(R)-5-(4-fluorophenyl)-1,1,3-trimethylbenzo[f]-thiazolo[4,3-a]isoindole-6,11(1H,3H)-dione | 1246308-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (R)-5-(4-fluorophenyl)-1,1,3-trimethylbenzo[f]-thiazolo[4,3-a]isoindole-6,11(1H,3H)-dione
• 英文别名: (14R)-16-(4-fluorophenyl)-12,12,14-trimethyl-13-thia-15-azatetracyclo[8.6.0.03,8.011,15]hexadeca-1(16),3,5,7,10-pentaene-2,9-dione
• CAS: 1246308-66-6
• 化学式: C₂₃H₁₈FNO₂S
• 分子量: 391.466
• InChiKey: JWQYCPZJNGUQJB-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸酐 、 1,4-萘醌 、 (+/-)-(2S,4R)-3-(4-fluorophenylcarbonyl)-2,5,5-trimethylthiazolidine-4-carboxylic acid 反应 2.0h， 以72%的产率得到(R)-5-(4-fluorophenyl)-1,1,3-trimethylbenzo[f]-thiazolo[4,3-a]isoindole-6,11(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of new naphthoquinone-containing pyrrolo-thiazoles as anticancer agents

  摘要：

  Abstract magnified image Naphthoquinones undergo 1,3‐dipolar cycloaddition with bicyclic münchnones generated from thiazolidines affording new pyrrolo‐thiazoles with a fused quinone nucleus. The products were obtained as single enantiomers in good yields. These benzo[f]thiazolo[4,3‐a]isoindole‐6,11(1H,3H)‐diones are comprised of four fused rings and present a very planar structure. The evaluation of their anticancer activity against melanoma A375 and colorectal adenocarcinoma WiDr human cell lines showed only moderate activity but gave insight into the modeling of new structures. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.] J. Heterocyclic Chem., (2010).

  DOI：

  10.1002/jhet.396

文献信息

• Synthesis and biological evaluation of new naphthoquinone-containing pyrrolo-thiazoles as anticancer agents
  作者：Susana M. M. Lopes、Mafalda Laranjo、Arménio C. Serra、Ana Margarida Abrantes、António M. d'A. Rocha Gonsalves、Maria Filomena Botelho、Ana Matos Beja、Manuela Ramos Silva、Teresa M. V. D. Pinho e Melo

  DOI：10.1002/jhet.396

  日期：——

  Abstract magnified image Naphthoquinones undergo 1,3‐dipolar cycloaddition with bicyclic münchnones generated from thiazolidines affording new pyrrolo‐thiazoles with a fused quinone nucleus. The products were obtained as single enantiomers in good yields. These benzo[f]thiazolo[4,3‐a]isoindole‐6,11(1H,3H)‐diones are comprised of four fused rings and present a very planar structure. The evaluation of their anticancer activity against melanoma A375 and colorectal adenocarcinoma WiDr human cell lines showed only moderate activity but gave insight into the modeling of new structures. [Color figure can be viewed in the online issue, which is available at www.interscience.wiley.com.] J. Heterocyclic Chem., (2010).