isopropyl (S)-2-(benzo[b]thiophene-2-carboxamido)-3-(1H-imidazol-1-yl)propanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: isopropyl (S)-2-(benzo[b]thiophene-2-carboxamido)-3-(1H-imidazol-1-yl)propanoate
• 英文别名: propan-2-yl (2S)-2-(1-benzothiophene-2-carbonylamino)-3-imidazol-1-ylpropanoate
• 化学式: C₁₈H₁₉N₃O₃S
• 分子量: 357.433
• InChiKey: BIMVZOFOEKGJNN-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基苯并噻吩-2-甲醛 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 isopropyl (S)-2-(benzo[b]thiophene-2-carboxamido)-3-(1H-imidazol-1-yl)propanoate
  参考文献：
  名称：

  Design, synthesis and evaluation of benzoheterocycle analogues as potent antifungal agents targeting CYP51

  摘要：

  To further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compound 1, a series of benzoheterocycle analogues were designed, synthesized and evaluated for their in vitro antifungal activity. The most promising compounds 13s and 14a exhibited excellent antifungal activity against C. albicans, C. neoformans, A. fumigatus and fluconazole-resistant C. albicans strains, that was superior or comparable to those of the reference drugs fluconazole and voriconazole. GC-MS analyses suggested that the novel compound 13s might have a similar mechanism to fluconazole by inhibiting fungal lanosterol 14 alpha-demethylase (CYP51). Furthermore, compounds 13s and 14a exhibited low inhibition profiles for various human cytochrome P450 isoforms as well as excellent blood plasma stability. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.04.054

文献信息

• Design, synthesis and evaluation of benzoheterocycle analogues as potent antifungal agents targeting CYP51
  作者：Shizhen Zhao、Peng Wei、Mengya Wu、Xiangqian Zhang、Liyu Zhao、Xiaolin Jiang、Chenzhou Hao、Xin Su、Dongmei Zhao、Maosheng Cheng

  DOI：10.1016/j.bmc.2018.04.054

  日期：2018.7

  To further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compound 1, a series of benzoheterocycle analogues were designed, synthesized and evaluated for their in vitro antifungal activity. The most promising compounds 13s and 14a exhibited excellent antifungal activity against C. albicans, C. neoformans, A. fumigatus and fluconazole-resistant C. albicans strains, that was superior or comparable to those of the reference drugs fluconazole and voriconazole. GC-MS analyses suggested that the novel compound 13s might have a similar mechanism to fluconazole by inhibiting fungal lanosterol 14 alpha-demethylase (CYP51). Furthermore, compounds 13s and 14a exhibited low inhibition profiles for various human cytochrome P450 isoforms as well as excellent blood plasma stability. (C) 2018 Elsevier Ltd. All rights reserved.