4-Hydroxy-7-methoxybenzo[h]chromen-2-one | 1092350-28-1

• 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: 4-Hydroxy-7-methoxybenzo[h]chromen-2-one
• CAS: 1092350-28-1
• 化学式: C₁₄H₁₀O₄
• 分子量: 242.231
• InChiKey: GSDMQOIRYYHLSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-7-methoxybenzo[h]chromen-2-one 、 一氯丙酮 在 ammonium acetate 、 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 25.0h， 以29%的产率得到6-methoxy-1-methyl-11H-benzo[h]furo[3,2-c]chromen-11-one
  参考文献：
  名称：

  Antitumor Agents. 272. Structure−Activity Relationships and In Vivo Selective Anti-Breast Cancer Activity of Novel Neo-tanshinlactone Analogues

  摘要：

  Neo-tanshinlactone (1) and its previously reported analogues, such as 2, are potent and selective in vitro antibreast cancer agents. The synthetic pathway to 2 was optimized from seven to five steps, with a better overall yield. Structure-activity relationships studies on these compounds revealed some key molecular determinants for this family of antibreast agents. Several derivatives (19-21 and 24) exerted potent and selective antibreast cancer activity with IC50 values of 0.3, 0.2, 0.1, and 0.1 mu g/mL, respectively, against the ZR-75-1 cell lines. Compound 24 was 2- to 3-fold more potent than I against SK-BR-3 and ZR-75-1. Importantly, 21 exhibited high selectivity; it was 23 times more active against ZR-75-1 than MCF-7. Compound 20 had an approximately 12-fold ratio of SK-BR-3/MCF-7 selectivity. In addition, analogue 2 showed potent activity against it ZR-75-1 xenograft model, but not PC-3 and MDA-MB-231 xenografts, as well as high selectivity against breast cancer cell line compared with normal breast tissue-derived cell lines. Further development of lead compounds 19-21 and 24 as clinical trial candidates is warranted.

  DOI：

  10.1021/jm1000858
• 作为产物：
  描述：

  丙二酸 、 5-甲氧基-1-萘酚 在 polyphosphoric acid 作用下， 反应 3.0h， 生成 4-Hydroxy-7-methoxybenzo[h]chromen-2-one
  参考文献：
  名称：

  Antitumor Agents. 272. Structure−Activity Relationships and In Vivo Selective Anti-Breast Cancer Activity of Novel Neo-tanshinlactone Analogues

  摘要：

  Neo-tanshinlactone (1) and its previously reported analogues, such as 2, are potent and selective in vitro antibreast cancer agents. The synthetic pathway to 2 was optimized from seven to five steps, with a better overall yield. Structure-activity relationships studies on these compounds revealed some key molecular determinants for this family of antibreast agents. Several derivatives (19-21 and 24) exerted potent and selective antibreast cancer activity with IC50 values of 0.3, 0.2, 0.1, and 0.1 mu g/mL, respectively, against the ZR-75-1 cell lines. Compound 24 was 2- to 3-fold more potent than I against SK-BR-3 and ZR-75-1. Importantly, 21 exhibited high selectivity; it was 23 times more active against ZR-75-1 than MCF-7. Compound 20 had an approximately 12-fold ratio of SK-BR-3/MCF-7 selectivity. In addition, analogue 2 showed potent activity against it ZR-75-1 xenograft model, but not PC-3 and MDA-MB-231 xenografts, as well as high selectivity against breast cancer cell line compared with normal breast tissue-derived cell lines. Further development of lead compounds 19-21 and 24 as clinical trial candidates is warranted.

  DOI：

  10.1021/jm1000858

文献信息

• Substituted furochromene compounds of antiinflammatory action
  申请人：Mercep Mladen

  公开号：US20060148890A1

  公开（公告）日：2006-07-06

  The present invention relates to novel compounds of the formula (I) including all stereoisomers and tautomers thereof, to the pharmaceutically acceptable salts and solvates thereof, to the processes and reactive intermediates for their preparation and to their use in the prophylaxis and treatment of asthma and other inflammatory diesases and/or conditions in humans.

  本发明涉及式（I）的新化合物，包括其所有立体异构体和互变异构体、药学上可接受的盐和溶剂合物，以及其制备过程和反应中间体，以及它们在预防和治疗人类哮喘和其他炎症性疾病和/或病况中的用途。
• US7208518B2
  申请人：——

  公开号：US7208518B2

  公开（公告）日：2007-04-24