(Z)-1-(5-chlorothien-2-yl)-2-(1H-imidazol-1-yl)ethanone 2,6-dichlorophenylhydrazone hydrochloride | 80168-45-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-1-(5-chlorothien-2-yl)-2-(1H-imidazol-1-yl)ethanone 2,6-dichlorophenylhydrazone hydrochloride
• 英文别名: 2,6-dichloro-N-[(Z)-[1-(5-chlorothiophen-2-yl)-2-imidazol-1-ylethylidene]amino]aniline;hydron;chloride
• CAS: 80168-45-2
• 化学式: C₁₅H₁₁Cl₃N₄S*ClH
• 分子量: 422.165
• InChiKey: ABBHTBYIHZTISS-GRWWMUSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  70.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-1-(5-氯-2-噻吩基-2-(1H)-咪唑-1-基)乙酮(2,6-二氯苯基)腙盐酸盐 在 1,2-二氯乙烷 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以8%的产率得到(Z)-1-(5-chlorothien-2-yl)-2-(1H-imidazol-1-yl)ethanone 2,6-dichlorophenylhydrazone hydrochloride
  参考文献：
  名称：

  Synthesis of (E)-1-(5-chlorothien-2-yl)-2-(1H-imidazol-1-yl)ethanone 2,6-dichlorophenylhydrazone hydrochloride, a novel, orally active antifungal agent

  摘要：

  The preparation, determination of isomeric configuration, and antifungal properties of (E)-1-(5-chlorothien-2-yl)-2-(1H-imidazol-1-yl)ethanone 2,6-dichlorophenylhydrazone hydrochloride (1) are described. In vitro, compound 1 has been shown to have activity against Candida albicans comparable with miconazole. When administered orally to animals with experimentally induced vaginal candidiasis or systemic candidiasis, compound 1 produced results approaching those produced by ketoconazole. In addition, topical administration of compound 1 to rats with vaginal candidiasis produced results comparable with those produced by similar administration of clotrimazole. Unlike ketoconazole, which is active by a mechanism that is essentially fungistatic, compound 1 shares with miconazole a mode of action that is fungicidal. However, unlike miconazole, compound 1 exhibits activity following oral administration. Compound 1 has been found to be negative in the Ames test.

  DOI：

  10.1021/jm00357a023

文献信息

• DYER, R. L.;ELLAMES, G. J.;HAMILL, B. J.;MANLEY, P. W.;POPE, A. M. S., J. MED. CHEM., 1983, 26, N 3, 442-445
  作者：DYER, R. L.、ELLAMES, G. J.、HAMILL, B. J.、MANLEY, P. W.、POPE, A. M. S.

  DOI：——

  日期：——
• US4871741A
  申请人：——

  公开号：US4871741A

  公开（公告）日：1989-10-03
• Synthesis of (E)-1-(5-chlorothien-2-yl)-2-(1H-imidazol-1-yl)ethanone 2,6-dichlorophenylhydrazone hydrochloride, a novel, orally active antifungal agent
  作者：R. L. Dyer、G. J. Ellames、B. J. Hamill、P. W. Manley、A. M. S. Pope

  DOI：10.1021/jm00357a023

  日期：1983.3

  The preparation, determination of isomeric configuration, and antifungal properties of (E)-1-(5-chlorothien-2-yl)-2-(1H-imidazol-1-yl)ethanone 2,6-dichlorophenylhydrazone hydrochloride (1) are described. In vitro, compound 1 has been shown to have activity against Candida albicans comparable with miconazole. When administered orally to animals with experimentally induced vaginal candidiasis or systemic candidiasis, compound 1 produced results approaching those produced by ketoconazole. In addition, topical administration of compound 1 to rats with vaginal candidiasis produced results comparable with those produced by similar administration of clotrimazole. Unlike ketoconazole, which is active by a mechanism that is essentially fungistatic, compound 1 shares with miconazole a mode of action that is fungicidal. However, unlike miconazole, compound 1 exhibits activity following oral administration. Compound 1 has been found to be negative in the Ames test.