1-hydroxy-4-thia-phenanthren-3-one | 32147-96-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-hydroxy-4-thia-phenanthren-3-one
• 英文别名: 4-Hydroxy-1-thia-7,8-benzcumarin
• CAS: 32147-96-9
• 化学式: C₁₃H₈O₂S
• 分子量: 228.271
• InChiKey: KEIJTWGHYZVDOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-hydroxy-4-thia-phenanthren-3-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8%的产率得到1-methyl-11H-benzo[h]furo[3,2-c]thiochromen-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：

  1-奈硫酚 、 丙二酸 在 polyphosphoric acid 作用下， 反应 3.0h， 生成 1-hydroxy-4-thia-phenanthren-3-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

• NEO-TANSHINLACTONE AND ANALOGS AS POTENT AND SELECTIVE ANTI-BREAST CANCER AGENTS
  申请人：Lee Kuo-Hsiung

  公开号：US20090118356A1

  公开（公告）日：2009-05-07

  Compounds of Formulas I-II are described, along with methods of using such compounds for the treatment of cancer and pharmaceutical formulations thereof.

  描述了I-II式化合物，以及使用这些化合物治疗癌症和制备制药配方的方法。
• THIOCHROMENE DERIVATIVES AS HIF HYDROXYLASE INHIBITORS
  申请人：Ho Wen-Bin

  公开号：US20110305776A1

  公开（公告）日：2011-12-15

  The present invention relates to novel compounds, methods, and compositions capable of decreasing HIF hydroxylase enzyme activity, thereby increasing the stability and/or activity of hypoxia inducible factor (HIF).

  本发明涉及新型化合物、方法和组合物，能够降低HIF羟化酶酶活性，从而增加缺氧诱导因子（HIF）的稳定性和/或活性。
• THIOCHROMENE DERIVATIVES AS HIP HYDROXYLASE INHIBITORS
  申请人：Fibrogen, Inc.

  公开号：EP2370422A1

  公开（公告）日：2011-10-05
• US7495026B2
  申请人：——

  公开号：US7495026B2

  公开（公告）日：2009-02-24
• US7795299B2
  申请人：——

  公开号：US7795299B2

  公开（公告）日：2010-09-14