2-(3'-iodobenzoyl)-3H-benzo[f]chromen-3-one | 1148118-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-(3'-iodobenzoyl)-3H-benzo[f]chromen-3-one
• 英文别名: 2-(3-Iodobenzoyl)benzo[f]chromen-3-one
• CAS: 1148118-66-4
• 化学式: C₂₀H₁₁IO₃
• 分子量: 426.21
• InChiKey: IGKRQNAOZCUCQP-UHFFFAOYSA-N

物化性质

• 熔点：
  237-239 °C
• 沸点：
  603.6±55.0 °C(predicted)
• 密度：
  1.716±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3'-iodobenzoyl)-3H-benzo[f]chromen-3-one 在 sodium tetrahydroborate 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以90%的产率得到2-(3'-iodobenzoyl)-1,2-dihydro-benzo[f]chromen-3-one
  参考文献：
  名称：

  Novel Cambinol Analogs as Sirtuin Inhibitors: Synthesis, Biological Evaluation, and Rationalization of Activity

  摘要：

  The tenovins and cambinol are two classes of sirtuin inhibitor that exhibit antitumor activity in preclinical models. This report describes modifications to the core structure of cambinol, in particular by incorporation of substitutents at the N1-position, which lead to increased potency and modified selectivity. These improvements have been rationalized using molecular modeling techniques. The expected functional selectivity in cells was also observed for both a SIRT1 and a SIRT2 selective analog.

  DOI：

  10.1021/jm8014298
• 作为产物：
  描述：

  (3-碘苯甲酰)乙酸乙酯 、 2-羟基-1-萘甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以80%的产率得到2-(3'-iodobenzoyl)-3H-benzo[f]chromen-3-one
  参考文献：
  名称：

  Novel Cambinol Analogs as Sirtuin Inhibitors: Synthesis, Biological Evaluation, and Rationalization of Activity

  摘要：

  The tenovins and cambinol are two classes of sirtuin inhibitor that exhibit antitumor activity in preclinical models. This report describes modifications to the core structure of cambinol, in particular by incorporation of substitutents at the N1-position, which lead to increased potency and modified selectivity. These improvements have been rationalized using molecular modeling techniques. The expected functional selectivity in cells was also observed for both a SIRT1 and a SIRT2 selective analog.

  DOI：

  10.1021/jm8014298

文献信息

• PYRIMIDINE DERIVATIVES AND THEIR PHARMACEUTICAL USE
  申请人：The University Court of the University of Dundee

  公开号：EP2344462B1

  公开（公告）日：2016-05-18
• Compounds
  申请人：Westwood Nicholas James

  公开号：US20110245282A1

  公开（公告）日：2011-10-06

  The invention provides a compound according to formula (I): wherein: X is O or S; Y is O or S; each Ar and Ar′ is independently a mono-, bi- or tricyclic aryl or heteroaryl group optionally substituted with one or more substituents selected from halo, alkyl, aryl, heteroaryl, hydroxyl, nitro, amino, alkoxy, alkylthio, cyano, thio, ester, acyl and amido; each R 2 is independently hydrogen, halo, alkyl, aryl, heteroaryl, hydroxyl, nitro, amino, alkoxy, alkylthio, cyano and thio; and R 1 is as defined herein, or a physiologically acceptable salt, solvate, ester, amide or other physiologically functional derivative thereof.
• US8563557B2
  申请人：——

  公开号：US8563557B2

  公开（公告）日：2013-10-22
• Novel Cambinol Analogs as Sirtuin Inhibitors: Synthesis, Biological Evaluation, and Rationalization of Activity
  作者：Federico Medda、Rupert J. M. Russell、Maureen Higgins、Anna R. McCarthy、Johanna Campbell、Alexandra M. Z. Slawin、David P. Lane、Sonia Lain、Nicholas J. Westwood

  DOI：10.1021/jm8014298

  日期：2009.5.14

  The tenovins and cambinol are two classes of sirtuin inhibitor that exhibit antitumor activity in preclinical models. This report describes modifications to the core structure of cambinol, in particular by incorporation of substitutents at the N1-position, which lead to increased potency and modified selectivity. These improvements have been rationalized using molecular modeling techniques. The expected functional selectivity in cells was also observed for both a SIRT1 and a SIRT2 selective analog.