3-Pyridin-2-yl-3-thiophen-3-yl-propionic acid ethyl ester | 425392-72-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-Pyridin-2-yl-3-thiophen-3-yl-propionic acid ethyl ester
• 英文别名: Ethyl 3-pyridin-2-yl-3-thiophen-3-ylpropanoate
• CAS: 425392-72-9
• 化学式: C₁₄H₁₅NO₂S
• 分子量: 261.345
• InChiKey: JVSFTBRIHYWZPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Pyridin-2-yl-3-thiophen-3-yl-propionic acid ethyl ester 在 CHIRALCEL OD 、 三甲基铝 作用下， 以 正庚烷 、 二乙胺 、 异丙醇 、 甲苯 为溶剂， 反应 1.0h， 生成 (+)-2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-(thiophen-3-yl)ethyl]pyridine
  参考文献：
  名称：

  Imidazolines as efficacious glucose-dependent stimulators of insulin secretion

  摘要：

  Synthesis of a series of imidazolines with glucose dependent effects on insulin exocytosis from pancreatic P-cells is reported. Regioisomers and enantionters were found to exhibit marked differences in exocytotic effects as well as different activities on the K-ATP-channel- the (R (+)) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-2-ylethyl]pyridine (4a) and the (+) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-3-yiethyl]pyridine (4d) were found to give a significant increase in insulin release in contrast to Findings for their enantiomers-without influence on the K-ATP-channel. The (+) isomer (4a) showed glucose dependent insulin release from P-cells at concentrations above 2.5 mM and a marked glucose lowering effect in ob/ob mice as well as in fed but not in fasted rats. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00041-2
• 作为产物：
  描述：

  pyridin-2-yl(thiophen-3-yl)methanone 在 palladium on activated charcoal 氢气 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 55.0 ℃ 、137.9 kPa 条件下， 反应 72.0h， 生成 3-Pyridin-2-yl-3-thiophen-3-yl-propionic acid ethyl ester
  参考文献：
  名称：

  Imidazolines as efficacious glucose-dependent stimulators of insulin secretion

  摘要：

  Synthesis of a series of imidazolines with glucose dependent effects on insulin exocytosis from pancreatic P-cells is reported. Regioisomers and enantionters were found to exhibit marked differences in exocytotic effects as well as different activities on the K-ATP-channel- the (R (+)) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-2-ylethyl]pyridine (4a) and the (+) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-3-yiethyl]pyridine (4d) were found to give a significant increase in insulin release in contrast to Findings for their enantiomers-without influence on the K-ATP-channel. The (+) isomer (4a) showed glucose dependent insulin release from P-cells at concentrations above 2.5 mM and a marked glucose lowering effect in ob/ob mice as well as in fed but not in fasted rats. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00041-2

文献信息

• Oral hypoglycaemic agents
  申请人：——

  公开号：US20020132812A1

  公开（公告）日：2002-09-19

  Compounds of formula (I) which are optionally substituted 2-(&ohgr;,&ohgr;-diarylalkyl)-4,5-dihydro-1H-imidazoles and 2-(&ohgr;,&ohgr;-diarylalkyl)-1,4,5,6-tetrahydropyrimidines and salts thereof with inorganic and organic acids have interesting pharmacological properties. Thus, the compounds are useful in the treatment of type 2 diabetes.

  式(I)的化合物，它们是可选择取代的2-(&ohgr;，&ohgr;-二芳基烷基)-4,5-二氢-1H-咪唑和2-(&ohgr;，&ohgr;-二芳基烷基)-1,4,5,6-四氢嘧啶及其与无机和有机酸的盐具有有趣的药理特性。因此，这些化合物在治疗2型糖尿病方面是有用的。
• [EN] 1,3-DIAZAHETEROCYCLIC COMPOUNDS AND THEIR USE AS ORAL HYPOGLYCAEMIC AGENTS<br/>[FR] COMPOSES 1,3 DIAZHETEROCYCLIQUES ET UTILISATION DE CES DERNIERS COMME AGENTS HYPOGLYCEMIANTS
  申请人：NOVO NORDISK AS

  公开号：WO2002038559A1

  公开（公告）日：2002-05-16

  A compound of formula (I) wherein Y is selected from the ring systems (a), (b); R?1 and R2¿ are independently phenyl, naphthyl, thienyl, thiazolyl, imidazolyl, pyrazolyl, triazolyl, pyridyl, pyrimidyl, pyridazinyl, pyrazinyl, quinolyl, 3-4-dihydroquinolyl, 5,6,7,8-tetrahydroquinolyl, isoquinolyl, 3,4-dihydroisoquinolyl, 5,6,7,8-tetrahydroisoquinolyl, indolyl, benzo[b]thienyl, benzimidazozyl, 5,6,7,8-tetrahydroimidazo[1,5-a]pyridyl or benzthiazolyl each of which is optionally substituted. R?3 and R5¿ are independently hydrogen, C¿1-6? alkyl or halogen or when taken together R?3 and R5¿ form an additional bond between the carbon atoms which they are attached; R¿4? is hydrogen, C1-6alkyl, arylC1-6alkyl, C1-6-C(O)- or arylC1-6alkyl-C(O)-, X is -CR?18R19¿- wherein R?18 and R19¿ are independently hydrogen or C¿1-6?alkyl; n is 0, 1 or 2. Thus, the compounds are useful in the treatment of type 2 diabetes.
• Imidazolines as efficacious glucose-dependent stimulators of insulin secretion
  作者：P Jakobsen

  DOI：10.1016/s0223-5234(03)00041-2

  日期：2003.4

  Synthesis of a series of imidazolines with glucose dependent effects on insulin exocytosis from pancreatic P-cells is reported. Regioisomers and enantionters were found to exhibit marked differences in exocytotic effects as well as different activities on the K-ATP-channel- the (R (+)) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-2-ylethyl]pyridine (4a) and the (+) isomer of 2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophene-3-yiethyl]pyridine (4d) were found to give a significant increase in insulin release in contrast to Findings for their enantiomers-without influence on the K-ATP-channel. The (+) isomer (4a) showed glucose dependent insulin release from P-cells at concentrations above 2.5 mM and a marked glucose lowering effect in ob/ob mice as well as in fed but not in fasted rats. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.