad 500 007
4India
5Medicinal Chemistry and Biotechnology, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India
6Department of Medicinal Chemistry
7Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad-500 037, India
8CSIR-Indian Institute of Chemical Technology;
9Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India
10Hyderabad-500007
11Catalytic Chemistry Research Chair, Chemistry Department, College of Science, King Saud University, Riyadh 11451, Saudi Arabia
12Chemistry Department,
13College of Science
14King Saud University
15Riyadh 11451
16CSIR-Centre for Cellular and Molecular Biology, Hyderabad 500 007, India

Tóm tắt

A facile one-pot, three component strategy has been developed for the construction oftrans-2,3-dihydrofuran derivatives. All the synthesized compounds have been evaluated for their cytotoxic activity.

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Tài liệu tham khảo

Cragg, 2009, Chem. Rev., 109, 3012, 10.1021/cr900019j

Solyanik, 2011, Exp. Oncol., 32, 181

Vijayaraghavalu, 2012, Mol. Pharm., 9, 2730, 10.1021/mp300281t

Holohan, 2013, Nat. Rev. Cancer, 13, 714, 10.1038/nrc3599

Riedl, 2011, Chem. Phys. Lipids, 164, 766, 10.1016/j.chemphyslip.2011.09.004

P. M. Dewick , Medicinal natural products: a biosynthetic approach, John Wiley & Sons, 2002

Michael, 2005, Nat. Prod. Rep., 22, 627, 10.1039/b413750g

Balderas-Renteria, 2012, Curr. Med. Chem., 19, 4377, 10.2174/092986712803251593

Garazd, 2003, Chem. Nat. Compd., 39, 54, 10.1023/A:1024140915526

Grundon, 1990, Nat. Prod. Rep., 7, 131, 10.1039/np9900700131

Spino, 1998, Bioorg. Med. Chem. Lett., 8, 3475, 10.1016/S0960-894X(98)00628-3

Nagamallu, 2016, Bioorg. Med. Chem. Lett., 26, 690, 10.1016/j.bmcl.2015.11.038

Osman, 2012, Chem. Cent. J., 6, 1, 10.1186/1752-153X-6-1

Greeff, 2012, Bioorg. Med. Chem., 20, 809, 10.1016/j.bmc.2011.11.068

Yu, 2005, J. Agric. Food Chem., 53, 2009, 10.1021/jf0484632

Kahriman, 2013, Eur. J. Med. Chem., 69, 348, 10.1016/j.ejmech.2013.08.050

Alexander, 1987, J. Med. Chem., 30, 1711, 10.1021/jm00393a004

Creaven, 2010, Polyhedron, 29, 813, 10.1016/j.poly.2009.11.002

Bayrak, 2009, Eur. J. Med. Chem., 44, 1057, 10.1016/j.ejmech.2008.06.019

Shi, 2011, Bioorg. Med. Chem. Lett., 21, 956, 10.1016/j.bmcl.2010.12.059

Liu, 2012, Bioorg. Med. Chem. Lett., 22, 5845, 10.1016/j.bmcl.2012.07.081

Hwu, 2008, Antiviral Res., 77, 157, 10.1016/j.antiviral.2007.09.003

Hwu, 2011, J. Med. Chem., 54, 2114, 10.1021/jm101337v

Guo, 2011, Eur. J. Med. Chem., 46, 307, 10.1016/j.ejmech.2010.11.019

Sagong, 2013, ACS Med. Chem. Lett., 4, 547, 10.1021/ml4001112

Hassan, 2016, Eur. J. Med. Chem., 123, 236, 10.1016/j.ejmech.2016.07.056

Wang, 2002, Cancer Lett., 183, 163, 10.1016/S0304-3835(02)00031-9

Carta, 2015, J. Med. Chem., 58, 7991, 10.1021/acs.jmedchem.5b00805

Chen, 2013, Bioorg. Med. Chem., 21, 5064, 10.1016/j.bmc.2013.06.046

Chang, 2009, J. Med. Chem., 52, 4883, 10.1021/jm900456w

Basanagouda, 2014, Eur. J. Med. Chem., 74, 225, 10.1016/j.ejmech.2013.12.061

Bisi, 2017, Eur. J. Med. Chem., 127, 577, 10.1016/j.ejmech.2017.01.020

Zhao, 2011, J. Med. Chem., 54, 3839, 10.1021/jm200148p

Zhao, 2005, J. Med. Chem., 48, 3463, 10.1021/jm0490538

Piccagli, 2010, Bioorg. Med. Chem., 18, 8341, 10.1016/j.bmc.2010.09.063

Murray, 1991, Prog. Chem. Org. Nat. Prod., 58, 83

Donnelly, 1998, Nat. Prod. Rep., 15, 241, 10.1039/a815241y

Michael, 1997, Nat. Prod. Rep., 14, 605, 10.1039/np9971400605

Wang, 2004, J. Med. Chem., 47, 5816, 10.1021/jm040112r

Dong, 2010, J. Med. Chem., 53, 2299, 10.1021/jm1000858

Marks, 2011, J. Nat. Prod., 74, 567, 10.1021/np100429s

Li, 2013, J. Pharm. Pharmacol., 65, 355, 10.1111/j.2042-7158.2012.01606.x

Openshaw, 1967, Alkaloids, 9, 223

Vaquette, 1976, Phytochemistry, 15, 743, 10.1016/S0031-9422(00)94434-0

Wu, 1999, Phytochemistry, 50, 509, 10.1016/S0031-9422(98)00519-6

Basco, 1994, Antimicrob. Agents Chemother., 38, 1169, 10.1128/AAC.38.5.1169

Butenschon, 2001, J. Med. Chem., 44, 1249, 10.1021/jm001007u

Rajski, 1998, Chem. Rev., 98, 2723, 10.1021/cr9800199

El-Gogary, 2003, Spectrochim. Acta, Part A, 59, 2635, 10.1016/S1386-1425(03)00038-6

Wang, 2008, J. Org. Chem., 73, 7088, 10.1021/jo800870z

Citterio, 1989, J. Org. Chem., 54, 2713, 10.1021/jo00272a047

Garzino, 2002, Tetrahedron Lett., 43, 5049, 10.1016/S0040-4039(02)01011-0

Zhang, 2003, Org. Lett., 5, 2363, 10.1021/ol034763d

Lee, 2000, Tetrahedron, 56, 8845, 10.1016/S0040-4020(00)00839-5

Wu, 2004, Tetrahedron, 60, 1841, 10.1016/j.tet.2003.12.035

Nair, 2001, Tetrahedron, 57, 7705, 10.1016/S0040-4020(01)00700-1

Lee, 2005, Eur. J. Org. Chem., 1568

Pirrung, 1999, J. Org. Chem., 64, 3642, 10.1021/jo982503h

Murakami, 2006, J. Organomet. Chem., 691, 3151, 10.1016/j.jorganchem.2006.03.011

Lee, 2002, Tetrahedron, 58, 2359, 10.1016/S0040-4020(02)00118-7

Cheng, 2006, J. Fluorine Chem., 127, 894, 10.1016/j.jfluchem.2006.03.020

Li, 2009, Tetrahedron Lett., 50, 2353, 10.1016/j.tetlet.2009.02.204

Lee, 2000, Tetrahedron, 56, 8845, 10.1016/S0040-4020(00)00839-5

Lee, 2000, Tetrahedron, 56, 3867, 10.1016/S0040-4020(00)00307-0

Jiang, 2002, Tetrahedron: Asymmetry, 13, 1033, 10.1016/S0957-4166(02)00239-2

Sun, 2008, Acc. Chem. Res., 41, 937, 10.1021/ar800108z

Fan, 2005, J. Org. Chem., 70, 8204, 10.1021/jo050903g

Yang, 2005, Tetrahedron, 61, 9140, 10.1016/j.tet.2005.07.009

Fan, 2005, Synthesis, 391

Redon, 2008, Tetrahedron, 64, 9293, 10.1016/j.tet.2008.07.025

Cao, 2004, Synth. Commun., 34, 1599, 10.1081/SCC-120030747

Qian, 2007, J. Fluorine Chem., 128, 207, 10.1016/j.jfluchem.2006.12.006

Moorhoff, 1996, Tetrahedron Lett., 37, 9349, 10.1016/S0040-4039(97)82961-9

Cao, 2008, Tetrahedron, 64, 163, 10.1016/j.tet.2007.10.073

Wang, 2009, J. Org. Chem., 74, 7403, 10.1021/jo901379h

Altieri, 2010, Tetrahedron, 66, 9493, 10.1016/j.tet.2010.10.023

Borah, 2015, Synth. Commun., 45, 1533, 10.1080/00397911.2015.1027405

Khan, 2013, Synthesis, 406, 10.1055/s-0032-1316837

Han, 2010, Synthesis, 406

Zhang, 2015, Macromolecules, 48, 3414, 10.1021/acs.macromol.5b00463

Ganem, 2009, Acc. Chem. Res., 42, 463, 10.1021/ar800214s

Ramón, 2005, Angew. Chem., Int. Ed., 44, 1602, 10.1002/anie.200460548

Dömling, 2006, Chem. Rev., 106, 17, 10.1021/cr0505728

Ye, 2010, J. Org. Chem., 75, 1760, 10.1021/jo902553k

Garzino, 2003, Eur. J. Org. Chem., 1410, 10.1002/ejoc.200390198

Yang, 2005, Tetrahedron, 61, 9140, 10.1016/j.tet.2005.07.009

Pohmakotr, 2003, Tetrahedron Lett., 44, 7937, 10.1016/j.tetlet.2003.09.005

Wang, 2007, J. Inorg. Biochem., 101, 1492, 10.1016/j.jinorgbio.2007.04.007

Barton, 1993, Biochemistry, 32, 2573, 10.1021/bi00061a015

Wu, 2009, Eur. J. Med. Chem., 44, 4153, 10.1016/j.ejmech.2009.05.006

Schäfe, 2007, Eur. J. Inorg. Chem., 19, 3034, 10.1002/ejic.200700206

Fukuda, 2002, Proc. Natl. Acad. Sci. U. S. A., 99, 12685, 10.1073/pnas.152456899

Mahaswari, 2004, Inorg. Chim. Acta, 357, 901, 10.1016/j.ica.2003.07.010

Kelly, 1985, Nucleic Acids Res., 13, 6017, 10.1093/nar/13.17.6017

Nitiss, 1996, Eur. J. Cancer, Part A, 32, 958, 10.1016/0959-8049(96)00056-1

Pommier, 2010, Chem. Biol., 17, 421, 10.1016/j.chembiol.2010.04.012

Jangir, 2012, J. Photochem. Photobiol., B, 114, 38, 10.1016/j.jphotobiol.2012.05.005

Liu, 1989, Annu. Rev. Biochem., 58, 351, 10.1146/annurev.bi.58.070189.002031

Waring, 1976, Eur. J. Cancer, 12, 995, 10.1016/0014-2964(76)90066-9

Elmore, 1988, Nucleic Acids Res., 16, 9707, 10.1093/nar/16.20.9707

Lipinski, 1997, Adv. Drug Delivery Rev., 23, 1, 10.1016/S0169-409X(96)00423-1

P. Ertl , Calculation of Molecular Properties and Bioactivity Score. Available online: http://www.molinspiration.com

Kumar, 2012, Green Chem., 14, 3269, 10.1039/c2gc36276g

Kumar, 2013, Synth. Commun., 43, 1802, 10.1080/00397911.2012.671435

Mosmann, 1983, J. Immunol. Methods, 65, 55, 10.1016/0022-1759(83)90303-4

Botta, 2007, Bioorg. Med. Chem. Lett., 17, 1579, 10.1016/j.bmcl.2006.12.101

Toshima, 2002, Bioorg. Med. Chem. Lett., 12, 671, 10.1016/S0960-894X(01)00828-9

Temperini, 2003, Nucleic Acids Res., 31, 1464, 10.1093/nar/gkg245

Morris, 2009, J. Comput. Chem., 30, 2785, 10.1002/jcc.21256

W. L. Delano , The PyMOL Molecular Graphics System, DeLano Scientific, San Carlos, CA, 2002

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Organic and Biomolecular Chemistry

Tập 15 Số 32

6837-6853

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