Synthesis, Crystal Structure and Antifungal Activities of 3-(CH2)nCO2C2H5-1,5-Benzothiazepines

doi:10.7503/cjcu20120781

Abstract

Abstract:

In order to find benzothiazepine derivatives with more effective activities against fungi and investigate the structure-activity relationship of ester-substituted 1,5-benzothiazepine derivatives(A), thirty-eight 3-(CH₂)_nCO₂C₂H₅-1,5-benzothiazepines(n=1, 2) 6 and 7 were synthesized and characterized by ¹H NMR, MS/HRMS, IR and elemental analysis. The crystal structures of compounds 6a and 7c were also studied by X-ray diffraction method and the results indicated that seven-membered ring in the molecules of compounds 6a and 7c adopts twist-boat conformation. The results of bioassay of compounds 6 and 7 showed that the antifungal activities decrease when the ethoxycarbonyl alkyl [(CH₂)_nCO₂C₂H₅] was at C3 position on the heterocyclic ring in these 1,5-benzothiazepine derivatives. Meanwhile, the Michael addition of thiophenol to α,β-unsaturated compounds catalyzed by CeCl₃·7H₂O-NaI was explored. The results show that the combination of CeCl₃·7H₂O-NaI can promote the conjugate addition of 2-aminothiophenol to α,β-unsaturated ketones with high steric hindrance efficiently. The condensation reactions of compounds 5 catalyzed by TiCl₄ were also studied. The results indicate that TiCl₄ is an efficient promoter for the reaction.

Key words: 1,5-Benzothiazepine, Antifungal activity, CeCl₃·7H₂O-NaI, Michael addition, Schiff base

CLC Number:

O626

TrendMD:

QIU Zhao-Lai, LI Wen-Hong, ZHU Hai-Fei, LIU Qian, LI Yuan. Synthesis, Crystal Structure and Antifungal Activities of 3-(CH₂)_nCO₂C₂H₅-1,5-Benzothiazepines[J]. Chem. J. Chinese Universities, 2013, 34(3): 579.

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Synthesis, Crystal Structure and Antifungal Activities of 3-(CH₂)_nCO₂C₂H₅-1,5-Benzothiazepines

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