3-氧代-4-(1H-咪唑-1-基)丁酸乙酯 | 103417-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-氧代-4-(1H-咪唑-1-基)丁酸乙酯
• 英文名称: ethyl 3-oxo-4-(1H-imidazol-1-yl)butanoate
• 英文别名: ethyl 4-(imidazol-1-yl) acetoacetate；ethyl 4-imidazol-1-yl-3-oxobutanoate
• CAS: 103417-70-5
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: LFXHAAPVAQEUOK-UHFFFAOYSA-N

物化性质

• 沸点：
  349.1±22.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  METHYL 2-{(4-NITROPHENYL)-METHYLENE}-3-OXOBUTYRATE 、 3-氧代-4-(1H-咪唑-1-基)丁酸乙酯 生成 2-Imidazol-1-ylmethyl-6-methyl-4-(2-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester
  参考文献：
  名称：

  摘要：

  DOI：
• 作为产物：
  描述：

  咪唑 、 4-氯乙酰乙酸乙酯 在 sodium hydride 作用下， 生成 3-氧代-4-(1H-咪唑-1-基)丁酸乙酯
  参考文献：
  名称：

  Design of an antithrombotic-antihypertensive agent (Wy 27569). Synthesis and evaluation of a series of 2-heteroaryl substituted dihydropyridines

  摘要：

  An approach to the design of potential combined antithrombotic-antihypertensive agents is described. A series of 1,4-dihydropyridines bearing a 1H-imidazol-1-yl or pyrid-3-yl substituted side chain in the 2-position were synthesized and tested for antihypertensive activity in spontaneously hypertensive rats and for inhibition of TXA2 synthetase in rabbit platelets, in vitro. 1,4-Dihydro-2-(1H-imidazol-1-ylmethyl)-6-methyl- 4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-ethyl 5-methyl diester (1) was shown to be similar in potency to nitrendipine as an antihypertensive agent. Compound 1 inhibited TXA2 synthetase in rabbit and human platelets in vitro and reduced plasma TXB2 levels in rats at antihypertensive dose levels. The reductions in thromboxane production observed in vivo and in vitro were accompanied by enhanced levels of 6-KPGF1 alpha, reflecting diversion of the arachidonic acid cascade toward prostacyclin synthesis.

  DOI：

  10.1021/jm00164a028

文献信息

• 1,4-dihydropyridines
  申请人：John Wyeth & Brother Limited

  公开号：US05064842A1

  公开（公告）日：1991-11-12

  The invention concerns compounds of formula ##STR1## or salts thereof; wherein: .alpha. and .beta. together represent a bond and additionally when B is an electron withdrawing group .alpha. can also represent OH and .beta. can represent hydrogen; Ar is an optionally substituted aryl or heteroaryl radical; R represents hydrogen or an optionally substituted alkyl or aralkyl group; R.sup.1 and R.sup.2 are the same or different and are selected from hydrogen and saturated or unsaturated, cyclic or acyclic aliphatic hydrocarbon residues optionally substituted by one or more groups selected from halogen, OH, carboxy, CN, alkoxy, alkylthio, aryloxy, alkoxycarbonyl, amino, substituted amino, and optioanlly substituted aryl or heteroaryl; A represents a group of formula --XR.sup.3 wherein X is a group of formula --(CHR.sup.6).sub.p --Y--(CHR.sup.7).sub.q -- in which formula: Y represents --O--, --S--, NR.sup.8 or a direct bond, p and q each represent 0, 1 or 2 R.sup.6, R.sup.7 and R.sup.8 independently represent hydrogen or lower alkyl and R.sup.3 is an optionally substituted nitrogen ring heteroaryl radical optionally containing other ring heteratoms selected from oxygen, nitrogen or sulphur; B represents haloalkyl, optionally substituted phenyl, --CN, --CHO, --CH(Oloweralkyl).sub.2 or --CH.sub.2 OH.

  本发明涉及以下式子的化合物或其盐：##STR1## 其中：.alpha.和.beta.一起代表一个键，此外，当B是一个电子提取基团时，.alpha.也可以代表OH，.beta.可以代表氢；Ar是一个可选的取代芳基或杂环芳基基团；R代表氢或一个可选的取代烷基或芳基烷基基团；R.sup.1和R.sup.2相同或不同，选择自氢和饱和或不饱和的、环状或非环状的脂肪烃残基，其可以被一个或多个从卤素、OH、羧基、CN、烷氧基、烷基硫基、芳基氧基、烷氧羰基、氨基、取代氨基和可选取代的芳基或杂环芳基中选择的基团所取代；A代表一个公式--XR.sup.3的基团，其中X代表一个公式--(CHR.sup.6).sub.p --Y--(CHR.sup.7).sub.q --，在该公式中：Y代表--O--、--S--、NR.sup.8或直接键，p和q分别代表0、1或2，R.sup.6、R.sup.7和R.sup.8独立地代表氢或低烷基，R.sup.3是一个可选的取代氮环杂芳基，其可以选自氧、氮或硫的其他环杂原子；B代表卤代烷基、可选取代的苯基、--CN、--CHO、--CH(O低烷基).sub.2或--CH.sub.2 OH。
• 1,4-Dihydropyridines
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0172029A1

  公开（公告）日：1986-02-19

  The invention concerns compounds of formula or salts thereof; wherein: Ar is an optionally substituted aryl radical; R represents hydrogen or an optionally substituted alkyl or aralkyl group; R' and R' are the same or different and are selected from hydrogen and saturated or unsaturated, cyclic or acyclic aliphatic hydrocarbon residues optionally substituted by one or more groups selected from halogen, OH, carboxy, CN, alkoxy, alkylthio, aryloxy, alkoxycarbonyl, amino, substituted amino, and optionally substituted aryl; A represents a group of formula -XR3 wherein X is (i) a group of formula - (CHR6)P-Y-(CHR7)q- or (ii) a group of formula - (CHR6)r-O-(CHR7) in which formulae: Y represents -S-, NR6 or a direct bond, p and q each represent O, or 2 providing that p and q do not both represent zero when Y is a direct bond; one or r and s represents O, or 2 and the other is zero; R6, R7 and R6 independently represent hydrogen or lower alkyl, and R3 is an optionally substituted nitrogen ring heteroaryl radical optionally containing other ring heteroatoms selected from oxygen, nitrogen or sulphur; B represents hydrogen, carboxyl, lower alkoxycarbonyl, lower alkyl optionally substituted by amino, lower alkoxy, lower alkoxycarbonyl or carboxyl, or amino optionally substituted by one or two lower alkyl groups, which compounds possess antihypertensive and antithrombotic activity.

  本发明涉及式 或其盐类；其中 Ar是任选取代的芳基；R代表氢或任选取代的烷基或芳烷基；R'和R'相同或不同，选自氢和饱和或不饱和、环状或非环状脂族烃残基，任选被一个或多个基团取代，这些基团选自卤素、OH、羧基、CN、烷氧基、烷硫基、芳氧基、烷氧基羰基、氨基、取代氨基和任选取代的芳基； A 代表式-XR3 的基团，其中 X 是 (i) 式-(CHR6)P-Y-(CHR7)q- 的基团，或 (ii) 式-(CHR6)r-O-(CHR7)的基团。 在这些式子中Y 代表-S-、NR6 或直接键，p 和 q 各自代表 O 或 2，条件是当 Y 为直接键时，p 和 q 不同时代表零；r 和 s 中的一个代表 O 或 2，另一个为零；R6、R7 和 R6 独立地代表氢或低级烷基，R3 是任选取代的氮环杂芳基，任选含有选自氧、氮或硫的其他环杂原子；B 代表氢、羧基、低级烷氧基羰基、任选被氨基取代的低级烷基、低级烷氧基、低级烷氧基羰基或羧基，或任选被一个或两个低级烷基取代的氨基，这些化合物具有抗高血压和抗血栓活性。
• ——
  作者：ARCHIBALD J. L.、 WARD T. J.、 OPALKO A.

  DOI：——

  日期：——
• US5068337A
  申请人：——

  公开号：US5068337A

  公开（公告）日：1991-11-26
• US5064842A
  申请人：——

  公开号：US5064842A

  公开（公告）日：1991-11-12