3-氨基-2-(3-氨基-4-甲氧苯基)-4H-色烯-4-酮 | 187585-11-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3-氨基-2-(3-氨基-4-甲氧苯基)-4H-色烯-4-酮
• 英文名称: 3,3'-Diamino-4'-methoxyflavone
• 英文别名: 3-amino-2-(3-amino-4-methoxyphenyl)chromen-4-one
• CAS: 187585-11-1
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: HSRUZXHIEFFBHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  87.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-硝基-4-甲氧基苯甲醛 在 palladium on activated charcoal potassium fluoride 、 氢气 、 盐酸二甲胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 xylene 为溶剂， 反应 69.0h， 生成 3-氨基-2-(3-氨基-4-甲氧苯基)-4H-色烯-4-酮
  参考文献：
  名称：

  Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones

  摘要：

  To further understand the molecular requirements for the antiproliferative activity of flavonoids, a series of 3-aminoflavones and some of their derivatives were prepared and evaluated using L1210 murine leukemia. Our novel five-step synthetic approach required easily available substituted aromatic aldehydes as starting materials and proved more convenient and more general than previously reported methods. Our results in the 3-aminoflavones series indicated that the 4'-methoxy group is important for cytotoxic activity. Moreover, for the flavone-8-acetic analogs, a marked increase in potency was observed with the addition of a 3-amino or a 3-nitro group, Methoxy groups on the 6 and 7 positions of flavonoids (as in cirsiliol) also appear to be important for antiproliferative activity. These results are essential for the further understanding of the critical molecular requirements that lead to antiproliferative properties in the flavonoid series.

  DOI：

  10.1016/s0223-5234(97)84363-2

文献信息

• CYCLOALKENYL HYDROXAMIC ACID DERIVATIVES AND THEIR USE AS HISTONE DEACETYLASE INHIBITORS
  申请人：THE BOARD INSTITUTE, INC.

  公开号：US20150368221A1

  公开（公告）日：2015-12-24

  The present invention provides compounds of formula (I) or a pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein W, X, n, s, t, and Ra are as described herein. The present invention relates generally to selective inhibitors of histone deacetylase and to methods of making and using them.

  本发明提供了公式(I)的化合物或其药学上可接受的盐、溶剂或前药，其中W、X、n、s、t和Ra如本文所述。本发明通常涉及组织脱乙酰化酶的选择性抑制剂以及制备和使用它们的方法。
• Cycloalkenyl hydroxamic acid derivatives and their use as histone deacetylase inhibitors
  申请人：The Broad Institute, Inc.

  公开号：US10793538B2

  公开（公告）日：2020-10-06

  The present invention provides compounds of formula (I): or a pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein W, X, n, s, t, and Ra are as described herein. The present invention relates generally to selective inhibitors of histone deacetylase and to methods of making and using them.

  本发明提供了式 (I) 的化合物： 或其药学上可接受的盐、溶液或原药，其中 W、X、n、s、t 和 Ra 如本文所述。本发明一般涉及组蛋白去乙酰化酶的选择性抑制剂及其制造和使用方法。
• US9914717B2
  申请人：——

  公开号：US9914717B2

  公开（公告）日：2018-03-13
• [EN] CYCLOALKENYL HYDROXAMIC ACID DERIVATIVES AND THEIR USE AS HISTONE DEACETYLASE INHIBITORS<br/>[FR] DÉRIVÉS D'ACIDE HYDROXAMIQUE CYCLOALCÉNYLE ET LEURS UTILISATIONS EN TANT QU'INHIBITEURS DE L'HISTONE DÉSACÉTYLASE
  申请人：BROAD INST INC

  公开号：WO2014100438A1

  公开（公告）日：2014-06-26

  The present invention provides compounds of formula (I) or a pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein W, X, n, s, t, and Ra are as described herein. The present invention relates generally to selective inhibitors of histone deacetylase and to methods of making and using them.
• Synthesis and in vitro cytotoxicity of a series of 3-aminoflavones
  作者：D Dauzonne、B Folléas、L Martinez、GG Chabot

  DOI：10.1016/s0223-5234(97)84363-2

  日期：1997.1

  To further understand the molecular requirements for the antiproliferative activity of flavonoids, a series of 3-aminoflavones and some of their derivatives were prepared and evaluated using L1210 murine leukemia. Our novel five-step synthetic approach required easily available substituted aromatic aldehydes as starting materials and proved more convenient and more general than previously reported methods. Our results in the 3-aminoflavones series indicated that the 4'-methoxy group is important for cytotoxic activity. Moreover, for the flavone-8-acetic analogs, a marked increase in potency was observed with the addition of a 3-amino or a 3-nitro group, Methoxy groups on the 6 and 7 positions of flavonoids (as in cirsiliol) also appear to be important for antiproliferative activity. These results are essential for the further understanding of the critical molecular requirements that lead to antiproliferative properties in the flavonoid series.