(2S,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(p-toluenesulfonyloxy)methyl]-1,3-dioxolane | 150034-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(p-toluenesulfonyloxy)methyl]-1,3-dioxolane
• 英文别名: [(2S,4R)-2-[2-(4-chlorophenyl)ethyl]-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 150034-35-8
• 化学式: C₂₃H₂₅ClN₂O₅S
• 分子量: 476.981
• InChiKey: WMPFDNQTDKVIHW-GGAORHGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(p-toluenesulfonyloxy)methyl]-1,3-dioxolane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 HemeOxDB18
  参考文献：
  名称：

  Imidazole−Dioxolane Compounds as Isozyme-Selective Heme Oxygenase Inhibitors

  摘要：

  Several imidazole-dioxolane compounds were synthesized and evaluated as novel inhibitors of heme oxygenase (HO). These compounds, which include (2R, 4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl) methyl]-4-methyl-1,3-dioxolane ( 1) hydrochloride, are structurally distinct from metalloporphyrin HO inhibitors and lack the aminothiophenol moiety of azalanstat. They were found to be highly selective for the HO-1 isozyme ( stress induced) and had substantially less inhibitory potency toward HO-2, the constitutive isozyme. These imidazole-dioxolane compounds are the first of their type known to exhibit this isozyme-selective HO inhibition.

  DOI：

  10.1021/jm0511435
• 作为产物：
  描述：

  4-(4-chlorophenyl)-1-(1H-imidazol-1-yl)-2-butanone 、 (R)-(-)-对甲基苯磺酸-2,2-二甲基-1,3-二氧戊环基-4-甲酯 在 对甲苯磺酸 、 正丁醇 作用下， 生成 (2S,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(p-toluenesulfonyloxy)methyl]-1,3-dioxolane 、 (2R,4R)-2-[2-(4-chlorophenyl)ethyl]-2-[(1H-imidazol-1-yl)methyl]-4-[(p-toluenesulfonyloxy)methyl]-1,3-dioxolane
  参考文献：
  名称：

  选择性抑制哺乳动物羊毛甾醇14α-脱甲基酶：降低胆固醇的可能策略。

  摘要：

  DOI：

  10.1021/jm00067a022

文献信息

• 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。
• Synthesis and evaluation of azalanstat analogues as heme oxygenase inhibitors
  作者：Jason Z. Vlahakis、Robert T. Kinobe、Raymond J. Bowers、James F. Brien、Kanji Nakatsu、Walter A. Szarek

  DOI：10.1016/j.bmcl.2004.12.075

  日期：2005.3

  Several analogues based on the lead structure of azalanstat were synthesized and evaluated as novel inhibitors of heme oxygenase (HO). A number of these compounds, which are structurally distinct from metalloporphyrin HO inhibitors, were found to be selective for the HO-1 isozyme (stress induced), and had substantially less inhibitory activity on HO-2, the constitutive isozyme. (c) 2005 Elsevier Ltd. All rights reserved.
• HEME-OXYGENASE INHIBITORS AND USE OF THE SAME IN THE TREATMENT OF CANCER AND DISEASES OF THE CENTRAL NERVOUS SYSTEM
  申请人：Osta Biotechnologies

  公开号：EP2173740A1

  公开（公告）日：2010-04-14
• US5158949A
  申请人：——

  公开号：US5158949A

  公开（公告）日：1992-10-27
• US7943650B2
  申请人：——

  公开号：US7943650B2

  公开（公告）日：2011-05-17