3-methoxy-4-nitro-N-(methylsulfonyl)benzenamine | 57165-05-6

• 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-methoxy-4-nitro-N-(methylsulfonyl)benzenamine
• 英文别名: 3-Methoxy-4-nitro-methansulfonanilid；N-(3-methoxy-4-nitrophenyl)methanesulfonamide
• CAS: 57165-05-6
• 化学式: C₈H₁₀N₂O₅S
• 分子量: 246.244
• InChiKey: TUYFHIKNEWGETD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-nitro-N-(methylsulfonyl)benzenamine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 N-(4-氨基-3-甲氧基苯基)甲磺酰胺
  参考文献：
  名称：

  Potential antitumor agents. 48. 3'-Dimethylamino derivatives of amsacrine: redox chemistry and in vivo solid tumor activity

  摘要：

  Structure-activity relationships for a series of acridine-substituted 3'-N(CH3)2 derivatives of the clinical antileukemic drug amsacrine (1) are reported. The parent (unsubstituted) compound 3 has activity against the Lewis lung solid tumor that is superior to amsacrine (1), the new clinical amsacrine analogue 4, and the recently developed 3'-NHCH3 derivative 2. Although the compounds generally bind less well to DNA and are less dose potent in vivo than either their amsacrine (3'-OCH3) or 3'-NHCH3 analogues, they show very high levels of antitumor activity, with the 4-OCH3 derivative capable of effecting 100% cures of the Lewis lung solid tumor. The broad structure-activity relationships for acridine substitution more closely resemble those of the amsacrine than the 3'-NHCH3 series, with 4-substituted and 4,5-disubstituted compounds showing the highest activity.

  DOI：

  10.1021/jm00387a012
• 作为产物：
  描述：

  N-(3-甲氧基-4-硝基苯基)乙酰胺 在 吡啶 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 3-methoxy-4-nitro-N-(methylsulfonyl)benzenamine
  参考文献：
  名称：

  Potential antitumor agents. 48. 3'-Dimethylamino derivatives of amsacrine: redox chemistry and in vivo solid tumor activity

  摘要：

  Structure-activity relationships for a series of acridine-substituted 3'-N(CH3)2 derivatives of the clinical antileukemic drug amsacrine (1) are reported. The parent (unsubstituted) compound 3 has activity against the Lewis lung solid tumor that is superior to amsacrine (1), the new clinical amsacrine analogue 4, and the recently developed 3'-NHCH3 derivative 2. Although the compounds generally bind less well to DNA and are less dose potent in vivo than either their amsacrine (3'-OCH3) or 3'-NHCH3 analogues, they show very high levels of antitumor activity, with the 4-OCH3 derivative capable of effecting 100% cures of the Lewis lung solid tumor. The broad structure-activity relationships for acridine substitution more closely resemble those of the amsacrine than the 3'-NHCH3 series, with 4-substituted and 4,5-disubstituted compounds showing the highest activity.

  DOI：

  10.1021/jm00387a012

文献信息

• CAIN B. F.; ATWELL G. J.; DENNY A. D., J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 11, 1110-1117
  作者：CAIN B. F.、 ATWELL G. J.、 DENNY A. D.

  DOI：——

  日期：——
• US4472582A
  申请人：——

  公开号：US4472582A

  公开（公告）日：1984-09-18
• Potential antitumor agents. 48. 3'-Dimethylamino derivatives of amsacrine: redox chemistry and in vivo solid tumor activity
  作者：Graham J. Atwell、Gordon W. Rewcastle、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00387a012

  日期：1987.4

  Structure-activity relationships for a series of acridine-substituted 3'-N(CH3)2 derivatives of the clinical antileukemic drug amsacrine (1) are reported. The parent (unsubstituted) compound 3 has activity against the Lewis lung solid tumor that is superior to amsacrine (1), the new clinical amsacrine analogue 4, and the recently developed 3'-NHCH3 derivative 2. Although the compounds generally bind less well to DNA and are less dose potent in vivo than either their amsacrine (3'-OCH3) or 3'-NHCH3 analogues, they show very high levels of antitumor activity, with the 4-OCH3 derivative capable of effecting 100% cures of the Lewis lung solid tumor. The broad structure-activity relationships for acridine substitution more closely resemble those of the amsacrine than the 3'-NHCH3 series, with 4-substituted and 4,5-disubstituted compounds showing the highest activity.