(±)-1-(2-azido-2-(2, 4-dichlorophenyl)ethyl)-1H-imidazole | 94038-18-3

• 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: (±)-1-(2-azido-2-(2, 4-dichlorophenyl)ethyl)-1H-imidazole
• 英文别名: 1-(2-azido-2-(2,4-dichlorophenyl)ethyl)-1H-imidazole；1-[2-Azido-2-(2,4-dichlorophenyl)ethyl]imidazole
• CAS: 94038-18-3
• 化学式: C₁₁H₉Cl₂N₅
• 分子量: 282.132
• InChiKey: ZYOZOFLDVWJMLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-1-(2-azido-2-(2, 4-dichlorophenyl)ethyl)-1H-imidazole 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 以77.4%的产率得到1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethylamine
  参考文献：
  名称：

  [EN] INHIBITORS OF ATP SYNTHASE - COSMETIC AND THERAPEUTIC USES
  [FR] INHIBITEURS D'UTILISATIONS COSMÉTIQUES ET THÉRAPEUTIQUES D'ATP SYNTHASE

  摘要：

  本公开教导了IF1蛋白活性是寿命的分子决定因素，通过支持实验数据解释了不同物种具有不同最大寿命的原因。本公开教导了使用IF1蛋白/片段（或其序列变体）或其融合蛋白作为减缓/延迟/减少受试者衰老的药剂，可选作为化妆品组分，可选用于治疗与年龄相关的疾病/失调。此外，本公开还教导了其他F1F0 ATP水解抑制剂，包括多种不同支架的小分子，用于此目的。此外，通过支持实验数据，本公开还教导了减缓ATP合成酶的ATP水解模式的化合物对于治疗各种疾病和失调的有用性，包括癌症，特别是利用Warburg效应的癌症。

  公开号：

  WO2022157548A1
• 作为产物：
  描述：

  2,2',4'-三氯苯乙酮 在 sodium tetrahydroborate 、 diazabicycloundecane 、 叠氮磷酸二苯酯 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 生成 (±)-1-(2-azido-2-(2, 4-dichlorophenyl)ethyl)-1H-imidazole
  参考文献：
  名称：

  N -[1-Aryl-2-(1-imidazolo)ethyl]-guanidine derivatives as potent inhibitors of the bovine mitochondrial F 1 F 0 ATP hydrolase

  摘要：

  A series of substituted guanidine derivatives were prepared and evaluated as potent and selective inhibitors of mitochondrial F1F0 ATP hydrolase. The initial thiourethane derived lead molecules possessed intriguing in vitro pharmacological profiles, though contained moieties considered non-drug-like. Analogue synthesis efforts led to compounds with maintained potency and superior physical properties. Small molecules in this series which potently and selectivity inhibit ATP hydrolase and not ATP synthase may have utility as cardioprotective agents. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.11.077

文献信息

• [EN] THERAPEUTIC INHIBITORS OF THE REVERSE MODE OF ATP SYNTHASE<br/>[FR] INHIBITEURS THÉRAPEUTIQUES DU MODE INVERSE DE L'ATP SYNTHASE
  申请人：FORREST MICHAEL DAVID

  公开号：WO2018134265A1

  公开（公告）日：2018-07-26

  Compounds of the following formula, and pharmaceutically-acceptable salts, solvates, hydrates and prodrugs thereof, formula (A) are useful to preferentially inhibit the ATP-hydrolysing mode of ATP synthase, and are thereby useful for treating various diseases and disorders including cancer, particularly cancers that utilise the Warburg effect.

  以下化合物的公式，以及其药用可接受的盐、溶剂合物、水合物和前药，公式（A）可用于优先抑制ATP合成酶的ATP水解模式，并因此可用于治疗各种疾病和紊乱，包括癌症，特别是利用Warburg效应的癌症。
• A convergent, scalable and stereoselective synthesis of azole CYP51 inhibitors
  作者：Galina Lepesheva、Plamen Christov、Gary A. Sulikowski、Kwangho Kim

  DOI：10.1016/j.tetlet.2017.09.070

  日期：2017.11

  azole-based CYP51 inhibitors is an active area of research across disciplines of biochemistry, pharmacology and infectious disease. Support of in vitro and in vivo studies require the development of robust asymmetric routes to single enantiomer products of this class of compounds. Herein, we describe a scalable and enantioselective synthesis to VNI and VFV, the two potent inhibitors of protozoan sterol

  唑基CYP51抑制剂的研究和开发是跨生物化学，药理学和传染病学科的活跃研究领域。体外和体内研究的支持要求开发出鲁棒的不对称途径，以制备此类化合物的单个对映体产物。在这里，我们描述了对VNI和VFV的可扩展和对映选择性合成，VNI和VFV是原生动物固醇14α-脱甲基酶（CYP51）的两种有效抑制剂，目前正考虑用于Chagas病的临床试验。关键的转化是雅各布森水解动力学拆分（HKR）反应。合成路线的实用性通过制备> 25 g的VNI和VFV单一对映体来说明。
• Azide-enolate 1,3-dipolar cycloaddition in the synthesis of novel triazole-based miconazole analogues as promising antifungal agents
  作者：Davir González-Calderón、María G. Mejía-Dionicio、Marco A. Morales-Reza、Alejandra Ramírez-Villalva、Macario Morales-Rodríguez、Bertha Jauregui-Rodríguez、Eduardo Díaz-Torres、Carlos González-Romero、Aydeé Fuentes-Benítes

  DOI：10.1016/j.ejmech.2016.02.013

  日期：2016.4

  Seven miconazole analogs involving 1,4,5-tri and 1,5-disubstituted triazole moieties were synthesized by azide-enolate 1,3-dipolar cycloaddition. The antifungal activity of these compounds was evaluated in vitro against four filamentous fungi, including Aspergillus fumigatus, Trichosporon cutaneum, Rhizopus oryzae, and Mucor hiemalis as well as three species of Candida spp. as yeast specimens. These pre-clinical studies suggest that compounds 4b, 4d and 7b can be considered as drug candidates for future complementary biological studies due to their good/excellent antifungal activities. (C) 2016 Elsevier Masson SAS. All rights reserved.
• STUETZ, A.;EGGER, H.
  作者：STUETZ, A.、EGGER, H.

  DOI：——

  日期：——
• Therapeutic Inhibitors of the Reverse Mode of ATP Synthase
  申请人：FORREST Michael David

  公开号：US20200247758A1

  公开（公告）日：2020-08-06

  Compounds of the following formula, and pharmaceutically-acceptable salts, solvates, hydrates and prodrugs thereof, formula (A) are useful to preferentially inhibit the ATP-hydrolysing mode of ATP synthase, and are thereby useful for treating various diseases and orders including cancer, particularly cancers that utilise the Warburg effect.