4-tolyl 4-aminobenzenesulfonate | 91813-07-9

• 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-tolyl 4-aminobenzenesulfonate
• 英文别名: sulfanilic acid p-tolyl ester；Sulfanilsaeure-p-tolylester；4-Methylphenyl 4-aminobenzene-1-sulfonate；(4-methylphenyl) 4-aminobenzenesulfonate
• CAS: 91813-07-9
• 化学式: C₁₃H₁₃NO₃S
• 分子量: 263.317
• InChiKey: LPCGQVZJMGBSSD-UHFFFAOYSA-N

物化性质

• 熔点：
  136.5 °C
• 沸点：
  453.5±45.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 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：
  77.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[7-(chlorosulfonyl)(2-naphthyl)]{[7-(chlorosulfonyl)(2-naphthyl)]amino}carboxamide 、 4-tolyl 4-aminobenzenesulfonate 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 4-methylphenyl 4-[({7-[({7-[({4-[(4-methylphenyl)oxysulfonyl]phenyl}amino)sulfonyl]-2-naphthyl}amino)carbonylamino]-2-naphthyl}sulfonyl)amino]benzenesulfonate
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Novel Insulin Receptor Tyrosine Kinase Activators

  摘要：

  A novel series of symmetrical ureas of [(7-amino(2-naphthyl))sulfonyl]phenylamines were designed, synthesized, and tested for their ability to increase glucose transport in mouse 3T3-L1 adipocytes, a surrogate readout for activation of the insulin receptor (IR) tyrosine kinase (IRTK). A structure-activity relationship was established that indicated glucose transport activity was dependent on the presence of two acidic functionalities, two sulfonamide linkages, and a central urea or 2-imidazolidinone core. Compound 30 was identified as a potent and selective IRTK activator. At low concentrations, 30 was able to increase the tyrosine phosphorylation of the IR stimulated by submaximal insulin. At higher concentrations, 30 was able to increase tyrosine the phosphorylation levels of the IR in the absence of insulin. When administered intraperitoneally (ip) and orally (po), 30 improved glucose tolerance in hypoinsulinemic, streptozotocin-treated rats. These data provide pharmacological validation that small molecule IRTK activators represent a potential new class of antidiabetic agents.

  DOI：

  10.1021/jm800600v
• 作为产物：
  描述：

  4-tolyl 4-nitrobenzenesulfonate 在 盐酸 、 tin(ll) chloride 作用下， 生成 4-tolyl 4-aminobenzenesulfonate
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationships of Novel Insulin Receptor Tyrosine Kinase Activators

  摘要：

  A novel series of symmetrical ureas of [(7-amino(2-naphthyl))sulfonyl]phenylamines were designed, synthesized, and tested for their ability to increase glucose transport in mouse 3T3-L1 adipocytes, a surrogate readout for activation of the insulin receptor (IR) tyrosine kinase (IRTK). A structure-activity relationship was established that indicated glucose transport activity was dependent on the presence of two acidic functionalities, two sulfonamide linkages, and a central urea or 2-imidazolidinone core. Compound 30 was identified as a potent and selective IRTK activator. At low concentrations, 30 was able to increase the tyrosine phosphorylation of the IR stimulated by submaximal insulin. At higher concentrations, 30 was able to increase tyrosine the phosphorylation levels of the IR in the absence of insulin. When administered intraperitoneally (ip) and orally (po), 30 improved glucose tolerance in hypoinsulinemic, streptozotocin-treated rats. These data provide pharmacological validation that small molecule IRTK activators represent a potential new class of antidiabetic agents.

  DOI：

  10.1021/jm800600v

文献信息

• [EN] SUBSTITUTED 2-IMIDAZOLIDONES AND ANALOGS<br/>[FR] 2-IMIDAZOLIDONES SUBSTITUES ET ANALOGUES
  申请人：UNIV LAVAL

  公开号：WO2011100840A1

  公开（公告）日：2011-08-25

  Compounds of formula (I): wherein R1, R2, R3, R4, R7, R6, R7, R8, R9, A, X and Y as defined herein are provided as useful for the treatment of cancer or for the manufacture of anti-cancer agents.

  式（I）的化合物：其中所述的R1、R2、R3、R4、R7、R6、R7、R8、R9、A、X和Y如本文所定义的那样，被提供为用于治疗癌症或用于制造抗癌药物。
• [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。
• Thienopyridine Derivatives for the Treatment and Prevention of Dengue Virus Infections
  申请人：Siga Technologies, Inc.

  公开号：US20130129677A1

  公开（公告）日：2013-05-23

  Methods and pharmaceutical compositions for treating viral infections, by administering certain thienopyridine derivative compounds in therapeutically effective amounts are disclosed. Methods of using the compounds and pharmaceutical compositions thereof are also disclosed. In particular, the treatment of viral infections such as caused by flavivirus is disclosed, i.e., including but not limited to, Dengue virus, West Nile virus, yellow fever virus, Japanese encephalitis virus, and tick-borne encephalitis virus.

  本发明揭示了使用某些噻唑吡啶衍生物化合物以治疗病毒感染的方法和制药组合物，通过以治疗有效剂量给药。同时还揭示了使用这些化合物和制药组合物的方法。具体地，揭示了治疗由黄热病毒、日本脑炎病毒、西尼罗河病毒、登革热病毒和蜱媒脑炎病毒等引起的病毒感染的方法。
• Verfahren zum Färben und Bedrucken von cellulosehaltigem Textilmaterial
  申请人：BASF Aktiengesellschaft

  公开号：EP0023601A1

  公开（公告）日：1981-02-11

  Die Erfindung betrifft ein Verfahren zum Färben und Bedrucken von cellulosehaltigem Textilmaterial, dadurch gekennzeichnet, dass man als Farbstoffe Verbindungen der allgemeinen Formel 1 verwendet, in der K der Rest einer Kupplungskomponente der Pyridon-, Pyrazol- oder Indolreihe, einer der Reste X, Y und Z eine Carbonestergruppe mit insgesamt 2 bis 19 C-Atomen, eine Carbonamidgruppe mit insgesamt 1-19 C-Atomen, eine gegebenenfalls substituierte Sulfonsäurephenylestergruppe oder eine Sulfonamidgruppe mit insgesamt 6 bis 18 C-Atomen und die restlichen Substituenten X, Y und Z Wasserstoff, Methyl, Chlor, Brom oder Nitro bedeuten.

  本发明涉及一种含纤维素纺织材料的染色和印花工艺，其特征在于使用通式 1 的化合物作为染料，其中 K 是吡啶酮、吡唑或吲哚系列偶联组分的基团，X、Y 和 Z 中的一个基团是碳原子总数为 2 至 19 个的碳酯基团、碳原子总数为 1 至 19 个的碳酰胺基团、任选取代的磺酸苯基酯基团或碳原子总数为 6 至 18 个的磺酰胺基团，其余取代基 X、Y 和 Z 为氢、甲基、氯、溴或硝基。
• 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.