Synthesis, characterization, antimicrobial activities and QSAR studies of some 10a-phenylbenzo[b]indeno[1,2-e][1,4]thiazin-11(10aH)-ones

European Journal of Medicinal Chemistry

Volumn 53, Issue , 2012, Pages 176-189

  Mor, Satbir ^a   Pahal, Preeti ^a   Narasimhan, Balasubramanian ^b  

^a GURU JAMBHESHWAR UNIVERSITY OF SCIENCE AND TECHNOLOGY   (India)

^b MAHARSHI DAYANAND UNIVERSITY   (India)

Author keywords

1,4 Benzothiazines; 2 Aminobenzenethiols; Antibacterial; Antifungal

Indexed keywords

10A (4 CHLOROPHENYL) 8 METHOXYBENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 10A (4 CHLOROPHENYL) 8 METHYLBENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 10A (4 CHLOROPHENYL)BENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 10A (4 METHOXYPHENYL) 8 METHYLBENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 10A (P TOLYL)BENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 10A PHENYLBENZO[B]INDENO [1,2 E][1,4] THIAZIN 11 (10AH) ONE; 8 BROMO 10A (4 CHLOROPHENYL)BENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 8 BROMO 10A (4 METHOXYPHENYL)BENZO[B]INDENO[1,2 E][1,4] THIAZIN 11(10AH) ONE; 8 BROMO 10A (P TOLYL)BENZO[B]INDENO[1,2 E][1,4] THIAZIN 11(10AH) ONE; 8 BROMO 10A PHENYLBENZO[B]INDENO[1,2 E][1,4 THIAZIN 11(10AH) ONE; 8 BROMO 10A PHENYLBENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 8 METHOXY 10A (4 METHOXYPHENYL)BENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 8 METHOXY 10A (P TOLYL)BENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 8 METHOXY 10A PHENYLBENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 8 METHYL 10A PHENYLBENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; 8 METHYL(P TOLYL)BENZO[B]INDENO[1,2 E][1,4]THIAZIN 11(10AH) ONE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; DRUG SYNTHESIS; ESCHERICHIA COLI; NONHUMAN; PSEUDOMONAS AERUGINOSA; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STAPHYLOCOCCUS AUREUS;

ANTI-INFECTIVE AGENTS; BACTERIA; CHEMISTRY TECHNIQUES, SYNTHETIC; FUNGI; MICROBIAL SENSITIVITY TESTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; THIAZINES;

EID: 84861596114     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.03.054     Document Type: Article

References (78)

1. S.J. Teague, A.M. Davis, P.D. Leeson, and T. Oprea Angew. Chem. Int. Ed. 38 1999 3743 3748
2. J.V. Cecchetti, V. Calderone, O. Tabarrini, S. Sabatini, E. Filipponi, L. Testai, R. Spogli, E. Martinotti, and A. Fravolini J. Med. Chem. 46 2003 3670 3679
3. T. Matasui, Y. Nakamura, H. Ishikawa, A. Matsuura, and F. Kobayashi Jpn. J. Pharmacol. 64 1994 115 124
4. U.R. Pratap, D.V. Jawale, B.S. Londhe, and R.A. Mane J. Mol. Catal. B: Enzym. 68 2011 94 97
5. P.I. Williams, and M. Smith Eur. J. Anaesthesiol. 16 1999 638 645
6. M. Fujita, S. Ito, A. Ota, N. Kato, K. Yamamoto, Y. Kawashima, H. Yamauchi, and J. Iwao J. Med. Chem. 33 1990 1898 1905
7. B. Baghernejad, M.M. Heravi, and H.A. Oskooie Synth. Commun. 41 2011 589 593
8. M.K. Nyati, C.M. Rajoria, R.R. Gupta, and P.K. Dev Anti-cancer Drugs 6 1995 693 696
9. Chem. Abstr. 124 1996 21034h
10. R.C. Millonig, M.B. Goldlust, W.E. Maguire, B. Rubin, E. Schulze, R.J. Wojnar, A.R. Turkheimer, W.F. Schreiber, and R.J. Brittain J. Med. Chem. 16 1973 780 782
11. S. Sabatini, G.W. Kaatz, G.M. Rossolini, D. Brandini, and A. Fravolini J. Med. Chem. 51 2008 4321 4330
12. Chem. Abstr. 86 1977 106504h
13. V. Cecchetti, A. Fravolini, F. Schiaffella, O. Tabarrini, W. Zhou, and P.G. Pagella J. Heterocycl. Chem. 29 1992 375 382
14. M.K. Schwarz, D. Tumelty, and M.A. Gallop J. Org. Chem. 64 1999 2219 2231
15. V. Calderone, R. Spogli, A. Martelli, G. Manfroni, L. Testai, S. Sabatini, T. Oriana, and V. Cecchetti J. Med. Chem. 51 2008 5085 5092
16. E.V. Nosova, G.N. Lipunova, V.N. Charushin, and O.N. Chupakhin J. Fluor. Chem. 131 2010 1267 1288
17. T. Kuroita, N. Marubayashi, M. Sano, K. Kanzaki, K. Inaba, and T. Kawakita Chem. Pharm. Bull. (Tokyo) 44 1996 2051 2060
18. S.N. Pandeya, D. Sriram, E.De. Clercq, and G. Nath Arzneim. Forsch. 50 2000 55 59
19. G. Grandolini, V. Ambrogi, L. Baiocchi, M. Giannangeli, A. Furlani, A. Papaioannou, L. Perioli, and V. Scarcia Heterocycl. Commun. 1 1995 265 280
20. T. Yamamoto, M. Hori, I. Watanabe, K. Harada, S. Ikeda, and H. Ohtaka Chem. Pharm. Bull. 48 2000 843 849
21. J.W. Constantine, and I.M. Purcell J. Pharmacol. Exp. Ther. 187 1973 653 665
22. M. Bakavoli, H. Sadeghian, Z. Tabatabaei, E. Rezaei, M. Rahimizadeh, and M. Nikpour J. Mol. Model. 14 2008 471 478
23. Chem. Abstr. 136 2002 340675n
24. A. Napolitano, S. Memoli, and G. Prota J. Org. Chem. 64 1999 3009 3011
25. S. Aloui, I. Forsal, M. Sfaira, M.E. Touhami, M. Taleb, M.F. Baba, and M. Daoudi Portu. Electrochim. Acta 27 2009 599 613
26. R. Mannhold Med. Chem. Rev. 24 2004 213 266
27. M. Kumar, K. Sharma, R.M. Samarth, and A. Kumar Eu. J. Med. Chem. 45 2010 4467 4472
28. Y.T. Ma, M.C. Huang, F.L. Hsu, and H.F. Chang Phytochemistry 48 1998 1083 1085
29. R. Podsiadły J. Photochem. Photobiol. A: Chem. 208 2009 147 153
30. C. Brown, and R.M. Davidson Adv. Heterocycl. Chem. 38 1985 135 176
31. G. Liso, G. Trapani, V. Berardi, A. Latrofa, and P. Marchini J. Heterocycl. Chem. 1980 793 796
32. E.L. Patmore, and H. Chafetz J. Org. Chem. 32 1967 1254 1255
33. A.R. Katritzky, C.W. Rees, and E.F.V. Scriven Comprehensive Heterocyclic Chemistry 1996 Elsevier Amsterdam
34. B.S. Rathore, and M. Kumar Bioorg. Med. Chem. 14 2006 5678 5682
35. P.R. Sharma, V. Gupta, D.C. Gautam, and R.R. Gupta Phosphorus Sulfur Silicon 178 2003 1483 1488
36. A.C. Bajji, S. Nanya, and Y. Butsugan J. Heterocycl. Chem. 30 1993 361 363
37. J. Mungalpara, A. Pandey, V. Jain, and C.G. Mohan J. Mol. Model. 16 2010 629 644
38. G. Vanags, and A. Arens Zhur. Obsh. Khim. 27 1957 1358
39. Chem. Abstr. 94 1981 103045d
40. S.L. Shapiro, K. Geiger, J. Youlus, and L. Freedman J. Org. Chem. 26 1961 3580 3582
41. N.E. Cundasawmy, and D.B. Maclean Canad. J. Chem. 50 1972 3028 3036
42. R.Q. Brewster, and F.B. Dains J. Am. Chem. Soc. 58 8 1936 1364 1366
43. R.L. Mital, and S.K. Jain J. Chem. Soc. (c) 1969 2148 2150
44. M. Matsui, Y. Marui, M. Kushida, K. Funabiki, H. Muramastu, K. Shibata, K. Hirota, M. Hosoda, and K. Tai Dyes Pigm. 38 1998 57 64
45. B.S. Holla, K.N. Poojary, B. Poojary, K.S. Bhat, and N.S. Kumari Ind. J. Chem. 44 B 2005 2114 2119
46. S.N. Dhawan, S. Mor, K. Sharma, A.D. Chawla, A. Saini, and S.C. Gupta Ind. J. Chem. 33 B 1994 38 42
47. H.C. Norman, and A.M. Ronald J. Org. Chem. 26 1961 3812 3817
48. F.E.M. El-Baih, S.I. Al-Aqeel, O.A. El-Sayed, and H.M. Al-Hazimi J. King Saud. Univ. (Science), Saudi Arabia 18 1 2005 1 17
49. H. Sheibani, M.R. Islami, A. Hassanpour, and K. Saidi Phosphorus Sulfur Silicon 3 2008 13 20
50. H. Sheibani, M.R. Islami, A. Hassanpour, and F.A. Hosseininasab Arkivoc. XV 2006 68 75
51. L. Filak, B.T. Gulbas, Z. Riedl, G.A. Vasko, O. Egyed, I. Yalcin, E.A. Sener, and G. Hajos Acta Chim. Slov. 56 2009 622 628
52. W.S. Saari, D.W. Cochran, Y.C. Lee, E.L. Cresson, J.P. Springer, M. Williams, J.A. Totaro, and G.G. Yarbrough J. Med. Chem. 26 1983 564 569
53. K.M. El-Shaieb J. Sulfur. Chem. 28 2007 223 229
54. K.R. Scott, M.L. Laws, R.R. Roberts, J.M. Nicholson, United States Patent 5994349 1999.
55. National Committee for Clinical Laboratory Standards (NCCLs) Standard methods for dilution antimicrobial susceptibility tests for bacteria, which grows aerobically Nat. Comm. Lab. Stands.Villanova 1982 242
56. C. Hansch, and T. Fujita J. Am. Chem. Soc. 86 1964 1616 1626
57. C. Hansch, A. Leo, S.H. Unger, K.H. Kim, D. Nikaitani, and E.J. Lien J. Med. Chem. 16 11 1973 1207 1216
58. L.B. Kier, and L.H. Hall Molecular Connectivity in Chemistry and Drug Research 1976 Academic Press New York
59. M. Randic J. Am. Chem. Soc. 97 1975 6609 6615
60. A.T. Balaban Chem. Phys. Lett. 89 1982 399 404
61. H. Wiener J. Am. Chem. Soc. 69 1947 17 20
62. M. Randic Croat. Chem. Acta 66 1993 289 312
63. E. Furusjo, A. Svenson, M. Rahmberg, and M. Andersson Chemosphere 63 2006 99 108
64. A. Golbraikh, and A. Tropsha J. Mol. Graph. Model. 20 4 2002 269 276
65. M. Heravi, and A. Kyani J. Chem. Inf. Comput. Sci. 44 2005 1328 1335
66. L.B. Kier, L.H. Hall, J. Devillers, A.T. Balaban (Eds.), Gordon and Breach Sci. Pub., Amsterdam, 1999, pp. 455-489.
67. S.P. Gupta, A.N. Kumar, A.N. Nagappa, D. Kumar, and S. Kumaran Eur. J. Med. Chem. 38 2003 867 873
68. A.D. Pillai, S. Rani, P.D. Rathod, F.P. Xavier, K.K. Vasu, H. Padh, and V. Sundarsanam Bioorg. Med. Chem. 13 2005 1275 1283
69. S. Bajaj, S.S. Sambi, and A.K. Madan Croat. Chem. Acta 78 2 2005 165 174
70. A. Kumar, P. Sharma, V.K. Gurram, and N. Rane Biororg. Med. Chem. Lett. 16 2006 2484 2491
71. P. Sharma, A. Kumar, and M. Sharma Eur. J. Med. Chem. 41 2006 833 840
72. S.A. Hatya, E. Aki-sener, B. Tekiner-Gulbas, I. Yildiz, O. Temiz-Arpaci, I. Yalcin, and N. Altanlar Eur. J. Med. Chem. 41 2006 1398 1404
73. A. Kumar, B. Narasimhan, and D. Kumar Bioorg. Med. Chem. 15 2007 4113 4124
74. B. Narasimhan, V. Judge, R. Narang, S. Ohlan, and R. Ohlan Bioorg. Med. Chem. Lett. 17 2007 5836 5845
75. Hyperchem 6.0 1993 Hypercube, Inc. Florida
76. TSAR 3D Version 3.3 2000 Oxford Molecular Limited
77. SPSS for Windows, Version 10.05 1999 SPSS Inc. Bangalore, India
78. K.J. Schaper Quant. Struct. Act. Relat. 18 1999 354 360