2-(1H-imidazol-1-yl)indan-1-one | 84391-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(1H-imidazol-1-yl)indan-1-one
• 英文别名: (+/-)-2,3-dihydro-2-(1H-imidazol-1-yl)-1H-inden-1-one；2-(1 H-1-imidazolyl)-1-indanone；2-Imidazol-1-yl-2,3-dihydroinden-1-one
• CAS: 84391-38-8
• 化学式: C₁₂H₁₀N₂O
• mdl: MFCD09031965
• 分子量: 198.224
• InChiKey: GKIFTFMJWDASNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1H-imidazol-1-yl)indan-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到2-(1H-imidazol-1-yl)indan-1-ol
  参考文献：
  名称：

  Synthesis and Evaluation of Heteroaryl-Substituted Dihydronaphthalenes and Indenes:  Potent and Selective Inhibitors of Aldosterone Synthase (CYP11B2) for the Treatment of Congestive Heart Failure and Myocardial Fibrosis

  摘要：

  In this study, the synthesis and biological evaluation of heteroaryl-substituted dihydronaphthalenes and indenes (1-16) is described. The compounds were tested for activity by use of human CYP11B2 expressed in fission yeast and V79 MZh cells and for selectivity by use of human CYP11B1, CYP17, and CYP19. The most active inhibitor was the 6-methoxydihydronaphthalene 4 (IC50 = 2 nM), showing a K-i value of 1.3 nM and a competitive type of inhibition. The 5-methoxyindene 3 was found to be the most selective CYP11B2 inhibitor (IC50 = 4 nM; CYP11B1 IC50 = 5684 nM), which also showed only marginal inhibition of human CYP3A4 and CYP2D6. Docking and molecular dynamics studies using our homology-modeled CYP11B2 structure were performed to understand some structure-activity relationships. Caco-2 cell experiments revealed highly cell-permeable compounds, and metabolic studies with 4 using rat liver microsomes showed sufficient stability.

  DOI：

  10.1021/jm060055x
• 作为产物：
  描述：

  咪唑 、 2-溴-1-茚满酮 以 N,N-二甲基甲酰胺 为溶剂， 以39%的产率得到2-(1H-imidazol-1-yl)indan-1-one
  参考文献：
  名称：

  Synthesis and Evaluation of Heteroaryl-Substituted Dihydronaphthalenes and Indenes:  Potent and Selective Inhibitors of Aldosterone Synthase (CYP11B2) for the Treatment of Congestive Heart Failure and Myocardial Fibrosis

  摘要：

  In this study, the synthesis and biological evaluation of heteroaryl-substituted dihydronaphthalenes and indenes (1-16) is described. The compounds were tested for activity by use of human CYP11B2 expressed in fission yeast and V79 MZh cells and for selectivity by use of human CYP11B1, CYP17, and CYP19. The most active inhibitor was the 6-methoxydihydronaphthalene 4 (IC50 = 2 nM), showing a K-i value of 1.3 nM and a competitive type of inhibition. The 5-methoxyindene 3 was found to be the most selective CYP11B2 inhibitor (IC50 = 4 nM; CYP11B1 IC50 = 5684 nM), which also showed only marginal inhibition of human CYP3A4 and CYP2D6. Docking and molecular dynamics studies using our homology-modeled CYP11B2 structure were performed to understand some structure-activity relationships. Caco-2 cell experiments revealed highly cell-permeable compounds, and metabolic studies with 4 using rat liver microsomes showed sufficient stability.

  DOI：

  10.1021/jm060055x

文献信息

• Heme Oxygenase Inhibition by 1-Aryl-2-(1H-imidazol-1-yl/1H-1,2,4-triazol-1-yl)ethanones and Their Derivatives
  作者：Gheorghe Roman、Jason Z. Vlahakis、Dragic Vukomanovic、Kanji Nakatsu、Walter A. Szarek

  DOI：10.1002/cmdc.201000120

  日期：2010.9.3

  been concerned with the design of selective inhibitors of heme oxygenases (HO‐1 and HO‐2). The majority of these were based on a four‐carbon linkage of an azole, usually an imidazole, and an aromatic moiety. In the present study, we designed and synthesized a series of inhibition candidates containing a shorter linkage between these groups, specifically, a series of 1‐aryl‐2‐(1H‐imidazol‐1‐yl/1H‐1

  我们研究小组先前的研究一直与血红素加氧酶选择性抑制剂（HO-1和HO-2）的设计有关。其中大多数是基于吡咯（通常是咪唑）和芳族部分的四碳键合。在本研究中，我们设计和合成了一系列抑制候选物，这些抑制物在这些基团之间具有较短的连接，特别是一系列的1-芳基-2-（1 H-咪唑-1-基/ 1 H-1,2,4-三唑-1-基）乙酮及其衍生物。关于HO-1抑制，发现产生最佳结果的芳族部分是卤素取代的残基，例如3-溴苯基，4-溴苯基和3,4-二氯苯基，或烃基残基，例如2-萘基，4-联苯基。 ，4-苄基苯基和4-（2-苯乙基）苯基。在咪唑酮中，发现有五个（36 – 39和44）对两种同功酶非常有效（IC 50 < 5μM）。相对于咪唑酮类，该系列相应的三唑酮的显示四种化合物（54，55，61，和62）的选择性指数> 50，而对HO-1有利。对于唑二氧戊环，发现其中两个（分别为80和85）分别具有2-萘基部分
• Novel Series of Imidazolyl Substituted Steroidal and Indan-1-One Derivatives
  申请人：Bansal Ranju

  公开号：US20090137541A1

  公开（公告）日：2009-05-28

  The present invention provides a novel series of imidazolyl substituted steroidal and indan-1-one derivatives and salts thereof having the following general structural formulae (A and B)

  本发明提供了一种新的咪唑基取代类固醇和茚环-1-酮衍生物及其盐，其具有以下一般结构式（A和B）。
• Compounds and Methods for Treating Cancer and Diseases of the Central Nervous System
  申请人：Gupta Ajay

  公开号：US20110319459A1

  公开（公告）日：2011-12-29

  Disclosed are compounds of the general formula (I): TC n D  (I), compositions comprising an effective amount of said compounds either alone or in combination with other chemotherapeutic agents, and methods useful for treating or preventing cancer and for inhibiting tumour tissue growth. These compounds attenuate the oxidative damage associated with increased heme-oxygenase activity and can reduce cell proliferation in transformed cells. In addition, the described compounds and compositions are useful as neuroprotectants and for treating or preventing neurodegenerative disorders and other diseases of the central nervous system.

  本发明涉及一般式（I）的化合物：TCnD（I），包括单独使用或与其他化疗药物联合使用的有效量的该化合物的组合物，以及用于治疗或预防癌症和抑制肿瘤组织生长的有用方法。这些化合物减弱了与增加血红素氧合酶活性相关的氧化损伤，并可以减少转化细胞中的细胞增殖。此外，所述化合物和组合物可用作神经保护剂，并用于治疗或预防中枢神经系统的神经退行性疾病和其他疾病。
• Imidazole hydrazone and hydrazine derivatives, production thereof and use in medicine
  申请人：G.D. Searle & Co.

  公开号：EP0057461A1

  公开（公告）日：1982-08-11

  Compounds of the general formulae: in which Ar and Ar1 which may be the same or different represent aromatic radicals optionally substituted once or more than by substituents selected from halogen. lower alkaly and lower alkoxy and Alk represents an alkylene group containing from 1 to 5 carbon atoms which alkylene group may be interrupted with a heteroatom: and acid addition salts thereof. These compounds have anti-anaerobe and also anti-fungal activity and are non-mutagenic.

  通式如下的化合物 其中 Ar 和 Ar1 可以相同或不同，代表芳香基，可任选被选自卤素、低级烷基和低级烷氧基的取代基一次或多次取代，Alk 代表含有 1 至 5 个碳原子的亚烷基，该亚烷基可被杂原子打断：及其酸加成盐。 这些化合物具有抗厌氧菌和抗真菌活性，并且不会产生突变。
• NOVEL SERIES OF IMIDAZOLYL SUBSTITUTED STEROIDAL AND INDAN-1-ONE DERIVATIVES
  申请人：Council of Scientific and Industrial Research

  公开号：EP1934241B1

  公开（公告）日：2012-11-14