1,4-dihydro-4-(3-aminophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid,dimethyl ester | 21835-63-2

• 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-aminophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid,dimethyl ester
• 英文别名: 4-(3-amino-phenyl)-2,6-dimethyl-3,5-bis(methoxycarbonyl)-1,4-dihydropyridine；4-(3-amino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid dimethyl ester；4-(3-Amino-phenyl)-2,6-dimethyl-1,4-dihydro-pyridin-3,5-dicarbonsaeure-dimethylester；4-(3-Aminophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylic acid, dimethyl ester；dimethyl 4-(3-aminophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 21835-63-2
• 化学式: C₁₇H₂₀N₂O₄
• 分子量: 316.357
• InChiKey: ORQGFSYSENCJLL-UHFFFAOYSA-N

物化性质

• 沸点：
  478.9±45.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  90.6
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4-dihydro-4-(3-aminophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid,dimethyl ester 以 四氢呋喃 、 甲苯 为溶剂， 反应 48.5h， 生成 1,4-dihydro-4-(3-isocyanatophenyl)-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：

  间硝基苯甲醛 在 palladium 10% on activated carbon 、 氨 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 15.0h， 生成 1,4-dihydro-4-(3-aminophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid,dimethyl ester
  参考文献：
  名称：

  新型同型喜树碱-二氢吡啶衍生物作为强拓扑异构酶I抑制剂的合成及药理评价

  摘要：

  同型喜树碱（hCPT）代表了针对DNA拓扑异构酶I的新一代抗肿瘤药物。与传统的六种抗肿瘤药物相比，表征hCPT的扩展的七元内酯E环增强了药物的血浆稳定性并增强了对拓扑异构酶I（Topo I）的抑制作用。成员的CPT。为了改善hCP的抗肿瘤活性，基于将7-甲酰基高喜树碱与不同的二氢吡啶衍生物偶联的合成路线，设计并合成了与二氢吡啶衍生物缀合的一系列新颖的hCPT衍生物。大多数合成的化合物对肿瘤细胞系A549，MDA-MB-435和HCT116表现出良好的细胞毒活性。此外，这类化合物显示出与CPT相当或更高的Topo I抑制活性。

  DOI：

  10.1071/ch11091

文献信息

• 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 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: 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。
• The synthesis of some dialkyl 4-(3-substituted amino)phenyl-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylates
  作者：Igor Simonič、Branko Stanovnik

  DOI：10.1002/jhet.5570340614

  日期：1997.11

  Dialkyl 4-(3-aminophenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylates 1 were transformed into alkyl 4-(3-(((2-benzoylamino-2-methoxycarbonyl)ethenyl)amino)phenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylates 4 and with 2,2-disubstituted-1-dimethylaminoethenes 7 into dimethyl 4-(3-(((2,2-diacyl- or 2-acyl-2-alkoxycarbonyl)ethenyl)amino)phenyl)-1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylates

  将4-（3-氨基苯基）-1,4-二氢-2,6-二甲基吡啶-3,5-二羧酸二烷基酯1转化为烷基4-（3-（（（（2-苯甲酰基氨基-2-甲氧基羰基）乙烯基）氨基）苯基）-1,4-二氢-2,6-二甲基吡啶-3,5-二羧酸酯4和2,2-二取代-1-二甲基氨基乙烯7变成二甲基4-（3-（（（2,2-二酰基或2-酰基-2-烷氧基羰基）乙烯基）氨基）苯基）-1,4-二氢-2,6-二甲基吡啶-3,5-二羧酸酯8及其乙基甲基类似物9。