3-(3-(3-(thien-2-yl)-1-propylthio)-1,2,5-thiadiazol-4-yl)pyridine | 165116-44-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(3-(3-(thien-2-yl)-1-propylthio)-1,2,5-thiadiazol-4-yl)pyridine
• 英文别名: 3-(3-(3-(2-thienyl)-1-propylthio)-1,2,5-thiadiazol-4-yl)pyridine；3-(3-(3-(2-Thienyl)-1-propylthio)-1,2,5-thiadiazol-4-yl) pyridine；3-pyridin-3-yl-4-(3-thiophen-2-ylpropylsulfanyl)-1,2,5-thiadiazole
• CAS: 165116-44-9
• 化学式: C₁₄H₁₃N₃S₃
• 分子量: 319.475
• InChiKey: LQKYMUZNUCKYKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(3-(3-(thien-2-yl)-1-propylthio)-1,2,5-thiadiazol-4-yl)pyridine 在 sodium tetrahydroborate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 16.5h， 生成 3-(3-(3-(2-Thienyl)-1-propylthio)-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydro-1-methylpyridine
  参考文献：
  名称：

  Muscarinic Analgesics with Potent and Selective Effects on the Gastrointestinal Tract:  Potential Application for the Treatment of Irritable Bowel Syndrome

  摘要：

  Irritable bowel syndrome (IBS) is a pathopysiolocal condition characterized by abnormal bowel habits that are frequently accompanied by abdominal pain. Current therapy based on reducing high-amplitude GI contractions with nonselective muscarinic antagonists is limited in efficacy due to typical muscarinic side effects and provides no pain relief. We have previously found potent antinociceptive agents acting through muscarinic receptors. In the present work, new 1,2,5-thiadiazole-based structures with muscarinic activity have been evaluated both for activity as analgesics in the mouse withing assay and for activity in normalizing spontaneous cluster contractions in ferret jejunum as a model of IBS in humans. (5R,6R)-exo-6-[4-[(4,4,4-Trifluorobutyl)thio]-1,2,5-thiadiazol-3-yl]-1-azabicyclo[3.2.1]octane (35, LY316108/NNC11-2192) was found to offer an exceptional profile combining analgesic potency in mouse writhing (ED(50) = 0.1 mg/kg) along with potency for normalization of GI motility (ED(50) = 0.17 mg/kg). This combination of GI and analgesic potency suggests 35 as an excellent candidate for evaluation as a potential treatment of IBS.

  DOI：

  10.1021/jm9602470
• 作为产物：
  描述：

  3-氯-4-(吡啶-3-基)-1,2,5-噻二唑 在 sodium hydrogensulfide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 3-(3-(3-(thien-2-yl)-1-propylthio)-1,2,5-thiadiazol-4-yl)pyridine
  参考文献：
  名称：

  Muscarinic Analgesics with Potent and Selective Effects on the Gastrointestinal Tract:  Potential Application for the Treatment of Irritable Bowel Syndrome

  摘要：

  Irritable bowel syndrome (IBS) is a pathopysiolocal condition characterized by abnormal bowel habits that are frequently accompanied by abdominal pain. Current therapy based on reducing high-amplitude GI contractions with nonselective muscarinic antagonists is limited in efficacy due to typical muscarinic side effects and provides no pain relief. We have previously found potent antinociceptive agents acting through muscarinic receptors. In the present work, new 1,2,5-thiadiazole-based structures with muscarinic activity have been evaluated both for activity as analgesics in the mouse withing assay and for activity in normalizing spontaneous cluster contractions in ferret jejunum as a model of IBS in humans. (5R,6R)-exo-6-[4-[(4,4,4-Trifluorobutyl)thio]-1,2,5-thiadiazol-3-yl]-1-azabicyclo[3.2.1]octane (35, LY316108/NNC11-2192) was found to offer an exceptional profile combining analgesic potency in mouse writhing (ED(50) = 0.1 mg/kg) along with potency for normalization of GI motility (ED(50) = 0.17 mg/kg). This combination of GI and analgesic potency suggests 35 as an excellent candidate for evaluation as a potential treatment of IBS.

  DOI：

  10.1021/jm9602470

文献信息

• Method of treating schizophrenia
  申请人：Novo Nordisk A/S

  公开号：US05750541A1

  公开（公告）日：1998-05-12

  The present invention relates to a novel method for treating a mammal suffering from or susceptible to schizophrenia and schizophreniform diseases by administering thiadiazole or oxadiazole compounds.

  本发明涉及一种通过给予噻二唑或氧二唑化合物治疗患有或易患精神分裂症和分裂形障碍的哺乳动物的新方法。
• Method of treating gastrointestinal motility disorders
  申请人：Novo Nordisk A/S

  公开号：US05545638A1

  公开（公告）日：1996-08-13

  The present invention relates to a novel method for treating a mammal suffering from gastrointestinal motility disorders.

  本发明涉及一种治疗患有胃肠蠕动障碍的哺乳动物的新方法。
• Heterocyclic compounds
  申请人：Novo Nordisk A/S

  公开号：US05376668A1

  公开（公告）日：1994-12-27

  The present invention relates to therapeutically active azacyclic compounds, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful as stimulants of the cognitive function of the forebrain and hippocampus of mammals and especially in the treatment of Alzheimer's disease, severe painful conditions and glaucoma.

  本发明涉及治疗活性的杂环化合物，一种制备这些化合物的方法以及包含这些化合物的药物组合物。这些新颖的化合物可用作哺乳动物前脑和海马体认知功能的刺激剂，特别适用于治疗阿尔茨海默病、严重疼痛症状和青光眼。
• Heterocyclic compounds and their preparation and use
  申请人：Novo Nordisk A/S

  公开号：US05658932A1

  公开（公告）日：1997-08-19

  The present invention relates to therapeutically active azacyclic compounds, a method of preparing the same and to pharmaceutical compositions comprising the compounds. The novel compounds are useful as stimulants of the cognitive function of the forebrain and hippocampus of mammals and especially in the treatment of Alzheimer's disease, severe painful conditions and glaucoma.

  本发明涉及治疗活性的氮杂环化合物，其制备方法以及包含这些化合物的制药组合物。这些新型化合物可用作哺乳动物前脑和海马的认知功能刺激剂，特别适用于治疗阿尔茨海默病、严重疼痛症状和青光眼。
• Treatment of Alzheimer's disease using azacyclic compounds
  申请人：Novo Nordisk A/S

  公开号：US05559136A1

  公开（公告）日：1996-09-24

  The present invention relates to therapeutically active azacyclic compounds. The novel compounds are useful as stimulants of the cognitive function of the forebrain and hippocampus of mammals and especially in the treatment of Alzheimer's disease, severe painful conditions and glaucoma.

  本发明涉及治疗活性的杂环氮化合物。这些新型化合物可用作哺乳动物前脑和海马的认知功能刺激剂，特别是在治疗阿尔茨海默病、严重疼痛和青光眼方面有用。