6-chloro-7-(5-phenyl-1,3,4-oxadiazol-2-yl)-3-methylthio-1,1-dioxo-1,4,2-benzodithiazine | 1318988-78-1

• 分子结构分类: 有机化合物
• 英文名称: 6-chloro-7-(5-phenyl-1,3,4-oxadiazol-2-yl)-3-methylthio-1,1-dioxo-1,4,2-benzodithiazine
• CAS: 1318988-78-1
• 化学式: C₁₆H₁₀ClN₃O₃S₃
• 分子量: 423.925
• InChiKey: KPKMBNSKYLPNJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  85.42
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  6-chloro-7-(5-phenyl-1,3,4-oxadiazol-2-yl)-3-methylthio-1,1-dioxo-1,4,2-benzodithiazine 在 ammonium hydroxide 、 盐酸羟胺 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成 1-{2-[(1,3-benzodioxol-5-yl)methylthio]-4-chloro-5-(5-phenyl-1,3,4-oxadiazol-2-yl)benzenesulfonyl}-3-hydroxyguanidine
  参考文献：
  名称：

  1-(2-Mercaptobenzenesulfonyl)-3-hydroxyguanidines – Novel potent antiproliferatives, synthesis and in vitro biological activity

  摘要：

  Twenty four 1-[2-alkylthio-5-(azol-2 or 5-yl)-4-chlorobenzenesulfonyl]-3-hydroxyguanidines 6a-x have been synthesized in order to evaluate their biological activity. Compounds 6a, 6c, 6d, 6f, 6g, 6i-p, 6r-t, and 6v-x were tested for their in vitro anticancer activity at the US National Cancer Institute. The highest in vitro anticancer activity was found for compounds 6d, 6g and 6k with GI(50) average value in the range 1.62-1.86 mu M, and TGI mean values 3.72-4.47 mu M, whereas the remaining compounds showed broad spectrum of anticancer activity at low micromolar GI(50) level against all tested cancer cell lines. These results were subjected to CoMSIA analysis to establish quantitative structure activity relationships. The results evidence that potency of these compounds correlates mainly with hydrophobic and polar surface properties of substituents located both at 2 and 5 positions of 1-(4-chlorobenzenesulfonyl) moiety of investigated 3-hydroxyguanidine series. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.042
• 作为产物：
  描述：

  6-chloro-3-(methylthio)-1,1-dioxo-1,4,2-benzodithiazine-7-carboxylic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 生成 6-chloro-7-(5-phenyl-1,3,4-oxadiazol-2-yl)-3-methylthio-1,1-dioxo-1,4,2-benzodithiazine
  参考文献：
  名称：

  Novel 3-Amino-6-chloro-7-(azol-2 or 5-yl)-1,1-dioxo-1,4,2-benzodithiazine Derivatives with Anticancer Activity: Synthesis and QSAR Study

  摘要：

  一系列新的 3-氨基-6-氯-7-(azol-2 或 5-yl)-1,1-二氧代-1,4,2-苯并二噻嗪衍生物 5a–j 已被合成并在体外评估美国国家癌症研究所的抗增殖活性。最活跃的化合物 5h 对卵巢癌 (OVCAR-3) 和乳腺癌 (MDA-MB-468) 表现出显着的细胞毒性作用（癌细胞死亡分别为 10% 和 47%），并对前列腺癌 (DU-145) 具有良好的选择性）、结肠（SW-620）和肾（TK-10）癌细胞系。为了更深入地了解新化合物 5a-j 的结构-活性关系，已经应用了 QSAR 研究。理论计算允许识别属于 RDF（分别在 MOLT-4 和 UO-31 QSAR 模型中的 RDF055p 和 RDF145m）和 3D-MorSE（MOLT-4 和 UO-31 QSAR 模型中的 Mor32m 和 Mor16e）描述符的分子描述符类。基于这些数据，获得了具有良好鲁棒性和预测能力的QSAR模型。

  DOI：

  10.3390/molecules201219821

文献信息

• Synthesis and Antitumor Activity of Novel N’-(2-Benzylthiobenzenesulfonyl)-1H-pyrazole-1-amidine Derivatives
  作者：Jarosław Sławiński、Kamil Brożewicz、Andrzej Fruziński、Marek L. Główka

  DOI：10.3987/com-11-12164

  日期：——

  A series of N'-(2-benzylthio-4-chlorobenzenesulfonyl)-1H-pyrazole-1-amidines (23-36) were synthesized by the reaction of 3-amino-2-(benzenesulfonyl)guanidines (18-22) with adequate 1,3-diketones. The compounds 23, 24, 26, 30, 31, 34 and 35 were tested in vitro in the full NCI 60 cell panel. The most potent compound in the series (26) showed substantial activity toward some cell lines of leukemia and cancer cells of lung, colon, CNS, melanoma, renal, prostate and breast (GI(50) in the range 2.30-9.47 mu M).