3-ethyl methyl 2-chloromethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate | 107812-63-5

• 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: 3-ethyl methyl 2-chloromethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
• 英文别名: 2-chloromethyl-3-carboethoxy-5-carbomethoxy-4-(m-nitro-phenyl)-6-methyl-1,4-dihydropyridine；3-ethyl 5-methyl 2-(chloromethyl)-1,4-dihydro-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate；3-Ethyl 5-methyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate；3-O-ethyl 5-O-methyl 2-(chloromethyl)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 107812-63-5
• 化学式: C₁₈H₁₉ClN₂O₆
• 分子量: 394.812
• InChiKey: JYPZKAWYVKYCOE-UHFFFAOYSA-N

物化性质

• 沸点：
  513.8±50.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：

  3-ethyl methyl 2-chloromethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 吡啶 为溶剂， 生成 2-chloromethyl-3-carboethoxy-5-carbomethoxy-4-(m-nitrophenyl)-6-methylpyridine
  参考文献：
  名称：

  Ca++-modulators. Unusual highly stereospecific hantzsch-like cyclization: first authenticated example of 2-chloromethylene-1,2,3,4-tetrahydropyridine

  摘要：

  DOI：

  10.1016/s0040-4039(00)82340-0
• 作为产物：
  描述：

  (3S,4R)-2-[1-Chloro-meth-(Z)-ylidene]-6-methyl-4-(3-nitro-phenyl)-1,2,3,4-tetrahydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester 以 氯仿 为溶剂， 反应 0.08h， 生成 3-ethyl methyl 2-chloromethyl-1,4-dihydro-6-methyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Ca++-modulators. Unusual highly stereospecific hantzsch-like cyclization: first authenticated example of 2-chloromethylene-1,2,3,4-tetrahydropyridine

  摘要：

  DOI：

  10.1016/s0040-4039(00)82340-0

文献信息

• Organic Nitrates II[1]. Synthesis and Biological Activities of 4-Nitrooxymethylphenyl-1,4-dihydropyridines
  作者：Jochen Lehmann、Rainer Kahlich、Christoph Meyer Zum Gottesberge、Uwe Fricke

  DOI：10.1002/ardp.19973300804

  日期：——

  Both 2‐nitrooxymethyl‐4‐phenyl‐ (2) and 4‐nitrooxymethylphenyl‐1,4‐dihydropyridines (3) represent new combinations of two different vasodilating structures. 2 could not be isolated due to its spontaneous lactonization. Derivatives of 3 were obtained via Hantzsch synthesis using nitrooxymethylated benzaldehydes. The inotropic potency in isolated porcine trabecular muscles and the vasodilator activity

  2-硝基氧甲基-4-苯基-(2)和4-硝基氧甲基苯基-1,4-二氢吡啶(3)都代表了两种不同血管舒张结构的新组合。2由于其自发内酯化而无法分离。使用硝基氧甲基化苯甲醛通过 Hantzsch 合成获得 3 的衍生物。测定了离体猪小梁肌中的正性肌力效力和四种硝基氧苯基二氢吡啶在离体猪冠状动脉中的血管扩张活性。尼群地平 (NTD) 和三硝酸甘油酯 (GTN) 用作参考。3 是负性肌力，然而，小于 NTD 并且 - 除了二氰基衍生物 3d - 大于 GTN。血管扩张剂的特性不如尼群地平和 GTN 明显。血管选择性低。
• 1,4-dihydropyridines
  申请人：Boehringer Biochemia Robin S.p.A.

  公开号：US04839348A1

  公开（公告）日：1989-06-13

  Dihydropyridines of formula I ##STR1## wherein R is hydrogen or lower alkyl; R.sub.1 is a CN, NO.sub.2, COCH.sub.3, COPh group, a carboalkoxy or carboamide group; R.sub.2 is an aromatic or heteroaromatic, mono- or bicyclic eventually substituted phenyl group; R.sub.3 is a carboalkoxy group; while A is a halogen atom or an ammonium or phosphonium residue. The compounds I are useful as antihypertensive, antitumoral, antimetastatic, antithrombotic, and/or antiischemic agent.

  式I的二氢吡啶类化合物，其中R是氢或较低烷基；R1是CN、NO2、COCH3、COPh基团、羧基烷氧基或羧酰胺基团；R2是芳香或杂环芳基，单环或双环，最终被取代的苯基基团；R3是羧基烷氧基；A是卤素原子或铵或膦残基。这些化合物I可用作抗高血压、抗肿瘤、抗转移、抗血栓和/或抗缺血剂。
• 2-selenomethyl-1,4-dihydropyridines having calcium-antagonistic
  申请人：Boehringer Biochemia Robin S.p.A.

  公开号：US04988713A1

  公开（公告）日：1991-01-29

  Compounds of formula I ##STR1## wherein R.sub.1 is a cyano, nitro, acetyl, benzoyl or alkoxycarbonyl group; R.sub.2 is an optionally substituted phenyl or heteroaryl group; R.sub.3 is an alkoxycarbonyl group; R.sub.4 is an alkyl group, optionally substituted by hydroxy, amino, phenyl, heterocyclic group; an optionally substituted phenyl group or an heterocyclic group. Compounds I are useful in human therapy as agents able to interact with CA.sup.++ -dependent systems and as anti-tumor agents.

  化合物I的式子为： ##STR1## 其中R.sub.1是氰基，硝基，乙酰基，苯甲酰基或烷氧羰基基团；R.sub.2是可选取的取代苯基或杂环基团；R.sub.3是烷氧羰基基团；R.sub.4是烷基基团，可选取羟基，氨基，苯基，杂环基团取代的烷基基团，可选取的苯基或杂环基团。化合物I可用于人类治疗，作为能够与CA.sup.++ -依赖性系统相互作用的药剂和抗肿瘤药剂。
• Design of an antithrombotic-antihypertensive agent (Wy 27569). Synthesis and evaluation of a series of 2-heteroaryl substituted dihydropyridines
  作者：John L. Archibald、Gerald Bradley、Albert Opalko、Terence J. Ward、Janet C. White、Christine Ennis、Nicholas B. Shepperson

  DOI：10.1021/jm00164a028

  日期：1990.2

  An approach to the design of potential combined antithrombotic-antihypertensive agents is described. A series of 1,4-dihydropyridines bearing a 1H-imidazol-1-yl or pyrid-3-yl substituted side chain in the 2-position were synthesized and tested for antihypertensive activity in spontaneously hypertensive rats and for inhibition of TXA2 synthetase in rabbit platelets, in vitro. 1,4-Dihydro-2-(1H-imidazol-1-ylmethyl)-6-methyl- 4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-ethyl 5-methyl diester (1) was shown to be similar in potency to nitrendipine as an antihypertensive agent. Compound 1 inhibited TXA2 synthetase in rabbit and human platelets in vitro and reduced plasma TXB2 levels in rats at antihypertensive dose levels. The reductions in thromboxane production observed in vivo and in vitro were accompanied by enhanced levels of 6-KPGF1 alpha, reflecting diversion of the arachidonic acid cascade toward prostacyclin synthesis.
• 2-Dithioalkyl-dihydropyridines, a method for their preparation and pharmaceutical compositions containing them
  申请人：BOEHRINGER MANNHEIM ITALIA S.P.A.

  公开号：EP0272694B1

  公开（公告）日：1992-03-18