5-O-benzyl 3-O-(2-cyanoethyl) 4-(1,3-benzodioxol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate | 210829-70-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-O-benzyl 3-O-(2-cyanoethyl) 4-(1,3-benzodioxol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 210829-70-2
• 化学式: C₂₆H₂₄N₂O₆
• 分子量: 460.486
• InChiKey: GCEQPPRKRCMBJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-O-benzyl 3-O-(2-cyanoethyl) 4-(1,3-benzodioxol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 甲酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.25h， 生成 2-Cyanoethyl 4-(1,3-benzodioxol-5-yl)-5-[3-(4,4-diphenylpiperidin-1-yl)propylcarbamoyl]-2,6-dimethyl-1,4-dihydropyridine-3-carboxylate
  参考文献：
  名称：

  Identification of a Dihydropyridine as a Potent α_1a Adrenoceptor-Selective Antagonist That Inhibits Phenylephrine-Induced Contraction of the Human Prostate

  摘要：

  A number of novel dihydropyridine derivatives based upon 1,4-dihydro-3-(methoxycarbonyl)-2,6-dimethyl-4-(4-nitrophenyl)-5-((3-(4, diphenylpiperdin-1-yl)propyl)aminocarbonyl)pyridine (4) have been synthesized and tested at cloned human a adrenoceptors as well as the rat L-type calcium channel. Within this compound series, 5-(aminocarbonyl)-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)- 3-((3-(4,4-diphenylpiperidin-1-yl)propyl)aminocarbonyl)pyridine (19) displayed good binding affinity and selectivity for the alpha(1a) adrenoceptor (pK(i) = 8.73) and potently inhibited (pA(2) = 9.23) phenylephrine-induced contraction of the human prostate.

  DOI：

  10.1021/jm980077m
• 作为产物：
  描述：

  乙酰丙酮苄酯 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 、 异丙醇 为溶剂， 反应 72.0h， 生成 5-O-benzyl 3-O-(2-cyanoethyl) 4-(1,3-benzodioxol-5-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Identification of a Dihydropyridine as a Potent α_1a Adrenoceptor-Selective Antagonist That Inhibits Phenylephrine-Induced Contraction of the Human Prostate

  摘要：

  A number of novel dihydropyridine derivatives based upon 1,4-dihydro-3-(methoxycarbonyl)-2,6-dimethyl-4-(4-nitrophenyl)-5-((3-(4, diphenylpiperdin-1-yl)propyl)aminocarbonyl)pyridine (4) have been synthesized and tested at cloned human a adrenoceptors as well as the rat L-type calcium channel. Within this compound series, 5-(aminocarbonyl)-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)- 3-((3-(4,4-diphenylpiperidin-1-yl)propyl)aminocarbonyl)pyridine (19) displayed good binding affinity and selectivity for the alpha(1a) adrenoceptor (pK(i) = 8.73) and potently inhibited (pA(2) = 9.23) phenylephrine-induced contraction of the human prostate.

  DOI：

  10.1021/jm980077m

文献信息

• Identification of a Dihydropyridine as a Potent α_1a Adrenoceptor-Selective Antagonist That Inhibits Phenylephrine-Induced Contraction of the Human Prostate
  作者：Wai C. Wong、George Chiu、John M. Wetzel、Mohammad R. Marzabadi、Dhanapalan Nagarathnam、Diana Wang、James Fang、Shou Wu Miao、Xingfang Hong、Carlos Forray、Pierre J.-J. Vaysse、Theresa A. Branchek、Charles Gluchowski、Rui Tang、Herbert Lepor

  DOI：10.1021/jm980077m

  日期：1998.7.1

  A number of novel dihydropyridine derivatives based upon 1,4-dihydro-3-(methoxycarbonyl)-2,6-dimethyl-4-(4-nitrophenyl)-5-((3-(4, diphenylpiperdin-1-yl)propyl)aminocarbonyl)pyridine (4) have been synthesized and tested at cloned human a adrenoceptors as well as the rat L-type calcium channel. Within this compound series, 5-(aminocarbonyl)-1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)- 3-((3-(4,4-diphenylpiperidin-1-yl)propyl)aminocarbonyl)pyridine (19) displayed good binding affinity and selectivity for the alpha(1a) adrenoceptor (pK(i) = 8.73) and potently inhibited (pA(2) = 9.23) phenylephrine-induced contraction of the human prostate.