2,6-dimethyl-3,5-dicyano-4-(4-pyridyl)-1,4-dihydropyridine | 64089-25-4

• 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-3,5-dicyano-4-(4-pyridyl)-1,4-dihydropyridine
• 英文别名: Pyridin-4-YL-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile；2,6-dimethyl-4-pyridin-4-yl-1,4-dihydropyridine-3,5-dicarbonitrile
• CAS: 64089-25-4
• 化学式: C₁₄H₁₂N₄
• 分子量: 236.276
• InChiKey: BGQJZHSJWQFXCP-UHFFFAOYSA-N

物化性质

• 熔点：
  234-236 °C
• 沸点：
  429.8±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dimethyl-3,5-dicyano-4-(4-pyridyl)-1,4-dihydropyridine 以85%的产率得到
  参考文献：
  名称：

  BALICKI R.; BLASZCZAK H.; NANTKA-NAMIRSKI P., ACTA POL. PHARM., 1980, 37, NO 1, 1-6

  摘要：

  DOI：
• 作为产物：
  描述：

  4-吡啶甲醛 、 3-氨基巴豆腈 以 乙醇 为溶剂， 生成 2,6-dimethyl-3,5-dicyano-4-(4-pyridyl)-1,4-dihydropyridine
  参考文献：
  名称：

  由含氰基和吡啶基的多齿配体生成的 银（i）超分子复合物†

  摘要：

  {[Ag（L1）] [X]} ∞类型的一系列银（I）配合物（L1 =2,6-二甲基-3,5-二氰基-4-（4-吡啶基）-1,4-二氢吡啶; X = BF 4 −，1 ; CLO 4 - ，2 ; 和NO 3 - ，3）; {[Ag 2（L2）4 ] [SO 4 ]} n，4 ; 和[Ag 2（L2）2（NO 3）2 ] n，5（L2 =2,6-二甲基-3,5-二氰基-4-（3-吡啶基）-1,4-二氢吡啶）是由各种Ag（I）盐与L1或L2在甲醇–高氧2。X射线晶体学已对所有配合物进行了结构表征，证实了配合物1-3是二维配位聚合物网，而配合物4和5是一维配位聚合物链。配合物1-3中的所有L1配体均充当三齿配体，以桥接Ag（I）离子。阴离子BF 4 -和C10 4 -中的复合物1和2未配位到的Ag（我）原子，同时NO 3 -中络合阴离子3通过三个氧原子之一与金属中心配位。配合物4中的三齿L2配体

  DOI：

  10.1039/c2nj40399d

文献信息

• Synthesis and calcium channel antagonist activity of dialkyl 1,4-dihydro-2,6-dimethyl-4-(pyridinyl)-3,5-pyridinedicarboxylates
  作者：Lina Dagnino、Moy Cheong Li-Kwong-Ken、Michael W. Wolowyk、Hla Wynn、Christopher R. Triggle、Edward E. Knaus

  DOI：10.1021/jm00162a016

  日期：1986.12

  3-aminocrotonate (4) and pyridinecarboxaldehydes 5 afforded the unsymmetrical alkyl methyl 1,4-dihydro-2,6-dimethyl-4-(pyridinyl)-3,5-pyridinedicarboxylates 6, whereas condensation of 3 with 5 and ammonium hydroxide gave the symmetrical dialkyl 1,4-dihydro-2,6-dimethyl-4-(pyridinyl)-3,5-pyridinedicarboxylates 7. The calcium channel antagonist activities of disubstituted 1,4-dihydro-3,5-pyridinedicarboxylates

  乙酰乙酸烷基酯3与3-氨基巴豆酸甲酯（4）和吡啶甲醛5的汉茨缩合反应得到不对称的1,4-二氢-2,6-二甲基-4-（吡啶基）-3,5-吡啶二甲酸烷基甲基酯6，而缩合反应3与5和氢氧化铵反应得到对称的1,4-二氢-2,6-二甲基-4-（吡啶基）-3,5-吡啶二羧酸二烷基酯7。二取代的1,4-二氢-3的钙通道拮抗剂活性使用豚鼠回肠纵向平滑肌的毒蕈碱受体介导的Ca2 +依赖性收缩测定1,5-吡啶二甲酸6,7和9。异构吡啶基类似物6和7的相对效价顺序是2-吡啶基大于3-吡啶基大于4-吡啶基。增加烷基酯取代基的大小可增强活性。具有相同酯取代基的化合物比具有相同酯取代基的化合物更有效。用氰基取代基代替C-3和/或C-5酯取代基明显降低了活性。观察到抑制[3H]硝苯地平结合的IC50值与抑制毒蕈碱诱导的收缩反应的补品成分之间的近似1：1关系。测试结果表明4-（吡啶基）取代基在1,4-二氢吡啶环系统上具有
• Structural Diversity in the Self-assembly of Cd(II) Complexes Containing 2,6-Dimethyl-3,5-dicyano-4-(4-pyridyl)-1,4-dihydropyridine
  作者：Chun-Wei Yeh、Fu-Chang Huang、Ay Jong、Chi-Hui Tsou、Maw-Cherng Suen

  DOI：10.1002/jccs.201300652

  日期：2014.5

  structures and properties of the complexes [CdBr2(L)2·4H2O]n [L = 2,6‐dimethyl‐3,5‐dicyano‐4‐(4‐pyridyl)‐1,4‐dihydropyridine], 1 and [Cd(SCN)2(L)2(H2O)]n, 2, are reported. In polymeric complexes 1 — 2, the L ligands bridge the metal centers through the pyrimidyl and cyano nitrogen atoms forming 1‐D double‐stranded chain and zigzag chain, respectively. The L ligands in complex 1 act as κ1, κ1‐bidentate bridging

  配合物[CdBr 2（L）2 ·4H 2 O] n的合成，结构和性质[ L = 2,6-二甲基-3,5-二氰基-4-（4-吡啶基）-1,4-二氢吡啶报道了[ ，] 1和[Cd（SCN）2（L）2（H 2 O）] n，2。在聚合物配合物1 - 2时，大号配体通过桥形成1-d双链链和锯齿形链，分别是嘧啶基和氰基的氮原子的金属中心。复合物中的L配体1充当κ1，κ1的架桥配体，而复合体2中的L配体充当κ1的单齿科和κ1，κ1的架桥的配体。这些配合物的分子通过形成堆积结构的各种弱相互作用相互连接。所有的配合物均表现出发射态，可将其暂定为配体内（IL）π→π*跃迁。
• Antihypertensive reduced pyridyl derivatives
  申请人：The Governors of the University of Alberta

  公开号：EP0239186A1

  公开（公告）日：1987-09-30

  Pharmaceutical compounds of the general formula (1): have been prepared and non-toxic pharmaceutically acceptable salts thereof, wherein the ring system is a 1,2- or 1,4-dihydropyridyl radical; R1 is a hydrogen, lower alkyl, lower alkyl carbonyl or lower alkoxy carbonyl substituent; R2 is a lower alkyl or phenyl substituent; R3 is a lower alkoxy carbonyl, (N,N-lower dialkylamino) lower alkoxy carbonyl, (N-loweralkyl-N-phenyl lower alkyl amino) lower alkoxy carbonyl, lower alkoxy lower alkoxy carbonyl, nitro or cyano substituent; R4 is a member selected from the group consisting of pyridyl, N-lower alkoxy carbonyl-1,2-dihydropyridyl, N-lower alkyl carbonyl-1,2-dihydropyridyl, N-phenyloxy carbonyl-1,2-dihydropyridyl, N-lower alkoxy carbonyl-1,6-dihydropyridyl, N-lower alkyl carbonyl-1,6-dihydropyridyl, N-lower alkyl carbonyl-1,6-dihydropyridyl, N-phenyloxy carbonyl-1,6-dihydropyridyl, N-lower alkoxy carbonyl-1,4-dihydropyridyl, N-lower alkyl carbonyl-1,4-dihydropyridyl, N-phenyloxy carbonyl-1,4-dihydropyridyl, N-lower alkyl 1,2,3,6-tetrahydropyridyl, N-lower alkoxy carbonyl-1,2,3,6-tetrahydropyridyl, N-lower alkyl carbonyl-1,2,3,6-tetrahydropyridyl, nitro substituted phenyl or trifluoromethyl substituted phenyl; Rs is a lower alkoxy carbonyl, (N,N-lowerdialkylamino) lower alkoxycarbonyl, (N-loweralkyl-N-phenyl lower alkyl amino) lower alkoxy carbonyl, lower alkoxy lower alkoxy carbonyl, nitro, or cyano substitutent; R6 is a lower alkyl, or phenyl substituent, lower denoting a straight or branched chain having from 1-6 carbon atoms. The compounds exhibit antihypertensive activity due to their ability to induce cerebral and peripheral vasodilation, decrease heart rate, and/or increase cardiac contractility, and are useful in the treatment of angina, arrhythmias, cerebralvascular disease and hypertension.

  通式(1)的药用化合物： 已制备出的药物化合物及其无毒的药学上可接受的盐，其中环系统是 1，2-或 1，4-二氢吡啶基；R1 是氢、低级烷基、低级烷基羰基或低级烷氧基羰基取代基；R2 是低级烷基或苯基取代基；R3 是低级烷氧基羰基、（N，N-低级二烷基氨基）低级烷氧基羰基、（N-低级烷基-N-苯基低级烷基氨基）低级烷氧基羰基、低级烷氧基低级烷氧基羰基、硝基或氰基取代基；R4 是选自吡啶基、N-低级烷氧基羰基-1,2-二氢吡啶基、N-低级烷基羰基-1,2-二氢吡啶基、N-苯基氧基羰基-1,2-二氢吡啶基、N-低级烷氧基羰基-1,6-二氢吡啶基、N-低级烷基羰基-1,6-二氢吡啶基、N-低级烷基羰基-1,6-二氢吡啶基、N-苯基氧基羰基-1、6-二氢吡啶基、N-低级烷氧基羰基-1,4-二氢吡啶基、N-低级烷基羰基-1,4-二氢吡啶基、N-苯氧基羰基-1,4-二氢吡啶基、N-低级烷基 1,2,3、1,2,3,6-四氢吡啶基、N-低级烷氧基羰基-1,2,3,6-四氢吡啶基、N-低级烷基羰基-1,2,3,6-四氢吡啶基、硝基取代的苯基或三氟甲基取代的苯基；Rs 是低级烷氧基羰基、（N,N-低级二烷基氨基）低级烷氧基羰基、（N-低级烷基-N-苯基低级烷基氨基）低级烷氧基羰基、低级烷氧基低级烷氧基羰基、硝基或氰基取代基；R6 是低级烷基或苯基取代基，低级表示具有 1-6 个碳原子的直链或支链。这些化合物具有抗高血压活性，因为它们能够诱导脑血管和外周血管扩张、降低心率和/或增加心脏收缩力，可用于治疗心绞痛、心律失常、脑血管疾病和高血压。
• Synthesis and calcium channel antagonist activity of dialkyl 4-(dihydropyridinyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates
  作者：Lina Dagnino、Moy Cheong Li-Kwong-Ken、Hla Wynn、Michael W. Wolowyk、Christopher R. Triggle、Edward E. Knaus

  DOI：10.1021/jm00387a010

  日期：1987.4

  The sodium borohydride reduction of 3,5-disubstituted 1,4-dihydro-2,6-dimethyl-4-(pyridinyl)pyridines 2 and 5 in the presence of methyl, phenyl, or tert-butyl chloroformate afforded the respective 4-(dihydropyridinyl)-1,4-dihydropyridines 4 and 6 in good yield. Products 4 comprised a mixture of the 1,2- and 1,6-dihydropyridinyl regioisomers 4a and 4b where 4a was always the predominant regioisomer. Compounds possessing a 4-[dihydro-1-(phenoxycarbonyl)-3-pyridinyl] substituent, such as 26, were also a mixture of two regioisomers 26a and 26b, and each regioisomer existed as a mixture of two rotamers in Me2SO-d6 at 25 degrees C (26a', 26a'', and 26b', 26b'') due to restricted rotation about the nitrogen-to-carbonyl carbamate bond. The calcium antagonist activities for 4 and 6 were determined by using the muscarinic receptor-mediated Ca2+-dependent contraction of guinea pig ileal longitudinal smooth muscle. The relative order of activities for the 4-(dihydropyridinyl) analogues was 4-(dihydro-3-pyridinyl) greater than 4-(dihydro-4-pyridinyl). Increasing the size of the C-3(5) alkyl ester substituents increased activity. Compounds having nonidentical ester substituents were more active than those having identical ester substituents. Replacement of the C-3 and/or C-5 ester substituents by a cyano substituent(s) decreased activity significantly. An approximate 1:1 correlation between the IC50 value for inhibition of [3H]nitrendipine binding and inhibition of the tonic component of the muscarinic-induced contractile response was observed. The test results suggest that a 4-(dihydropyridinyl) substituent is bioisosteric with a 4-(nitrophenyl) substituent on a 1,4-dihydropyridine ring where m- and p-nitrophenyl are bioisosteric with the 4-[1,2(1,6)-dihydro-3-pyridinyl] 4 and 4-(1,2-dihydro-4-pyridinyl) 6 isomers, respectively.
• DAGNINO L.; LI-KWONG-KEN MOY CH.; WYNN HLA; WOLOWYK M. W.; TRIGGLE CH. R.+, J. MED. CHEM., 30,(1987) N 4, 640-646
  作者：DAGNINO L.、 LI-KWONG-KEN MOY CH.、 WYNN HLA、 WOLOWYK M. W.、 TRIGGLE CH. R.+

  DOI：——

  日期：——