isopropyl (-)-1,4-dihydro-2,6-dimethyl-3-(1,3,4-oxadiazol-2-yl)-4-(2,3-dichlorophenyl)-pyridine-5-carboxylate | 121578-24-3

• 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: isopropyl (-)-1,4-dihydro-2,6-dimethyl-3-(1,3,4-oxadiazol-2-yl)-4-(2,3-dichlorophenyl)-pyridine-5-carboxylate
• 英文别名: Seladipine；Isopropyl (-)-1,4-dihydro-2,6-dimethyl-3-(1,3,4-oxadiazol-2-yl)-4-(2,3-dichlorophenyl)-pyridine-5-carboxylate；isopropyl 1,4-dihydro-2,6-dimethyl-4-(2,3-dichlorophenyl)-5-(1,3,4-oxadiazol-2-yl)pyridine-3-carboxylate；Propan-2-yl 4-(2,3-dichlorophenyl)-2,6-dimethyl-5-(1,3,4-oxadiazol-2-yl)-1,4-dihydropyridine-3-carboxylate；propan-2-yl 4-(2,3-dichlorophenyl)-2,6-dimethyl-5-(1,3,4-oxadiazol-2-yl)-1,4-dihydropyridine-3-carboxylate
• CAS: 121578-24-3
• 化学式: C₁₉H₁₉Cl₂N₃O₃
• 分子量: 408.284
• InChiKey: DOHODEQEZBYMTK-UHFFFAOYSA-N

物化性质

• 沸点：
  508.0±60.0 °C(Predicted)
• 密度：
  1.302±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-1-ethoxycarbonyl-ethyl (-)-1,4-dihydro-2,6-dimethyl-3-(1,3,4-oxadiazol-2-yl)-4-(2,3-dichlorophenyl)-pyridine-5-carboxylate 在 lithium 作用下， 以 ice-water 、 异丙醇 为溶剂， 生成 isopropyl (-)-1,4-dihydro-2,6-dimethyl-3-(1,3,4-oxadiazol-2-yl)-4-(2,3-dichlorophenyl)-pyridine-5-carboxylate
  参考文献：
  名称：

  Optically active, substituted 1,4-dihydropyridines and their use as

  摘要：

  具有钙拮抗作用的光学活性取代的1,4-二氢吡啶式I的化合物，其中R代表具有1至5个C原子的烷基，具有1至4个C原子的烷氧基和2至4个C原子的烷基部分，具有总共3至6个C原子的两个烷基基团作为氨基团上的取代基，其中每个烷基基团具有1至3个C原子，或在光学活性（R）-形式中为--CH（CH.sub.3）CO.sub.2R.sup.5，R.sup.1代表苯基，其单取代基为氰基，硝基或氯原子，或双取代基为氯原子，R.sup.2代表噻二唑基，或被甲基，乙基，异丙基，叔丁基，苄基，甲硫基，异丙硫基，氨基羰硫基或甲氧基甲基取代的噻二唑基，R.sup.5代表具有1至4个C原子的烷基，以及它们的酸加成盐。

  公开号：

  US04760147A1

文献信息

• Calcium- and calmodulin-antagonism of elnadipine derivatives: comparative SAR
  作者：R Mannhold、B Jablonka、W Voigt、K Schönafinger、E Schraven

  DOI：10.1016/0223-5234(92)90006-m

  日期：1992.4

  The Ca2+-antagonistic properties of elnadipine derivatives have been quantified by means of binding experiments in bovine cerebral cortex membranes using H-3-nitrendipine. Competition experiments have shown a 308-fold concentration range of K(i)-values (2.9 x 10(-10) to 8.9 x 10(-8)) for elnadipine derivatives and a eudismic ratio for elnadipine and its (+)-enantiomer of 448. Calmodulin (CaM)-antagonistic properties have been measured in the test system of CaM-stimulated phosphodiesterase. The concentration range of IC50 values only amounts to 9 (5 x 10(-7) to 4.5 x 10(-6) M). In contrast to Ca2+-antagonism, enantioselectivity of CaM-inhibition by elnadipine is negligible. CaM-antagonistic potency of elnadipine derivatives is diminished by a factor of 10 to 5000 as compared to their Ca2+-antagonistic potency. The following conclusions regarding structural determinants of Ca2+- and CaM-antagonistic properties can be made: lipophilic substituents of the oxadiazole in 5-position of the dihydropyridine (DHP) ring increase the CaM-antagonistic and decrease the Ca2+-antagonistic potency: correspondingly the unsubstituted compound is the strongest Ca2+- and the weakest CaM-antagonist; 1,3,4-oxadiazole substitution is superior to 1,2,4-oxadiazole as regards Ca2+- and CaM-antagonistic potency.
• US4558058A
  申请人：——

  公开号：US4558058A

  公开（公告）日：1985-12-10
• US4760147A
  申请人：——

  公开号：US4760147A

  公开（公告）日：1988-07-26
• Optically active, substituted 1,4-dihydropyridines and their use as
  申请人：Cassella Aktiengesellschaft

  公开号：US04760147A1

  公开（公告）日：1988-07-26

  Optically active substituted 1,4-dihydropyridines of the formula I having calcium antogonistic properties: ##STR1## wherein R denotes alkyl with 1 to 5 C atoms, alkoxy-alkyl with 1 to 4 C atoms, in the alkoxy part and 2 to 4 C atoms in the alkyl part, dialkylaminioalkyl with a total of 3 to 6 C atoms each of the alkyl groups as substituents on the amino group having 1 to 3 C atoms, or --CH(CH.sub.3)CO.sub.2 R.sup.5 in the optically active (R)-forms, R.sup.1 denotes phenyl which is monosubstituted by cyano, nitro or chlorine or is disubstituted by chlorine, R.sup.2 denotes oxadiazolyl, or an oxadiaxolyl which is substituted by methyl, ethyl, i-propyl, tert.-butyl, benzyl, methylthio, i-propylthio, aminocarbonylthio or methoxymethyl, R.sup.5 denotes alkyl with 1 to 4 C atoms, and acid-addition salts thereof, and acid addition salts thereof.

  具有钙拮抗作用的光学活性取代的1,4-二氢吡啶式I的化合物，其中R代表具有1至5个C原子的烷基，具有1至4个C原子的烷氧基和2至4个C原子的烷基部分，具有总共3至6个C原子的两个烷基基团作为氨基团上的取代基，其中每个烷基基团具有1至3个C原子，或在光学活性（R）-形式中为--CH（CH.sub.3）CO.sub.2R.sup.5，R.sup.1代表苯基，其单取代基为氰基，硝基或氯原子，或双取代基为氯原子，R.sup.2代表噻二唑基，或被甲基，乙基，异丙基，叔丁基，苄基，甲硫基，异丙硫基，氨基羰硫基或甲氧基甲基取代的噻二唑基，R.sup.5代表具有1至4个C原子的烷基，以及它们的酸加成盐。