S-propan-2-yl 3-aminobut-2-enethioate | 1088254-73-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: S-propan-2-yl 3-aminobut-2-enethioate
• CAS: 1088254-73-2
• 化学式: C₇H₁₃NOS
• 分子量: 159.252
• InChiKey: YYEYIXXMFJLPMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S-propan-2-yl 3-aminobut-2-enethioate 、 (2-氟苯甲酰)乙酸乙酯 、 丙醛 以 乙醇 为溶剂， 生成 Ethyl 4-ethyl-2-(2-fluorophenyl)-6-methyl-5-propan-2-ylsulfanylcarbonyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Structure–activity relationships of 1,4-dihydropyridines that act as enhancers of the vanilloid receptor 1 (TRPV1)

  摘要：

  Vanilloid agonists such as capsaicin activate ion flux through the TRPV1 channel, a heat- and ligand-gated cation channel that transduces painful chemical or thermal stimuli applied to peripheral nerve endings in skin or deep tissues. We have probed the SAR of a variety of 1,4-dihydropyridine (DHP) derivatives as novel 'enhancers' of TRPV1 activity by examining changes in capsaicin-induced elevations in Ca-45(2+)-uptake in either cells ectopically expressing TRPV1 or in cultured dorsal root ganglion (DRG) neurons. The enhancers increased the maximal capsaicin effect on Ca-45(2+)-uptake by typically 2- to 3-fold without producing an action when used alone. The DHP enhancers contained 6-aryl substitution and small alkyl groups at the 1 and 4 positions, and a 3-phenylalkylthioester was tolerated. Levels of free intracellular Ca2+, as measured by calcium imaging, were also increased in DRG neurons when exposed to the combination of capsaicin and the most efficacious enhancer 23 compared to capsaicin alone. Thus, DHPs can modulate TRPV1 channels in a positive fashion. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.08.048
• 作为产物：
  描述：

  β-Keto-thiobuttersaeure-S-isopropylester 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 生成 S-propan-2-yl 3-aminobut-2-enethioate
  参考文献：
  名称：

  Structure–activity relationships of 1,4-dihydropyridines that act as enhancers of the vanilloid receptor 1 (TRPV1)

  摘要：

  Vanilloid agonists such as capsaicin activate ion flux through the TRPV1 channel, a heat- and ligand-gated cation channel that transduces painful chemical or thermal stimuli applied to peripheral nerve endings in skin or deep tissues. We have probed the SAR of a variety of 1,4-dihydropyridine (DHP) derivatives as novel 'enhancers' of TRPV1 activity by examining changes in capsaicin-induced elevations in Ca-45(2+)-uptake in either cells ectopically expressing TRPV1 or in cultured dorsal root ganglion (DRG) neurons. The enhancers increased the maximal capsaicin effect on Ca-45(2+)-uptake by typically 2- to 3-fold without producing an action when used alone. The DHP enhancers contained 6-aryl substitution and small alkyl groups at the 1 and 4 positions, and a 3-phenylalkylthioester was tolerated. Levels of free intracellular Ca2+, as measured by calcium imaging, were also increased in DRG neurons when exposed to the combination of capsaicin and the most efficacious enhancer 23 compared to capsaicin alone. Thus, DHPs can modulate TRPV1 channels in a positive fashion. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.08.048