Synthesis and in vitro antimycobacterial and isocitrate lyase inhibition properties of novel 2-methoxy-2′-hydroxybenzanilides, their thioxo analogues and benzoxazoles

European Journal of Medicinal Chemistry

Volumn 56, Issue , 2012, Pages 108-119

  Kozic, Ján ^a   Novotná, Eva ^a   Volková, Marie ^a   Stolaříková, Jiřina ^b   Trejtnar, František ^a   Wsól, Vladimír ^a   Vinšová, Jarmila ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b Zdravotniho ustavu se sidlem v Ostrave   (Czech Republic)

Author keywords

Antimycobacterial activity; Benzanilide; E, Z conformation of thiobenzanilide; Isocitrate lyase; Thiobenzanilide; Tuberculosis

Indexed keywords

2 METHOXY 2' HYDROXYBENZANILIDE DERIVATIVE; 3 NITROPROPIONIC ACID; 4 CHLORO N [2 HYDROXY 4 (TRIFLUOROMETHYL)PHENYL] 2 METHOXYBENZOTHIOAMIDE; 5 CHLORO N (4 CHLORO 2 HYDROXYPHENYL) 2 METHOXYBENZAMIDE; 5 CHLORO N [2 HYDROXY 4 (TRIFLUOROMETHYL)PHENYL] 2 METHOXYBENZOTHIOAMIDE; ANTIMYCOBACTERIAL AGENT; BENZOXAZOLE DERIVATIVE; ISOCITRATE LYASE; LYASE INHIBITOR; N (4 BROMO 2 HYDROXYPHENYL) 5 CHLORO 2 METHOXYBENZAMIDE; N (5 BROMO 2 HYDROXYPHENYL) 5 CHLORO 2 METHOXYBENZAMIDE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIUM ISOLATE; CHEMICAL BOND; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; INFRARED SPECTROMETRY; MYCOBACTERIUM AVIUM; MYCOBACTERIUM KANSASII; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

ANILIDES; ANTINEOPLASTIC AGENTS; BENZOXAZOLES; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; HEP G2 CELLS; HUMANS; ISOCITRATE LYASE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84865745744     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.08.016     Document Type: Article

References (31)

1. K.R. Desai, M.S. Shaikh, and E.C. Coutinho Molecular modeling studies, synthesis and biological evaluation of derivatives of N-phenylbenzamide as Plasmodium falciparum dihydroorotate dehydrogenase (PfDHODH) inhibitors Med. Chem. Res. 20 2011 321 332
2. T. Ertan, I. Yildiz, S. Ozkan, O. Temiz-Arpaci, F. Kaynak, I. Yalcin, E. Aki-Sener, and U. Abbasoglu Synthesis and biological evaluation of new N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamides and phenylacetamides as antimicrobial agents Bioorgan. Med. Chem. 15 2007 2032 2044
3. I.Y. Oren, E. Aki-Sener, C. Ertas, O.T. Arpaci, I. Yalcin, and N. Altanlar Synthesis and microbiological activity of some substituted N-(2-hydroxy-4-nitrophenyl)benzamides and phenylacetamides as possible metabolites of antimicrobial active benzoxazoles Turk. J. Chem. 28 2004 441 449
4. E. Aki-Sener, K.K. Bingol, O. Temiz-Arpaci, I. Yalcin, and N. Altanlar Synthesis and microbiological activity of some N-(2-hydroxy-4-substitutedphenyl) benzamides, phenylacetamides and furamides as the possible metabolites of antimicrobial active benzoxazoles Il Farmaco 57 2002 451 456
5. E.A. Sener, K.K. Bingol, I. Oren, O.T. Arpaci, I. Yalcin, and N. Altanlar Synthesis and microbiological activity of some N-(o-hydroxyphenyl)benzamides and phenylacetamides as the possible metabolites of antimicrobial active benzoxazoles: part II Il Farmaco 55 2000 469 476
6. G. Biagi, I. Giorgi, O. Livi, A. Nardi, V. Calderone, A. Martelli, E. Martinotti, and O.L. Salerni Synthesis and biological activity of novel substituted benzanilides as potassium channel activators. V Eur. J. Med. Chem. 39 2004 491 498
7. V. Calderone, A. Coi, F.L. Fiamingo, I. Giorgi, M. Leonardi, O. Livi, A. Martelli, and E. Martinotti Structural modifications of benzanilide derivatives, effective potassium channel openers. X Eur. J. Med. Chem. 41 2006 1421 1429
8. G. Brunhofer, N. Handler, K. Leisser, C.R. Studenik, and T. Erker Benzanilides with spasmolytic activity: chemistry, pharmacology, and SAR Bioorgan. Med. Chem. 16 2008 5974 5981
9. A.E. Philip, J.H. Poupaert, G. Cheve, G. Muccioli, D. Lambert, and C.R. McCurdy Structure-activity relationship of phenytoinergic antiepileptic drugs related to ameltolide Med. Chem. Res. 16 2007 130 135
10. J.V. Allen, C. Bardelle, K. Blades, D. Buttar, L. Chapman, N. Colclough, A.G. Dossetter, A.P. Garner, A. Girdwood, C. Lambert, A.G. Leach, B. Law, J. Major, H. Plant, and A.M. Slater The discovery of benzanilides as c-Met receptor tyrosine kinase inhibitors by a directed screening approach Bioorg. Med. Chem. Lett. 21 2011 5224 5229
11. WHO report Global Tuberculosis Control 2011 http://www.who.int/tb/ publications/global report/2011/gtbr11 full.pdf
12. P.E.A. Da Silva, and J.C. Palomino Molecular basis and mechanisms of drug resistance in Mycobacterium tuberculosis: classical and new drugs J. Antimicrob. Chemother. 66 2011 1417 1430
13. L.G. Dover, and G.D. Coxon Current status and research strategies in tuberculosis drug development J. Med. Chem. 54 2011 6157 6165
14. D. Sriram, P. Yogeeswari, P. Senthilkumar, D. Sangaraju, R. Nelli, D. Banerjee, P. Bhat, and T.H. Manjashetty Synthesis and antimycobacterial evaluation of novel phthalazin-4-ylacetamides against log- and starved phase cultures Chem. Biol. Drug Des. 75 2010 381 391
15. V. Sharma, S. Sharma, K.H.Z. Bentrup, J.D. McKinney, D.G. Russell, W.R. Jacobs, and J.C. Sacchettini Structure of isocitrate lyase, a persistence factor of Mycobacterium tuberculosis Nat. Struct. Biol. 7 2000 663 668
16. K. Waisser, O. Bures, P. Holy, J. Kunes, R. Oswald, L. Jiraskova, M. Pour, V. Klimesova, L. Kubicova, and J. Kaustova Relationship between the structure and antimycobacterial activity of substituted salicylanilides Arch. Pharm. 336 2003 53 71
17. R. Lok, R.E. Leone, and A.J. Williams Facile rearrangements of alkynylamino heterocycles with noble metal cations J. Org. Chem. 61 1996 3289 3297
18. R. Dolezal, K. Waisser, E. Petrlikova, J. Kunes, L. Kubicova, M. Machacek, J. Kaustova, and H.M. Dahse N-Benzylsalicylthioamides: highly active potential antituberculotics Arch. Pharm. 342 2009 113 119
19. L. Chabaud, J. Clayden, M. Helliwell, A. Page, J. Raftery, and L. Vallverdu Conformational studies of tertiary oligo-m-benzanilides and oligo-p-benzanilides in solution Tetrahedron 66 2010 6936 6957
20. M.K. Kesharwani, and B. Ganguly Probing the structural and electronic effects to stabilize nonplanar forms of thioamide derivatives: a computational study J. Comput. Chem. 32 2011 2170 2176
21. D. Lauvergnat, and P.C. Hiberty Role of conjugation in the stabilities and rotational barriers of formamide and thioformamide. An ab initio valence-bond study J. Am. Chem. Soc. 119 1997 9478 9482
22. R.D. Parra, H.Q. Zeng, J. Zhu, C. Zheng, X.C. Zeng, and B. Gong Stable three-center hydrogen bonding in a partially rigidified structure Chem. Eur. J. 7 2001 4352 4357
23. B. Gong Hollow crescents, helices, and macrocycles from enforced folding and folding-assisted macrocyclization Acc. Chem. Res. 41 2008 1376 1386
24. Y. Otani, T. Hori, M. Kawahata, K. Yamaguchi, and T. Ohwada Secondary structure of homo-thiopeptides based on a bridged beta-proline analogue: preferred formation of extended strand structures with trans-thioamide bonds Tetrahedron 68 2012 4418 4428
25. D.A. Nugiel, K. Jacobs, L. Cornelius, C.H. Chang, P.K. Jadhav, E.R. Holler, R.M. Klabe, L.T. Bacheler, B. Cordova, S. Garber, C. Reid, K.A. Logue, L.J. Gorey-Feret, G.N. Lam, S. Erickson-Viitanen, and S.P. Seitz Improved P1/P1'substituents for cyclic urea based HIV-1 protease inhibitors: synthesis, structure-activity relationship, and X-ray crystal structure analysis J. Med. Chem. 40 1997 1465 1474
26. Y.H. Shen, Q. Xie, M. Norberg, E. Sausville, G.V. Woude, and D. Wenkert Geldanamycin derivative inhibition of HGF/SF-mediated Met tyrosine kinase receptor-dependent urokinase-plasminogen activation Bioorgan. Med. Chem. 13 2005 4960 4971
27. A. Naganawa, T. Matsui, T. Saito, M. Ima, T. Tatsumi, S. Yamamoto, M. Murota, H. Yamamoto, T. Maruyama, S. Ohuchida, H. Nakai, K. Kondo, and M. Toda Discovery of heteroaryl sulfonamides as new EP1 receptor selective antagonistse Bioorgan. Med. Chem. 14 2006 6628 6639
28. 3 receptor partial agonists in the gut J. Med. Chem. 41 1998 3015 3021
29. I. Ott, B. Kircher, G. Heinisch, and B. Matuszczak Substituted pyridazino[3,4-b][1,5]benzoxazepin-5(6H)ones as multidrug resistance modulating agents J. Med. Chem. 47 2004 4627 4630
30. M.M. Bradford Rapid and sensitive method for quantitation of microgram quantities of protein utilizing principle of protein-dye binding Anal. Biochem. 72 1976 248 254
31. G.H. Dixon, and H.L. Kornberg Assay methods for key enzymes of the glyoxylate cycle, Proceedings of the Biochemical Society Biochem. J. 72 1959 3P