N-methyl-(7-isopropoxycarbonyl-6-methyl-2,3,5,6-tetrahydropyrrolo[2,1-b]thiazol-3-ylidene)acetamide | 170951-02-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: N-methyl-(7-isopropoxycarbonyl-6-methyl-2,3,5,6-tetrahydropyrrolo[2,1-b]thiazol-3-ylidene)acetamide
• 英文别名: propan-2-yl (3E)-6-methyl-3-[2-(methylamino)-2-oxoethylidene]-5,6-dihydropyrrolo[2,1-b][1,3]thiazole-7-carboxylate
• CAS: 170951-02-7
• 化学式: C₁₄H₂₀N₂O₃S
• 分子量: 296.39
• InChiKey: YDORIQRKHGPPSQ-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diisopropyl ethylidenemalonate 在 镍 劳森试剂 、 氢气 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 水 、 异丙醇 、 苯 为溶剂， 反应 65.0h， 生成 N-methyl-(7-isopropoxycarbonyl-6-methyl-2,3,5,6-tetrahydropyrrolo[2,1-b]thiazol-3-ylidene)acetamide
  参考文献：
  名称：

  Synthesis and Pharmacological Activities of Novel Bicyclic Thiazoline Derivatives as Hepatoprotective Agents. II. (7-Alkoxycarbonyl-2,3,5,6-tetrahydropyrrolo(2,1-b)thiazol-3-ylidene)acetamide Derivatives.

  摘要：

  合成了一系列外甲基双环噻唑啉衍生物（3a-i），并评估了它们对半乳糖胺诱导的大鼠急性肝损伤和单克隆抗体诱导的大鼠急性肝损伤的保肝活性。研究了结构-活性关系。在合成的化合物中，N-甲基-(7-异丙氧羰基-6, 6-二甲基-2, 3, 5, 6-四氢吡咯并[2, 1-b]噻唑-3-亚基)乙酰胺（3i）表现出最强的保肝活性。根据血清转氨酶活性的变化，口服 100 毫克/千克该化合物可抑制半乳糖胺诱导的肝损伤，腹腔注射 30 毫克/千克可进一步防止单克隆抗体诱导的肝损伤。

  DOI：

  10.1248/cpb.43.1125

文献信息

• Pyrrolo(2,1-B)thiazole derivatives
  申请人：Daiichi Pharmaceutical Co., Ltd.

  公开号：US05098919A1

  公开（公告）日：1992-03-24

  A compound represented by the following formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom, an alkyl group or a cyclic alkyl group; R.sub.2 represents a hydroxyl group, an alkoxy group which may have one to three substituents in the alkyl group moiety, an arylthio group which may have one or more substituents in the aryl group moiety, an aryloxy group which may have one or more substituents in the aryl group moiety, an amino group, an alkylamino group or a cyclic amino group which may contain other hetero atoms as ring atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom; R.sub.3 represents a hydrogen atom, an alkyl group, an aryl group which may have one or more substituents, or a hetero aryl group which may have one or more substituents; m represents 1 or 2 and represents a single bond or a double bond; salts thereof, and pharmaceutical preparations for preventing and treating hepatic diseases containing the compound of the formula (I) or salts thereof as an active ingredient are disclosed.

  以下式子(I)所表示的化合物：##STR1## 其中，R.sub.1代表氢原子、烷基或环烷基；R.sub.2代表羟基、烷氧基，该烷氧基中的烷基部分可以有一到三个取代基，还可以是苯硫基，该苯硫基中的苯基部分可以有一个或多个取代基，也可以是苯氧基，该苯氧基中的苯基部分可以有一个或多个取代基，还可以是氨基、烷基氨基或环状氨基，该环状氨基可以包含其他杂原子作为环原子，所选的杂原子包括氮原子、氧原子和硫原子；R.sub.3代表氢原子、烷基、苯基，该苯基可以有一个或多个取代基，或杂环苯基，该杂环苯基可以有一个或多个取代基；m代表1或2，表示单键或双键；其盐以及作为活性成分的具有预防和治疗肝病作用的药物制剂，其中所述药物制剂包含式(I)中的化合物或其盐。
• Pyrrolo [2,1-b]thiazole derivatives
  申请人：DAIICHI PHARMACEUTICAL CO., LTD.

  公开号：EP0410224A1

  公开（公告）日：1991-01-30

  A novel compound represented by the following formula (I): wherein R₁ represents a hydrogen atom, an alkyl group or a cyclic alkyl group; R₂ represents a hydroxyl group, an alkoxy group which may have one to three substituents in the alkyl group moiety, an arylthio group which may have one or more substituents in the aryl group moiety, an aryloxy group which may have one or more substituents in the aryl group moiety, an amino group, an alkylamino group or a cyclic amino group which may contain other hetero atoms as ring atoms selected from a nitrogen atom, an oxygen atom and a sulfur atom; R₃ represents a hydrogen atom, an alkyl group, an aryl group which may have one or more substituents, or a hetero aryl group which may have one or more substituents; and ----- represents a single bond or a double bond; salts thereof, and pharmaceutical preparations for preventing and treating hepatic diseases containing the compound of the formula (I) or salts thereof as an active ingredient are disclosed.

  由下式(I)代表的新型化合物： 其中 R₁ 代表氢原子、烷基或环烷基； R₂代表羟基、烷氧基（可在烷基分子中具有一至三个取代基）、芳硫基（可在芳基分子中具有一个或多个取代基）、芳氧基（可在芳基分子中具有一个或多个取代基）、氨基、烷基氨基或环状氨基（可含有其他杂原子作为选自氮原子、氧原子和硫原子的环原子）； R₃ 代表氢原子、烷基、芳基（可有一个或多个取代基）或杂芳基（可有一个或 多个取代基）；以及 ----- 代表单键或双键；公开了含有式 (I) 化合物或其盐作为活性成分的其盐和用于预防和治疗肝病的药物制剂。
• US5098919A
  申请人：——

  公开号：US5098919A

  公开（公告）日：1992-03-24
• Synthesis and Pharmacological Activities of Novel Bicyclic Thiazoline Derivatives as Hepatoprotective Agents. II. (7-Alkoxycarbonyl-2,3,5,6-tetrahydropyrrolo(2,1-b)thiazol-3-ylidene)acetamide Derivatives.
  作者：Masashi HASEGAWA、Atsushi NAKAYAMA、Shuichi YOKOHAMA、Toru HOSOKAMI、Yoichi KUREBAYASHI、Takuya IKEDA、Yoshimasa SHIMOTO、Shoichiro IDE、Yuko HONDA、Norio SUZUKI

  DOI：10.1248/cpb.43.1125

  日期：——

  A series of exomethylenic bicyclic thiazoline derivatives (3a-i) was synthesized and evaluated for hepatoprotective activity against galactosamine-induced and monoclonal antibody-induced acute liver injuries in rats. The structure-activity relationships were investigated. Among the compounds synthesized, N-methyl-(7-isopropoxycarbonyl-6, 6-dimethyl-2, 3, 5, 6-tetrahydropyrrolo[2, 1-b]thiazol-3-ylidene)acetamide (3i) exhibited the most potent hepatoprotective activity. This compound suppressed galactosamine-induced hepatic injury at 100 mg/kg by oral administration and further prevented monoclonal antibody-induced hepatic injury at 30 mg/kg by intraperitoneal injection, as judged from the changes in serum transaminase activities.

  合成了一系列外甲基双环噻唑啉衍生物（3a-i），并评估了它们对半乳糖胺诱导的大鼠急性肝损伤和单克隆抗体诱导的大鼠急性肝损伤的保肝活性。研究了结构-活性关系。在合成的化合物中，N-甲基-(7-异丙氧羰基-6, 6-二甲基-2, 3, 5, 6-四氢吡咯并[2, 1-b]噻唑-3-亚基)乙酰胺（3i）表现出最强的保肝活性。根据血清转氨酶活性的变化，口服 100 毫克/千克该化合物可抑制半乳糖胺诱导的肝损伤，腹腔注射 30 毫克/千克可进一步防止单克隆抗体诱导的肝损伤。