Synthesis, structure-activity relationship of iodinated-4-aryloxymethyl- coumarins as potential anti-cancer and anti-mycobacterial agents

European Journal of Medicinal Chemistry

Volumn 74, Issue , 2014, Pages 225-233

  Basanagouda, Mahantesha ^a   Jambagi, Vishwanath B ^a   Barigidad, Nivedita N ^a   Laxmeshwar, Sandeep S ^b   Devaru, Venkatesh ^c   Narayanachar, ^c  

^a P C JABIN SCIENCE COLLEGE   (India)

^b UNIVERSITY OF MYSORE   (India)

^c L v D College   (India)

Author keywords

Anti mycobacterial; Anticancer; Coumarin; Heterocycles; Iodine; SAR

Indexed keywords

1 (3 IODO PHENOXYMETHYL)BENZO[F]CHROMEN 3 ONE; 1 (4 IODO PHENOXYMETHYL)BENZO[F]CHROMEN 3 ONE; 4 (2 IODO PHENOXYMETHYL) 6 METHOXY CHROMEN 2 ONE; 4 (2 IODO PHENOXYMETHYL) 7 METHOXY CHROMEN 2 ONE; 4 (2 IODO PHENOXYMETHYL)BENZO[F]CHROMEN 3 ONE; 4 (2 IODO PHENOXYMETHYL)BENZO[H]CHROMEN 2 ONE; 4 (3 IODO PHENOXYMETHYL) 6 METHOXY CHROMEN 2 ONE; 4 (3 IODO PHENOXYMETHYL) 6 METHYL CHROMEN 2 ONE; 4 (3 IODO PHENOXYMETHYL) 7 METHOXY CHROMEN 2 ONE; 4 (3 IODO PHENOXYMETHYL) 7 METHYL CHROMEN 2 ONE; 4 (3 IODO PHENOXYMETHYL) 7,8 DIMETHYL CHROMEN 2 ONE; 4 (3 IODO PHENOXYMETHYL)BENZO[F]CHROMEN 2 ONE; 4 (4 IODO PHENOXYMETHYL) 6 METHOXY CHROMEN 2 ONE; 4 (4 IODO PHENOXYMETHYL) 6 METHYL CHROMEN 2 ONE; 4 (4 IODO PHENOXYMETHYL) 7 METHOXY CHROMEN 2 ONE; 4 (4 IODO PHENOXYMETHYL) 7 METHYL CHROMEN 2 ONE; 4 (4 IODO PHENOXYMETHYL) 7,8 DIMETHYL CHROMEN 2 ONE; 4 (4 IODO PHENOXYMETHYL)BENZO[H]CHROMEN 2 ONE; 6 BROMO 4 (2 IODO PHENOXYMETHYL)CHROMEN 2 ONE; 6 BROMO 4 (3 IODO PHENOXYMETHYL)CHROMEN 2 ONE; 6 CHLORO 4 (2 IODO PHENOXYMETHYL)CHROMEN 2 ONE; 6 CHLORO 4 (3 IODO PHENOXYMETHYL)CHROMEN 2 ONE; 6 CHLORO 4 (4 IODO PHENOXYMETHYL)CHROMEN 2 ONE; 7 CHLORO 4 (2 IODO PHENOXYMETHYL)CHROMEN 2 ONE; 7 CHLORO 4 (3 IODO PHENOXYMETHYL)CHROMEN 2 ONE; 7 CHLORO 4 (4 IODO PHENOXYMETHYL)CHROMEN 2 ONE; COUMARIN DERIVATIVE; PYRAZINAMIDE; STREPTOMYCIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTITUBERCULAR ACTIVITY; ARTICLE; BREAST ADENOCARCINOMA; CANCER CELL CULTURE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IN VITRO STUDY; LUNG CARCINOMA; MYCOBACTERIUM PHLEI; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE ACTIVITY RELATION;

ANTI-MYCOBACTERIAL; ANTICANCER; COUMARIN; HETEROCYCLES; IODINE; SAR;

ANTINEOPLASTIC AGENTS; ANTITUBERCULAR AGENTS; CELL LINE, TUMOR; COUMARINS; HUMANS; IODINE; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84893055680     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.12.061     Document Type: Article

References (46)

1. S.K. Arya, and S. Bhansali Lung cancer and its early detection using biomarker-based biosensors Chem. Rev. 111 2011 6783 6809
2. M. Ljungman Targeting the DNA damage response in cancer Chem. Rev. 109 2009 2929 2950
3. M. Jeyachandran, P. Ramesh, D. Sriram, P. Senthilkumar, and P. Yogeeswari Synthesis and in vitro antitubercular activity of 4-aryl/ alkylsulfonylmethylcoumarins as inhibitors of mycobacterium tuberculosis Bioorg. Med. Chem. Lett. 22 2012 4807 4809
4. A. Lacy Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer Curr. Pharm. Des. 10 2004 3797 3811 (Pubitemid 39409871)
5. F. Borges, F. Roleira, N. Milhazes, L. Santana, and E. Uriarte Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity Curr. Med. Chem. 12 2005 887 916 (Pubitemid 40443846)
6. I. Kostova Synthetic and natural coumarins as cytotoxic agents Anti-Cancer Agents Med. Chem. 5 2005 29 46 (Pubitemid 40081292)
7. M.V. Kulkarni, G.M. Kulkarni, C.H. Lin, and C.M. Sun Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents Curr. Med. Chem. 13 2006 2795 2818 (Pubitemid 44509726)
8. M.A. Musa, J.S. Cooperwood, and M.O.F. Khan A review of coumarin derivatives in pharmacotherapy of breast cancer Curr. Med. Chem. 15 2008 2664 2679
9. L. Wu, X. Wang, W. Xu, F. Farzaneh, and R. Xu The structure and pharmacological functions of coumarins and their derivatives Curr. Med. Chem. 16 2009 4236 4260
10. M.E. Riveiro, N.D. Kimpe, A. Moglioni, R. Vazquez, F. Monczor, C. Shayo, and C. Davio Coumarins: old compounds with novel promising therapeutic perspectives Curr. Med. Chem. 17 2010 1325 1338
11. C. Kontogiorgis, A. Detsi, and D.H. Litina Coumarin-based drugs: a patent review (2008-present) Expert Opin. Ther. Pat. 22 2012 437 454
12. X.M. Peng, G.L.V. Damu, and C.H. Zhou Current developments of coumarin compounds in medicinal chemistry Curr. Pharm. Des. 19 2013 3884 3930
13. L.W.L. Woo, A. Purohit, B. Malini, M.J. Reed, and B.V.L. Potter Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates Chem. Biol. 7 2000 773 791
14. B. Malini, A. Purohit, D. Ganeshapillai, L.W.L. Woo, B.V.L. Potter, and M.J. Reed Inhibition of steroid sulphatase activity by tricyclic coumarin sulphamates J. Steroid Biochem. Mol. Biol. 75 2000 253 258 (Pubitemid 32244254)
15. A. Purohit, L.W.L. Woo, B.V.L. Potter, and M.J. Reed In vivo inhibition of estrone sulfatase activity and growth of nitrosomethylureainduced mammary tumors by 667 COUMATE Cancer Res. 60 2000 3394 3396 (Pubitemid 30482153)
16. F. Meggio, M.A. Pagano, S. Moro, G. Zagotto, M. Ruzzene, S. Sarno, G. Cozza, J. Bain, M. Elliott, A.D. Deana, A.M. Brunati, and L.A. Pinna Inhibition of protein kinase CK2 by condensed polyphenolic derivatives. An in vitro and in vivo study Biochemistry 43 2004 12931 12936 (Pubitemid 39331813)
17. A. Chilin, R. Battistutta, A. Bortolato, G. Cozza, S. Zanatta, G. Poletto, M. Mazzorana, G. Zagotto, E. Uriarte, A. Guiotto, L.A. Pinna, F. Meggio, and S. Moro Coumarin as attractive casein kinase 2 (CK2) inhibitor scaffold: an integrate approach to elucidate the putative binding motif and explain structure-activity relationships J. Med. Chem. 51 2008 752 759 (Pubitemid 351304684)
18. G.L. Bras, C. Radanyi, J.F. Peyrat, J.D. Brion, M. Alami, V. Marsaud, B. Stella, and J.M. Renoir New novobiocin analogues as antiproliferative agents in breast cancer cells and potential inhibitors of heat shock protein 90 J. Med. Chem. 50 2007 6189 6200
19. A.C. Donnelly, J.R. Mays, J.A. Burlison, J.T. Nelson, G. Vielhauer, J. Holzbeierlein, and B.S.J. Blagg The design, synthesis, and evaluation of coumarin ring derivatives of the novobiocin scaffold that exhibit antiproliferative activity J. Org. Chem. 73 2008 8901 8920
20. H.P. Zhao, A.C. Donnelly, B.R. Kusuma, G.E.L. Brandt, D. Brown, R.A. Rajewski, G. Vielhauer, J. Holzbeierlein, M.S. Cohen, and B.S.J. Blagg Engineering an antibiotic to fight cancer: optimization of the novobiocin scaffold to produce anti-proliferative agents J. Med. Chem. 54 2011 3839 3853
21. H.P. Zhao, B. Yan, L.B. Peterson, and B.S.J. Blagg 3-Arylcoumarin derivatives manifest anti-proliferative activity through Hsp90 inhibition ACS Med. Chem. Lett. 3 2012 327 331
22. S. Ananthan, E.R. Faaleolea, R.C. Goldman, J.V. Hobrath, C.D. Kwong, B.E. Laughon, J.A. Maddry, A. Mehta, L. Rasmussen, R.C. Reynolds, J.A. Secrist III, N. Shindo, D.N. Showe, M.I. Sosa, W.J. Suling, and E.L. White High-throughput screening for inhibitors of mycobacterium tuberculosis H37Rv Tuberculosis 89 2009 334 353
23. R.C. Reynolds, S. Ananthan, E. Faaleolea, J.V. Hobrath, C.D. Kwong, C. Maddox, L. Rasmussen, M.I. Sosa, E. Thammasuvimol, E.L. White, W. Zhang, and J.A. Secrist III High throughput screening of a library based on kinase inhibitor scaffolds against Mycobacterium tuberculosis H37Rv Tuberculosis 92 2012 72 83
24. H. Kohno, R. Suzuki, M. Curini, F. Epifano, F. Maltese, S.P. Gonzales, and T. Tanaka Dietary administration with prenyloxycoumarins, auraptene and collinin, inhibits colitis-related colon carcinogenesis in mice Int. J. Cancer 118 2006 2936 2942
25. W. Liu, J. Hua, J. Zhou, H. Zhang, H. Zhu, Y. Cheng, and R. Gust Synthesis and in vitro antitumor activity of novel scopoletin derivatives Bioorg. Med. Chem. Lett. 22 2012 5008 5012
26. K.V. Sashidhara, S.R. Avula, K. Sharma, G.R. Palnati, and S.R. Bathula Discovery of coumarin-monastrol hybrid as potential antibreast tumor-specific agent Eur. J. Med. Chem. 60 2013 120 127
27. Z.Q. Xu, W.W. Barrow, W.J. Suling, L. Westbrook, E. Barrow, Y.M. Lin, and M.T. Flavin Anti-HIV natural product (+)-calanolide A is active against both drug-susceptible and drug-resistant strains of Mycobacterium tuberculosis Bioorg. Med. Chem. 12 2004 1199 1207 (Pubitemid 38251310)
28. A. Manvar, A. Malde, J. Verma, V. Virsodia, A. Mishra, K. Upadhyay, H. Acharya, E. Coutinho, and A. Shah Synthesis, anti-tubercular activity and 3D-QSAR study of coumarin-4-acetic acid benzylidene hydrazides Eur. J. Med. Chem. 43 2008 2395 2403
29. S.H. Cardoso, M.B. Barreto, M.C.S. Lourenco, M.G.M.O. Henriques, A.L.P. Candea, C.R. Kaiser, and M.V.N. Souza Antitubercular activity of new coumarins Chem. Biol. Drug Des. 77 2011 489 493
30. R.J. Naik, M.V. Kulkarni, K.S.R. Pai, and P.G. Nayak Click chemistry approach for bis-chromenyl triazole hybrids and their antituberculosis activity Chem. Biol. Drug Des. 80 2012 516 523
31. Y. Lu, Y. Wang, and W. Zhu Nonbonding interactions of organic halogens in biological systems: implications for drug discovery and biomolecular design Phys. Chem. Chem. Phys. 12 2010 4543 4551
32. Y. Lu, T. Shi, Y. Wang, H. Yang, X. Yan, X. Luo, H. Jiang, and W. Zhu Halogen bonding-a novel interaction for rational drug design? J. Med. Chem. 52 2009 2854 2862
33. S. Arnold, F. Goglia, and B. Kadenbach 3,5-Diiodothyronine binds to subunit Va of cytochrome-c oxidase and abolishes the allosteric inhibition of respiration by ATP Eur. J. Biochem. 252 1998 325 330 (Pubitemid 28102010)
34. R. Lan, Q. Liu, P. Fan, S. Lin, S.R. Fernando, D. McCallion, R. Pertwee, and A. Makriyannis Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists J. Med. Chem. 42 1999 769 776 (Pubitemid 29110792)
35. R. Wilcken, X. Liu, M.O. Zimmermann, T.J. Rutherford, A.R. Fersht, A.C. Joerger, and F.M. Boeckler Halogen-enriched fragment libraries as leads for drug rescue of mutant p53 J. Am. Chem. Soc. 134 2012 6810 6818
36. V.Y. Su, Y.W. Hu, K.T. Chou, S.M. Ou, Y.C. Lee, E.Y. Lin, T.J. Chen, C.H. Tzeng, and C.J. Liu Amiodarone and the risk of cancer Cancer 2003 1699 1705
37. B. Carlsson, B.N. Singh, M. Temciuc, S. Nilsson, Y.L. Li, C. Mellin, and J. Malm Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone J. Med. Chem. 45 2002 623 630 (Pubitemid 34145708)
38. F. Borrelli, C. Campagnuolo, R. Capasso, E. Fattorusso, and O.T. Scafati Iodinated indole alkaloids from plakortis simplex - new plakohypaphorines and an evaluation of their antihistamine activity Eur. J. Org. Chem. 2004 3227 3232
39. M. Basanagouda, M.V. Kulkarni, D. Sharma, V.K. Gupta, Pranesha, P. Sandhyarani, and V.P. Rasal Synthesis of some new 4-aryloxymethylcoumarins and examination of their antibacterial and antifungal activities J. Chem. Sci. 121 2009 485 495
40. M. Basanagouda, K. Shivashankar, M.V. Kulkarni, V.P. Rasal, H. Patel, S.S. Mutha, and A.A. Mohite Synthesis and antimicrobial studies on novel sulfonamides containing 4-azidomethylcoumarin Eur. J. Med. Chem. 45 2010 1151 1157
41. M. Basanagouda, V.B. Jadhav, M.V. Kulkarni, and R.N. Rao Computer aided prediction of biological activity spectra: study of correlation between predicted and observed activities for coumarin-4-acetic acids Indian J. Pharm. Sci. 73 2011 88 92
42. S.N. Makandar, M. Basanagouda, M.V. Kulkarni, Pranesha, and V.P. Rasal Synthesis and anti-microbial studies of some 4-aryloxymethylcoumamrins obtained by reaction of 4-bromomethyl coumarins with aromatic bidentate nucleophiles Med. Chem. Res. 21 2012 2603 2614
43. M. Basanagouda, and M.V. Kulkarni Novel one-pot synthesis for 2,5-diaryl and 5-aryl-pyridazin-3(2H)-ones Synth. Commun. 41 2011 2569 2582
44. A. Burger, and G.E. Ullyot Analgesic studies. β-ethyl and β-isopropylamine derivatives of pyridine and thiazole J. Org. Chem. 12 1947 342 355
45. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays J. Immunol. Methods 65 1983 55 63 (Pubitemid 14203433)
46. M.C.S. Lourenco, M.V.N. deSouza, A.C. Pinheiro, M.L. Ferreira, R.B. Goncalves, T.C.M. Nogneira, and M.A. Peralta Evaluation of anti-tubercular activity of nicotinic and isoniazid analogues Arkivoc 15 2007 181 191