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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

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Abstract

Reaction of 1,5-benzothiazepines, containing 2-phenyl-1,2,3-triazole 2a–d, with aryl nitrile oxides in CH2 Cl2 at room temperature leads to a series of novel 1,2,4-oxadiazolo[4,5-d]-1,5-benzothiazepine derivatives 3a-l in good yields. The products were characterized by IR, 1H NMR, MS, elemental analyses, X-ray and their spectrum characters were discussed.

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References

  1. Kumari N, Saini RK, Joshi YC (2007) Synthesis of novel derivative of 1,5-benzothiazepines from 1,3-diketones and their antibacterial activity. Orient J Chem 23: 731–734

    CAS  Google Scholar 

  2. Fan B, Li J, Li Y, Yin S (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

    CAS  Google Scholar 

  3. Pant S, Sharma P, Sharma A, Pant UC (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

    CAS  Google Scholar 

  4. Nikalje AP, Mane R, Ingle D (2006) Synthesis and antimicrobial activity of new 4-thiazolidinonyl-1,5-benzothiazepines. Int J Chem Sci 4: 145–150

    CAS  Google Scholar 

  5. Nikalje AG, Mane RA, Ingle DB (2006) Synthesis of new 1,5-benzothiazepines as prospective antimicrobial agents. Indian J Heterocycl Chem 15: 309–310

    CAS  Google Scholar 

  6. Shetgiri NP, Nayak BK (2003) Synthesis of some benzothiazepines and their antimicrobial activities. Indian J Chem B Org Chem 42: 683–687

    Google Scholar 

  7. Richard S (2005) Vascular effects of calcium channel antagonists: New evidence Drugs 65: 1–10. doi:10.2165/00003495-200565002-00002

    CAS  Google Scholar 

  8. Ansari FL, Umbreen S, Hussain L, Makhmoor T, Nawaz SA, Lodhi MA et al (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. doi:10.1002/cbdv.200590029

    Article  PubMed  CAS  Google Scholar 

  9. Jiang L, Wan X, Xu H, Bian J, Han W, Zhu K et al (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. doi:10.1016/S1000-1948(07)60046-X

    Article  CAS  Google Scholar 

  10. Zhu S (2004) Canadian multicenter clentiazem angina trial. S Chin J Card Dis 10: 72

    Google Scholar 

  11. Xu F, Liu F, Shen L, Liu G, Yang C, Chen Q (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

    CAS  Google Scholar 

  12. Kamal A, Shankaraiah N, Devaiah V, Reddy KL, Juvekar A, Sen S et al (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. doi:10.1016/j.bmcl.2007.12.063

    Article  PubMed  CAS  Google Scholar 

  13. Zhu X, Chen X, Yan M, Shi D, Ding K (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. doi:10.1002/hc.20367

    Article  CAS  Google Scholar 

  14. Aufort M, Herscovici J, Bouhours P, Moreau N, Girard C (2008) Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives. Bioorg Med Chem Lett 18: 1195–1198. doi:10.1016/j.bmcl.2007.11.111

    Article  PubMed  CAS  Google Scholar 

  15. Gallardo H, Conte G, Bryk F, Lourenco MCS, Costa MS, Ferreira VF (2007) Synthesis and evaluation of 1-alkyl-4-phenyl-[1,2,3]-triazole derivatives as antimycobacterial agent. J Braz Chem Soc 18: 1285–1291. doi:10.1590/S0103-50532007000600027

    Article  CAS  Google Scholar 

  16. Liu F, Wang B, Li Y (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

    CAS  Google Scholar 

  17. Liu F, Wang B, Zhang Z, Sun W (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

    CAS  Google Scholar 

  18. Chimirri A, Gitto R, Grasso S, Monforte P, Zappalà M (1994) 5H-[1,2,4]oxadiazolo[5,4-d][1,5]benzothiazepines: synthesis and stereo-chemistry. Heterocycles 38: 2289–2293

    Article  CAS  Google Scholar 

  19. Yang D, Liu F, Xu F, Yang C (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. doi:10.1007/s10870-007-9269-7

    Article  CAS  Google Scholar 

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Correspondence to Fang-Ming Liu.

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Yang, DB., Liu, FM., Xu, F. et al. 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. Mol Divers 12, 103–109 (2008). https://doi.org/10.1007/s11030-008-9082-z

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  • DOI: https://doi.org/10.1007/s11030-008-9082-z

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