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(E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(naphthalen-2-yl)prop-2-enone | 1332222-87-3

中文名称
——
中文别名
——
英文名称
(E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(naphthalen-2-yl)prop-2-enone
英文别名
(E)-3-(2-butyl-5-chloro-3-methylimidazol-4-yl)-1-naphthalen-2-ylprop-2-en-1-one
(E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(naphthalen-2-yl)prop-2-enone化学式
CAS
1332222-87-3
化学式
C21H21ClN2O
mdl
——
分子量
352.864
InChiKey
BGZSMCMUMZCHBD-OUKQBFOZSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    5.8
  • 重原子数:
    25
  • 可旋转键数:
    6
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.24
  • 拓扑面积:
    34.9
  • 氢给体数:
    0
  • 氢受体数:
    2

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(naphthalen-2-yl)prop-2-enone溶剂黄146一水合肼 作用下, 以91%的产率得到1-(5-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-3-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone
    参考文献:
    名称:
    Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors
    摘要:
    A series of novel 2-butyl-4-chloro-1-methylimidazole embedded aryl and heteroaryl derived chalcones and pyrazoles were synthesized and evaluated for their angiotensin converting enzyme (ACE) inhibitory activity. The condensation of 2-butyl-4-chloro-1-methylimidazole-5-carboxaldehyde with various aryl and heteroaryl methyl ketones in the presence of 10% aqueous NaOH in methanol proceeded efficiently to give the respective chalcones in very good yields. Further, the reaction of chalcones with hydrazine hydrate in acetic acid gave substituted pyrazole analogues. Screening all 36 new compounds using ACE inhibition assay, resulted chalcones with better ACE inhibitory activity compared to the respective pyrazole analogues. Among the chalcones 4a-r, three compounds, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(5-chlorothiophen-2-yl)prop-2-enone 4i, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(1H-pyrrol-2-yl)prop-2-enone 4l, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(dibenzo[b,d] thiophen-2-yl)prop-2-enone 4q were resulted as most active ACE inhibitors with IC50 of 3.60 mu M, 2.24 mu M, and 2.68 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2011.06.085
  • 作为产物:
    描述:
    咪唑醛 在 sodium hydride 、 sodium hydroxide 作用下, 以 甲醇N,N-二甲基甲酰胺 为溶剂, 反应 4.0h, 生成 (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(naphthalen-2-yl)prop-2-enone
    参考文献:
    名称:
    Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors
    摘要:
    A series of novel 2-butyl-4-chloro-1-methylimidazole embedded aryl and heteroaryl derived chalcones and pyrazoles were synthesized and evaluated for their angiotensin converting enzyme (ACE) inhibitory activity. The condensation of 2-butyl-4-chloro-1-methylimidazole-5-carboxaldehyde with various aryl and heteroaryl methyl ketones in the presence of 10% aqueous NaOH in methanol proceeded efficiently to give the respective chalcones in very good yields. Further, the reaction of chalcones with hydrazine hydrate in acetic acid gave substituted pyrazole analogues. Screening all 36 new compounds using ACE inhibition assay, resulted chalcones with better ACE inhibitory activity compared to the respective pyrazole analogues. Among the chalcones 4a-r, three compounds, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(5-chlorothiophen-2-yl)prop-2-enone 4i, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(1H-pyrrol-2-yl)prop-2-enone 4l, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(dibenzo[b,d] thiophen-2-yl)prop-2-enone 4q were resulted as most active ACE inhibitors with IC50 of 3.60 mu M, 2.24 mu M, and 2.68 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
    DOI:
    10.1016/j.bmc.2011.06.085
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文献信息

  • Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors
    作者:Srinivas Kantevari、Dinesh Addla、Pankaj K. Bagul、Balasubramanian Sridhar、Sanjay K. Banerjee
    DOI:10.1016/j.bmc.2011.06.085
    日期:2011.8
    A series of novel 2-butyl-4-chloro-1-methylimidazole embedded aryl and heteroaryl derived chalcones and pyrazoles were synthesized and evaluated for their angiotensin converting enzyme (ACE) inhibitory activity. The condensation of 2-butyl-4-chloro-1-methylimidazole-5-carboxaldehyde with various aryl and heteroaryl methyl ketones in the presence of 10% aqueous NaOH in methanol proceeded efficiently to give the respective chalcones in very good yields. Further, the reaction of chalcones with hydrazine hydrate in acetic acid gave substituted pyrazole analogues. Screening all 36 new compounds using ACE inhibition assay, resulted chalcones with better ACE inhibitory activity compared to the respective pyrazole analogues. Among the chalcones 4a-r, three compounds, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(5-chlorothiophen-2-yl)prop-2-enone 4i, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(1H-pyrrol-2-yl)prop-2-enone 4l, (E)-3-(2-butyl-4-chloro-1-methyl-1H-imidazol-5-yl)-1-(dibenzo[b,d] thiophen-2-yl)prop-2-enone 4q were resulted as most active ACE inhibitors with IC50 of 3.60 mu M, 2.24 mu M, and 2.68 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
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