8-bromo-3-hydroxy-4-methyl-6H-benzo[c]chromen-6-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-bromo-3-hydroxy-4-methyl-6H-benzo[c]chromen-6-one
• 英文别名: 8-bromo-3-hydroxy-4-methylbenzo[c]chromen-6-one
• 化学式: C₁₄H₉BrO₃
• 分子量: 305.128
• InChiKey: FTLWRBYUURZGIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,5-二溴苯甲酸 、 2,6-二羟基甲苯 在 sodium hydroxide 、 copper(II) sulfate 作用下， 生成 8-bromo-3-hydroxy-4-methyl-6H-benzo[c]chromen-6-one
  参考文献：
  名称：

  6H-Benzo[c]chromen-6-one derivatives as selective ERβ agonists

  摘要：

  A series of 6H-benzo[c]chromen-6-one and 6H-benzo[c]chromene derivatives were prepared, and the affinity and selectivity for ER alpha and ER beta was measured. Many of the analogs were found to be potent and selective ER beta agonists. Bis hydroxyl at positions 3 and 8 is essential for activity in a HTRF coactivator recruitment assay. Additional modifications at both phenyl rings led to compounds with ER beta < 10 nM potency and > 100-fold selectivity over ER alpha. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.057

文献信息

• [EN] ESTROGEN RECEPTOR MODULATORS<br/>[FR] MODULATEURS DE RECEPTEUR D'OESTROGENES
  申请人：MERCK & CO INC

  公开号：WO2004073612A2

  公开（公告）日：2004-09-02

  The present invention relates to compounds and derivatives thereof, their synthesis, and their use as estrogen receptor modulators. The compounds of the instant invention are ligands for estrogen receptors and as such may be useful for treatment or prevention of a variety of conditions related to estrogen functioning including: bone loss, bone fractures, osteoporosis, metastatic bone disease, Paget s disease, periodontal disease, cartilage degeneration, endometriosis, uterine fibroid disease, hot flashes, increased levels of LDL cholesterol, cardiovascular disease, impairment of cognitive functioning, cerebral degenerative disorders, restenosis, gynecomastia, vascular smooth muscle cell proliferation, obesity, incontinence, and cancer.
• 6H-Benzo[c]chromen-6-one derivatives as selective ERβ agonists
  作者：Wanying Sun、Lovji D. Cama、Elizabeth T. Birzin、Sudha Warrier、Louis Locco、Ralph Mosley、Milton L. Hammond、Susan P. Rohrer

  DOI：10.1016/j.bmcl.2005.12.057

  日期：2006.3

  A series of 6H-benzo[c]chromen-6-one and 6H-benzo[c]chromene derivatives were prepared, and the affinity and selectivity for ER alpha and ER beta was measured. Many of the analogs were found to be potent and selective ER beta agonists. Bis hydroxyl at positions 3 and 8 is essential for activity in a HTRF coactivator recruitment assay. Additional modifications at both phenyl rings led to compounds with ER beta < 10 nM potency and > 100-fold selectivity over ER alpha. (C) 2006 Elsevier Ltd. All rights reserved.