1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethylamine | 94038-16-1

• 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-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethylamine
• 英文别名: 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethylamine；1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanamine
• CAS: 94038-16-1
• 化学式: C₁₁H₁₁Cl₂N₃
• 分子量: 256.134
• InChiKey: YJJZWYYPULSCCK-UHFFFAOYSA-N

物化性质

• 沸点：
  446.9±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethylamine 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 反应 28.0h， 生成 Biphenyl-4-ylmethyl-[1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl]-amine
  参考文献：
  名称：

  Fioravanti, Rossella; Biava, Mariangela; Porretta, Giulio Cesare, Medicinal Chemistry Research, 1997, vol. 7, # 2, p. 87 - 97

  摘要：

  DOI：
• 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 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 生成 1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethylamine
  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。
• (1-phenyl-2-heteroaryl)ethyl-guanidine compounds as inhibitors of mitochondrial F1F0 ATP hydrolase
  申请人：——

  公开号：US20040039033A1

  公开（公告）日：2004-02-26

  Compounds having the formula (I), and pharmaceutically acceptable salts thereof, 1 are useful for modulating mitochondrial F 1 F 0 ATPase activity and treating ischemic conditions including myocardial infarction, congestive heart failure, and cardiac arrhythmias.

  具有化学式（I）的化合物及其药用盐对调节线粒体F1F0ATP酶活性和治疗包括心肌梗死、充血性心力衰竭和心律失常在内的缺血性疾病具有用处。
• Structure-Activity Relationships of a New Antifungal Imidazole, AFK-108, and Related Compounds.
  作者：Kimihiko HORI、Akira SAKAGUCHI、Michinari KUDOH、Koichi ISHIDA、Yuri AOYAMA、Yuzo YOSHIDA

  DOI：10.1248/cpb.48.60

  日期：——

  Fungicidal activity of widely used imidazole antifungal drugs in topical applications is not so strong in spite of their potent fungistatic activities against dermatophytes and pathogenic yeasts. In order to improve fungicidal activity of imicazole antifungal agents, a series of novel imidazole derivatives having a hydrophobic substituent derived from isoprenoid were synthesized. The efficacy of these compounds was evaluated with respect to direct cell-membrane damaging activity, ergosterol biosynthesis inhibition, minimum growth-inhibitory concentration (MIC) and therapeutic effect for experimental dermatophytosis of guinea pigs. Among the newly synthesized compounds, the geranyl derivative named AFK-108 (2a) showed the highest in vivo fungicidal activity with both cell membrane damaging activity and ergosterol biosynthesis inhibition in vitro.

  尽管广泛使用的咪唑类抗真菌药物对皮癣菌和致病性酵母菌具有很强的杀真菌活性，但其局部应用的杀真菌活性并不强。为了提高咪唑类抗真菌药物的杀真菌活性，我们合成了一系列新型咪唑衍生物，这些衍生物具有来自异肾上腺素的疏水取代基。评估了这些化合物在直接破坏细胞膜活性、麦角甾醇生物合成抑制、最低生长抑制浓度（MIC）以及对豚鼠实验性皮癣病的治疗效果等方面的功效。在新合成的化合物中，名为 AFK-108 （2a）的香叶基衍生物显示出最高的体内杀真菌活性，同时具有细胞膜破坏活性和体外麦角甾醇生物合成抑制作用。
• (1-phenyl-2-heteoaryl)ethyl-guanidine compounds as inhibitors of mitochondrial F1F0 ATP hydrolase
  申请人：Atwal Karnail S.

  公开号：US06916813B2

  公开（公告）日：2005-07-12

  Compounds having the formula (I), and pharmaceutically acceptable salts thereof, are useful for modulating mitochondrial F 1 F 0 ATPase activity and treating ischemic conditions including myocardial infarction, congestive heart failure, and cardiac arrhythmias.

  具有式(I)的化合物及其药学上可接受的盐，对于调节线粒体F1F0ATP酶活性和治疗缺血性疾病，包括心肌梗死、充血性心力衰竭和心律失常，具有用途。
• [EN] INHIBITORS OF ATP SYNTHASE - COSMETIC AND THERAPEUTIC USES<br/>[FR] INHIBITEURS D'UTILISATIONS COSMÉTIQUES ET THÉRAPEUTIQUES D'ATP SYNTHASE
  申请人：FORREST MICHAEL DAVID

  公开号：WO2022157548A1

  公开（公告）日：2022-07-28

  With supporting experimental data, this disclosure teaches that IF1 protein activity is a molecular determinant of lifespan, therein explaining why different species have different maximal lifespans, and it teaches a IF1 protein/fragment (or sequence variant thereof), or a fusion protein thereof, optionally a fusion protein comprising a Cell Penetrating Peptide (CPP) sequence, as an agent to slow/delay/reduce aging in a subject, optionally as a component of a cosmetic, optionally to treat an age-correlated disease/disorder. Moreover it teaches other inhibitors of F1F0 ATP hydrolysis, including small molecules, of a number of different scaffolds, for this purpose. Furthermore, with supporting experimental data, it teaches that compounds that slow the ATP-hydrolysing mode of ATP synthase are useful for treating various diseases and disorders, including cancer, particularly cancers that utilise the Warburg effect.

  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。