cyclopentyl 3-aminocrotonate | 61312-61-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: cyclopentyl 3-aminocrotonate
• 英文别名: Cyclopentyl 3-aminobut-2-enoate
• CAS: 61312-61-6
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: SCFWSXWPGYNVRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclopentyl 3-aminocrotonate 、 (E)-3-(2-Oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-(2-trifluoromethyl-phenyl)-but-3-en-2-one 以 异丙醇 为溶剂， 以56%的产率得到2,6-Dimethyl-5-(2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-yl)-4-(2-trifluoromethyl-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid cyclopentyl ester
  参考文献：
  名称：

  Synthesis and antihypertensive activities of 1,4-dihydropyridine-5-phosphonate derivatives. II.

  摘要：

  合成了一系列1,4-二氢吡啶-5-环状磷酸酯衍生物，作为1,4-二氢吡啶-3,5-二羧酸钙拮抗剂的类似物，并对其抗高血压活性进行了检查。几种化合物在降低正常血压和自发性高血压大鼠（SHR）的血压方面被证明具有优于或可比于硝苯地平的活性。在这些化合物中，甲基2,6-二甲基-5-(2-氧-1,3,2-二氧磷烷-2-基)-4-(2-硝基苯基)-1,4-二氢吡啶-3-羧酸酯（31，DHP-218）在SHR中的活性约为硝苯地平的7倍，并被选为进一步开发和临床评估的候选化合物。讨论了结构-活性关系。

  DOI：

  10.1248/cpb.35.4144

文献信息

• 4-Chromenonyl-1,4-dihydropyridines and their use
  申请人：Kuhl Alexander

  公开号：US20100022484A1

  公开（公告）日：2010-01-28

  The present application relates to novel 4-chromenonyl-1,4-dihydropyridines, process for their preparation, their use for the treatment and/or prophylaxis of diseases, and their use for the manufacture of medicaments for the treatment and/or prophylaxis of diseases, especially cardiovascular disorders.

  本申请涉及新型4-氧杂环己烯基-1,4-二氢吡啶，其制备方法，其用于治疗和/或预防疾病的用途，以及其用于制造治疗和/或预防疾病的药物的用途，特别是心血管疾病。
• 4-Chromenonyl-1,4-dihydropyridinecarbonitriles and the use thereof
  申请人：Kuhl Alexander

  公开号：US20090214675A1

  公开（公告）日：2009-08-27

  The present application relates to novel 4-chromenonyl-1,4-dihydropyridinecarbonitriles, processes for their preparation, pharmaceutical compositions containing them, and their use for the treatment and/or prophylaxis of diseases, especially cardiovascular disorders.

  本申请涉及新型4-咔唑基-1,4-二氢吡啶基碳腈化合物，其制备方法，含有它们的药物组合物，以及它们用于治疗和/或预防疾病，特别是心血管疾病的用途。
• Synthesis and Calcium Channel-Modulating Effects of Alkyl (or Cycloalkyl) 1,4-Dihydro-2,6-dimethyl-3-nitro-4-pyridyl-5-pyridinecarboxylate Racemates and Enantiomers
  作者：Manian Ramesh、Wandikayi C. Matowe、Murthy R. Akula、Dean Vo、Lina Dagnino、Moy Cheong Li-Kwong-Ken、Michael W. Wolowyk、Edward E. Knaus

  DOI：10.1021/jm9704006

  日期：1998.2.1

  that the 2-pyridyl isomers acted as dual cardioselective calcium channel agonists (GPLA)/smooth muscle selective calcium channel antagonists (GPILSM). In contrast, the 3-pyridyl and 4-pyridyl isomers acted as calcium channel agonists on both GPLA and GPILSM. In the C-4 2-pyridyl group of compounds, the size of the C-5 alkyl (or cycloalkyl) ester substituent was a determinant of GPILSM antagonist activity

  一组外消旋烷基（或环烷基）1,4-二氢-2,6-二甲基-3-硝基-4-（2-，3-或4-吡啶基）-5-吡啶羧酸酯异构体（6-14）为使用改进的Hantzsch反应制备的方法，该反应涉及硝基丙酮与3-氨基巴豆酸烷基酯（或环烷基）和2-，3-或4-吡啶甲醛的缩合反应。使用豚鼠回肠纵向平滑肌（GPILSM）和豚鼠左心房（GPLA）分析测定其体外钙通道调节活性，结果表明2-吡啶基异构体可作为双心脏选择性钙通道激动剂（GPLA）/平滑肌选择性钙通道拮抗剂（GPILSM）。相反，3-吡啶基和4-吡啶基异构体在GPLA和GPILSM上均充当钙通道激动剂。在化合物的C-4 2-吡啶基中 C-5烷基（或环烷基）酯取代基的大小是GPILSM拮抗剂活性的决定因素，其中相对活性分布为环戊基和环己基> t-Bu，i-Bu，并且Et> MeOCH2CH2> Me。C-4吡啶基取代基的连接点是GPLA激动剂活性的决定因
• Calcium antagonist 2-fluoroalkyl-1,4-dihydropyridines
  申请人：Fisons plc

  公开号：US04686217A1

  公开（公告）日：1987-08-11

  There are described compounds of formula I, ##STR1## in which R.sub.1 represents benzofurazanyl, pyridyl or phenyl, the pyridyl or phenyl being substituted, --COOR.sub.2 and --COOR.sub.3 are various ester groups, one of R.sub.7 and R.sub.8 represents alkyl Cl to 6 and the other represents --CONR.sub.10 R.sub.11 ; --CSNH.sub.2 ; --C(.dbd.NH)SR.sub.9 ; --S(O).sub.m R.sub.9 ; phenyl optionally substituted by one or more of alkyl Cl to 6, halogen, alkoxy Cl to 6 or nitro; alkyl Cl to 6 substituted by halogen; or furanyl; m is 0 or 1 R.sub.9 is alkyl Cl to 6, and R.sub.10 and R.sub.11 each independently represent hydrogen or alkyl Cl to 6, or together with the nitrogen atom to which they are attached form a 5 or 6 membered heterocyclic ring. There are also described processes for making the compounds, and pharmaceutical, e.g. calcium antagonist, formulations containing them.

  描述了一系列化合物的化学式I，其中R.sub.1代表苯并呋喃基、吡啶基或苯基，吡啶基或苯基被取代，--COOR.sub.2和--COOR.sub.3是不同的酯基，R.sub.7和R.sub.8中的一个代表烷基Cl至6，另一个代表--CONR.sub.10 R.sub.11；--CSNH.sub.2；--C(.dbd.NH)SR.sub.9；--S(O).sub.mR.sub.9；苯基选择性地被取代为1个或多个烷基Cl至6、卤素、烷氧基Cl至6或硝基；被卤素取代的烷基Cl至6；或呋喃基；m为0或1，R.sub.9为烷基Cl至6，R.sub.10和R.sub.11各自独立地表示氢或烷基Cl至6，或者与它们所附着的氮原子一起形成5或6元杂环环。还描述了制备这些化合物的过程以及包含它们的制药配方，例如钙拮抗剂。
• Pharmaceutically active dihydropyridines
  申请人：FISONS plc

  公开号：EP0125803A2

  公开（公告）日：1984-11-21

  There are described compounds of formula I, in which R1 represents benzofurazanyl, pyridyl or phenyl, the pyridyl or phenyl being substituted, -COOR2 and -COOR3 are various ester groups, Yand Ztogetherform a bond, and additionally, when R. is an electron withdrawing group Y may be hydrogen and Z may be hydroxy, one of R7 and R. represents alkyl Cl to 6 and the other represents -CONR10R11; -CSNH2; -C(=NN)SR9; -S(O)mR9; phenyl optionally substituted by one or more of alkyl Cl to 6, halogen, alkoxy CI to 6 or nitro; alkyl Cl to 6 substituted by halogen; or furanyl, or R7 and R. may be the same or different and each represents phenyl optionally substituted by one or more of alkyl CI to 6, halogen, alkoxy Cl to 6 or nitro; amino; alkyl CI to 6 substituted by halogen; -CN; -CH2OH; -CHO or-CH(OR9)2, m is 0 or 1 R9 is alkyl CI to 6, and R10 and R11 each independently represent hydrogen or alkyl Cl to 6, or together with the nitrogen atom to which they are attached form a 5 or 6 membered heterocyclic ring. There are also described processes for making the compounds, and pharmaceutical, eg calcium antagonist, formulations containing them.

  所述化合物为式 I、 其中 R1 代表苯并呋喃基、吡啶基或苯基，吡啶基或苯基被取代、 -COOR2和-COOR3是各种酯基、 Y和Z共同构成键，此外，当R.是取电子基团时，Y可以是氢，Z可以是羟基、 R7 和 R. 中的一个代表 Cl 至 6 烷基，另一个代表-CONR10R11；-CSNH2；-C(=NN)SR9；-S(O)mR9；任选被 Cl 至 6 烷基、卤素、CI 至 6 烷氧基或硝基中的一个或多个取代的苯基；被卤素取代的 Cl 至 6 烷基；或呋喃基、 或 R7 和 R.可以相同或不同，且各自代表被以下一种或多种任选取代的苯基：CI 至 6 号烷基、卤素、CI 至 6 号烷氧基或硝基；氨基；被卤素取代的 CI 至 6 号烷基；-CN；-CH2OH；-CHO 或-CH(OR9)2、 m为0或1 R9 是 CI-6 烷基，和 R10和R11各自独立地代表氢或Cl至6的烷基，或与它们所连接的氮原子一起形成5或6个成员的杂环。 此外，还介绍了制造这些化合物的工艺，以及含有这些化合物的药物制剂（如钙拮抗剂）。