2,2-dimethyl-4-(phenylthio)-3,4-dihydro-2H-benzo[g]chromene-5,10-dione | 1569313-66-1

• 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: 2,2-dimethyl-4-(phenylthio)-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
• 英文别名: 2,2-Dimethyl-4-phenylsulfanyl-3,4-dihydrobenzo[g]chromene-5,10-dione；2,2-dimethyl-4-phenylsulfanyl-3,4-dihydrobenzo[g]chromene-5,10-dione
• CAS: 1569313-66-1
• 化学式: C₂₁H₁₈O₃S
• 分子量: 350.438
• InChiKey: VTBOXOMZJLVZRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  ALPHA-拉杷醌 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 生成 2,2-dimethyl-4-(phenylthio)-3,4-dihydro-2H-benzo[g]chromene-5,10-dione
  参考文献：
  名称：

  1,2,3-Triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: Potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones

  摘要：

  1,2,3-Triazole-, arylamino- and thio-substituted naphthoquinones (24, 8, and 2 representatives, respectively) were synthesized in moderate yields and evaluated against several human cancer cell lines (blood, ovarian, breast, central nervous system, colon, and prostate cancers and melanoma), showing, for some of them, IC50 values below 2 mu M. The cytotoxic potential of the tested naphthoquinones was also assayed on non-tumor cells such as human peripheral blood mononucluear cells (PBMC) and two murine fibroblast lines (L929 and V79 cells). alpha-Lapachone-and nor-alpha-lapachone-based 1,2,3-triazoles and arylamino-substituted naphthoquinones showed potent cytotoxicity against different cancer cell lines. The compounds may represent promising new lead derivatives for anticancer drug development. The electrochemical properties of selected compounds were evaluated in an attempt to correlate them with antitumor activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.01.033

文献信息

• 1,2,3-Triazole-, arylamino- and thio-substituted 1,4-naphthoquinones: Potent antitumor activity, electrochemical aspects, and bioisosteric replacement of C-ring-modified lapachones
  作者：Eduardo H.G. da Cruz、Caio M.B. Hussene、Gleiston G. Dias、Emilay B.T. Diogo、Isadora M.M. de Melo、Bernardo L. Rodrigues、Mauro G. da Silva、Wagner O. Valença、Celso A. Camara、Ronaldo N. de Oliveira、Yen G. de Paiva、Marilia O.F. Goulart、Bruno C. Cavalcanti、Claudia Pessoa、Eufrânio N. da Silva Júnior

  DOI：10.1016/j.bmc.2014.01.033

  日期：2014.3

  1,2,3-Triazole-, arylamino- and thio-substituted naphthoquinones (24, 8, and 2 representatives, respectively) were synthesized in moderate yields and evaluated against several human cancer cell lines (blood, ovarian, breast, central nervous system, colon, and prostate cancers and melanoma), showing, for some of them, IC50 values below 2 mu M. The cytotoxic potential of the tested naphthoquinones was also assayed on non-tumor cells such as human peripheral blood mononucluear cells (PBMC) and two murine fibroblast lines (L929 and V79 cells). alpha-Lapachone-and nor-alpha-lapachone-based 1,2,3-triazoles and arylamino-substituted naphthoquinones showed potent cytotoxicity against different cancer cell lines. The compounds may represent promising new lead derivatives for anticancer drug development. The electrochemical properties of selected compounds were evaluated in an attempt to correlate them with antitumor activity. (C) 2014 Elsevier Ltd. All rights reserved.