(-)-(S)-2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-(thiophen-2-yl)ethyl]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (-)-(S)-2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-(thiophen-2-yl)ethyl]pyridine
• 英文别名: 2-[(1S)-2-(4,5-dihydro-1H-imidazol-2-yl)-1-thiophen-2-ylethyl]pyridine
• 化学式: C₁₄H₁₅N₃S
• 分子量: 257.359
• InChiKey: AZHGJEKRUSUJPB-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氰基吡啶 在 palladium on activated charcoal 正丁基锂 、 CHIRALCEL OD 、 potassium tert-butylate 、 氢气 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 正庚烷 、 二乙胺 、 异丙醇 为溶剂， -78.0~160.0 ℃ 、550.0 kPa 条件下， 反应 105.0h， 生成 (-)-(S)-2-[2-(4,5-dihydro-1H-imidazol-2-yl)-1-(thiophen-2-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

文献信息

• 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.