3-(1H-imidazol-5-yl)propanethioamide | 176860-52-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1H-imidazol-5-yl)propanethioamide
• CAS: 176860-52-9
• 化学式: C₆H₉N₃S
• 分子量: 155.224
• InChiKey: SZVAOKBEKRXLQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-氯-3-(4-氯苯基)丙烷-2-酮 、 3-(1H-imidazol-5-yl)propanethioamide 以 甲醇 为溶剂， 生成 4-[(4-chlorophenyl)methyl]-2-[2-(1H-imidazol-5-yl)ethyl]-1,3-thiazole
  参考文献：
  名称：

  Novel 1, 2, 4-oxadiazoles as potent and selective histamine H3 receptor antagonists

  摘要：

  Replacement of the isothiourea moiety of known histamine H-3 antagonists by certain 5-membered heteroaromatic systems can give compounds with an improved activity profile. One of these, 3-[(4-chlorophenyl)methyl]-5-[2-(1H-imidazol-4-yl)ethyl] 1,2,4-oxadiazole (GR175737) is a potent, selective, orally active and centally penetrating H-3 antagonist. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00122-9
• 作为产物：
  描述：

  3-(1H-咪唑-4-基)-丙酸乙酯 在 劳森试剂 、 氨 作用下， 以 水 为溶剂， 生成 3-(1H-imidazol-5-yl)propanethioamide
  参考文献：
  名称：

  Novel 1, 2, 4-oxadiazoles as potent and selective histamine H3 receptor antagonists

  摘要：

  Replacement of the isothiourea moiety of known histamine H-3 antagonists by certain 5-membered heteroaromatic systems can give compounds with an improved activity profile. One of these, 3-[(4-chlorophenyl)methyl]-5-[2-(1H-imidazol-4-yl)ethyl] 1,2,4-oxadiazole (GR175737) is a potent, selective, orally active and centally penetrating H-3 antagonist. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00122-9

文献信息

• New thiazole derivatives as potent and selective 5-hydroxytriptamine 3 (5-HT 3 ) receptor agonists for the treatment of constipation
  作者：Naoki Imanishi、Kiyoshi Iwaoka、Hiroyuki Koshio、Shin-ya Nagashima、Ken-ichi Kazuta、Mitsuaki Ohta、Shuichi Sakamoto、Hiroyuki Ito、Shinobu Akuzawa、Tetsuo Kiso、Shin-ichi Tsukamoto、Toshiyasu Mase

  DOI：10.1016/s0968-0896(02)00557-6

  日期：2003.4

  The syntheses and biological evaluation of a series of novel indeno[1,2-d]thiazole derivatives are described. Several groups reported 5-HT3 receptor agonists which were mainly evaluated for their activities on the von Bezold-Jarisch reflex (B-J reflex). We discovered that tetrahydrothiazolopyridine derivative 1b had a contractile effect on the isolated guinea pig colon with weak B-J reflex. Our efforts to find a new type of 5-HT3 receptor agonists on the isolated guinea pig colon focused on the synthesis of a fused thiazole derivative 1d modified from 1b and reverse-fused thiazole derivatives (7-10). In this series, 10f (YM-31636) showed high affinity and selectivity for the cloned human 5-HT3 receptor; furthermore, it showed potent and selective 5-HT3 receptor agonistic activity. YM-31636 was examined for its effects on defecation in animals, thus evaluating the compound as an agent against constipation. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Novel 1, 2, 4-oxadiazoles as potent and selective histamine H3 receptor antagonists
  作者：J.W. Clitherow、P. Beswick、W.J. Irving、D.I.C. Scopes、J.C. Barnes、J. Clapham、J.D. Brown、D.J. Evans、A.G. Hayes

  DOI：10.1016/0960-894x(96)00122-9

  日期：1996.4

  Replacement of the isothiourea moiety of known histamine H-3 antagonists by certain 5-membered heteroaromatic systems can give compounds with an improved activity profile. One of these, 3-[(4-chlorophenyl)methyl]-5-[2-(1H-imidazol-4-yl)ethyl] 1,2,4-oxadiazole (GR175737) is a potent, selective, orally active and centally penetrating H-3 antagonist. Copyright (C) 1996 Elsevier Science Ltd