3-tolyl 4-nitrobenzenesulfonate | 1350461-85-6

• 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-tolyl 4-nitrobenzenesulfonate
• 英文别名: (3-Methylphenyl) 4-nitrobenzenesulfonate
• CAS: 1350461-85-6
• 化学式: C₁₃H₁₁NO₅S
• 分子量: 293.3
• InChiKey: GSNKDRDBHUDJHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-tolyl 4-nitrobenzenesulfonate 在 盐酸 、 铁粉 作用下， 以 乙醇 、 水 为溶剂， 以92%的产率得到3-tolyl 4-aminobenzenesulfonate
  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：

  间甲酚 、 对硝基苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以97%的产率得到3-tolyl 4-nitrobenzenesulfonate
  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

• SUBSTITUTED 2-IMIDAZOLIDONES AND ANALOGS
  申请人：Gaudreault René C.

  公开号：US20120309777A1

  公开（公告）日：2012-12-06

  Compounds of formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 7 , R 6 , R 7 , R 8 , R 9 , A, X and Y as defined herein are provided as useful for the treatment of cancer or for the manufacture of anti-cancer agents.
• US9034888B2
  申请人：——

  公开号：US9034888B2

  公开（公告）日：2015-05-19
• [EN] NON-IONIC PHOTOACID GENERATORS WITH IMPROVED QUANTUM EFFICIENCY<br/>[FR] GENERATEURS DE PHOTOACIDES NON IONIQUES PRESENTANT UNE EFFICACITE QUANTIQUE AMELIOREE
  申请人：PPG INDUSTRIES, INC.

  公开号：WO1997048677A1

  公开（公告）日：1997-12-24

  (EN) Photoacid generator compounds are 2,6-dinitrobenzyl sulfonates substituted at the 4 position of the dinitrobenzyl group with an electron donating phenoxymethyl group. Also disclosed are methods of synthesizing the photoreactive compounds from 2,6-dinitro-1,4-bis(haloalkyl)benzene.(FR) L'invention concerne des composés générateurs de photoacides. Ces composés sont des 2,6-dinitrobenzyle sulfonates substitués à la position 4 du groupe dinitrobenzyle par un groupe phénoxyméthyle donneur d'électrons. L'invention traite aussi de procédés pour assurer la synthèse des composés photoréactifs à partir du 2,6-dinitro-1,4-bis(haloalkyle)benzène.
• 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.