2-(3-Phenylpiperidin-1-yl)-5-(4-piperidin-1-ylpiperidin-1-yl)-1,3,4-thiadiazole | 1222994-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(3-Phenylpiperidin-1-yl)-5-(4-piperidin-1-ylpiperidin-1-yl)-1,3,4-thiadiazole
• CAS: 1222994-37-7
• 化学式: C₂₃H₃₃N₅S
• 分子量: 411.615
• InChiKey: UKXQJJDASUHIPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-苯基哌啶 、 2-bromo-5-(4-piperidinopiperidino)-1,3,4-thiadiazole 在 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 三氟甲苯 为溶剂， 反应 3.0h， 生成 2-(3-Phenylpiperidin-1-yl)-5-(4-piperidin-1-ylpiperidin-1-yl)-1,3,4-thiadiazole
  参考文献：
  名称：

  Discovery of a Potent Thiadiazole Class of Histamine H₃ Receptor Antagonist for the Treatment of Diabetes

  摘要：

  A series of novel 2-piperidinopiperidine thiadiazoles were synthesized and evaluated as new leads of histamine H-3 receptor antagonists. The 4-(5-([1,4'-bipiperidin]-1'-yl)-1,3,4-thiadiazol-2-yl)-2-(pyridin-2-yl)morpholine (5u) displayed excellent potency and ex vivo receptor occupancy. Compound 5u was also evaluated in vivo for antidiabetic efficacy in STZ diet-induced obesity type 2 diabetic mice for 2 or 12 days. Non-fasting glucose levels were significantly reduced as compared with vehicle-treated mice. In addition, 5u dose dependently blocked the increase of HbA(1c) after 12 days of treatment.

  DOI：

  10.1021/ml200250t

文献信息

• PYRROLIDINE, PIPERIDINE AND PIPERAZINE DERIVATIVES AND METHODS OF USE THEREOF
  申请人：Palani Anandan

  公开号：US20110224187A1

  公开（公告）日：2011-09-15

  The present invention relates to novel Pyrrolidine, Piperidine and Piperazine Derivatives, pharmaceutical compositions comprising the Pyrrolidine, Piperidine and Piperazine Derivatives and the use of these compounds for treating or preventing treating allergy, an allergy-induced airway response, congestion, a cardiovascular disease, an inflammatory disease, a gastrointestinal disorder, a neurological disorder, a metabolic disorder, obesity, an obesity-related disorder, diabetes, a diabetic complication, impaired glucose tolerance or impaired fasting glucose.
• Discovery of a Potent Thiadiazole Class of Histamine H₃ Receptor Antagonist for the Treatment of Diabetes
  作者：Ashwin U. Rao、Ning Shao、Robert G. Aslanian、Tin-Yau Chan、Sylvia J. Degrado、Li Wang、Brian McKittrick、Mary Senior、Robert E. West、Shirley M. Williams、Ren-Long Wu、Joyce Hwa、Bhuneshwari Patel、Shuqin Zheng、Christopher Sondey、Anandan Palani

  DOI：10.1021/ml200250t

  日期：2012.3.8

  A series of novel 2-piperidinopiperidine thiadiazoles were synthesized and evaluated as new leads of histamine H-3 receptor antagonists. The 4-(5-([1,4'-bipiperidin]-1'-yl)-1,3,4-thiadiazol-2-yl)-2-(pyridin-2-yl)morpholine (5u) displayed excellent potency and ex vivo receptor occupancy. Compound 5u was also evaluated in vivo for antidiabetic efficacy in STZ diet-induced obesity type 2 diabetic mice for 2 or 12 days. Non-fasting glucose levels were significantly reduced as compared with vehicle-treated mice. In addition, 5u dose dependently blocked the increase of HbA(1c) after 12 days of treatment.