1,2,3-triazole tethered Indole-3-glyoxamide derivatives as multiple inhibitors of 5-LOX, COX-2 & tubulin: Their anti-proliferative & anti-inflammatory activity

Bioorganic Chemistry - Tập 81 - Trang 1-20 - 2018
Fatima Naaz1, M Pallavi2, Syed Shafi3, Naveen Mulakayala4, Mohammad Shahar Yar1, H. M. Sampath Kumar2
1Department of Pharmaceutical Chemistry, School of Pharmaceutical Education and Research, Jamia Hamdard, New Delhi, India
2Immunochemistry Lab, Natural Product Division, ACSIR-IICT-Hyderabad, India
3Department of Chemistry, School of Chemical and Lifescience, Jamia Hamdard, New Delhi, India
4SVAK Life Sciences, Pragati Nagar, Hyderabad 500090, India

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Whiteman, 2016, The fractions of cancer attributable to modifiable factors: a global review, Cancer Epidemiol., 44, 203, 10.1016/j.canep.2016.06.013

Nagle, 2006, Antimitotic agents of natural origin, Curr. Drug Target., 7, 305, 10.2174/138945006776054933

Perez, 2009, Microtubule inhibitors: differentiating tubulin-inhibiting agents based on mechanisms of action, clinical activity, and resistance, Mol. Cancer Ther., 8, 2086, 10.1158/1535-7163.MCT-09-0366

Stanton, 2011, Drugs that target dynamic microtubules: a new molecular perspective, Med. Res. Rev., 31, 443, 10.1002/med.20242

Simona, 2008, Licofelone, a dual COX/5-LOX inhibitor, induces apoptosis in HCA-7 colon cancer cells through the mitochondrial pathway independently from its ability to affect the arachidonic acid cascade, Carcinogenesis, 29, 371, 10.1093/carcin/bgm265

Gregor, 2005, Effects of selective COX-2 and 5-LOX inhibition on prostaglandin and leukotriene synthesis in ductal pancreatic cancer in Syrian hamster, Prostaglandins Leukot. Essent. Fatty Acids, 73, 89, 10.1016/j.plefa.2005.04.016

R. Wisastra, F.J. Dekker, Inflammation, cancer and oxidative lipoxygenase activity are intimately linked, in:Cancers 6 (2014) 1500–1521.

Sameena, 2011, Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agent, Eur. J. Med. Chem., 46, 5763, 10.1016/j.ejmech.2011.08.015

Parveen, 2015, Synthesis, characterization and cytotoxic investigations of novel bis(indole) analogues besides antimicrobial study, Arabian J. Chem., 1878

Hao, 2016, Discovery of novel hybrids of diaryl-1,2,4-triazoles and caffeic acid as dual inhibitors of cyclooxygenase-2 and 5-lipoxygenase for cancer therapy, Eur. J. Med. Chem., 108, 89, 10.1016/j.ejmech.2015.11.013

Nagendra, 2016, Synthesis of new secretory phospholipase A2-inhibitory indole containing isoxazole derivatives as anti-inflammatory and anticancer agents, Eur. J. Med. Chem., 12, 289

Narsimha, 2013, 5-((1-Aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones as potential anticancer agents with anti-inflammatory properties, Bioorg. Med. Chem. Lett., 23, 1442, 10.1016/j.bmcl.2012.12.053

Bhale, 2017, Synthesis of extended conjugated indolyl chalcones as potent anti-breast cancer, anti-inflammatory and antioxidant agents, Bioorg. Med. Chem. Lett., 27, 1502, 10.1016/j.bmcl.2017.02.052

Nasir, 2013, Chemistry and biology of indoles and indazoles: a mini-review, Mini Rev. Med. Chem., 13, 1792, 10.2174/1389557511313120009

Antonio, 2011, Molecular modelling studies on Arylthioindoles as potent inhibitors of tubulin polymerization, Eur. J. Med. Chem., 46, 3519, 10.1016/j.ejmech.2011.05.020

Sultan, 2014, Synthesis, biological evaluation and molecular docking studies of trans-indole-3-acrylamide derivatives, a new class of tubulin polymerization inhibitors, Bioorg. Med. Chem., 22, 3096, 10.1016/j.bmc.2014.04.027

Dalip, 2014, Synthesis and identification of α-cyano bis(indolyl)chalcones as novel anticancer agents, Bioorg. Med. Chem. Lett., 24, 5170, 10.1016/j.bmcl.2014.09.085

Guangcheng, 2014, Design, synthesis and biological evaluation of a series of pyrano chalcone derivatives containing indole moiety as novel anti-tubulin agents, Bioorg. Med. Chem., 22, 2060, 10.1016/j.bmc.2014.02.028

Srinivasa, 2016, Synthesis of new secretory phospholipase A2-inhibitory indole containing isoxazole derivatives as anti-inflammatory and anticancer agents, Eur. J. Med. Chem., 112, 289, 10.1016/j.ejmech.2016.02.025

Syed, 2012, Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: their anti-inflammatory and anti-nociceptive activities, Eur. J. Med. Chem., 49, 324, 10.1016/j.ejmech.2012.01.032

Palwinder, 2015, Indole based peptidomimetics as anti-inflammatory and anti-hyperalgesic agents: dual inhibition of 5-LOX and COX-2 enzymes, Eur. J. Med. Chem., 97, 104, 10.1016/j.ejmech.2015.04.044

Copeland, 1994, Mechanism of selective inhibition of the inducible isoform of prostaglandin G/H synthase, Proc. Natl. Acad. Sci., 23, 11202, 10.1073/pnas.91.23.11202

Pagels, 1983, Immunochemical evidence for the involvement of prostaglandin H synthase in hydroperoxide-dependent oxidations by ram seminal vesicle microsomes, J. Biol. Chem., 258, 6517, 10.1016/S0021-9258(18)32442-6

Egan, 1976, Mechanism for irreversible self-deactivation of prostaglandin synthetase, J. Biol. Chem., 251, 7329, 10.1016/S0021-9258(17)32853-3

Winter, 1962, Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs, Proc. Soc. Exp. Biol. Med., 111, 544, 10.3181/00379727-111-27849

Ferreira, 1979, A new method for measuring variations of rat paw volume, J. Pharm. Pharmacol., 31, 648, 10.1111/j.2042-7158.1979.tb13616.x

Daidone, 1994, Synthesis and pharmacological study of ethyl 1-methyl-5-[2-substituted-4-oxo-3(4H)-quinazolinyl]-1H-pyrazole-4-acetates, Eur. J. Med. Chem., 29, 707, 10.1016/0223-5234(94)90033-7

Ahmed, 2016, Combretastatin linked 1,3,4-oxadiazole conjugates as a Potent Tubulin Polymerization inhibitors, Bioorg. Chem., 65, 126, 10.1016/j.bioorg.2016.02.007

Smaranda, 2017, COX inhibition profile and molecular docking studies of some 2-(Trimethoxyphenyl)-thiazoles, Molecules, 22, 1507, 10.3390/molecules22091507

Parteek, 2014, Lead modification: amino acid appended indoles as highly effective 5-LOX inhibitors, Bioorg. Med. Chem., 22, 1642, 10.1016/j.bmc.2014.01.027

Lu, 2017, Structure of 4'-demethylepipodophyllotoxin in complex with tubulin provides a rationale for drug design, Biochem. Biophys. Res. Commun., 493, 718, 10.1016/j.bbrc.2017.08.125

Kolb, 2003, The growing impact of click chemistry on drug discovery, Drug Discov. Today, 24, 1128, 10.1016/S1359-6446(03)02933-7

Hélio, 2013, One-pot three-component synthesis of indole-3-glyoxyl derivatives and indole-3-glyoxyl triazoles, Tetrahedron Lett., 43, 5821

Mangiatordi, 2017, Novel chemotypes targeting tubulin at the colchicine binding site and unbiasing P-glycoprotein, Eur. J. Med. Chem., 139, 792, 10.1016/j.ejmech.2017.07.037