1,3-di(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one | 131637-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1,3-di(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one
• 英文别名: 1,3-bis(prop-2-ynyl)-1H-1,3-benzimidazol-2(3H)-one；1,3-bis(prop-2-ynyl)benzimidazol-2-one
• CAS: 131637-62-2
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: KEFAURQXASTDLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-azidomethyl-2(1H)-quinolinone 、 1,3-di(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one 在 copper(ll) sulfate pentahydrate 、 sodium carbonate 、 维生素 C 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以85%的产率得到4-((4-((2-oxo-3-((1-((2-oxo-1,2-dihydroquinolin-4-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)-2,3-dihydrobenzo[d]imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)methyl)quinolin-2(1H)-one
  参考文献：
  名称：

  A click chemistry approach for the synthesis of cyclic ureido tethered coumarinyl and 1-aza coumarinyl 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis H37Rv and their in silico studies

  摘要：

  Nucleoside bases like uracil, pharmacophoric triazoles and benzimidazolones have been used during the present study to design molecular matrices for antitubercular activity, employing Click Chemistry. Click triazoles 4/7/10 have been obtained by the reaction of 4-(Azidomethyl)-2H-chromen-2-ones/quinolin-2(1H)-ones 3 and propargyl ethers 2/6/9 derived from theophylline/6-methyl uracil/2-benzimidazolone respectively. In addition to spectral data structures have been confirmed by single crystal X-ray diffraction studies in case of uracil bis alkyne (6) and theophylline mono triazole (4c). Theophylline linked mono triazoles, 4(a-d) and 6-methyl uracil linked bis triazoles, 7(a-e) have been found to inhibit Mycobacterium tuberculosis H37Rv with MIC values in the range 55.62-115.62 mu M. Benzimidazolone bis triazoles, 10(a-n) showed better activity with MIC in the range 2.33-18.34 mu M. Molecular modeling studies using Surflex-Dock algorithm supported our results.

  DOI：

  10.1016/j.bmc.2019.115054
• 作为产物：
  描述：

  乙基(2-氨基苯基)氨基甲酸酯 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 1,3-di(prop-2-yn-1-yl)-1,3-dihydro-2H-benzimidazol-2-one
  参考文献：
  名称：

  在转移催化条件下通过1,3-二氢-2H-苯并咪唑-2-酮与一些烷基卤的烷基化反应合成结构新颖的N-单和N，N'-二取代的苯并咪唑-2-酮衍生物

  摘要：

  通过将1,3-二氢-2H-苯并咪唑-2-并合反应并制得一系列N-单-和N，N'-二取代的苯并咪唑-2-一衍生物，它们任选地被两个仲胺官能团取代。在相转移催化条件下分别用各种烷基卤进行两步反应。一种合成的N，N-二取代的苯并咪唑-2-酮衍生物之一在其侧烯丙基取代基上进行了区域特异性的1,3-偶极环加成反应，并从4-氯苯并肟中原位生成了4-氯苄腈N-氧化物，得到了良好的产生相应的N，N'在侧链之一中包含2,5-二氢-异恶唑核的二取代衍生物。所有新化合物均通过物理和光谱数据充分表征。

  DOI：

  10.1002/jhet.3289

文献信息

• Triazolobenzo- and triazolothienodiazepines as potent antagonists of platelet activating factor
  作者：Armin Walser、Thomas Flynn、Carl Mason、Herman Crowley、Catherine Maresca、Bob Yaremko、Margaret O'Donnell

  DOI：10.1021/jm00107a048

  日期：1991.3

  A series of [1,2,4]triazolo[4,3-alpha][1,4]benzodiazepines bearing an ethynyl functionality at the 8-position and the isosteric thieno[3,2-f][1,2,4]triazolo[4,3-alpha][1,4]diazepines were prepared and evaluated as antagonists of platelet activating factor. The effects of substitution were explored in in vitro and in vivo test systems designed to measured PAF-antagonistic activity. Results are discussed and compared with previously published data. Many of the compounds had activity superior to WEB 2086, compound 1. In general, the thieno analogues exhibited better oral activity than the corresponding benzodiazepines. The duration of activity upon oral administration was modulated by the substitution on the acetylenic side chain. Compounds 71 and 81 were selected for further pharmacological evaluation as a result of their good oral potency and exceptionally long duration of action.
• Bis-7-hydroxy coumarinyl 1,2,3-triazole derived from benzimidazol-2-one as a water sensor: A fluorescence investigation
  作者：Netravati Khanapurmath、Madhuri D. Prabhu、Jayashree Tonannavar、Jagdish Tonannavar、Manohar V. Kulkarni

  DOI：10.1016/j.molliq.2020.113620

  日期：2020.9

  A click triazole derived from 4-azidomethyl-7-hydroxy-coumarin and 1,3-di(prop-2-ynyl)-1H-benzo[d] imidazol-2(3H)-one was found to exhibit ratiometric fluorescence response to water in DMF. Photophysical studies carried out for methoxy analogue of the title compound and analytical techniques employed in the study support involvement of water induced proton and photo induced electron transfer (PET) processes. Further, anion of the title compound generated in situ exhibited 'turn off' fluorescence for Fe3+, Cu2+, Hg2+ and Zn2+. PET on and off processes are also supported by DFT calculations. (C) 2020 Elsevier B.V. All rights reserved.
• WALSER, ARMIN;FLYNN, THOMAS;MASON, CARL;CROWLEY, HERMAN;MARESCA, CATHERIN+, J. MED. CHEM., 34,(1991) N, C. 1209-1221
  作者：WALSER, ARMIN、FLYNN, THOMAS、MASON, CARL、CROWLEY, HERMAN、MARESCA, CATHERIN+

  DOI：——

  日期：——