Synthesis of some halogen-containing 1,2,4-triazolo-1,3,4-thiadiazines and their antibacterial and anticancer screening studies--part I.

作者: Bantval Shivarama Holla , Balladka Kunhanna Sarojini , Balikekodi Sooryanarayana Rao , Padiyath Mohammed Akberali , Nalilu Suchetha Kumari

DOI: 10.1016/S0014-827X(01)01094-1

关键词: Organic chemistryCytotoxicityAntibacterial agentChemical synthesisBicyclic moleculeProton NMRAntibacterial activityIn vitroBacteriaChemistry

摘要: Abstract A series of 7-arylidene-6-(2,4-dichloro-5-fluorophenyl)-3-substituted-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (3) were prepared by the condensation 4-amino-5-mercapto-3-substituted-1,2,4-triazoles (1) and 3-aryl-1-(2,4-dichloro-5-fluorophenyl)-2-bromo-2-propen-1-one (2). An alternative route for synthesis title compound 3 has been described. The newly synthesised compounds characterised on basis N-analyses, IR, 1H NMR mass spectral data. Some tested their antibacterial activities against Gram +ve −ve bacteria. Among 3n showed highest degree activity S. aureus evaluation LD50 value this was carried out. also screened anticancer activities. these, 3b, 3g, 3p are found to be active NCI-H460 (lung), MCF7 (breast), SF 268 (CNS) in preliminary screening studies. Further, 60-cell-line studies these results such discussed paper.

参考文章(13)
BS Holla, B Kalluraya, KR Sridhar, E Drake, LM Thomas, KK Bhandary, MJ Levine, Synthesis, structural characterization, crystallographic analysis and antibacterial properties of some nitrofuryl triazolo[3,4-b]-1,3,4-thiadiazines European Journal of Medicinal Chemistry. ,vol. 29, pp. 301- 308 ,(1994) , 10.1016/0223-5234(94)90100-7
Takashi Hirota, Kenji Sasaki, Hiroshi Yamamoto, Taiji Nakayama, Polycyclic N‐hetero compounds. XXXVI. Syntheses and antidepressive evaluation of 11,13,15,17‐tetraazasteroids and their 17‐oxides Journal of Heterocyclic Chemistry. ,vol. 28, pp. 257- 261 ,(1991) , 10.1002/JHET.5570280209
B. N. Goswami, J. C. S. Kataky, J. N. Baruah, Synthesis and biological activity of bridgehead nitrogen heterocycles Journal of Heterocyclic Chemistry. ,vol. 23, pp. 1439- 1442 ,(1986) , 10.1002/JHET.5570230538
N. F. Eweiss, A. A. Bahajaj, E. A. Elsherbini, SYNTHESIS OF HETEROCYCLES (PART VI [1]); SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF 4-AMINO-5-ARYL-1,2,4-TRIZOLE-3-THIONES AND THEIR DERIVATIVES Journal of Heterocyclic Chemistry. ,vol. 23, pp. 1451- 1458 ,(1986) , 10.1002/JHET.5570230540
L. C. Miller, M. L. Tainter, Estimation of the ED50 and Its Error by Means of Logarithmic-Probit Graph Paper.∗: Experimental Biology and Medicine. ,vol. 57, pp. 261- 264 ,(1944) , 10.3181/00379727-57-14776
Jack R. Reid, Ned D. Heindel, Improved syntheses of 5‐substituted‐4‐amino‐3‐mercapto‐(4H)‐1,2,4‐triazoles Journal of Heterocyclic Chemistry. ,vol. 13, pp. 925- 926 ,(1976) , 10.1002/JHET.5570130450
S. KUMARI, S. PARKASH, V. K. GOEL, Synthesis of Substituted Pyrrolo(1,2-a)quinolines. ChemInform. ,vol. 28, ,(1997) , 10.1002/CHIN.199713121
B. Kalluraya, B. S. Holla, A. D'souza, SYNTHESIS AND STRUCTURAL CHARACTERIZATION OF SOME NITROTHIENYL-TRIAZOLO3,4-B-1,3,4-THIADIAZINES Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal Chemistry. ,vol. 34, pp. 939- 943 ,(1995)
S. Parkash, S. Kumari, Vijender Kumar Goel, SYNTHESIS OF SUBSTITUTED PYRROLO1,2-AQUINOLINES Indian Journal of Chemistry Section B-organic Chemistry Including Medicinal Chemistry. ,vol. 35, pp. 1329- 1330 ,(1996)