1-(4-氨基苯基)-2-(1H-咪唑-1-基)乙酮 | 73932-42-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-氨基苯基)-2-(1H-咪唑-1-基)乙酮
• 英文名称: 1-(4-aminophenyl)-2-(1H-imidazol-1-yl)ethanone
• 英文别名: 1-(4-aminophenyl)-2-imidazol-1-ylethanone
• CAS: 73932-42-0
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: QRMNVYHFJCGDDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  60.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基磺酰氯 、 1-(4-氨基苯基)-2-(1H-咪唑-1-基)乙酮 在 吡啶 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 6.0h， 以37%的产率得到N-[4-(2-咪唑-1-基乙酰基)苯基]甲烷磺酰胺
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of N-(benzoylalkyl)imidazoles and N-(.omega.-phenyl-.omega.-hydroxyalkyl)imidazoles

  摘要：

  A novel series of N-(benzoylalkyl)imidazoles and N-(omega-phenyl-omega-hydroxyalkyl)imidazoles was synthesized and evaluated for anticonvulsant activity in mice against maximal electroshock induced seizures. Some of the compounds showed an activity comparable to or better than phenytoin and phenobarbital. The N-[beta-[4-(beta-phenylethyl)phenyl]-beta-hydroxyethyl]imidazole (38) was selected for further studies; preclinical toxicology and additional efficacy evaluations are in progress. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00138a017
• 作为产物：
  描述：

  α-imidazolyl-(4-nitroacetophenone) hydrochloride 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以54%的产率得到1-(4-氨基苯基)-2-(1H-咪唑-1-基)乙酮
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of N-(benzoylalkyl)imidazoles and N-(.omega.-phenyl-.omega.-hydroxyalkyl)imidazoles

  摘要：

  A novel series of N-(benzoylalkyl)imidazoles and N-(omega-phenyl-omega-hydroxyalkyl)imidazoles was synthesized and evaluated for anticonvulsant activity in mice against maximal electroshock induced seizures. Some of the compounds showed an activity comparable to or better than phenytoin and phenobarbital. The N-[beta-[4-(beta-phenylethyl)phenyl]-beta-hydroxyethyl]imidazole (38) was selected for further studies; preclinical toxicology and additional efficacy evaluations are in progress. Structure-activity relationships are discussed.

  DOI：

  10.1021/jm00138a017

文献信息

• Imidazolium salts, intermediates thereto and their use
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0131302A2

  公开（公告）日：1985-01-16

  The imidazolium salts described are useful as antiarrhythmic agents. A method of treating arrhythmia by increasing the refractoriness of cardiac tissue is provided as well as pharmaceutical formulations containing such imidazolium salts.

  所述咪唑盐可用作抗心律失常药物。本文提供了一种通过增加心脏组织的折射性来治疗心律失常的方法，以及含有此类咪唑鎓盐的药物制剂。
• Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer
  作者：Bin Sun、Juma Hoshino、Katie Jermihov、Laura Marler、John M. Pezzuto、Andrew D. Mesecar、Mark Cushman

  DOI：10.1016/j.bmc.2010.05.042

  日期：2010.7

  A series of new resveratrol analogues were designed and synthesized and their inhibitory activities against aromatase were evaluated. The crystal structure of human aromatase (PDB 3eqm) was used to rationalize the mechanism of action of the aromatase inhibitor 32 (IC50 0.59 mu M) through docking, molecular mechanics energy minimization, and computer graphics molecular modeling, and the information was utilized to design several very potent inhibitors, including compounds 82 (IC50 70 nM) and 84 (IC50 36 nM). The aromatase inhibitory activities of these compounds are much more potent than that for the lead compound resveratrol, which has an IC50 of 80 mu M. In addition to aromatase inhibitory activity, compounds 32 and 44 also displayed potent QR2 inhibitory activity (IC50 1.7 mu M and 0.27 mu M, respectively) and the high-resolution X-ray structures of QR2 in complex with these two compounds provide insight into their mechanism of QR2 inhibition. The aromatase and quinone reductase inhibitors resulting from these studies have potential value in the treatment and prevention of cancer. (C) 2010 Elsevier Ltd. All rights reserved.
• Salerno; Sorrenti; Guerrera, Pharmazie, 1999, vol. 54, # 9, p. 685 - 690
  作者：Salerno、Sorrenti、Guerrera、Sarva、Siracusa、Di Giacomo、Vanella

  DOI：——

  日期：——
• NARDI, D.;TAJANA, A.;LEONARDI, A.;PENNINI, R.;PORTIOLI, F.;MAGISTRETTI, M+, J. MED. CHEM., 1981, 24, N 6, 727-731
  作者：NARDI, D.、TAJANA, A.、LEONARDI, A.、PENNINI, R.、PORTIOLI, F.、MAGISTRETTI, M+

  DOI：——

  日期：——
• US4581370A
  申请人：——

  公开号：US4581370A

  公开（公告）日：1986-04-08