5-(5-chloro-2-methoxyphenoxy)isophthalonitrile | 895572-34-6

• 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: 5-(5-chloro-2-methoxyphenoxy)isophthalonitrile
• 英文别名: 5-(5-Chloro-2-methoxyphenoxy)benzene-1,3-dicarbonitrile
• CAS: 895572-34-6
• 化学式: C₁₅H₉ClN₂O₂
• 分子量: 284.702
• InChiKey: OPWLKVIPVFJGAX-UHFFFAOYSA-N

物化性质

• 沸点：
  398.0±42.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(5-chloro-2-methoxyphenoxy)isophthalonitrile 在 偶氮二甲酸二异丙酯 、 三溴化硼 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 5-(2-(2-bromoethoxy)-5-chlorophenoxy)isophthalonitrile
  参考文献：
  名称：

  Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents

  摘要：

  A 5-mu M docking hit has been optimized to an extraordinarily potent (55 pM) non-nucleoside inhibitor of HIV reverse transcriptase. Use of free energy perturbation (PEP) calculations to predict relative free energies of binding aided the optimizations by identifying optimal substitution patterns for phenyl rings and a linker. The most potent resultant catechol diethers feature terminal uracil and cyanovinylphenyl groups. A halogen bond with Pro95 likely contributes to the extreme potency of compound 42. In addition, several examples are provided illustrating failures of attempted grafting of a substructure from a very active compound onto a seemingly related scaffold to improve its activity.

  DOI：

  10.1021/jm201134m
• 作为产物：
  描述：

  3,5-二氰基氟苯 、 5-氯-2-甲氧基-苯酚 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以50%的产率得到5-(5-chloro-2-methoxyphenoxy)isophthalonitrile
  参考文献：
  名称：

  Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents

  摘要：

  A 5-mu M docking hit has been optimized to an extraordinarily potent (55 pM) non-nucleoside inhibitor of HIV reverse transcriptase. Use of free energy perturbation (PEP) calculations to predict relative free energies of binding aided the optimizations by identifying optimal substitution patterns for phenyl rings and a linker. The most potent resultant catechol diethers feature terminal uracil and cyanovinylphenyl groups. A halogen bond with Pro95 likely contributes to the extreme potency of compound 42. In addition, several examples are provided illustrating failures of attempted grafting of a substructure from a very active compound onto a seemingly related scaffold to improve its activity.

  DOI：

  10.1021/jm201134m

文献信息

• CHEMICAL COMPOUNDS
  申请人：Jones Lyn Howard

  公开号：US20090264425A1

  公开（公告）日：2009-10-22

  This invention relates to biaryl ether derivatives of formula (I) wherein R 1 , R 3 , R 4 , X, W, Y and m are defined in the description, and to compositions containing them and the uses of such derivatives. The compounds of the present invention bind to the enzyme reverse transcriptase and are modulators, especially inhibitors thereof.

  本发明涉及公式（I）的二芳基醚衍生物，其中R1、R3、R4、X、W、Y和m在说明中定义，并涉及含有它们的组合物以及这些衍生物的用途。本发明的化合物与酶逆转录酶结合，并且是其调节剂，特别是抑制剂。
• CATECHOL DIETHERS AS POTENT ANTI-HIV AGENTS
  申请人：YALE UNIVERSITY

  公开号：US20140288017A1

  公开（公告）日：2014-09-25

  The present invention is directed to novel catechol diether compounds, pharmaceutical compositions therefrom and methods for inhibiting reverse transcriptase and treating HIV infections, especially included drug resistant strains of HIV 1 and 2 and/or secondary disease states and/or conditions which occur as a consequence of HIV infection.

  本发明涉及新型儿茶酚二醚化合物、其制药组合物以及抑制反转录酶和治疗HIV感染的方法，特别包括抗药性HIV 1和2以及/或作为HIV感染后果的二级疾病状态和/或条件。
• [EN] CATECHOL DIETHERS AS POTENT ANTI-HIV AGENTS<br/>[FR] DIÉTHERS DE CATÉCHOL COMME AGENTS ANTI-HIV PUISSANTS
  申请人：UNIV YALE

  公开号：WO2013056003A3

  公开（公告）日：2013-06-20
• NONNUCLEOSIDE INHIBITORS OF HIV-1 REVERSE TRANSCRIPTASE
  申请人：Pfizer Limited

  公开号：EP1831157A2

  公开（公告）日：2007-09-12
• US9487476B2
  申请人：——

  公开号：US9487476B2

  公开（公告）日：2016-11-08