2,2-dimethyl-3-(phenylthio)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione

• 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-3-(phenylthio)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
• 英文别名: 2,2-Dimethyl-3-phenylsulfanyl-3,4-dihydrobenzo[h]chromene-5,6-dione；2,2-dimethyl-3-phenylsulfanyl-3,4-dihydrobenzo[h]chromene-5,6-dione
• 化学式: C₂₁H₁₈O₃S
• 分子量: 350.438
• InChiKey: YPMRQCFLHXEFQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-3-(phenylthio)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 在 sodium periodate 、 ruthenium(III) trichloride hydrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 以92 %的产率得到2,2-dimethyl-3-(phenylsulfonyl)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
  参考文献：
  名称：

  醌的电化学磺化/环化：快速、绿色、高效地获取细胞毒性化合物

  摘要：

  利用完整的电化学电池进行磺化反应，制备具有有效生物活性的含硫萘醌。

  DOI：

  10.1002/ejoc.202300506
• 作为产物：
  描述：

  二苯硫醚 、 黄钟花醌 在 碘 、 二甲基亚砜 作用下， 反应 0.17h， 以52%的产率得到2,2-dimethyl-3-(phenylthio)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
  参考文献：
  名称：

  Hybrid compounds with two redox centres: Modular synthesis of chalcogen-containing lapachones and studies on their antitumor activity

  摘要：

  Chalcogen-containing beta-lapachone derivatives were synthesized using a straightforward methodology and evaluated against several cancer cell lines (leukaemia, human colon carcinoma, prostate, human metastatic prostate, ovarian, central nervous system and breast), showing, in some cases, IC50 values below 1 mu M. The cytotoxic potential of the lapachones evaluated was also assayed using non-tumor cells: human peripheral blood mononuclear cells, two murine fibroblast lines (L929 and V79 cells) and MDCK (canine kidney epithelial cells). These compounds could provide promising new lead derivatives for anticancer drug development. This manuscript reports important findings since few authors have described C-3 substituted beta-lapachone with potent antitumor activity. The methodology employed allowed the preparation of the compounds from lapachol within a few minutes in a green approach. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.06.044

文献信息

• On the investigation of hybrid quinones: synthesis, electrochemical studies and evaluation of trypanocidal activity
  作者：Guilherme A. M. Jardim、Wallace J. Reis、Matheus F. Ribeiro、Flaviano M. Ottoni、Ricardo J. Alves、Thaissa L. Silva、Marilia O. F. Goulart、Antonio L. Braga、Rubem F. S. Menna-Barreto、Kelly Salomão、Solange L. de Castro、Eufrânio N. da Silva Júnior

  DOI：10.1039/c5ra16213k

  日期：——

  Thirty-eight compounds were evaluated against T. cruzi and six were found to be more potent against trypomastigotes than benznidazole.

  三十八种化合物被评估对抗克氏锥虫，其中六种被发现对游离子比苯硝唑更有效。