2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 3-chloropropyl ester | 91116-19-7

• 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: 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 3-chloropropyl ester
• 英文别名: 3-Chloropropyl Methyl 1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate；1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinecarboxylic acid methyl ester 2-chloroethyl ester；(3-chloropropyl) methyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate；3-chloropropyl methyl 1,4dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate；5-O-(3-chloropropyl) 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 91116-19-7
• 化学式: C₁₉H₂₁ClN₂O₆
• 分子量: 408.839
• InChiKey: KZTKWAQYHLCYTD-UHFFFAOYSA-N

物化性质

• 熔点：
  125-130 °C(Solvent: Ethanol)
• 沸点：
  548.4±50.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 3-chloropropyl ester 生成 3-O-methyl 5-O-[3-[methyl-[2-(N-methylanilino)ethyl]amino]propyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  POINDEXTER, GRAHAM S.

  摘要：

  DOI：
• 作为产物：
  描述：

  β-氨基巴豆酸甲酯 、 3-chloropropyl 2-(3-nitrobenzyliden)acetoacetate 以 乙醇 为溶剂， 反应 6.0h， 以81%的产率得到2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid methyl ester 3-chloropropyl 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

• Dihydropyridin-3,5-dicarboxylates incorporating aryloxypropanolamine
  申请人：Bristol-Myers Company

  公开号：US04994476A1

  公开（公告）日：1991-02-19

  A series of compounds useful in treating cardiovascular disorders due to the combined expression of both .beta.-block and calcium-block activity by these agents. This useful combination of actions is effected by a novel combination of structural subunits forming these compounds. Essentially, .beta.-blocking aryloxypropanolamine moieties are attached via their aryl ring or amino nitrogen at one of the carboxylate groups of calcium-blocking 4-aryl-1,4-dihydropyridine-3,5-dicarboxylates. These compounds are prepared from new 4-aryl-1,4-dihydropyridine intermediate compounds.

  一系列化合物对治疗心血管疾病有用，因为这些药物通过结合表达β-阻滞和钙通道阻滞活性来发挥作用。这种有用的作用组合是通过形成这些化合物的结构亚单位的新组合来实现的。基本上，β-阻滞芳基氧丙胺基团通过它们的芳基环或氨基氮之一连接到钙通道阻滞的4-芳基-1,4-二氢吡啶-3,5-二羧酸酯的羧酸基团之一。这些化合物是从新的4-芳基-1,4-二氢吡啶中间体化合物制备的。
• Carbostyril derivative
  申请人：Otsuka Pharmaceutical Co., Ltd.

  公开号：US04564619A1

  公开（公告）日：1986-01-14

  Carbostyril derivative or a pharmaceutically acceptable acid addition salt thereof, having excellent platelate aggregation inhibitory effect, calcium antagonism, hypotensive effect and phosphodiesterase inhibitory effect are useful as prophylactic or treating agents for thrombosis, circulation improving agents for coronary blood flow such as coronary vasodilators, hypotensive agents and phosphodiesterase inhibitors. Furthermore, the carbostyril derivatives are weak in heart rate increasing activity and also in cardiac muscle contraction increasing activity, and the carbostyril derivatives are useful agents for curing and treating heart diseases such as cardiac angina and myocardial infarction caused by hypercoagulability of the platelets. Processes are disclosed for preparation of the carbostyril derivatives.

  羧基喹啉衍生物或其药用酸盐，具有出色的血小板聚集抑制作用、钙拮抗作用、降压作用和磷酸二酯酶抑制作用，可用作预防或治疗血栓症的药物、改善冠状动脉血流的循环药物，如冠状血管扩张剂、降压药物和磷酸二酯酶抑制剂。此外，羧基喹啉衍生物在增加心率活性和心肌收缩活性方面较弱，且对治疗由血小板高凝造成的心脏病如心绞痛和心肌梗死有用。公开了制备羧基喹啉衍生物的方法。
• Pharmaceutically useful dihydropyridinyldicarboxylate amides and esters
  申请人：Bristol-Myers Company

  公开号：US04755512A1

  公开（公告）日：1988-07-05

  A series of 1,4-dihydropyridin-3,5-yl dicarboxylic acid amides and esters incorporating an arylpiperazinylalkyl moiety have been prepared possessing the general formula ##STR1## wherein R.sup.4 is cycloalkyl, aryl or hetaryl, generally with electronwithdrawing substituents; R.sup.2 and R.sup.6 are lower alkyl, alkanol, alkoxyalkyl, or alkylaminoalkyl; R.sup.5 is R.sup.2 or arylpiperazinylalkyl; X is 0 or NH; Y is lower alkylene, alkoxyalkylene, alkylaminoalkylene; and Z is phenyl, substituted phenyl, pyridinyl, substituted pyridinyl, or pyrimidinyl. Compounds of this series demonstrate activity as calcium and alphaadrenergic blockers in in vitro testing and antihypertensive, antiischemic, and platelet function inhibiting actions in in vivo screens.

  已翻译完成： 一系列包含芳基哌嗪基烷基基团的1,4-二氢吡啶-3,5-二羧酸酰胺和酯已经合成，具有一般化学式##STR1## 其中R.sup.4为环烷基、芳基或杂芳基，通常带有电子吸引基团；R.sup.2和R.sup.6为较低的烷基、烷醇、烷氧基烷基或烷基氨基烷基；R.sup.5为R.sup.2或芳基哌嗪基烷基；X为0或NH；Y为较低的烷基、烷氧基烷基、烷基氨基烷基；Z为苯基、取代苯基、吡啶基、取代吡啶基或嘧啶基。该系列化合物在体外测试中表现出作为钙通道和α肾上腺素受体拮抗剂的活性，并且在体内筛选中显示出抗高血压、抗缺血和抑制血小板功能的作用。
• Dihydro-3,5-dicarboxylates
  申请人：Bristol-Myers Company

  公开号：US04814455A1

  公开（公告）日：1989-03-21

  A series of compounds of the 1,4-dihydropyridine class with a 3-carboxylate group linked to an alkyleneaminoalkylene heteroatom have been prepared possessing the general formula ##STR1## wherein R.sup.2, R.sup.5 and R.sup.6 are independently selected from lower (C.sub.1-4)alkyl, hydroxy-lower-alkylene, lower alkoxy-lower-alkylene, lower alkylamino-lower-alkylene or lower dialkyl-amino-lower-alkylene; R.sup.7 is selected from hydrogen, lower alkyl, phenyl-lower-alkylene, or phenylthio-lower-alkylene; n is the integer 2 or 3; X is a chemical bond, --O--, --S--, ##STR2## or --NR.sup.9 -- wherein R.sup.9 is hydrogen, lower alkyl, phenyl, or phenyl-lower-alkylene with the proviso that when X is a chemical bond, Z is a 3-indolyl ring; and Z is selected from the group consisting of phenyl substituted with 1 to 3 substituents independently chosen from among hydrogen, lower alkyl, or lower alkoxy, phenyl-lower-alkylene, or 3-indolyl. Compounds of this series possess calcium channel blocking properties, afford protection against ischemia and inhibit aggregation of blood platelets.

  一系列1,4-二氢吡啶类化合物已经制备，其具有通式##STR1##其中，R.sup.2、R.sup.5和R.sup.6分别从较低的（C.sub.1-4）烷基、羟基-较低烷基、较低烷氧基-较低烷基、较低烷基氨基-较低烷基或较低二烷基氨基-较低烷基中独立选择；R.sup.7从氢、较低烷基、苯-较低烷基或苯硫-较低烷基中选择；n为整数2或3；X为化学键、-O-、-S-、##STR2##或-NR.sup.9-，其中R.sup.9为氢、较低烷基、苯或苯-较低烷基，但当X为化学键时，Z为3-吲哚基环；Z从苯基被1至3个独立选择的取代基中选择，所述取代基为氢、较低烷基或较低烷氧基、苯-较低烷基或3-吲哚基。该系列化合物具有钙通道阻滞性能，可提供缺血保护并抑制血小板聚集。
• 3,5-Diacyl-4-aryl-1,4 dihydropyridine derivatives, their uses and
  申请人：Ciba-Geigy Corporation

  公开号：US04853393A1

  公开（公告）日：1989-08-01

  Compounds of the formula ##STR1## in which R represents a carbocyclic or heterocyclic aryl radical, R.sub.1 represents lower alkyl, one of the groups R.sub.2 and R.sub.3 represents lower alkyl and the other represents lower alkyl, cyano or amino, X represents oxygen or the group --NH--, and Alk represents lower alkylene which separates the group X from the ring nitrogen atom by at least two carbon atoms, Y represents the group --CHOH-- or --(C.dbd.O)--, and Ar.sub.1 represents a monocyclic aryl or heteroaryl radical, Ar.sub.1 being other than unsubstituted phenyl if R.sub.1, R.sub.2 and R.sub.3 each represents lower alkyl, X represents oxygen, Alk represents straight-chain alkylene having from 2 to 4 carbon atoms, Y represents the group --(C.dbd.O)-- and R has the meaning given, and salts thereof have cardiovascular, especially coronary-dilatory and antihypertensive properties.

  式为##STR1##的化合物，其中R代表碳环或杂环芳基基团，R.sub.1代表较低的烷基，R.sub.2和R.sub.3中的一个代表较低的烷基，另一个代表较低的烷基、氰基或氨基，X代表氧或--NH--基团，Alk代表较低的烷基，将基团X与环氮原子隔开至少两个碳原子，Y代表--CHOH--或--(C.dbd.O)--基团，Ar.sub.1代表单环芳基或杂环芳基基团，如果R.sub.1、R.sub.2和R.sub.3每个代表较低的烷基，X代表氧，Alk代表具有2至4个碳原子的直链烷基，Y代表--(C.dbd.O)--基团，R具有所给的含义，以及其盐具有心血管、特别是冠脉扩张和降压作用。