Synthesis and structure characterization of new 1,2,4-oxadiazolo[4,5-d]-1, 5-benzothiazepines derivatives containing 2-phenyl-1,2,3-triazole through 1,3-dipolar cycloaddition reaction

Molecular Diversity

Volumn 12, Issue 2, 2008, Pages 103-109

  Yang, De Bao ^a   Liu, Fang Ming ^a,b   Xu, Feng ^b   Yang, Chun ^a   Ye, Jia Wei ^b   Shen, Song Wei ^a   Zhou, Ying Lei ^a   Li, Wei ^a  

^a HANGZHOU NORMAL UNIVERSITY   (China)

^b XINJIANG UNIVERSITY   (China)

Author keywords

1,2,4 Oxadiazole; 1,5 Benzothiazepine 2 phenyl 1,2,3 triazole; Crystal structure; Cycloaddition

Indexed keywords

1 (4 METHOXYPHENYL) 5 NITRO 3A (2 PHENYL 2H 1,2,3 TRIAZO 4 YL) 4,5 DIHYDRO 3AH BENZO[B][1,2,4]OXADIAZOLO[4,5 D][1,4]THIAZEPINE; 1 (4 METHOXYPHENYL) 5 PHENYL 3A (2 PHENYL 2H 1,2,3 TRIAZO 4 YL) 4,5 DIHYDRO 3AH BENZO[B][1,2,4]OXADIAZOLO[4,5 D][1,4]THIAZEPINE; 1 CHLORO 5 NITRO 3A (2 PHENYL 2H 1,2,3 TRIAZOL 4 YL) 4,5 DIHYDRO 3AH BENZO[B][1,2,4]OXADIAZOLO[4,5 D][1,4]THIAZEPINE; 1 PHENYL 5 NITRO 3A (2 PHENYL 2H 1,2,3 TRIAZOL 4 YL) 4,5 DIHYDRO 3AH BENZO[B][1,2,4]OXADIAZOLO[4,5 D][1,4]THIAZEPINE; 1,5 BISCHLORO 3A (2 PHENYL 2H 1,2,3 TRIAZOL 4 YL) 4,5 DIHYDRO 3AH BENZO[B][1,2,4]OXADIAZOLO[4,5 D][1,4]THIAZEPINE; 1,5 BISPHENYL 3A (2 PHENYL 2H 1,2,3 TRIAZOL 4 YL) 4,5 DIHYDRO 3AH BENZO[B][1,2,4]OXADIAZOL[4,5 D][1,4]THIAZEPINE; 1,5 DI(4 METHYLOXYPHENYL) 3A (2 PHENYL 1,2,3 TRIAZOL 4 YL) 4,5 DIHYDRO 1,2 4 OXADIAZOLO[4,5 D][1,5]BENZOTHIAZEPINE; 2 (4 METHOXYPHENYL) 4 (2 PHENYL 1,2,3 TRIAZOLE 4 YL) 2,3 DIHYDRO[1,5]BENZOTHIAZEPINE; 2 CHLORO 4 (2 PHENYL 1,2,3 TRIAZOLE 4 YL) 2,3 DIHYDRO[1,5]BENZOTHIAZEPINE; 2 NITRO 4 (2 PHENYL 1,2,3 TRIAZOLE 4 YL) 2,3 DIHYDRO[1,5]BENZOTHIAZEPINE; 2 PHENYL 4 (2 PHENYL 1,2,3 TRIAZOLE 4 YL) 2,3 DIHYDRO[1,5]BENZOTHIAZEPINE; BENZOTHIAZEPINE DERIVATIVE; NITRILE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED RADIATION; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; X RAY DIFFRACTION;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; THIAZEPINES; TRIAZOLES;

EID: 50849084811     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-008-9082-z     Document Type: Article

References (19)

1. N Kumari RK Saini YC Joshi 2007 Synthesis of novel derivative of 1,5-benzothiazepines from 1,3-diketones and their antibacterial activity Orient J Chem 23 731 734
2. B Fan J Li Y Li S Yin 2007 Synthesis and calm activity of 2-(4-β-D-allopyranosyloxyphenyl)-4-aryl-2,3-dihydro-1,5-benzothiazepine Chin J Org Chem 27 1150 1154
3. S Pant P Sharma A Sharma UC Pant 2007 Synthesis of 1,5-benzothiazepines. Part XXXV. Synthesis and antimicrobial studies of 8-substituted-2-(2- chlorophenyl)-2,5-dihydro-4-(phenyl/1-naphthyl)-1,5-benzothiazepines Indian J Heterocycl Chem 16 345 348
4. AP Nikalje R Mane D Ingle 2006 Synthesis and antimicrobial activity of new 4-thiazolidinonyl-1,5-benzothiazepines Int J Chem Sci 4 145 150
5. AG Nikalje RA Mane DB Ingle 2006 Synthesis of new 1,5-benzothiazepines as prospective antimicrobial agents Indian J Heterocycl Chem 15 309 310
6. NP Shetgiri BK Nayak 2003 Synthesis of some benzothiazepines and their antimicrobial activities Indian J Chem B Org Chem 42 683 687
7. S Richard 2005 Vascular effects of calcium channel antagonists: New evidence Drugs 65 1 10 10.2165/00003495-200565002-00002
8. FL Ansari S Umbreen L Hussain T Makhmoor SA Nawaz MA Lodhi 2005 Syntheses and biological activities of chalcone and 1,5-benzothiazepine derivatives. Promising new free-radical scavengers, and esterase, urease, and α-glucosidase inhibitors Chem Biodivers 2 487 495 10.1002/cbdv.200590029
9. L Jiang X Wan H Xu J Bian W Han K Zhu 2007 Effect of diltiazem and lidocaine on arterial pressure or heart rate and the quality of extubation in patients undergoing uvulopalato-pharyngoplasty J Med Coll PLA 22 230 233 10.1016/S1000-1948(07)60046-X
10. S Zhu 2004 Canadian multicenter clentiazem angina trial S Chin J Card Dis 10 72
11. F Xu F Liu L Shen G Liu C Yang Q Chen 2007 Synthesis and crystal structure of 2-p-methyloxyphenyl-3a-(2-phenyl-1,2,3-triazole-4-yl)-3,4-dihydro- 1,2,4-oxa-diazolo[4,5-d] [1,5]benzothiazepine Chin J Struct Chem 26 1061 1065
12. A Kamal N Shankaraiah V Devaiah KL Reddy A Juvekar S Sen 2008 Synthesis of 1,2,3-triazole-linked pyrrolobenzodiazepine conjugates employing 'click' chemistry: DNA-binding affinity and anticancer activity Bioorg Med Chem Lett 18 1468 1473 10.1016/j.bmcl.2007.12.063
13. X Zhu X Chen M Yan D Shi K Ding 2008 Stereoselective synthesis and biological activities of O-(E)-1-{1-[(6-chloropyridin-3-yl)methyl]-5-methyl-1H- 1,2,3-triazol-4-yl}ethyleneamino-O-ethyl-O-arylphosphorothioates Heteroatom Chem 19 15 20 10.1002/hc.20367
14. M Aufort J Herscovici P Bouhours N Moreau C Girard 2008 Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives Bioorg Med Chem Lett 18 1195 1198 10.1016/j.bmcl.2007.11.111
15. H Gallardo G Conte F Bryk MCS Lourenco MS Costa VF Ferreira 2007 Synthesis and evaluation of 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives as antimycobacterial agent J Braz Chem Soc 18 1285 1291 10.1590/S0103- 50532007000600027
16. F Liu B Wang Y Li 2002 Synthesis of new 1,2,4-oxadiazolo[4,5-d][1,5] benzothiazepine derivatives containing 2-phenyl-1,2,3-triazole through 1,3-dipolar cycloaddition reaction Chem Res Chin Univ 23 2097 2101
17. F Liu B Wang Z Zhang W Sun 2002 Synthesis of new 1,5-benzothiazepines containing 2-phenyl-1,2,3-triazole and their β-lactam derivatives Acta Chimi Sin 60 1095 1101
18. A Chimirri R Gitto S Grasso P Monforte M Zappalà 1994 5H-[1,2,4]oxadiazolo[5,4-d][1,5]benzothiazepines: synthesis and stereo-chemistry Heterocycles 38 2289 2293
19. D Yang F Liu F Xu C Yang 2008 Synthesis and crystal structure of compound 1,5-bis(4-methoxyphenyl)-3a-(2-phenyl-2H-1,2,3-triazol-4-yl)-4,5-dihydro-3aH- benzo[b][1,2,4]oxadiazolo[4,5-d][1,4]thiazepine J Chem Crystallogr 38 97 101 10.1007/s10870-007-9269-7