3-amino-2-(4-chloro-5-methyl-2-methylthiobenzenesulfonyl)guanidine | 852289-49-7

• 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: 3-amino-2-(4-chloro-5-methyl-2-methylthiobenzenesulfonyl)guanidine
• 英文别名: 1-amino-2-(4-chloro-5-methyl-2-methylsulfanylphenyl)sulfonylguanidine
• CAS: 852289-49-7
• 化学式: C₉H₁₃ClN₄O₂S₂
• 分子量: 308.813
• InChiKey: QOVMTGICEZINIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-2-(4-chloro-5-methyl-2-methylthiobenzenesulfonyl)guanidine 、 方酸 以 乙醇 为溶剂， 以37%的产率得到4-chloro-5-methyl-2-methylthio-N-(1,2-dihydroxycyclobuta[e]1,2,4-triazin-3-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, molecular structure, and in vitro antitumor activity of new 4-chloro-2-mercaptobenzenesulfonamide derivatives

  摘要：

  The reaction of 3-amino-2-(2-alkylthio-4-chlorobenzenesulfonyl)guanidines 2a-j with 1,2-dicarbonyl compounds are described. Depending on structure of 1,2-dicarbonyl reagent novel 2-alkylthio-5-chloro-N-(1,2,4-triazin-3-yl)benzenesulfonamides 3-15, 1-(2-alkylthio-4chlorobenzenesulfonyl)-3-(2-oxobutane-3-ylidenoimino)guanidines 16-18 and 2-alkylthio-4-chloro-N-(1,2-dihydroxycyclobuta[e]1,2,4triazin-3-yl)benzenesulfonamides 19-21 are obtained. The structures of these compounds were confirmed on the basis of elemental analysis, spectral data and X-ray analysis. The compounds 4, 5, 7, 9, 10, 12-15, 17, 18 and 20 were screened at the National Cancer Institute (NCI) for their in vitro activities against a panel of 56 tumor cell lines and relationship between structure and antitumor activity are discussed. The compounds 10, 12, 17 and 20 were inactive, whereas the other compounds exhibited reasonable activity against one or more human tumor cell lines. The prominent compound 18 showed significant activity against cell lines of colon cancer (HCT- 116), renal cancer (786-0) and melanoma (M14) (GI(50), in the range 0.33-1.08 mu M) as well as good selectivity toward non-small cell lung cancer (HOP-62) cells (GI(50) = 0.05 PM, TGI = 0.38 mu M and LC51 = 4.83 mu M). (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.11.014
• 作为产物：
  描述：

  N-(4-chloro-2-methylthio-5-methylbenzenesulfonyl)cyanamide potassium salt 在 盐酸肼 作用下， 以 1,4-二氧六环 为溶剂， 以76%的产率得到3-amino-2-(4-chloro-5-methyl-2-methylthiobenzenesulfonyl)guanidine
  参考文献：
  名称：

  Synthesis, molecular structure, and in vitro antitumor activity of new 4-chloro-2-mercaptobenzenesulfonamide derivatives

  摘要：

  The reaction of 3-amino-2-(2-alkylthio-4-chlorobenzenesulfonyl)guanidines 2a-j with 1,2-dicarbonyl compounds are described. Depending on structure of 1,2-dicarbonyl reagent novel 2-alkylthio-5-chloro-N-(1,2,4-triazin-3-yl)benzenesulfonamides 3-15, 1-(2-alkylthio-4chlorobenzenesulfonyl)-3-(2-oxobutane-3-ylidenoimino)guanidines 16-18 and 2-alkylthio-4-chloro-N-(1,2-dihydroxycyclobuta[e]1,2,4triazin-3-yl)benzenesulfonamides 19-21 are obtained. The structures of these compounds were confirmed on the basis of elemental analysis, spectral data and X-ray analysis. The compounds 4, 5, 7, 9, 10, 12-15, 17, 18 and 20 were screened at the National Cancer Institute (NCI) for their in vitro activities against a panel of 56 tumor cell lines and relationship between structure and antitumor activity are discussed. The compounds 10, 12, 17 and 20 were inactive, whereas the other compounds exhibited reasonable activity against one or more human tumor cell lines. The prominent compound 18 showed significant activity against cell lines of colon cancer (HCT- 116), renal cancer (786-0) and melanoma (M14) (GI(50), in the range 0.33-1.08 mu M) as well as good selectivity toward non-small cell lung cancer (HOP-62) cells (GI(50) = 0.05 PM, TGI = 0.38 mu M and LC51 = 4.83 mu M). (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.11.014

文献信息

• Synthesis, molecular structure, and in vitro antitumor activity of new 4-chloro-2-mercaptobenzenesulfonamide derivatives
  作者：Jarosław Sławiński、Maria Gdaniec

  DOI：10.1016/j.ejmech.2004.11.014

  日期：2005.4

  The reaction of 3-amino-2-(2-alkylthio-4-chlorobenzenesulfonyl)guanidines 2a-j with 1,2-dicarbonyl compounds are described. Depending on structure of 1,2-dicarbonyl reagent novel 2-alkylthio-5-chloro-N-(1,2,4-triazin-3-yl)benzenesulfonamides 3-15, 1-(2-alkylthio-4chlorobenzenesulfonyl)-3-(2-oxobutane-3-ylidenoimino)guanidines 16-18 and 2-alkylthio-4-chloro-N-(1,2-dihydroxycyclobuta[e]1,2,4triazin-3-yl)benzenesulfonamides 19-21 are obtained. The structures of these compounds were confirmed on the basis of elemental analysis, spectral data and X-ray analysis. The compounds 4, 5, 7, 9, 10, 12-15, 17, 18 and 20 were screened at the National Cancer Institute (NCI) for their in vitro activities against a panel of 56 tumor cell lines and relationship between structure and antitumor activity are discussed. The compounds 10, 12, 17 and 20 were inactive, whereas the other compounds exhibited reasonable activity against one or more human tumor cell lines. The prominent compound 18 showed significant activity against cell lines of colon cancer (HCT- 116), renal cancer (786-0) and melanoma (M14) (GI(50), in the range 0.33-1.08 mu M) as well as good selectivity toward non-small cell lung cancer (HOP-62) cells (GI(50) = 0.05 PM, TGI = 0.38 mu M and LC51 = 4.83 mu M). (c) 2005 Elsevier SAS. All rights reserved.