4-(2-氯-1-亚氨基乙基)苯-1,3-二醇 | 755722-84-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(2-氯-1-亚氨基乙基)苯-1,3-二醇
• 英文名称: imine
• 英文别名: 4-(2-Chloroethanimidoyl)benzene-1,3-diol
• CAS: 755722-84-0
• 化学式: C₈H₈ClNO₂
• 分子量: 185.61
• InChiKey: APJAKRAXUALELR-UHFFFAOYSA-N

物化性质

• 沸点：
  371.3±34.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2-氯-1-亚氨基乙基)苯-1,3-二醇 在 盐酸 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 7-methoxy-2-(2-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Inhibitory effect of flavonoids on human glutaminyl cyclase

  摘要：

  Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4' (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.064
• 作为产物：
  描述：

  氯乙腈 、 间苯二酚 在 盐酸 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 生成 4-(2-氯-1-亚氨基乙基)苯-1,3-二醇
  参考文献：
  名称：

  新型吡唑衍生物的合成及其对肿瘤细胞生长的抑制活性。

  摘要：

  为了找到新的抗肿瘤药，设计并合成了一系列1H-苯并呋喃[3,2-c]吡唑衍生物4a-e。用LiHMDS在无水四氢呋喃（THF）中处理6-甲氧基苯并呋喃-3（2H）-one 3，然后与3-取代的异硫氰酸苯酯反应，得到硫酰胺中间体，将其与肼一水合物在二恶烷/乙醇中缩合（1：1 ），以提供苯并呋喃并吡唑衍生物4a welle和意外的吡唑衍生物5a⁻e。在肿瘤细胞生长抑制试验中，所有苯并呋喃并吡唑衍生物对乳腺癌MCF-7细胞均无活性，只有4a对白血病K562（GI50 = 0.26μM）和肺肿瘤A549细胞具有高活性，并且比ABT-751更有效（GI50 = 0.19μM），而其他苯并呋喃并吡唑类药物的抑制活性非常弱。相反，吡唑5a-e通常比苯并呋喃吡唑4a⁻e更有效。化合物5a显示出与4a相似的趋势，对K562和A549细胞具有高效力，但对MCF-7细胞的作用较弱。吡唑5b和5e均显示出对K56

  DOI：

  10.3390/molecules24020279

文献信息

• Antidiabetic bicyclic compounds
  申请人：Ge Min

  公开号：US20070265332A1

  公开（公告）日：2007-11-15

  Tricyclic compounds containing a cyclopropyl carboxylic acid or carboxylic acid derivative (e.g. amide) fused to a bicyclic ring, including pharmaceutically acceptable salts and prodrugs thereof, are agonists of G-protein coupled receptor 40 (GPR40) and are useful as therapeutic compounds, particularly in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

  含有环丙基羧酸或羧酸衍生物（如酰胺）的三环化合物与融合到双环环上的G蛋白偶联受体40（GPR40）是激动剂，并且可用作治疗化合物，特别是在治疗2型糖尿病方面，以及与该疾病常相关的病症，包括肥胖和脂质紊乱，如混合性或糖尿病性脂质代谢异常、高血脂、高胆固醇血症和高甘油三酯血症。
• Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase
  作者：Romain Haudecoeur、Abdelhakim Ahmed-Belkacem、Wei Yi、Antoine Fortuné、Rozenn Brillet、Catherine Belle、Edwige Nicolle、Coralie Pallier、Jean-Michel Pawlotsky、Ahcène Boumendjel

  DOI：10.1021/jm200242p

  日期：2011.8.11

  We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 mu M and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indo1-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 mu M. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.
• US7442808B2
  申请人：——

  公开号：US7442808B2

  公开（公告）日：2008-10-28
• [EN] ANTIDIABETIC BICYCLIC COMPOUNDS<br/>[FR] COMPOSÉS BICYCLIQUES ANTIDIABÉTIQUES
  申请人：MERCK & CO INC

  公开号：WO2007136572A2

  公开（公告）日：2007-11-29

  [EN] Tricyclic compounds containing a cyclopropyl carboxylic acid or carboxylic acid derivative (e.g. amide) fused to a bicyclic ring, including pharmaceutically acceptable salts and prodrugs thereof, are agonists of G-protein coupled receptor 40 (GPR40) and are useful as therapeutic compounds, particularly in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.
  [FR] L'invention concerne des composés tricycliques comportant un acide carboxylique de cyclopropyle ou un dérivé de cet acide carboxylique (par ex. un amide) condensé avec un anneau bicyclique, ainsi que des sels pharmaceutiquement acceptables et des promédicaments de ces composés, qui constituent des agonistes du récepteur couplé à la protéine G 40 (GPR40) et peuvent servir de composés thérapeutiques, en particulier pour traiter le diabète sucré de type 2, ainsi que des états qui sont souvent associés à cette maladie, parmi lesquels figurent l'obésité et les troubles lipidiques tels que la dyslipidémie mixte ou diabétique, l'hyperlipidémie, l'hypercholestérolémie, et l'hypertriglycéridémie.