2,2-dimethyl-3-(phenylselanyl)-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-(phenylselanyl)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione
• 英文别名: 2,2-Dimethyl-3-phenylselanyl-3,4-dihydrobenzo[h]chromene-5,6-dione；2,2-dimethyl-3-phenylselanyl-3,4-dihydrobenzo[h]chromene-5,6-dione
• 化学式: C₂₁H₁₈O₃Se
• 分子量: 397.332
• InChiKey: DNWGOVCPCLJUDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-3-(phenylselanyl)-3,4-dihydro-2H-benzo[h]chromene-5,6-dione 在 盐酸羟胺 、 sodium acetate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以60%的产率得到6-(hydroxyimino)-2,2-dimethyl-3-(phenylselanyl)-2,3,4,6-tetrahydro-5H-benzo[h]chromen-5-one
  参考文献：
  名称：

  醌的电化学硒化/环化：快速，绿色和有效地获得功能化的锥虫和抗肿瘤化合物

  摘要：

  在未分开的电化学池中进行电化学硒化可以制备具有强生物活性的含硒萘醌。快速，绿色和高效的方案避免了化学氧化剂，并能够以快速可靠的方式合成目标分子。

  DOI：

  10.1002/ejoc.202000216
• 作为产物：
  描述：

  二苯硒醚 、 黄钟花醌 在 碘 、 二甲基亚砜 作用下， 反应 0.17h， 以66%的产率得到2,2-dimethyl-3-(phenylselanyl)-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。
• Catalytic Chalcogenylation under Greener Conditions: A Solvent-Free Sulfur- and Seleno-functionalization of Olefins via I₂/DMSO Oxidant System
  作者：André A. Vieira、Juliano B. Azeredo、Marcelo Godoi、Claudio Santi、Eufrânio N. da Silva Júnior、Antonio L. Braga

  DOI：10.1021/jo502621a

  日期：2015.2.20

  Herein, we report a solvent- and metal-free methodology for the alkoxy-chalcogenylation of styrenes, using molecular iodine as a catalyst, DMSO as a stoichiometric oxidant, and different nucleophiles under microwave irradiation. This eco-friendly approach afforded the desired products in good to excellent yields in only 10 min. In addition, using the same protocol, we carried out the cyclization reaction of relevant molecules, such as lapachol derivatives.
• Electrochemical Selenation/Cyclization of Quinones: A Rapid, Green and Efficient Access to Functionalized Trypanocidal and Antitumor Compounds
  作者：Ammar Kharma、Claus Jacob、Ícaro A. O. Bozzi、Guilherme A. M. Jardim、Antonio L. Braga、Kelly Salomão、Claudia C. Gatto、Maria Francilene S. Silva、Claudia Pessoa、Maximilian Stangier、Lutz Ackermann、Eufrânio N. da Silva Júnior

  DOI：10.1002/ejoc.202000216

  日期：2020.8.9

  Electrochemical selenation in undivided electrochemical cells allows the preparation of selenium‐containing naphthoquinones with potent bioactivity. The rapid, green and efficient protocol avoids chemical oxidants and enables the synthesis of target molecules in a fast and reliable way.

  在未分开的电化学池中进行电化学硒化可以制备具有强生物活性的含硒萘醌。快速，绿色和高效的方案避免了化学氧化剂，并能够以快速可靠的方式合成目标分子。
• Hybrid compounds with two redox centres: Modular synthesis of chalcogen-containing lapachones and studies on their antitumor activity
  作者：André A. Vieira、Igor R. Brandão、Wagner O. Valença、Carlos A. de Simone、Bruno C. Cavalcanti、Claudia Pessoa、Teiliane R. Carneiro、Antonio L. Braga、Eufrânio N. da Silva

  DOI：10.1016/j.ejmech.2015.06.044

  日期：2015.8

  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.