3-methyl 5-{2-[4-(2-tolyl)-1-piperazinyl]-ethyl} (+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate | 90096-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 3-methyl 5-{2-[4-(2-tolyl)-1-piperazinyl]-ethyl} (+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate
• 英文别名: methyl 2-[4-(2-methylphenyl)-1-piperazinyl]ethyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate；3-O-methyl 5-O-[2-[4-(2-methylphenyl)piperazin-1-yl]ethyl] 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 90096-00-7
• 化学式: C₂₉H₃₄N₄O₆
• 分子量: 534.612
• InChiKey: OXCYMRNWHJHIHA-UHFFFAOYSA-N

物化性质

• 沸点：
  678.6±55.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-(2-羟基乙基)-4-(O-甲苯基)哌嗪 以 异丙醇 为溶剂， 生成 3-methyl 5-{2-[4-(2-tolyl)-1-piperazinyl]-ethyl} (+)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  具有强效和持久降压作用的新型1,4-二氢吡啶衍生物。

  摘要：

  在寻找对心血管系统具有长效作用的新的1,4-二氢吡啶衍生物时，合成并测试了一系列在哌嗪环的4-氮上带有亲脂性取代基的吡哆酯类化合物I对自发性高血压大鼠(SHR)的降压效果。化合物I，尤其是那些在哌嗪环上有二苯甲基部分的化合物，显示出极其强大且长效的降压特性。还制备了与I相关的类似物，并讨论了结构-活性关系。

  DOI：

  10.1248/cpb.33.3787

文献信息

• Dihydropyridine derivatives, their production and use
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0094159A1

  公开（公告）日：1983-11-16

  Dihydropyridine derivatives and acid addition salts thereof which are of use as prophylactic or/and therapeutic drugs for cardiovascular diseases, said dihydropyridine derivatives having the formula (wherein R', R2 and R3 are the same or different and each is alkyl, cycloalkyl or alkoxyalkyl; R4 and R5 are the same or different and each is hydrogen, halogen, nitro, trifluoromethyl, alkyl, cycloalkyl, alkoxy, cyano, alkoxycarbonyl or alkylthio; R6 is hydrogen, alkyl, cycloalkyl, aralkyl, aryl or a pyridyl; X is oxygen, sulfur, vinylene, azomethine or a group of the formula A is alkylene; Ar is aryl or a pyridyl; m is an integer of 1 to 3; n is an integer of 0 to 2).

  可用作心血管疾病的预防或/和治疗药物的二氢吡啶衍生物及其酸加成盐，所述二氢吡啶衍生物具有以下式子 (其中 R'、R2 和 R3 相同或不同，各自为烷基、环烷基或烷氧基烷基；R4 和 R5 相同或不同，各自为氢、卤素、硝基、三氟甲基、烷基、环烷基、烷氧基、氰基、烷氧羰基或烷基硫基；R6 为氢、烷基、环烷基、芳烷基、芳基或吡啶基；X 为氧、硫、乙烯基、偶氮甲基或式中的基团 A 是亚烷基；Ar 是芳基或吡啶基；m 是 1 至 3 的整数；n 是 0 至 2 的整数）。
• Dihydropyridines with an antagonistic activity to calcium, process for their preparation, and pharmaceutical compositions containing them
  申请人：Pierrel S.p.A.

  公开号：EP0097821A2

  公开（公告）日：1984-01-11

  Basic esters of 1,4-dihydropyridine-3,5-dicarboxylic acid of formula (I) are described, in which R' is a linear or branched alkyl radical containing 1-5 carbon atoms which is unsubstituted or substituted by an alkoxy group; R2 is a phenyl or a nitrophenyl radical; R3 is phenyl, phenyl substituted by one to three radicals selected from (C1-4)alkyl, (C1-4)alkoxy, fluoro, chloro, bromo, nitro, cyano, carb(C1-4)alkoxy, trifluoromethyl, hydroxy, amino, mono- or di-alkylamino, mono- or di-acylamino, mercapto, S(O)n-alkyl with n = 0,1 or 2, (C1-C5)acyl, carbamoyl, ureido or R3 is a 5 or 6 membered heteroaryl monocyclic radical which contains one or more heteroatoms which are N, 0 or S such as unsubstituted pyridyl, pirazinyl, pyrimidyl, furyl, imidazolyl, thienyl, thiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl or mono-, di- or tri-substituted with alkyl, alkoxy, halogen or trifluoromethyl; X is a linear or branched alkylen radical containing between 2 and 5 carbon atems which is unsubstituted or substituted by an alkoxy group and their racemates, enantiomers and diastereoisomers and addition salts thereof with a pharmaceutically acceptable acid. The novel compounds exhibit calcium antagonistic activity.

  描述了式(I)的 1,4-二氢吡啶-3,5-二羧酸碱式酯。 其中 R' 是含有 1-5 个碳原子的直链或支链烷基，未被取代或被烷氧基取代；R2 是苯基或硝基苯基；R3 是苯基、被一至三个基团取代的苯基，这些基团选自(C1-4)烷基、(C1-4)烷氧基、氟基、氯基、溴基、硝基、氰基、碳(C1-4)烷氧基、三氟甲基、羟基、氨基、单或双烷基氨基、单或双酰基氨基、巯基、S(O)n-烷基（n = 0、1 或 2）、(C1-C5)酰基、氨基甲酰基、脲基或 R3 是脲基、脲基或 R3 是含有一个或多个杂原子（N、0 或 S）的 5 或 6 位杂芳基单环基，如未取代的吡啶基、吡嗪基、嘧啶基、呋喃基、咪唑基、噻吩基、噻唑基、1,2,3-三唑基、1,2,4-三唑基，或由烷基、烷氧基、卤素或三氟甲基单取代、二取代或三取代的烷基；X 是含有 2 至 5 个碳原子的直链或支链烯基，未被烷氧基取代或被烷氧基取代，以及它们的外消旋体、对映体和非对映异构体及其与药学上可接受的酸的加成盐。这些新型化合物具有钙拮抗活性。
• US4894460A
  申请人：——

  公开号：US4894460A

  公开（公告）日：1990-01-16
• US4892875A
  申请人：——

  公开号：US4892875A

  公开（公告）日：1990-01-09
• New 1,4-dihydropyridine derivatives with potent and long-lasting hypotensive effect.
  作者：KANJI MEGURO、MASAHIRO AIZAWA、TAKASHI SOHDA、YUTAKA KAWAMATSU、AKINOBU NAGAOKA

  DOI：10.1248/cpb.33.3787

  日期：——

  In a search for new 1, 4-dihydropyridine derivatives with a long-lasting effect on the cardiovascular system, a series of piperazinylalkyl esters (I) bearing a lipophilic substituent on the 4-nitrogen of the piperazine ring was synthesized and tested for hypotensive effect in spontaneously hypertensive rats (SHR). Compounds I, especially those having a diphenylmethyl moiety on the piperazine ring, showed extremely potent and long-lasting hypotensive properties. Analogues related to I were also prepared, and the structure-activity relationships are discussed.

  在寻找对心血管系统具有长效作用的新的1,4-二氢吡啶衍生物时，合成并测试了一系列在哌嗪环的4-氮上带有亲脂性取代基的吡哆酯类化合物I对自发性高血压大鼠(SHR)的降压效果。化合物I，尤其是那些在哌嗪环上有二苯甲基部分的化合物，显示出极其强大且长效的降压特性。还制备了与I相关的类似物，并讨论了结构-活性关系。