1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid, n-butyl methyl ester

• 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-nitrophenyl)-3,5-pyridinedicarboxylic acid, n-butyl methyl ester
• 英文别名: 5-O-butyl 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 化学式: C₂₀H₂₄N₂O₆
• 分子量: 388.42
• InChiKey: ALGSDTURVYWVEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid, n-butyl methyl ester 在 铁粉 、 氯化铵 作用下， 以 甲醇 为溶剂， 生成 4-(3-Amino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-butyl ester 5-methyl ester
  参考文献：
  名称：

  Dihydropyridine Neuropeptide Y Y1 Receptor Antagonists

  摘要：

  Dihydropyridine 5a was found to be an inhibitor of neuropeptide Y-1 binding in a high throughput I-125-PYY screening assay. Structure-activity studies around certain portions of the dihydropyridine chemotype identified BMS-193885 (6e) as a potent and selective Y-1 receptor antagonist. In a forskolin-stimulated c-AMP production assay using CHO cells expressing the human Y-1 receptor, 6e demonstrated full functional antagonism (K-b = 4.5 nM). Compound 6e inhibited NPY-induced feeding in satiated rats when dosed at 3.0 and 10.0 mg/kg (ip), and also decreased spontaneous overnight food consumption in rats at doses of 10 and 20 mg/kg (ip). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00761-2
• 作为产物：
  描述：

  乙酰乙酸正丁酯 、 β-氨基巴豆酸甲酯 、 间硝基苯甲醛 在 SiO2 、 乙酸乙酯 作用下， 以 异丙醇 为溶剂， 反应 34.0h， 以to furnish the product in 49% yield as low melting, yellow solid的产率得到1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid, n-butyl methyl ester
  参考文献：
  名称：

  Dihydropyridine NPY antagonists: nitrogen heterocyclic derivatives

  摘要：

  一系列非肽类NPY拮抗剂已被合成，包括4-苯基-1,4-二氢吡啶的氮杂环衍生物，其化学式为(I)。作为NPY诱导的进食行为的拮抗剂，这些化合物预计将作为有效的厌食剂，促进减重和治疗进食障碍。

  公开号：

  US05554621A1

文献信息

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

  公开号：US05554621A1

  公开（公告）日：1996-09-10

  A series of non-peptidergic antagonists of NPY have been synthesized and are comprised of nitrogen heterocyclic 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Formula (I)的4-苯基-1,4-二氢吡啶的氮杂环衍生物组成。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，在促进减重和治疗进食障碍方面发挥作用。
• Dihydropyridine NPY antagonists: piperidine derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US05668151A1

  公开（公告）日：1997-09-16

  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. ##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Formula I的哌啶和四氢吡啶衍生物以及4-苯基-1,4-二氢吡啶组成。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，促进减重和治疗进食障碍。
• Dihydropyridine npy antagonists: piperazine derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US05635503A1

  公开（公告）日：1997-06-03

  A series of non-peptidergic antagonists of NPY have been synthesized and are comprised of piperazine and homopiperazine 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-1,4-二氢吡啶的哌嗪和同哌嗪衍生物组成。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 Y1 Receptor Antagonists
  作者：Graham S. Poindexter、Marc A. Bruce、Karen L. LeBoulluec、Ivo Monkovic、Scott W. Martin、Eric M. Parker、Larry G. Iben、Rachel T. McGovern、Astrid A. Ortiz、Jennifer A. Stanley、Gail K. Mattson、Michael Kozlowski、Meredith Arcuri、Ildiko Antal-Zimanyi

  DOI：10.1016/s0960-894x(01)00761-2

  日期：2002.2

  Dihydropyridine 5a was found to be an inhibitor of neuropeptide Y-1 binding in a high throughput I-125-PYY screening assay. Structure-activity studies around certain portions of the dihydropyridine chemotype identified BMS-193885 (6e) as a potent and selective Y-1 receptor antagonist. In a forskolin-stimulated c-AMP production assay using CHO cells expressing the human Y-1 receptor, 6e demonstrated full functional antagonism (K-b = 4.5 nM). Compound 6e inhibited NPY-induced feeding in satiated rats when dosed at 3.0 and 10.0 mg/kg (ip), and also decreased spontaneous overnight food consumption in rats at doses of 10 and 20 mg/kg (ip). (C) 2002 Elsevier Science Ltd. All rights reserved.