n-decyl 3-aminocrotonate | 52937-92-5

• 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: n-decyl 3-aminocrotonate
• 英文别名: Decyl 3-aminobut-2-enoate；decyl 3-aminobut-2-enoate
• CAS: 52937-92-5
• 化学式: C₁₄H₂₇NO₂
• 分子量: 241.374
• InChiKey: IJBRUUXJLQCDOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  2-(3-硝基苯亚甲基)乙酰乙酸甲酯 、 n-decyl 3-aminocrotonate 以 乙醇 为溶剂， 反应 6.0h， 以74.2%的产率得到5-n-decyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Synthesis and antihypertensive activity evaluation in spontaneously hypertensive rats of nitrendipine analogues

  摘要：

  The antihypertensive activity of nitrendipine analogues can be improved by properly lengthening its alkyl chain in 3- or 5-position. Nitrendipine and its seven analogues were synthesized, and their antihypertensive activities in spontaneously hypertensive rats (SHR) were evaluated by ig administration. It was found that 5-n-heptyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [(+/-)-5] exhibited the strongest antihypertensive effect amongst eight compounds. (+)-5-n-heptyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [(+)-5] was also prepared. Antihypertensive activities of (+/-)-5 and (+)-5 in SHR were compared. The results showed that (+/-)-5 and (+)-5 had a higher potency than nitrendipine, and (+)-isomer was 1.79-fold the raceme at a dose of 2 mg/kg.

  DOI：

  10.1007/s00044-010-9477-0

文献信息

• Synthesis of 1,4-Dihydropyridine-5-phosphonates and Their Calcium-Antagonistic and Antihypertensive Activities. Novel Calcium-Antagonist 2-(Benzyl(phenly)amino)ethyl 5-(5,5-Dimethyl-2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylate Hydrochloride Ethanol(NZ-105) and Its Crystal Structure.
  作者：Ryozo SAKODA、Yoshimasa KAMIKAWAJI、Kiyotomo SETO

  DOI：10.1248/cpb.40.2362

  日期：——

  The effect of the 3-carboxylic-ester variation in 2, 2-dimethyltrimethylene 3-alkoxycarbonyl-4-aryl-1, 4-dihydro-2, 6-dimethyl-5-pyridinephosphonates (1) was investigated with relation to the calcium-antagonistic and antihypertensive activities : the analogs contaning the alkyl groups of not more than 12 carbons and an amino functionality in the carboxylic-ester moiety were synthesized to be examined for biological activities. Among them, 2-[benzyl(phenyl)amino]-ethyl 5(5, 5-dimethyl-2-oxo-1, 3, 2-dioxaphosphorinan-2-yl)-1, 4-dihydro-2, 6-dimethyl-4-(3-nitrophenyl)-3-phridine-carboxylate hydrochloride ethanol (NZ-105) showed particularly beneficial activities and was selected for further pharmacological studies and clinical development. Some aspects of the structure-activity relationships and solid-state structure of NZ-105 by X-ray crystallographic analysis were described.

  研究了3-羧酸酯变体在2,2-二甲基三甲基烯-3-烷氧羰基-4-芳基-1,4-二氢-2,6-二甲基-5-吡啶膦酸酯(1)中与钙拮抗和降压活性相关的影响：合成了含有不超过12个碳的烷基和羧酸酯部分含有氨基功能团的类似物，以检测其生物活性。其中，2-[苄基(苯基)氨基]乙基5-(5,5-二甲基-2-氧-1,3,2-二氧膦杂环己烷-2-基)-1,4-二氢-2,6-二甲基-4-(3-硝基苯基)-3-吡啶羧酸酯盐酸盐乙醇(NZ-105)显示出特别有益的活性，并被选中进行进一步的药理学研究和临床开发。描述了通过X射线晶体学分析获得的NZ-105的结构-活性关系和固态结构的一些方面。
• 1,4-dihydropyridine derivatives
  申请人：FUJIREBIO INC.

  公开号：EP0400660A1

  公开（公告）日：1990-12-05

  1,4-Dihydropyridine derivatives of formula (I): wherein Ar1 and Ar2 each represent an unsubstituted or substituted aromatic hydrocarbon or aromatic heterocyclic group; and R1 represents -C02R2, -SO2R3, -COR4, -CON(R5)2, -CN or -NO2 in which R2 is hydrogen, a straight chain, branched chain or cyclic saturated hydrocarbon group, which may have a substituent or a straight chain, branched chain or cyclic unsaturated hydrocarbon group having 2 to 10 carbon atoms, which may have a substituent, R3 is an alkyl group having 1 to 4 carbon atoms, R4 is an alkyl group having 1 to 4 carbon atoms or a phenyl group; and R5 is an alkyl group having 1 to 4 carbon atoms.

  式(I)的 1,4-二氢吡啶衍生物： 其中 Ar1 和 Ar2 各自代表未取代或取代的芳香烃或芳香杂环基团； 和 R1 代表-C02R2、-SO2R3、-COR4、-CON(R5)2、-CN 或 -NO2，其中 R2 是氢、直链、支链或环状饱和烃基（可有取代基）或具有 2 至 10 个碳原子的直链、支链或环状不饱和烃基（可有取代基），R3 是具有 1 至 4 个碳原子的烷基，R4 是具有 1 至 4 个碳原子的烷基或苯基； R5 是具有 1 至 4 个碳原子的烷基。
• US4622332A
  申请人：——

  公开号：US4622332A

  公开（公告）日：1986-11-11
• US5276150A
  申请人：——

  公开号：US5276150A

  公开（公告）日：1994-01-04
• Synthesis and antihypertensive activity evaluation in spontaneously hypertensive rats of nitrendipine analogues
  作者：Kai Zhou、Xiao-meng Wang、Yi-zhi Zhao、Yong-xiao Cao、Qiang Fu、San-qi Zhang

  DOI：10.1007/s00044-010-9477-0

  日期：2011.11

  The antihypertensive activity of nitrendipine analogues can be improved by properly lengthening its alkyl chain in 3- or 5-position. Nitrendipine and its seven analogues were synthesized, and their antihypertensive activities in spontaneously hypertensive rats (SHR) were evaluated by ig administration. It was found that 5-n-heptyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [(+/-)-5] exhibited the strongest antihypertensive effect amongst eight compounds. (+)-5-n-heptyl 3-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate [(+)-5] was also prepared. Antihypertensive activities of (+/-)-5 and (+)-5 in SHR were compared. The results showed that (+/-)-5 and (+)-5 had a higher potency than nitrendipine, and (+)-isomer was 1.79-fold the raceme at a dose of 2 mg/kg.