4,4'-(6-hydroxybenzofuran-2,3-diyl)diphenol | 120990-53-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 4,4'-(6-hydroxybenzofuran-2,3-diyl)diphenol
• 英文别名: 2,3-Bis(4-hydroxyphenyl)-1-benzofuran-6-ol
• CAS: 120990-53-6
• 化学式: C₂₀H₁₄O₄
• 分子量: 318.329
• InChiKey: CFJDFWALJNSBPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-bis(4-methoxyphenyl)-6-hydroxy-1-benzofuran 在 sodium hydroxide 、 吡啶盐酸盐 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4,4'-(6-hydroxybenzofuran-2,3-diyl)diphenol
  参考文献：
  名称：

  Structure-activity relationship of antiestrogens. A study using triarylbutenone, benzofuran, and triarylfuran analogs as models for triarylethylenes and triarylpropenones

  摘要：

  In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constrained models for triarylethylene (TAE) and triarylpropenone (TAP) prototypes. The position-specific contributions of substituents to receptor affinity and to agonist-antagonist profiles were used as aids in characterizing the relative binding orientation of the prototypes. Although most compounds were found to be weak receptor ligands and poorly active in vivo, the following conclusions could be drawn about their SAR: (i) (Z)-TAPs and TAEs interact with the receptor in an analogous manner using the trans-stilbene core, with their agonist-antagonist profiles depending on the nature of other substructures. (ii) Incorporation into the benzofuran framework introduces a stereoelectronic constraint that compromises the normal binding interactions of TAE, as well as TAP, prototypes, resulting in their poor affinities and weak biological activities. (iii) (E)-TAPs can interact with the receptor through their S-cis conformation, but such a binding mode is unlikely to account for their behavior as antagonists.

  DOI：

  10.1021/jm00128a006

文献信息

• Natural product inspired library synthesis - Identification of 2,3-diarylbenzofuran and 2,3-dihydrobenzofuran based inhibitors of Chlamydia trachomatis
  作者：Michael Saleeb、Sergio Mojica、Anna U. Eriksson、C. David Andersson、Åsa Gylfe、Mikael Elofsson

  DOI：10.1016/j.ejmech.2017.11.099

  日期：2018.1

  A natural product inspired library was synthesized based on 2,3-diarylbenzofuran and 2,3-diaryl-2,3-dihydrobenzofuran scaffolds. The library of forty-eight compounds was prepared by utilizing Pd-catalyzed one-pot multicomponent reactions and ruthenium-catalyzed intramolecular carbenoid C-H insertions. The compounds were evaluated for antibacterial activity in a panel of test systems including phenotypic

  基于2，3-二芳基苯并呋喃和2，3-二芳基-2，3-二氢苯并呋喃支架合成了天然产物启发的文库。通过利用Pd催化的一锅多组分反应和钌催化的分子内类胡萝卜素CH插入制备了48种化合物的库。在包括表型，生化和基于图像的筛选测定在内的一系列测试系统中评估了这些化合物的抗菌活性。我们鉴定阻断致病的细胞内复制几种强效的抑制剂沙眼衣原体与IC 50  ≤3μM。这些新型沙眼衣原体抑制剂可以作为开发特定治疗方法的起点，从而减轻沙眼衣原体的全球负担 感染。
• DURANI, NEELAM;JAIN, RAKA;SAEED, ASHRAF;DIKSHIT, DINESH K.;DURANI, SUSHEE+, J. MED. CHEM., 32,(1989) N, C. 1700-1707
  作者：DURANI, NEELAM、JAIN, RAKA、SAEED, ASHRAF、DIKSHIT, DINESH K.、DURANI, SUSHEE+

  DOI：——

  日期：——
• Structure-activity relationship of antiestrogens. A study using triarylbutenone, benzofuran, and triarylfuran analogs as models for triarylethylenes and triarylpropenones
  作者：Neelam Durani、Raka Jain、Ashraf Saeed、Dinesh K. Dikshit、Susheel Durani、Randhir S. Kapil

  DOI：10.1021/jm00128a006

  日期：1989.8

  In a study of the structure-activity relationship (SAR) of antiestrogens use has been made of certain 1,2,3-triarylbutenones, of 2-arylbenzofurans carrying aryl or aroyl substituents at C3, and of 2,3,4-triarylfurans as conformationally constrained models for triarylethylene (TAE) and triarylpropenone (TAP) prototypes. The position-specific contributions of substituents to receptor affinity and to agonist-antagonist profiles were used as aids in characterizing the relative binding orientation of the prototypes. Although most compounds were found to be weak receptor ligands and poorly active in vivo, the following conclusions could be drawn about their SAR: (i) (Z)-TAPs and TAEs interact with the receptor in an analogous manner using the trans-stilbene core, with their agonist-antagonist profiles depending on the nature of other substructures. (ii) Incorporation into the benzofuran framework introduces a stereoelectronic constraint that compromises the normal binding interactions of TAE, as well as TAP, prototypes, resulting in their poor affinities and weak biological activities. (iii) (E)-TAPs can interact with the receptor through their S-cis conformation, but such a binding mode is unlikely to account for their behavior as antagonists.