7a-(4-Chlorophenyl)tetrahydropyrrolo[2,1-b][1,3]thiazol-5(6H)-one | 182957-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 7a-(4-Chlorophenyl)tetrahydropyrrolo[2,1-b][1,3]thiazol-5(6H)-one
• 英文别名: 7a-(4-chlorophenyl)-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]thiazol-5-one
• CAS: 182957-13-7
• 化学式: C₁₂H₁₂ClNOS
• 分子量: 253.752
• InChiKey: VEGSAUDLLSXLHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7a-(4-Chlorophenyl)tetrahydropyrrolo[2,1-b][1,3]thiazol-5(6H)-one 在 sodium hydroxide 、 氨 、 triethyloxonium fluoroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (7aR)-7a-(4-chlorophenyl)-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]thiazol-5-one
  参考文献：
  名称：

  Synthesis of chiral tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones

  摘要：

  In our investigations of potential hypoglycemic agents,(2) it was desired to evaluate optically pure tetrahydropyrrolo[2,1-beta]thiazol-5-ones. A novel, practical synthesis of each enantiomer of 1 via formation, separation, and hydrolysis of diastereomeric amidine derivatives is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01962-5
• 作为产物：
  描述：

  3-(4-氯苯甲酰)丙酸 、 半胱胺盐酸盐 在 sodium hydroxide 、 对甲苯磺酸 作用下， 生成 7a-(4-Chlorophenyl)tetrahydropyrrolo[2,1-b][1,3]thiazol-5(6H)-one
  参考文献：
  名称：

  Substituted Tetrahydropyrrolo[2,1-b]oxazol-5(6H)-ones and Tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones as Hypoglycemic Agents

  摘要：

  A series of substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-one and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones was synthesized from amino alcohols or amino thiols and keto acids. A pharmacological model based on the results obtained with these compounds led to the synthesis and evaluation of a series of isoxazoles and other monocyclic compounds. These were evaluated for their ability to enhance glucose utilization in cultured L6 myocytes. The in vivo hypoglycemic efficacy and potency of these compounds were evaluated in a model of type 2 diabetes mellitus (non-insulin-dependent diabetes mellitus), the ob/ob mouse. 25a(2S) (SDZ PGU 693) was selected for further pharmacological studies.

  DOI：

  10.1021/jm9803121

文献信息

• Synthesis and Anticonvulsant Activity of Some 1,2,3,3<i>a</i>-Tetrahydropyrrolo[2,1-<i>b</i>]-benzothiazol-, -thiazol-or -oxazol−1−ones in Rodents
  作者：Giuseppe Trapani、Massimo Franco、Andrea Latrofa、Angelo Carotti、Saverio Cellamare、Mariangela Serra、Cristina A Ghiani、Graziella Tuligi、Giovanni Biggio、Gaetano Liso

  DOI：10.1111/j.2042-7158.1996.tb03984.x

  日期：2011.4.12

  To identify more potent anticonvulsant agents and to gain insights into the structural properties determining the potency of a new class of anticonvulsants, some 3a-substituted tetrahydropyrrolo[2,1-b]benzothiazol-1-ones (1a-d) and the thiazole and oxazole analogues (2a-c and 3a-c, respectively) have been synthesized and tested for anticonvulsant activity against isoniazid-induced seizures in rodents

  为了确定更有效的抗惊厥药，并深入了解确定新型抗惊厥药效能的结构性质，一些3a取代的四氢吡咯并[2,1-b]苯并噻唑-1-酮（1a-d）和噻唑和已合成恶唑类似物（分别为2a-c和3a-c），并测试了其对啮齿动物中异烟肼诱发的癫痫发作的抗惊厥活性。活性更强的化合物2a在小鼠和大鼠中的中位有效剂量（ED50，ip）分别为24.3 mg kg-1和15.9 mg kg-1，经过更广泛的研究，发现其增强了地西epa的作用。在化合物1-3的抗惊厥活性和亲脂性分子之间没有观察到明显的相关性。分子模型研究证明了抗癫痫药物苯巴比妥和化合物1-3之间的结构相似性，并用于推导初步的结构活性关系。结果表明2a作为抗惊厥药是有吸引力的候选药物，值得进一步研究，可能有助于其他抗惊厥药的设计。
• Synthesis of chiral tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones
  作者：Thomas D. Aicher、Douglas C. Knorr、Howard C. Smith

  DOI：10.1016/s0040-4039(98)01962-5

  日期：1998.11

  In our investigations of potential hypoglycemic agents,(2) it was desired to evaluate optically pure tetrahydropyrrolo[2,1-beta]thiazol-5-ones. A novel, practical synthesis of each enantiomer of 1 via formation, separation, and hydrolysis of diastereomeric amidine derivatives is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Substituted Tetrahydropyrrolo[2,1-<i>b</i>]oxazol-5(6<i>H</i>)-ones and Tetrahydropyrrolo[2,1-<i>b</i>]thiazol-5(6<i>H</i>)-ones as Hypoglycemic Agents
  作者：Thomas D. Aicher、Bork Balkan、Philip A. Bell、Leonard J. Brand、S. H. Cheon、Rhonda O. Deems、Jay B. Fell、William S. Fillers、James D. Fraser、Jiaping Gao、Douglas C. Knorr、Gerald G. Kahle、Christina L. Leone、Jeffrey Nadelson、Ronald Simpson、Howard C. Smith

  DOI：10.1021/jm9803121

  日期：1998.11.1

  A series of substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-one and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones was synthesized from amino alcohols or amino thiols and keto acids. A pharmacological model based on the results obtained with these compounds led to the synthesis and evaluation of a series of isoxazoles and other monocyclic compounds. These were evaluated for their ability to enhance glucose utilization in cultured L6 myocytes. The in vivo hypoglycemic efficacy and potency of these compounds were evaluated in a model of type 2 diabetes mellitus (non-insulin-dependent diabetes mellitus), the ob/ob mouse. 25a(2S) (SDZ PGU 693) was selected for further pharmacological studies.