4-benzoyl-5-methyl-1H-imidazol-2(3H)-one | 75237-40-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-benzoyl-5-methyl-1H-imidazol-2(3H)-one
• 英文别名: 4-benzoyl-5-methyl-1,3-dihydro-imidazol-2-one；4-Benzoyl-5-methyl-1,3-dihydro-imidazol-2-on；4-benzoyl-1,3-dihydro-5-methyl-2H-imidazol-2-one；4-Benzoyl-5-methyl-1,3-dihydro-2H-imidazol-2-one；4-benzoyl-5-methyl-1,3-dihydroimidazol-2-one
• CAS: 75237-40-0
• 化学式: C₁₁H₁₀N₂O₂
• 分子量: 202.213
• InChiKey: KFDCBUKKFPXAJS-UHFFFAOYSA-N

物化性质

• 熔点：
  255.5-258 °C
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-benzoyl-5-methyl-1H-imidazol-2(3H)-one 在 palladium on activated charcoal 、 溶剂黄146 作用下， 生成 4-benzyl-5-methyl-1,3-dihydro-imidazol-2-one
  参考文献：
  名称：

  dl-desthiobiotin和相关物质的简单合成。

  摘要：

  DOI：

  10.1021/ja01228a008
• 作为产物：
  描述：

  (E)-3-(dimethylamino)-1-phenylbut-2-ene-1-one 在 盐酸 、 甲醇 、 ammonium acetate 、 水 、 potassium hydroxide 、 sodium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 64.5h， 生成 4-benzoyl-5-methyl-1H-imidazol-2(3H)-one
  参考文献：
  名称：

  通过烯胺酮从芳基甲基酮简单合成 4-aroyl-5-methyl-1H-imidazol-2(3H)-one 衍生物（Enoxymone 类似物）

  摘要：

  芳基甲基酮 1a-e 与 N,N-二甲基乙酰胺二甲基乙缩醛 (DMADMA) (E)-1aryl-3-(二甲氨基)-but-2-en-1-ones 2a-e 一起得到。在与乙酸铵的反应中取代 N,N-(二甲氨基) 基团得到相应的 (Z)-3-氨基-1-芳基-丁-2-烯-1 酮 3a-e。在 3a-e 与偶氮二羧酸二乙酯的反应中，形成了中间体 4a-e，在大多数情况下，它们无需分离就环化为乙基（5-芳酰基-4-甲基-2-氧代-2,3-二氢-1H-咪唑-1-基)氨基甲酸酯5a-e。酯基水解，然后中间体 6a-c,e 脱羧和脱氨基，生成 4-aroyl-5-methyl-1 Himidazol-2(3H)-ones 7a-c,e。

  DOI：

  10.3998/ark.5550190.p008.236

文献信息

• 4-Aroylimidazol-2-ones and their use as pharmaceuticals
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04405635A1

  公开（公告）日：1983-09-20

  Novel 4-aroylimidazol-2-ones of the following general structure which are useful as antihypertensives, cardiotonics, antithrombotics, bronchodilators and uterospasmolytics ##STR1## 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, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, methylenedioxy, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulfoxide, C.sub.1-4 alkylsulfone, CF.sub.3, --SO.sub.2 N(R.sub.2).sub.2, NR.sub.3 R.sub.4, pyrrolidino, piperidino, morpholino, piperazino or N'-alkyl-piperazino, R is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkylcarbonyl or benzyl; each of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are hydrogen or C.sub.1-4 alkyl; and the pharmaceutically acceptable salts thereof.

  以下是上述结构的4-芳基咪唑啉-2-酮类化合物的中文翻译：Ar为2-呋喃基、2-噻吩基或苯基，后者可以选择性地用一个或两个X基团取代；X为卤素、羟基、C.sub.1-4烷基、C.sub.1-4烷氧基、亚甲二氧基、C.sub.1-4烷硫基、C.sub.1-4烷基亚氧基、C.sub.1-4烷基磺醚基、CF.sub.3、--SO.sub.2 N(R.sub.2).sub.2、NR.sub.3 R.sub.4、吡咯啉基、哌啶基、吗啉基、哌嗪基或N'-烷基-哌嗪基，R为氢、C.sub.1-4烷基、C.sub.1-4烷基羰基或苄基；R.sub.1、R.sub.2、R.sub.3和R.sub.4中的每一个均为氢或C.sub.1-4烷基；以及其药学上可接受的盐。
• 4-(4-Guanidinobenzoyl)-2-imidazolones and Related Compounds: Phosphodiesterase Inhibitors and Novel Cardiotonics with Combined Histamine H2 Receptor Agonist and PDE III Inhibitor Activity
  作者：D. Glaß、A. Buschauer、H. Tenor、S. Bartel、L. Will-Shahab、E.-G. Krause

  DOI：10.1002/ardp.19953281005

  日期：——

  phosphodiesterase (PDE) inhibitor enoximone and guanidine‐type histamine H2 receptor agonists such as arpromidine. All compounds are para‐substituted 4‐benzoyl‐5‐alkyl‐2‐imidazolones. H2 agonism was incorporated by p‐(hetero)arylalkyl substituents, in particular by an imidazolylpropyl guanidine group. In addition analogous ureas, cyanoguanidines, alkyl guanidine carboxylates, and amides were prepared. These

  合成了一系列新型正性肌力药物，旨在结合咪唑酮型磷酸二酯酶（PDE）抑制剂依诺昔酮和胍型组胺 H2 受体激动剂阿普米啶的药效团。所有化合物都是对位取代的 4-苯甲酰基-5-烷基-2-咪唑酮。通过对（杂）芳基烷基取代基，特别是通过咪唑基丙基胍基团引入 H2 激动作用。此外，还制备了类似的脲、氰基胍、烷基胍羧酸盐和酰胺。这些官能团要么直接连接到苯环上，要么通过适当的间隔基连接。筛选化合物在分离的电刺激豚鼠乳头肌中的正性肌力活性和抑制 PDE III（cGMP 抑制的 cAMP PDE，从豚鼠心脏分离）。获得的强心剂要么是 PDE III 抑制剂，其中一些药物的效力是依诺昔酮的 3 倍，要么是结合了 PDE III 抑制剂和组胺 H2 受体激动剂活性的药理学杂种。这些混合物是乳头肌中最有效的正性肌力物质，可能是由于它们的协同作用机制。通过用 H2 拮抗剂法莫替丁 (10 μM) 预处理以及使用离体
• 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-(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。
• 4-Aroyl-1,3-dihydro-2H-imidazol-2-ones, a new class of cardiotonic agents
  作者：Richard A. Schnettler、Richard C. Dage、J. Martin Grisar

  DOI：10.1021/jm00354a017

  日期：1982.12

  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.