1',4'-Dihydro-2',6'-dimethyl-<3,4'-bipyridin>-3',5'-dicarbonsaeuredimethylester | 73349-75-4

• 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: 1',4'-Dihydro-2',6'-dimethyl-<3,4'-bipyridin>-3',5'-dicarbonsaeuredimethylester
• 英文别名: 4-(3-pyridyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-bis(methoxycarbonyl)；1,4-dihydro-2,6-dimethyl-4-(pyridin-3-yl)pyridine3,5-dicarboxylic acid dimethyl ester；dimethyl 2,6-dimethyl-4-(3'-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylate；1,4-dihydro-2,6-dimethyl-4-(3-pyridyl)pyridine3,5-dicarboxylic acid dimethyl ester；Dimethyl 2,6-dimethyl-4-pyridin-3-yl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 73349-75-4
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: HQPKQZOVCGHZFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1',4'-Dihydro-2',6'-dimethyl-<3,4'-bipyridin>-3',5'-dicarbonsaeuredimethylester 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 dimethyl 1,1',2,4',5,6-hexahydro-1,2',6'-trimethyl<3,4'-bipyridine>-3',5'-dicarboxylate
  参考文献：
  名称：

  Synthesis and calcium channel antagonist activity of dialkyl hexahydro-1,2′,6′-trimethyl[bipyridine]-3′,5′-dicarboxylates

  摘要：

  DOI：

  10.1016/0223-5234(87)90289-3
• 作为产物：
  描述：

  3-吡啶甲醛 、 3-氨基巴豆酸甲酯 在 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 生成 1',4'-Dihydro-2',6'-dimethyl-<3,4'-bipyridin>-3',5'-dicarbonsaeuredimethylester
  参考文献：
  名称：

  烟碱醛基1,4-二氢吡啶二羧酸酯的合成及生物活性

  摘要：

  摘要 1,4-二氢吡啶羧酸盐是通过烟醛与氨基巴豆酸酯在室温下在p- TsOH存在下反应制备的。对制备的化合物进行了抗微生物、自由基清除和α-葡萄糖苷酶抑制活性的评估。化合物 2,6-二苯基-4-(吡啶-3-基)-1,4-二氢吡啶-3,5-二羧酸二乙酯和4-(2-氯-5-(4-氟苯基)吡啶-3-基二乙酯)-2,6-二苯基-1,4-二氢吡啶-3,5-二羧酸酯被鉴定为有效的抗真菌剂。化合物2,6-二甲基-4-(吡啶-3-基)-1,4-二氢吡啶-3,5-二甲酸二乙酯、4-(2-氯吡啶-3-基)-2,6-二甲基- 1,4-二氢吡啶-3,5-二羧酸酯和 2,6-二甲基-4-(吡啶-4-基)-1,4-二氢吡啶-3,5-二羧酸二乙酯被鉴定为\({\text{ABT}}{{{\text{S}}}^{{\centerdot + }}}\)自由基清除剂。化合物4-(2-氯-5-苯基吡啶-3-基)-2,6-二苯基-1

  DOI：

  10.1134/s1068162021060224

文献信息

• Chemical compounds having ion channel blocking activity for the treatment of immune dysfunction
  申请人：——

  公开号：US20020119989A1

  公开（公告）日：2002-08-29

  The present invention relates to chemical compounds having inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca), and the use of such compounds for the treatment or alleviation of diseases or conditions relating to immune dysfunction. Moreover, the invention relates to a method of screening a chemical compound for inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca).

  本发明涉及具有对中间电导性Ca2+激活钾通道（IK Ca）具有抑制活性的化合物，以及利用这种化合物治疗或缓解与免疫功能紊乱相关的疾病或症状。此外，本发明涉及一种筛选化合物对中间电导性Ca2+激活钾通道（IK Ca）具有抑制活性的方法。
• 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
• Evaluation of Antiradical Activity and Reducing Capacity of Synthesised Bispyridinium Dibromides Obtained by Quaternisation of 4-Pyridyl-1,4-dihydropyridines with Propargyl Bromide
  作者：Martins Rucins、Marina Gosteva、Sergey Belyakov、Arkadij Sobolev、Karlis Pajuste、Mara Plotniece、Brigita Cekavicus、Dace Tirzite、Aiva Plotniece

  DOI：10.1071/ch14033

  日期：——

  New bispyridinium dibromides based on the 1,4-dihydropyridine (1,4-DHP) cycle were synthesised in the reaction between 4-pyridyl-1,4-DHP derivatives and propargyl bromide. It has been shown that variation of the substituent position on the pyridine as well as small changes in the electronic nature of the 1,4-DHP cycle as a result of the substituent nature at the 3 and 5 positions do not affect the course of the reaction and in all cases the corresponding bispyridinium dibromides 4a–e were formed. The antiradical activity, using 1,1-diphenyl-2-picrylhydrazine as a free radical scavenger, and the reducing capacity using phosphomolybdenum complexes have been evaluated for the newly synthesised compounds 4a–e. It has been shown that all tested 1,4-DHP bispyridinium dibromides 4a–e possess reducing capacity and antiradical properties. Moreover, the reducing capacity results could be explained by the influence of the electronic nature of the substituent at the 3 and 5 positions of the 1,4-DHP cycle.

  通过 4-吡啶基-1,4-DHP 衍生物与溴化丙炔的反应，合成了基于 1,4-二氢吡啶（1,4-DHP）循环的新型双吡啶二溴化物。研究表明，吡啶上取代基位置的变化以及 1,4-DHP循环电子性质的微小变化不会影响反应的进程，而且在所有情况下都会生成相应的双吡啶二溴化物 4a-e。利用 1,1-二苯基-2-苦肼作为自由基清除剂，对新合成的化合物 4a-e 的抗自由基活性进行了评估，并利用磷钼络合物对其还原能力进行了评估。结果表明，所有测试的 1,4-二氯丙醇双吡啶二溴化物 4a-e 都具有还原能力和抗自由基特性。此外，1,4-DHP 周期 3 和 5 位上的取代基的电子性质也可以解释还原能力的结果。
• 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。
• Shinde, D. B.; Shinde, N. D.; Shingare, M. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 10, p. 920 - 922
  作者：Shinde, D. B.、Shinde, N. D.、Shingare, M. S.、Dubey, M. P.、Patnaik, G. K.

  DOI：——

  日期：——