9-methyl-6H-dibenzo[c,h]chromen-6-one | 59115-64-9

• 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: 9-methyl-6H-dibenzo[c,h]chromen-6-one
• 英文别名: 9-Methylnaphtho[1,2-c]isochromen-6-one
• CAS: 59115-64-9
• 化学式: C₁₈H₁₂O₂
• 分子量: 260.292
• InChiKey: KTZMZHKFHWMARF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  naphthalen-1-yl 2-bromo-4-methylbenzoate 在 PdCl(OAc) 、 sodium acetate 、 三苯基膦 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 3.0h， 以65%的产率得到9-methyl-6H-dibenzo[c,h]chromen-6-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

• Enaminone-directed ruthenium(<scp>ii</scp>)-catalyzed C–H activation and annulation of arenes with diazonaphthoquinones for polycyclic benzocoumarins
  作者：Sudeshna Mondal、Chandan Kumar Giri、Mahiuddin Baidya

  DOI：10.1039/d3cc03999d

  日期：——

  coordinating enaminone functionality has been leveraged for a C–H bond activation strategy under ruthenium catalysis and employed in the regioselective annulative coupling of arenes with diazonaphthoquinones, offering polycyclic benzocoumarins in very high yields. The enaminone motif plays a dual role and the protocol operates through a Ru(II)/Ru(IV) catalytic pathway which is amenable to the diversification

  弱配位烯胺酮官能团已被用于钌催化下的C-H键活化策略，并用于芳烃与重氮萘醌的区域选择性环偶联，以非常高的产率提供多环苯并香豆素。烯胺酮基序发挥双重作用，该方案通过 Ru( II )/Ru( IV ) 催化途径进行操作，该途径适合各种药效团偶联底物的多样化。
• Antitumor Agents. 272. Structure−Activity Relationships and In Vivo Selective Anti-Breast Cancer Activity of Novel Neo-tanshinlactone Analogues
  作者：Yizhou Dong、Qian Shi、Huei-Chen Pai、Chieh-Yu Peng、Shiow-Lin Pan、Che-Ming Teng、Kyoko Nakagawa-Goto、Donglei Yu、Yi-Nan Liu、Pei-Chi Wu、Kenneth F. Bastow、Susan L. Morris-Natschke、Arnold Brossi、Jing-Yu Lang、Jennifer L. Hsu、Mien-Chie Hung、Eva Y.-H. P. Lee、Kuo-Hsiung Lee

  DOI：10.1021/jm1000858

  日期：2010.3.11

  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.