6-chloroethylureidopropylquinobenzothiazine | 1443133-64-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-chloroethylureidopropylquinobenzothiazine
• 英文别名: 1-(2-Chloroethyl)-3-(3-quinolino[3,2-b][1,4]benzothiazin-6-ylpropyl)urea；1-(2-chloroethyl)-3-(3-quinolino[3,2-b][1,4]benzothiazin-6-ylpropyl)urea
• CAS: 1443133-64-9
• 化学式: C₂₁H₂₁ClN₄OS
• 分子量: 412.943
• InChiKey: AYGICOKFLVCYGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  82.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6H-quino[3,2-b]benzo[1,4]thiazine 在 sodium hydride 、 肼 作用下， 以 乙醇 、 正己烷 、 水 、 甲苯 为溶剂， 反应 51.5h， 生成 6-chloroethylureidopropylquinobenzothiazine
  参考文献：
  名称：

  Synthesis and selected immunological properties of substituted quino[3,2-b]benzo[1,4]thiazines

  摘要：

  A new type of azaphenothiazines - tetracyclic quino[3,2-b]benzo[1,4]thiazines, possessing common substituents (H, CH3, Cl, Br, F, CF3, SCH3) in positions 8-10 and pharmacophoric aminoalkyl substituents in position 6, were-obtained from-diquinodithiin and 2,2'-dichloro-3,3'-diquinolinyl disulfide in several-step syntheses. Sixty one compounds, grouped as the 6H, 6-dialkylaminoalkyl, 6-acylaminoalkyl and sulfonylaminoalkyl derivatives, were tested for cytotoxicity, their effects on phytohemagglutin A (PHA)-induced proliferative response of human peripheral blood mononuclear cells (PBMC) and lipopolysaccharide (LPS)-induced tumor necrosis factor alpha (TNF-alpha) production by these cells. The compounds exhibited differential inhibitory activities in these tests and significantly varied in terms of cytotoxicity. The most promising compounds were tested for growth inhibition of leukemia L-1210 cells, colon cancer SV-948 cells and epidermal carcinoma A-341 cells. The most active compounds exhibited anticancer activity against these cell lines comparable to that of cisplatin. The structure-activity relationship of the compounds were discussed. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.02.023

文献信息

• Synthesis and selected immunological properties of substituted quino[3,2-b]benzo[1,4]thiazines
  作者：Małgorzata Jeleń、Krystian Pluta、Michał Zimecki、Beata Morak-Młodawska、Jolanta Artym、Maja Kocięba

  DOI：10.1016/j.ejmech.2013.02.023

  日期：2013.5

  A new type of azaphenothiazines - tetracyclic quino[3,2-b]benzo[1,4]thiazines, possessing common substituents (H, CH3, Cl, Br, F, CF3, SCH3) in positions 8-10 and pharmacophoric aminoalkyl substituents in position 6, were-obtained from-diquinodithiin and 2,2'-dichloro-3,3'-diquinolinyl disulfide in several-step syntheses. Sixty one compounds, grouped as the 6H, 6-dialkylaminoalkyl, 6-acylaminoalkyl and sulfonylaminoalkyl derivatives, were tested for cytotoxicity, their effects on phytohemagglutin A (PHA)-induced proliferative response of human peripheral blood mononuclear cells (PBMC) and lipopolysaccharide (LPS)-induced tumor necrosis factor alpha (TNF-alpha) production by these cells. The compounds exhibited differential inhibitory activities in these tests and significantly varied in terms of cytotoxicity. The most promising compounds were tested for growth inhibition of leukemia L-1210 cells, colon cancer SV-948 cells and epidermal carcinoma A-341 cells. The most active compounds exhibited anticancer activity against these cell lines comparable to that of cisplatin. The structure-activity relationship of the compounds were discussed. (C) 2013 Elsevier Masson SAS. All rights reserved.