3-nitro-N-(2-propylphenyl)benzenesulfonamide | 1383607-74-6

• 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-nitro-N-(2-propylphenyl)benzenesulfonamide
• CAS: 1383607-74-6
• 化学式: C₁₅H₁₆N₂O₄S
• 分子量: 320.369
• InChiKey: OZTRIDKUOBQACC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitro-N-(2-propylphenyl)benzenesulfonamide 在 吡啶 、 盐酸 、 铁粉 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 168.0h， 生成 3-(3-ethylureido) N-(2-propylphenyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Structure–Activity Relationships of Novel Substituted N-Phenyl Ureidobenzenesulfonate Derivatives Blocking Cell Cycle Progression in S-Phase and Inducing DNA Double-Strand Breaks

  摘要：

  Twenty-eight new substituted N-phenyl ureido-benzenesulfonate (PUB-SO) and 18 N-phenylureidobenzene-sulfonamide (PUB-SA) derivatives were prepared. Several PUB-SOs exhibited antiproliferative activity at the micromolar level against the HT-29, M21, and MCF-7 cell lines and blocked cell cycle progression in S-phase similarly to cisplatin. In addition, PUB-SOs induced histone H2AX (gamma H2AX) phosphorylation, indicating that these molecules induce DNA double-strand breaks. In contrast, PUB-SAs were less active than PUB-SOs and did not block cell cycle progression in S-phase. Finally, PUB-SOs 4 and 46 exhibited potent antitumor activity in HT-1080 fibrosarcoma cells grafted onto chick chorioallantoic membranes, which was similar to cisplatin and combretastatin A-4 and without significant toxicity toward chick embryos. These new compounds are members of a promising new class of anticancer agents.

  DOI：

  10.1021/jm3006492
• 作为产物：
  描述：

  2-丙基苯胺 、 3-硝基苯磺酰氯 在 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以55%的产率得到3-nitro-N-(2-propylphenyl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, Biological Evaluation, and Structure–Activity Relationships of Novel Substituted N-Phenyl Ureidobenzenesulfonate Derivatives Blocking Cell Cycle Progression in S-Phase and Inducing DNA Double-Strand Breaks

  摘要：

  Twenty-eight new substituted N-phenyl ureido-benzenesulfonate (PUB-SO) and 18 N-phenylureidobenzene-sulfonamide (PUB-SA) derivatives were prepared. Several PUB-SOs exhibited antiproliferative activity at the micromolar level against the HT-29, M21, and MCF-7 cell lines and blocked cell cycle progression in S-phase similarly to cisplatin. In addition, PUB-SOs induced histone H2AX (gamma H2AX) phosphorylation, indicating that these molecules induce DNA double-strand breaks. In contrast, PUB-SAs were less active than PUB-SOs and did not block cell cycle progression in S-phase. Finally, PUB-SOs 4 and 46 exhibited potent antitumor activity in HT-1080 fibrosarcoma cells grafted onto chick chorioallantoic membranes, which was similar to cisplatin and combretastatin A-4 and without significant toxicity toward chick embryos. These new compounds are members of a promising new class of anticancer agents.

  DOI：

  10.1021/jm3006492

文献信息

• [EN] ALKYLUREA DERIVATIVES ACTIVE AGAINST CANCER CELLS<br/>[FR] DÉRIVÉS D'ALKYLURÉE ACTIFS CONTRE LES CELLULES CANCÉREUSES
  申请人：UNIV LAVAL

  公开号：WO2012142698A1

  公开（公告）日：2012-10-26

  Compounds of formula (I) : wherein A, m, n, R1, X, Y, R2, R3, R4, R5 and R6, as defined herein are provided as useful for the treatment of cancer or for the manufacture of anti-cancer agents.

  化合物的化学式（I）：其中A、m、n、R1、X、Y、R2、R3、R4、R5和R6的定义如下，在此处被提供作为治疗癌症或制造抗癌药物的有用化合物。
• Synthesis, Biological Evaluation, and Structure–Activity Relationships of Novel Substituted <i>N</i>-Phenyl Ureidobenzenesulfonate Derivatives Blocking Cell Cycle Progression in S-Phase and Inducing DNA Double-Strand Breaks
  作者：Vanessa Turcotte、Sébastien Fortin、Florence Vevey、Yan Coulombe、Jacques Lacroix、Marie-France Côté、Jean-Yves Masson、René C.-Gaudreault

  DOI：10.1021/jm3006492

  日期：2012.7.12

  Twenty-eight new substituted N-phenyl ureido-benzenesulfonate (PUB-SO) and 18 N-phenylureidobenzene-sulfonamide (PUB-SA) derivatives were prepared. Several PUB-SOs exhibited antiproliferative activity at the micromolar level against the HT-29, M21, and MCF-7 cell lines and blocked cell cycle progression in S-phase similarly to cisplatin. In addition, PUB-SOs induced histone H2AX (gamma H2AX) phosphorylation, indicating that these molecules induce DNA double-strand breaks. In contrast, PUB-SAs were less active than PUB-SOs and did not block cell cycle progression in S-phase. Finally, PUB-SOs 4 and 46 exhibited potent antitumor activity in HT-1080 fibrosarcoma cells grafted onto chick chorioallantoic membranes, which was similar to cisplatin and combretastatin A-4 and without significant toxicity toward chick embryos. These new compounds are members of a promising new class of anticancer agents.