2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester | 92130-26-2

• 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: 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester
• 英文别名: methyl 2-chloroethyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-pyridine-3,5-dicarboxylate；2-Chloroethyl methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate；5-O-(2-chloroethyl) 3-O-methyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 92130-26-2
• 化学式: C₁₈H₁₉ClN₂O₆
• 分子量: 394.812
• InChiKey: JVIPBKGLWYAXGE-UHFFFAOYSA-N

物化性质

• 沸点：
  528.0±50.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester 在 silver nitrate 作用下， 以 乙腈 为溶剂， 以40%的产率得到methyl 2-nitro-oxyethyl 1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Certain nitratoalkyl ester dihydropyridines having antihypertensive

  摘要：

  式为##STR1##的二氢吡啶，其中R为芳基或杂环基，R.sup.1、R.sup.2和R.sup.3分别为氢或不同的有机基团，Y为氧，或者选择性地取代的--NH--，Z为--O--NO.sub.2或--O--NO，X为--COR.sup.4，--COOR.sup.5或--CO--Y--A--Z，R.sup.4为烷基，苯基，苄基或氨基基团，而R.sup.5为有机基团，或其药学上可接受的酸盐加成物，表现出循环活性，例如它们可用作降压剂，外周和脑血管扩张剂以及冠状动脉治疗药物。

  公开号：

  US04565824A1
• 作为产物：
  描述：

  β-氨基巴豆酸甲酯 、 2-[1-(2-Nitro-phenyl)-meth-(Z)-ylidene]-3-oxo-butyric acid 2-chloro-ethyl ester 以 异丙醇 为溶剂， 反应 3.0h， 以38%的产率得到2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-chloroethyl)ester-5-methyl ester
  参考文献：
  名称：

  Asymmetric N-(3,3-diphenylpropyl)aminoalkyl esters of 4-aryl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acids with antihypertensive activity

  摘要：

  A series of asymmetric 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates characterized by the presence of a 3,3-diphenyl-propylamino moiety in one of the ester groups were synthesized. They exhibited remarkable antihypertensive activity in spontaneously hypertensive rats as well as affinity for the 1,4-dihydropyridines binding site labelled by H-3-nitrendipine in the calcium channel. Introduction of this bulky and lipophilic amine confers to the whole series an elevated level of antihypertensive activity and a long duration of action, a structure-dependent modulation of the activity being found only in the subset characterized by the presence of a branched propylene bridge between the ester and the amino groups. The presence of the amino group is essential for oral activity. Out of this series, compound 9u (Rec 15/2375-lercanidipine) was selected for clinical development and obtained marketing authorization as an antihypertensive in several countries. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80015-9

文献信息

• 1,4-dihydropyridine derivatives, and pharmaceutical compositions
  申请人：Nisshin Flour Milling Co., Ltd.

  公开号：US04757071A1

  公开（公告）日：1988-07-12

  2,6-Dimethyl-4-(2- or 3-substituted phenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diesters, having vasodilating and blood pressure lowering effects, in the ester moiety at the 3-position of which a heterocyclic group is linked to an alkylene group through an ester bond (carbonyloxy group). The diesters are used for treatment of cardiac diseases, cerebrovascular diseases and hypertension.

  2,6-二甲基-4-(2-或3-取代苯基)-1,4-二氢吡啶-3,5-二羧酸二酯具有扩张血管和降低血压的作用，在其酯基中，异环群通过酯键（羰氧基团）连接到烷基上的3-位。这些二酯用于治疗心脏疾病、脑血管疾病和高血压。
• Asymmetrical diesters of 1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylic acid
  申请人：RECORDATI S.A. CHEMICAL and PHARMACEUTICAL COMPANY

  公开号：EP0153016A2

  公开（公告）日：1985-08-28

  Compounds I (Ph = phenyl; Ar = 2 - nitrophenyl, 3-nitrophenyl, 2,3-dichlorphenyl or benzofurazan-4-yl; A = C2 - C6 alkylene; R = C1 - C6 alkyl optionally C1 - C6 alkoxy monosubstituted; R1 = H, OH or C1- C4 alkyl; R2 = H or CH3) have antihypertensive activity and are effective against coronary heart diseases. They are prepared starting from the aldehyde ArCHO and esters of acetoacetic acid and 3-amino-crotonic acid. Pharmaceutical preparations containing them are also described.

  化合物 I（Ph =苯基；Ar = 2-硝基苯基、3-硝基苯基、2,3-二氯苯基或苯并呋咱-4-基；A = C2 - C6 亚烷基；R = C1 - C6 烷基，可选 C1 - C6 烷氧基单取代；R1 = H、OH 或 C1 - C4 烷基；R2 = H 或 CH3）具有抗高血压活性，对冠心病有效。 它们是由醛 ArCHO 以及乙酰乙酸酯和 3-氨基巴豆酸酯制备而成。 此外，还介绍了含有这些化合物的药物制剂。
• Process for the preparation of 1,4-dihydropyridine derivatives
  申请人：NISSHIN FLOUR MILLING CO., LTD.

  公开号：EP0371492B1

  公开（公告）日：1995-06-21
• SATOH, HIROAKI;KOYAMA, HIROYASU;SUZUKI, YOSHIKUNI;SUGAI, TOSHIJI;WATANABE+
  作者：SATOH, HIROAKI、KOYAMA, HIROYASU、SUZUKI, YOSHIKUNI、SUGAI, TOSHIJI、WATANABE+

  DOI：——

  日期：——
• 1,4-Dihydropyridine derivatives, processes for their preparation and pharmaceutical compositions containing same
  申请人：NISSHIN FLOUR MILLING CO., LTD.

  公开号：EP0184841B1

  公开（公告）日：1992-11-11