(1H-benzo[d]imidazol-2-yl)(4-methoxyphenyl)methanone | 15449-89-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1H-benzo[d]imidazol-2-yl)(4-methoxyphenyl)methanone
• 英文别名: 2-(p-Methoxybenzoyl)-benzimidazol；2-(4-Methoxy-benzoyl)-benzimidazol；2-<4-Methoxy-benzoyl>-benzimidazol；2-(4-methoxybenzoyl)benzimidazole；(1H-benzoimidazol-2-yl)-(4-methoxy-phenyl)-methanone；1H-benzimidazol-2-yl-(4-methoxyphenyl)methanone
• CAS: 15449-89-5
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: UBLNXNMKBFDVMO-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C(Solv: 1,4-dioxane (123-91-1))
• 沸点：
  487.8±47.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1H-benzo[d]imidazol-2-yl)(4-methoxyphenyl)methanone 在 三溴化硼 、 sodium hydride 、 potassium carbonate 、 caesium carbonate 作用下， 以 正己烷 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 95.75h， 生成 (4-((3-bromopyridin-2-yl)oxy)phenyl)(1-methyl-1H-benzo[d]imidazol-2-yl)methanone
  参考文献：
  名称：

  Synthesis and in vitro characterization of cinnoline and benzimidazole analogues as phosphodiesterase 10A inhibitors

  摘要：

  Fifteen cinnoline analogues and six benzimidazole phosphodiesterase 10A (PDE10A) inhibitors were synthesized as potential PET radiopharmaceuticals and their in vitro activity as PDE10A inhibitors was determined. Nine out of twenty-one compounds were potent inhibitors of PDE10A with IC50 values ranging from 1.5 to 18.6 nM. Notably, the IC50 values of compounds 26a, 26b, and 33c were 1.52 +/- 0.18, 2.86 +/- 0.10, and 3.73 +/- 0.60 nM, respectively; these three compounds also showed high in vitro selectivity (> 1000-fold) for PDE10A over PDE 3A/3B, PDE4A/4B. The high potency and selectivity of these three compounds suggests that they could be radiolabeled with PET radionuclides for further evaluation of their in vivo pharmacological behavior and ability to quantify PDE10A in the brain. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.054
• 作为产物：
  描述：

  2-(4-methoxybenzyl)-1H-benzo[d]imidazole 在 N-羟基邻苯二甲酰亚胺 、 氧气 、 cobalt(II) diacetate tetrahydrate 作用下， 以 乙酸丁酯 为溶剂， 反应 12.0h， 以92%的产率得到(1H-benzo[d]imidazol-2-yl)(4-methoxyphenyl)methanone
  参考文献：
  名称：

  Co/NHPI 介导的药物相关分子中苄基 C-H 键的有氧氧化†

  摘要：

  已经确定了一种简单的钴（ II ）/ N-羟基邻苯二甲酰亚胺催化剂体系，用于将药学相关的（杂）芳烃中的苄基亚甲基选择性转化为相应的（杂）芳基酮。自由基反应途径可耐受电子多样化的苄基 C-H 键，这与最近由苄基 C-H 键去质子化引发的氧化反应形成鲜明对比。反应在实际反应条件下进行（1 M 底物在 BuOAc 或 EtOAc 溶剂中，12 小时，90–100 °C），并且它们耐受常见的杂环，例如吡啶和咪唑。一种无钴、电化学、NHPI 催化氧化方法克服了抑制化学反应的螯合底物所遇到的挑战。有氧氧化方法的实用性在与工艺相关的反应条件下对候选药物 ( AMG 579 ) 的关键中间体进行多克合成中得到了体现。

  DOI：

  10.1039/c6sc03831j

文献信息

• Microwave supported synthesis of some novel 1,3-Diarylpyrazino[1,2-a]benzimidazole derivatives and investigation of their anticancer activities
  作者：Seref Demirayak、Ismail Kayagil、Leyla Yurttas

  DOI：10.1016/j.ejmech.2010.11.007

  日期：2011.1

  The syntheses of 1,3-diarylpyrazino[1,2-a]benzimidazole derivatives and the investigation of their anticancer activities were studied. For this, 2-aryloylbenzimidazole derivatives were reacted with 2-bromoacetophenones in acetone to give 1-(2-aryl-2-oxoethyl)-2-aryloylbenzimidazoles. The resulting materials were reacted with ammonium acetate in acetic acid to obtain the aimed compound. In this reaction

  研究了1，3-二芳基吡嗪并[1,2-a]苯并咪唑衍生物的合成及其抗癌活性。为此，使2-芳基苯并咪唑衍生物与2-溴苯乙酮在丙酮中反应，得到1-（2-芳基-2-氧代乙基）-2-芳基苯并咪唑。使所得物质与乙酸铵在乙酸中反应，得到目标化合物。在该反应中，采用微波辐射法作为反应条件。研究了所得化合物的抗癌活性。观察到某些化合物显示出显着的抗癌活性。
• Synthesis of 1-aryl-3H-[1,2,5]triazepino[5,4-a]benzimidazol-4(5H)-ones and quantum chemical investigation of the rotamers of the Boc-protected hydrazide key intermediate
  作者：Mátyás Milen、Tímea Szabó、András Dancsó、Péter Ábrányi-Balogh、Balázs Volk

  DOI：10.1016/j.mencom.2019.05.017

  日期：2019.5

  4-a]benzimidazol-4(5H)-ones were obtained in five steps involving C-acylation of benzimidazole, its N-alkylation with ethyl bromoacetate, the ester hydrolysis, condensation with BocNHNH2, and the acid-catalyzed heterocyclization of thus obtained 2-(2-aroyl-1H-benzimidazol-1-yl)-N′-(tert-butoxycarbonyl)acetohydrazides. The geometry of tert-butyl carbazate rotamers was estimated with quantum chemical

  在五个步骤中获得了3H- [1,2,5]三唑并[5,4-a]苯并咪唑-4（5H）-，这些步骤涉及苯并咪唑的C-酰化，溴乙酸乙酯的N-烷基化，酯水解，缩合。用BocNHNH 2，并由此酸催化2-（2-芳酰基-1H-苯并咪唑-1-基）-N′-（叔丁氧基羰基）乙酰肼。氨基甲酸叔丁酯旋转异构体的几何形状是通过量子化学计算来估计的。
• The design, synthesis, and biological evaluation of potent receptor tyrosine kinase inhibitors
  作者：Moon H. Kim、Amy Lew Tsuhako、Erick W. Co、Dana T. Aftab、Frauke Bentzien、Jason Chen、Wei Cheng、Stefan Engst、Levina Goon、Rhett R. Klein、Donna T. Le、Morrison Mac、Jason J. Parks、Fawn Qian、Monica Rodriquez、Thomas J. Stout、Jeffrey H. Till、Kwang-Ai Won、Xiang Wu、F. Michael Yakes、Peiwen Yu、Wentao Zhang、Yeping Zhao、Peter Lamb、John M. Nuss、Wei Xu

  DOI：10.1016/j.bmcl.2012.06.029

  日期：2012.8

  Variously substituted indolin-2-ones were synthesized and evaluated for activity against KDR, Flt-1, FGFR-1 and PDGFR. Extension at the 5-position of the oxindole ring with ethyl piperidine (compound 7i) proved to be the most beneficial for attaining both biochemical and cellular potencies. Further optimization of 7i to balance biochemical and cellular potencies with favorable ADME/ PK properties led to the identification of 8h, a compound with a clean CYP profile, acceptable pharmacokinetic and toxicity profiles, and robust efficacy in multiple xenograft tumor models. (c) 2012 Elsevier Ltd. All rights reserved.
• Dostert; Langlois; Guerret, European Journal of Medicinal Chemistry, 1980, vol. 15, # 3, p. 199 - 205
  作者：Dostert、Langlois、Guerret、et al.

  DOI：——

  日期：——