1,4-dihydro-2,6-dimethyl-4-[3-[methylamino]phenyl]-3,5-pyridinedicarboxylic acid dimethyl ester | 97804-84-7

• 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-2,6-dimethyl-4-[3-[methylamino]phenyl]-3,5-pyridinedicarboxylic acid dimethyl ester
• 英文别名: 1,4-Dihydro-2,6-dimethyl-4-[3-(methylamino)phenyl]-3,5-pyridinedicarboxylic acid, dimethyl ester；1,4-Dihydro-2,6-dimethyl-4-[3-(methylamino)phenyl]-3,5-pyridinedicarboxylic acid,dimethyl ester；dimethyl 2,6-dimethyl-4-[3-(methylamino)phenyl]-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 97804-84-7
• 化学式: C₁₈H₂₂N₂O₄
• 分子量: 330.384
• InChiKey: RONJIKRQBBHCPF-UHFFFAOYSA-N

物化性质

• 熔点：
  182-184 °C
• 沸点：
  480.5±45.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-dihydro-2,6-dimethyl-4-[3-[methylamino]phenyl]-3,5-pyridinedicarboxylic acid dimethyl ester 在 potassium carbonate 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成
  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-2,6-dimethyl-4-[3-[methyl(trifluoroacetyl)amino]phenyl]-3,5-pyridinedicarboxylic acid dimethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以86%的产率得到1,4-dihydro-2,6-dimethyl-4-[3-[methylamino]phenyl]-3,5-pyridinedicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Dihydropyridine NPY antagonists: cyanoguanidine derivatives

  摘要：

  一系列非肽类NPY拮抗剂已经合成，由式(I)的4-苯基-1,4-二氢吡啶的氰胍酸衍生物组成。作为NPY诱导的进食行为的拮抗剂，预计这些化合物将作为有效的压食剂药物，促进减重和治疗进食障碍。

  公开号：

  US06001836A1

文献信息

• Dihydropyridine NPY antagonists: cyanoguanidine derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US06001836A1

  公开（公告）日：1999-12-14

  A series of non-peptidergic antagonists of NPY have been synthesized and are comprised of cyanoguanidine derivatives of 4-phenyl-1,4-dihydropyridines of Formula (I). ##STR1## 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.

  一系列非肽类NPY拮抗剂已经合成，由式(I)的4-苯基-1,4-二氢吡啶的氰胍酸衍生物组成。作为NPY诱导的进食行为的拮抗剂，预计这些化合物将作为有效的压食剂药物，促进减重和治疗进食障碍。
• 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.