8-bromo-6-hydroxycoumarin | 885025-16-1

• 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-6-hydroxycoumarin
• 英文别名: 8-bromo-6-hydroxy-chromen-2-one；8-bromo-6-hydroxychromen-2-one
• CAS: 885025-16-1
• 化学式: C₉H₅BrO₃
• 分子量: 241.041
• InChiKey: AGMIBZQWJCKHIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-bromo-6-hydroxycoumarin 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-benzyloxy-8-bromo-chromen-2-one
  参考文献：
  名称：

  WO2006/44176

  摘要：

  公开号：
• 作为产物：
  描述：

  6-benzyloxy-8-bromo-chromen-2-one 在 三溴化硼 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 8-bromo-6-hydroxycoumarin
  参考文献：
  名称：

  WO2006/44176

  摘要：

  公开号：

文献信息

• Substituted Benzopyrans as Selective Estrogen Receptor-Beta Agonists
  申请人：Norman Hurst Bryan

  公开号：US20080064742A1

  公开（公告）日：2008-03-13

  The present invention relates to novel benzopyran ER-β agonist compounds, pharmaceutical compositions thereof, and use of these compounds to treat a ER-β mediated disease such as nocturia, obstructive uropathy, benign prostatic hypertrophy, obesity, dementia, hypertension, incontinence, colon cancer, prostate cancer, infertility, depression, leukemia, inflammatory, bowel disease, and arthritis. Formula (I), wherein G is —O—, —S(O)—, —CF 2 —, —C(O)—, —CR 1 H— or —CR 2 (OH)—; R is halo, (C 1 -C 4 )alkyl or R 2 —(CH 2 ) m —; R 1 is F, hydroxyl, cyano, trifluoromethyl, (C 1 -C 4 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )alkycarbonyloxy or benzyl; R 2 is trifluoromethyl or (C 1 -C 4 )alkyl; R 3 is cyano, hydroxyl, (C 2 -C 4 )alkenyl, (C 1 -C 4 )alkoxy or (C 1 -C 4 )alkoxycarbonyl; n is 0, 1 or 2; and m is 0, 1 or 2; and pharmaceutically acceptable salts thereof.

  本发明涉及新型苯并吡喃ER-β激动剂化合物，其制备的药物组合物，以及使用这些化合物治疗ER-β介导的疾病，如夜尿症，梗阻性尿路病，良性前列腺增生，肥胖症，痴呆症，高血压，失禁，结肠癌，前列腺癌，不育，抑郁症，白血病，炎症性肠病和关节炎。其中，公式（I）中，G为—O—，—S（O）—，—CF2—，—C（O）—，—CR1H—或—CR2（OH）—；R为卤素，（C1-C4）烷基或R2—（CH2）m—；R1为F，羟基，氰基，三氟甲基，（C1-C4）烷基，（C2-C4）烯基，（C2-C4）炔基，（C1-C4）烷氧基，（C1-C4）烷基羧酸酯或苯甲基；R2为三氟甲基或（C1-C4）烷基；R3为氰基，羟基，（C2-C4）烯基，（C1-C4）烷氧基或（C1-C4）烷氧羰基；n为0，1或2；m为0，1或2；以及其药学上可接受的盐。
• Substituted benzopyrans as selective estrogen receptor-beta agonists
  申请人：Eli Lilly and Company

  公开号：US07354951B2

  公开（公告）日：2008-04-08

  The present invention relates to novel benzopyran ER-β agonist compounds, pharmaceutical compositions thereof, and use of these compounds to treat a ER-β mediated disease such as nocturia, obstructive uropathy, benign prostatic hypertrophy, obesity, dementia, hypertension, incontinence, colon cancer, prostate cancer, infertility, depression, leukemia, inflammatory bowel disease, and arthritis. Formula (I), wherein G is —O—, —S(O)n, —CF2—, —C(O)—, —CR1H— or —CR2(OH)—; R is halo, (C1-C4)alkyl or R3—(CH2)m—; R1 is F, hydroxyl, cyano, trifluoromethyl, (C1-C4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl, (C1-C4)alkoxy, (C1-C4)alkylcarbonyloxy or benzyl; R2 is trifluoromethyl or (C1-C4)alkyl; R3 is cyano, hydroxyl, (C2-C4)alkenyl, (C1-C4)alkoxy or (C1-C4)alkoxycarbonyl; n is 0, 1 or 2; and m is 0, 1 or 2; and pharmaceutically acceptable salts thereof.

  本发明涉及新型苯并吡喃ER-β激动剂化合物、其制药组合物以及利用这些化合物治疗ER-β介导的疾病，如夜尿症、梗阻性尿路病、前列腺增生症、肥胖症、痴呆症、高血压、失禁、结肠癌、前列腺癌、不孕症、抑郁症、白血病、炎症性肠病和关节炎。其中，公式（I）中，G为—O—、—S(O)n、—CF2—、—C(O)—、—CR1H—或—CR2(OH)—；R为卤素、（C1-C4）烷基或R3—（CH2）m—；R1为F、羟基、氰基、三氟甲基、（C1-C4）烷基、（C2-C4）烯基、（C2-C4）炔基、（C1-C4）烷氧基、（C1-C4）烷基羰基氧基或苄基；R2为三氟甲基或（C1-C4）烷基；R3为氰基、羟基、（C2-C4）烯基、（C1-C4）烷氧基或（C1-C4）烷氧羰基；n为0、1或2；m为0、1或2；以及其药学上可接受的盐。
• Benzopyrans as selective estrogen receptor β agonists (SERBAs). Part 5: Combined A- and C-ring structure–activity relationship studies
  作者：Timothy I. Richardson、Jeffrey A. Dodge、Yong Wang、Jim D. Durbin、Venkatesh Krishnan、Bryan H. Norman

  DOI：10.1016/j.bmcl.2007.08.009

  日期：2007.10

  Benzopyrans are selective estrogen receptor (ER) beta agonists (SERBAs), which bind the ER subtypes alpha and beta in opposite orientations. Here we describe the synthesis of a late stage intermediate that allowed us to combine A-ring and C-ring modifications and carry out simultaneous SAR studies at both positions. Modification of both positions proved additive, maintaining affinity and improving ERbeta selectivity up to 83-fold. An X-ray cocrystal structure confirms the previously observed binding mode in ERbeta.
• SUBSTITUTED BENZOPYRANS AS SELECTIVE ESTROGEN RECEPTOR-BETA AGONISTS
  申请人：ELI LILLY AND COMPANY

  公开号：EP1805160B1

  公开（公告）日：2011-04-06
• US7354951B2
  申请人：——

  公开号：US7354951B2

  公开（公告）日：2008-04-08