1-allyl-3-amino-2-(4-chloro-5-methyl-2-methylthiobenzenesulphonyl)guanidine | 483305-10-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-allyl-3-amino-2-(4-chloro-5-methyl-2-methylthiobenzenesulphonyl)guanidine
• 英文别名: 1-allyl-3-amino-2-[4-chloro-5-methyl-2-(methylsulfanyl)benzenesulfonyl]guanidine；1-Amino-3-(4-chloro-5-methyl-2-methylsulfanylphenyl)sulfonyl-2-prop-2-enylguanidine
• CAS: 483305-10-8；950186-14-8
• 化学式: C₁₂H₁₇ClN₄O₂S₂
• 分子量: 348.878
• InChiKey: JRPAJDOSIWKVKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-硝基糠醛 、 1-allyl-3-amino-2-(4-chloro-5-methyl-2-methylthiobenzenesulphonyl)guanidine 以 乙醇 为溶剂， 反应 7.0h， 以92%的产率得到1-Allyl-2-(4-chloro-5-methyl-2-methylthiobenzenesulfonyl)-3-(5-nitro-2-furfulidenimino)-guanidine
  参考文献：
  名称：

  Synthesis of novel 3-amino-2-(4-chloro-2-mercaptobenzenesulfonyl)-guanidine derivatives as potential antitumor agents

  摘要：

  Novel 3-amino-2-(4-chloro-2-mercaptobenzenesulfonyl)guanidine derivatives have been synthesized as potential anticancer agents. The in vitro antitumor activity of these compounds has been evaluated in the US National Cancer Institute (NCI), and relationships between structure and antitumor activity are discussed. The prominent compound was 1-allyl-2-[4-chloro-5-(4-chlorophenylcarbamoyl)-2-methylthiobenzenesulfonyl]-3-(5-nitrofurfurylideneamino)guanidine (8) with remarkable activity against 21 human tumor cell lines representing leukemia, lung, colon, melanoma, ovarian, renal, prostate and breast (GI(50) = 0.3-3.0 mu M), and selectivity toward leukemia RPMI-8226 cell line (GI(50) = 0.3 VM, TGI = 1.4 mu M). (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.01.020
• 作为产物：
  描述：

  3-allylamino-6-chloro-7-methyl-1,4,2-benzodithiazine-1,1-dioxide 在 sodium hydroxide 、 一水合肼 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 1-allyl-3-amino-2-(4-chloro-5-methyl-2-methylthiobenzenesulphonyl)guanidine
  参考文献：
  名称：

  Synthesis, molecular structure and anticancer activity of 1-allyl-3-amino-2-(4-chloro-2-mercaptobenzenesulphonyl)guanidine derivatives

  摘要：

  A series of 3-allylamino-6-chloro-7-R-1.1-dioxo-1.4.2-benzodithiazines (2a-e) vas obtained by the reaction of 6-chloro-3-methylthio- 1.4.2-benzodithiazine-1. 1-dioxides (1a-e) with allylamine. Selective hydrazinolysis of the allylaminobenzodithiazines (2a-e) gave the appropriate 1-allyl 1-3-amino-2-(4-chloro-2-mercaptobenzenesulphonyl)guanidines (3a-e) in good yields. The reaction of 3a with dimethylsulphate under alkaline conditions provided the methylthio derivative 4. The structures of these compounds were confirmed on the basis of elemental analysis. spectral data (IR. H-1- and C-13-NMR) and X-ray analysis. Screening data indicated that the compounds 3a and 3d exhibited significant in vitro activities against numerous human tumour cell lines, whereas compounds 3b and 3c showed a moderate activity. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01341-7