4-(3-{3-[4-(3-Methoxy-phenyl)-piperidin-1-yl]-propoxycarbonylamino}-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(3-{3-[4-(3-Methoxy-phenyl)-piperidin-1-yl]-propoxycarbonylamino}-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 4-[3-[3-[4-(3-methoxyphenyl)piperidin-1-yl]propoxycarbonylamino]phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• 化学式: C₃₃H₄₁N₃O₇
• 分子量: 591.704
• InChiKey: CXRFWSIJKODLFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1,4-dihydro-4-(3-aminophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid,dimethyl ester 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 50.5h， 生成 4-(3-{3-[4-(3-Methoxy-phenyl)-piperidin-1-yl]-propoxycarbonylamino}-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic 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

文献信息

• Dihydropyridine NPY antagonists: piperidine derivatives
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0747357A2

  公开（公告）日：1996-12-11

  A series of non-peptidergic antagonists of NPY have been synthesized and are comprised of piperidine and tetrahydropyridine derivatives of 4-phenyl-1,4-dihydropyridines of Formula I. As antagonists of NPY-induced feeding behavior, these compounds are expected to act as effective anorexiant agents in promoting weight loss and treating eating disorders.

  一系列 NPY 非肽能拮抗剂已经合成，它们由式 I 的 4-苯基-1,4-二氢吡啶的哌啶和四氢吡啶衍生物组成。 作为 NPY 诱导的摄食行为的拮抗剂，这些化合物有望成为促进减肥和治疗饮食失调的有效厌食剂。
• Dihydropyridine neuropeptide Y Y 1 receptor antagonists 2
  作者：Graham S Poindexter、Marc A Bruce、J.Guy Breitenbucher、Mendi A Higgins、S.-Y Sit、Jeffrey L Romine、Scott W Martin、Sally A Ward、Rachel T McGovern、Wendy Clarke、John Russell、Ildiko Antal-Zimanyi

  DOI：10.1016/j.bmc.2003.10.016

  日期：2004.1

  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.