1,3-dihydro-4-(3,4-dimethoxybenzoyl)-5-methyl-2H-imidazol-2-one | 82709-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dihydro-4-(3,4-dimethoxybenzoyl)-5-methyl-2H-imidazol-2-one
• 英文别名: 4-(3,4-Dimethoxybenzoyl)-5-methyl-1,3-dihydroimidazol-2-one
• CAS: 82709-62-4
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: PRICITVOSXJGJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基-1,3-二氢咪唑-2-酮 、 3,4-二甲氧基苯甲酰氯 在 三氯化铝 作用下， 以 硝基苯 为溶剂， 反应 6.0h， 以32%的产率得到1,3-dihydro-4-(3,4-dimethoxybenzoyl)-5-methyl-2H-imidazol-2-one
  参考文献：
  名称：

  4-Aroyl-1,3-dihydro-2H-imidazol-2-ones, a new class of cardiotonic agents

  摘要：

  A series of 4-aroyl-1,3-dihydro-2H-imidazol-2-ones was synthesized and evaluated for pharmacological activity in the anesthetized dog. Most members of this series produced dose-related increases in cardiac contractile force as well as relatively minor increases in heart rate and decreases in systemic arterial blood pressure that were not blocked by propranolol. In general, 4-methoxy or 4-methylthiobenzoyl substitution afforded compounds of greatest inotropic potency. 1,3-Dihydro-4-(4-methoxybenzoyl)-5-methyl-2H-imidazol-one (6) was shown to produce a dose-related positive inotropic effect and reverse the depressant effect of pentobarbital on cardiac pump function in the dog heart-lung preparation. The cardiotonic activity of this series may have important utility in the treatment of congestive heart failure. 1,3-Dihydro-4-[4-(methylthio)benzoyl]-5-methyl-2H-imidazol-2-one (17) was chosen for human studies and is currently undergoing clinical trials.

  DOI：

  10.1021/jm00354a017

文献信息

• Novel 4-aroylimidazol-2-ones
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0058435A2

  公开（公告）日：1982-08-25

  Novel 4-aroylimidazol-2-ones of the following general structure which are useful as antihypertensives, cardiotonics and antithrombotics wherein Ar is 2-furyl, 2-thienyl or phenyl, the latter of which may optionally be substituted with one or two X groups; X is halogen, hydroxy, C1-4 alkyl, C1-4 alkoxy, methylenedioxy, C1-4 alkylthio, C1-4 alkylsulfoxide, C1-4 alkylsufone, CF3, -SO2N(R2)2, NR3R4, pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino, R is hydrogen, C1-4 alkyl, C1-4 alkylcarbonyl or benzyl; each of R1, R2, R3 and R4 are hydrogen or C1-4 alkyl; and the pharmaceutically acceptable salts thereof.

  具有以下一般结构的新型 4-芳基咪唑-2-酮，可用作抗高血压药、强心剂和抗血栓药 其中 Ar 是 2-呋喃基、2-噻吩基或苯基，后者可任选被一个或两个 X 基团取代；X 是卤素、羟基、C1-4 烷基、C1-4 烷氧基、亚甲基二氧基、C1-4 烷硫基、C1-4 烷基亚砜、C1-4 烷基砜、CF3、-SO2N(R2)2、NR3R4、吡咯烷基、哌啶基、吗啉基、哌嗪基或 N'- 烷基哌嗪基，R 是氢、C1-4 烷基、C1-4 烷基羰基或苄基；R1、R2、R3 和 R4 各为氢或 C1-4 烷基；及其药学上可接受的盐类。
• 4-Aminomethyl-5-acyl-1,3-dihydro-2H-imidazol-2-ones
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0064704A1

  公开（公告）日：1982-11-17

  1,3-Dihydro-2H-imidazol-2-ones having 5-acyl and 4-(substituted amino) methyl substituents, are useful as cardiotonics, antihypertensives and antithrombotic agents. The compounds are obtained by the reaction of an appropriate amine with a substituted 4-bromomethyl-1,3-dihydro-2H-imidazol-2-one.

  具有 5-酰基和 4-（取代氨基）甲基取代基的 1,3-二氢-2H-咪唑-2-酮可用作强心剂、降压药和抗血栓药。这些化合物是通过适当的胺与取代的 4-溴甲基-1,3-二氢-2H-咪唑-2-酮反应得到的。
• 4-(4-Phenyl-1-piperidinyl)methyl-5-acyl-1,3-dihydro-2H-imidazol-2-ones
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0064707A1

  公开（公告）日：1982-11-17

  1,3-Dihydro-2H-imidazol-2-ones having 5-acyl and 4-(4-phenyl-1-piperidinyl)methyl substituents, are useful as cardiotonics, antihypertensives and antithrombotic agents. The compounds are obtained by the reaction of an appropriate substituted piperidine with a substituted 4-bromomethyl-1,3-dihydro-2H-imidazol-2-one.

  具有 5-酰基和 4-(4-苯基-1-哌啶基)甲基取代基的 1,3-二氢-2H-咪唑-2-酮可用作强心剂、抗高血压药和抗血栓药。 这些化合物是由适当的取代哌啶与取代的 4-溴甲基-1,3-二氢-2H-咪唑-2-酮反应而得。
• SCHNETTLER, R. A.;DAGE, R. C.;GRISAR, J. M., J. MED. CHEM., 1982, 25, N 12, 1477-1481
  作者：SCHNETTLER, R. A.、DAGE, R. C.、GRISAR, J. M.

  DOI：——

  日期：——
• 5-Oxymethyl-4-acyl-1,3-dihydro-2H-imidazol-2-ones
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0065165B1

  公开（公告）日：1986-06-18