1,4-dihydro-4-[3-[isothiocyanato]phenyl]-2,6-dimethyl-3,5-pyridinedicarboxylic acid dimethyl ester | 86880-84-4

• 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: 1,4-dihydro-4-[3-[isothiocyanato]phenyl]-2,6-dimethyl-3,5-pyridinedicarboxylic acid dimethyl ester
• CAS: 86880-84-4
• 化学式: C₁₈H₁₈N₂O₄S
• 分子量: 358.418
• InChiKey: AEPYEJIRQFAKHA-UHFFFAOYSA-N

物化性质

• 熔点：
  163-166 °C
• 沸点：
  508.2±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  76.99
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1,4-dihydro-4-[3-[isothiocyanato]phenyl]-2,6-dimethyl-3,5-pyridinedicarboxylic acid dimethyl ester 在 sodium ethanolate 、 mercury dichloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 1.5h， 生成 1,4-dihydro-4-[3-[[3-[4-(3-methoxyphenyl)-1-piperidinyl]propylamino](cyanoimino)methyl]aminophenyl]-2,6-dimethyl-3,5-pyridinedicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Dihydropyridine neuropeptide Y Y 1 receptor antagonists 2

  摘要：

  Structure-activity studies around the urea linkage in BMS-193885 (4a) identified the cyanoguanidine moiety as an effective urea replacement in a series of dihydropyridine NPY Y-1 receptor antagonists. In comparison to urea 4a (K-i = 3.3 nM), cyanoguanidine 20 (BMS-205749) displayed similar binding potency at the Y-1 receptor (K-i = 5.1 nM) and full functional antagonism (K-b = 2.6 nM) in SK-N-MC cells. Cyanoguanidine 20 also demonstrated improved permeability properties in Caco-2 cells in comparison to urea 4a (43 vs 19 nm/s). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.016
• 作为产物：
  描述：

  1,4-dihydro-4-(3-aminophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid,dimethyl ester 、 N,N'-硫羰基二咪唑 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以75%的产率得到1,4-dihydro-4-[3-[isothiocyanato]phenyl]-2,6-dimethyl-3,5-pyridinedicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Dihydropyridine neuropeptide Y Y 1 receptor antagonists 2

  摘要：

  Structure-activity studies around the urea linkage in BMS-193885 (4a) identified the cyanoguanidine moiety as an effective urea replacement in a series of dihydropyridine NPY Y-1 receptor antagonists. In comparison to urea 4a (K-i = 3.3 nM), cyanoguanidine 20 (BMS-205749) displayed similar binding potency at the Y-1 receptor (K-i = 5.1 nM) and full functional antagonism (K-b = 2.6 nM) in SK-N-MC cells. Cyanoguanidine 20 also demonstrated improved permeability properties in Caco-2 cells in comparison to urea 4a (43 vs 19 nm/s). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.016