2-[2-(4-Chloro-phenoxy)-acetylamino]-benzoic acid methyl ester | 303794-72-1

• 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: 2-[2-(4-Chloro-phenoxy)-acetylamino]-benzoic acid methyl ester
• 英文别名: Methyl 2-{[(4-chlorophenoxy)acetyl]amino}benzoate；methyl 2-[[2-(4-chlorophenoxy)acetyl]amino]benzoate
• CAS: 303794-72-1
• 化学式: C₁₆H₁₄ClNO₄
• mdl: MFCD00573336
• 分子量: 319.744
• InChiKey: AWXAWMBJMXVXBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  528.7±40.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-(4-Chloro-phenoxy)-acetylamino]-benzoic acid methyl ester 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 NNI-5
  参考文献：
  名称：

  Pd（OAc）2催化一锅法制备无环不饱和β-烯胺酸酯的邻氨基苯甲酸酯

  摘要：

  首次实现了由无环不饱和β-烯胺酸酯与催化量的Pd（OAc）2的一锅法合成邻氨基苯甲酸酯。关键催化反应的底物易于从乙酰乙酸酯和胺中制备，并以中等至良好的化学收率获得官能化的邻氨基苯甲酸酯。通过应用此协议演示了13 C标记的邻氨基苯甲酸的简单组装。另外，使用该催化方法合成了生物活性NNI-5。

  DOI：

  10.1016/j.tetlet.2020.151659
• 作为产物：
  描述：

  对氯苯氧乙酸 在 氯化亚砜 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 1.0h， 生成 2-[2-(4-Chloro-phenoxy)-acetylamino]-benzoic acid methyl ester
  参考文献：
  名称：

  Design, synthesis and antihistaminic (H1) activity of some condensed 3-aminopyrimidin-4(3H)-ones

  摘要：

  A novel series of condensed 3-amino-2-(substituted)methylpyrimidin-4(3H)-ones is reported with potential H-1 receptor antagonistic activity. The IC50 values for 23 compounds were found to be in the micromolar range. Five lead compounds (10c, e, g, r and t), when evaluated by the in vivo method were found to protect guinea-pigs from the histamine induced asphyxia and antagonized histamine in a competitive and reversible manner. With a pA(2) value of 8.7 and protection time of 9.5 min (in vivo test), compound 10g was the most active amongst these five compounds. The isosteric replacement of the side chain -NH- in series 1, by oxygen and -NHSO2- functions, was undertaken to investigate the role of two amino functions in the receptor binding. This isosteric replacement with -O- does not affect thr antihistaminic activity and the sedative potential of the series. Preliminary molecular modelling studies indicate that the compounds with -NHSO2- in the side chain exhibit a closer fit with temelastine than their -O- isosteres. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00128-8

文献信息

• Identification of Anthranilic Acid Derivatives as a Novel Class of Allosteric Inhibitors of Hepatitis C NS5B Polymerase
  作者：Thomas Nittoli、Kevin Curran、Shabana Insaf、Martin DiGrandi、Mark Orlowski、Rajiv Chopra、Atul Agarwal、Anita Y. M. Howe、Amar Prashad、M. Brawner Floyd、Bernard Johnson、Alan Sutherland、Karen Wheless、Boris Feld、John O'Connell、Tarek S. Mansour、Jonathan Bloom

  DOI：10.1021/jm061428x

  日期：2007.5.1

  A series of potent anthranilic acid-based inhibitors of the hepatitis C NS5B polymerase has been identified. The inhibitors bind to a site on NS5B between the thumb and palm regions adjacent to the active site as determined by X-ray crystallography of the enzyme-inhibitor complex. Guided by both molecular modeling and traditional SAR, the enzyme activity of the initial hit was improved by approximately

  已鉴定出一系列强效邻氨基苯甲酸丙型肝炎 NS5B 聚合酶抑制剂。通过酶抑制剂复合物的 X 射线晶体学测定，抑制剂与 NS5B 上拇指和手掌区域之间与活性位点相邻的位点结合。在分子建模和传统 SAR 的指导下，初始命中的酶活性提高了约 100 倍，产生了一系列有效且选择性的 NS5B 抑制剂，IC50 值低至 10 nM。这些化合物也是培养的 HUH7 细胞中 HCV 复制子的抑制剂。
• COMPOUNDS THAT INHIBIT HIF-1 ACTIVITY, THE METHOD FOR PREPARATION THEREOF AND THE PHARMACEUTICAL COMPOSITION CONTAINING THEM AS AN EFFECTIVE COMPONENT
  申请人：Lee Jung Joon

  公开号：US20090306078A1

  公开（公告）日：2009-12-10

  Disclosed herein are an HIF-1 inhibitor, a method for the preparation thereof, and a pharmaceutical composition comprising the same as an active ingredient. The HIF-1 inhibitor shows anticancer activity thanks to the inhibition activity against HIF-1, a transcription factor which plays an important role in the growth and metastasis of cancer, but not to general cytotoxicity. Thus, the HIF-inhibitor and a pharmaceutically acceptable salt thereof can be used as a therapeutic for various cancers such as liver cancer; stomach cancer and breast cancer. Also, the compound having inhibition activity against HIF-1 is useful in the treatment of diabetic retinopathy and arthritis, which are aggravated by HIF-1-mediated VEGF expression.

  本文披露了一种HIF-1抑制剂，其制备方法，以及包含其作为活性成分的药物组合物。该HIF-1抑制剂显示抗癌活性，这归功于其对HIF-1的抑制活性，HIF-1是一种在癌症生长和转移中起重要作用的转录因子，但不具有一般细胞毒性。因此，HIF抑制剂及其药用可接受的盐可用作治疗各种癌症，如肝癌、胃癌和乳腺癌的治疗药物。此外，具有对HIF-1抑制活性的化合物在治疗由HIF-1介导的VEGF表达加重的糖尿病视网膜病变和关节炎方面是有用的。
• Anthranilic acid derivatives useful in treating infection with hepatitis C virus
  申请人：Bloom D. Jonathan

  公开号：US20050004192A1

  公开（公告）日：2005-01-06

  The present invention provides pharmaceutical compositions useful in treating hepatitis C infection. The present invention also provides methods of treating hepatitis C infection by administering to a mammal the pharmaceutical compositions of the present invention.

  本发明提供了可用于治疗丙型肝炎感染的药物组合物。本发明还提供了通过向哺乳动物施用本发明的药物组合物来治疗丙型肝炎感染的方法。
• ANTHRANILIC ACID DERIVATIVES USEFUL IN TREATING INFECTION WITH HEPATITIS C VIRUS
  申请人：Bloom Jonathan D.

  公开号：US20080269333A1

  公开（公告）日：2008-10-30

  The present invention provides pharmaceutical compositions useful in treating hepatitis C infection. The present invention also provides methods of treating hepatitis C infection by administering to a mammal the pharmaceutical compositions of the present invention.
• US7408078B2
  申请人：——

  公开号：US7408078B2

  公开（公告）日：2008-08-05