Department of Organic Chemistry, Medical University of Silesia, ul. Jagiellońska 4, 41-200 Sosnowiec, Poland.
Eur J Med Chem. 2010 Nov;45(11):4733-9. doi: 10.1016/j.ejmech.2010.07.035. Epub 2010 Jul 24.
A novel method of synthesizing 1,4-thiazine ring has led to the series of 5-alkyl-12(H)-quino[3,4-b][1,4]benzothiazinium salts. The derivatives containing a butyl or decyl substituents on the quinoline nitrogen atom were obtained by alkylation of 12(H)-quino[3,4-b][1,4]benzothiazine with alkyl bromides. Antiproliferative activity in vitro of the compounds (3) was assessed using two cancer cell lines (Hct116 and LLC) and doxorubicin as a reference. Most of the studied phenothiazine derivatives showed activity against both cell lines investigated (2.2-19.6 μg/mL concentration range). A structure-activity relationship was established. Only the compounds with substituents in the 11-position of the quinobenzothiazine ring did not exhibit activity against either cell line.
一种合成 1,4-噻嗪环的新方法导致了一系列 5-烷基-12（H）-喹诺[3,4-b][1,4]苯并噻嗪鎓盐的产生。通过用烷基溴对 12（H）-喹诺[3,4-b][1,4]苯并噻嗪进行烷基化，得到了在喹啉氮原子上带有丁基或癸基取代基的衍生物。使用两种癌细胞系（Hct116 和 LLC）和阿霉素作为参考，评估了化合物（3）的体外抗增殖活性。研究的吩噻嗪衍生物大多数对两种被研究的细胞系都表现出活性（浓度范围为 2.2-19.6μg/mL）。建立了构效关系。只有在喹苯并噻嗪环的 11 位带有取代基的化合物对两种细胞系均无活性。
