4-Chloro-5-methyl-2-[4-nitrophenylhydrazone N-(4-methoxybenzylidenethio)]benzenesulfonamide

• 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: 4-Chloro-5-methyl-2-[4-nitrophenylhydrazone N-(4-methoxybenzylidenethio)]benzenesulfonamide
• 英文别名: (5-chloro-4-methyl-2-sulfamoylphenyl) (1Z)-4-methoxy-N-(4-nitroanilino)benzenecarboximidothioate
• 化学式: C₂₁H₁₉ClN₄O₅S₂
• 分子量: 506.991
• InChiKey: XCUYMSJMZMQDSE-DAFNUICNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-chloro-2-mercapto-5-methylbenzenesulfonamide 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 7.5h， 以76%的产率得到4-Chloro-5-methyl-2-[4-nitrophenylhydrazone N-(4-methoxybenzylidenethio)]benzenesulfonamide
  参考文献：
  名称：

  Synthesis of a new series of 4-chloro-2-mercapto-5-methylbenzenesulfonamide derivatives with potential antitumor activity

  摘要：

  The syntheses of S-(5-chloro-4-methyl-2-sulfamoylptienyl)alkanethio (or benzothio)hydrazonates (3a-3o) and potassium S-(5-chloro-2-cyanoamidatesulfonyl-4-methylphenyl)alkanethio (or benzothio)hydrazonates (4-10) are described. The compounds 3e, 3i-3o, 7 and 8 were screened at the National Cancer Institute (NCI) for their activities against a panel of 59 tumor cell lines and relationships between Structure and antitumor activity in vitro are discussed. The Compounds 3e, 3j, 3l-3o and 7 exhibited reasonable activity against numerous human tumor cell lines. The prominent compound 3l showed significant activity against some cell lines of leukemia (SR), melanoma (SK-MEL-5), CNS cancer (SF-539), ovarian cancer (OVCAR-3, OVCAR-4) and breast cancer (MDA-MB-231/ACTT) (GI(50) values in the range, 0.3-0.9 muM). Furthermore, compound 8 exhibited the high selectivity against renal cancer (A498) cells (GI(50) < 0.01 muM, TGI = 2.3 muM and LC50 = 35.7 muM). (C) 2003 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2003.09.013

文献信息

• Synthesis of a new series of 4-chloro-2-mercapto-5-methylbenzenesulfonamide derivatives with potential antitumor activity
  作者：Jarosław Sławiński

  DOI：10.1016/j.ejmech.2003.09.013

  日期：2004.2

  The syntheses of S-(5-chloro-4-methyl-2-sulfamoylptienyl)alkanethio (or benzothio)hydrazonates (3a-3o) and potassium S-(5-chloro-2-cyanoamidatesulfonyl-4-methylphenyl)alkanethio (or benzothio)hydrazonates (4-10) are described. The compounds 3e, 3i-3o, 7 and 8 were screened at the National Cancer Institute (NCI) for their activities against a panel of 59 tumor cell lines and relationships between Structure and antitumor activity in vitro are discussed. The Compounds 3e, 3j, 3l-3o and 7 exhibited reasonable activity against numerous human tumor cell lines. The prominent compound 3l showed significant activity against some cell lines of leukemia (SR), melanoma (SK-MEL-5), CNS cancer (SF-539), ovarian cancer (OVCAR-3, OVCAR-4) and breast cancer (MDA-MB-231/ACTT) (GI(50) values in the range, 0.3-0.9 muM). Furthermore, compound 8 exhibited the high selectivity against renal cancer (A498) cells (GI(50) < 0.01 muM, TGI = 2.3 muM and LC50 = 35.7 muM). (C) 2003 Elsevier SAS. All rights reserved.