toluene-4-sulfonic acid-(4-amino-2-methyl-anilide) | 35481-04-0

• 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: toluene-4-sulfonic acid-(4-amino-2-methyl-anilide)
• 英文别名: Toluol-4-sulfonsaeure-(4-amino-2-methyl-anilid)；5-Amino-2-p-toluolsulfamino-toluol；N-(4-Amino-2-methylphenyl)-4-methylbenzenesulfonamide；4-(N-p-toluenesulfonyl)amino-3-methylaniline
• CAS: 35481-04-0
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: VLFFFVDXAWBIDV-UHFFFAOYSA-N

物化性质

• 沸点：
  455.2±55.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid-(4-amino-2-methyl-anilide) 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 生成 6-(toluene-4-sulfonylamino)-toluene-3-diazonium-betaine
  参考文献：
  名称：

  Morgan; Micklethwait, Chemische Berichte, 1906, vol. 39, p. 2872

  摘要：

  DOI：
• 作为产物：
  描述：

  4-硝基-2-甲苯胺 在 铁粉 、 碳酸氢钠 、 氯化铵 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 toluene-4-sulfonic acid-(4-amino-2-methyl-anilide)
  参考文献：
  名称：

  设计和合成磺酰胺取代的二苯基嘧啶（SFA-DPPYs）作为有效的Bruton酪氨酸激酶（BTK）抑制剂，对B细胞淋巴细胞白血病具有增强的活性。

  摘要：

  通过将功能性磺酰胺引入嘧啶模板的C-2苯胺部分，合成了一系列新的二苯基嘧啶衍生物（SFA-DPPYs），然后对其进行生物学评估，认为其是有效的Bruton酪氨酸激酶（BTK）抑制剂。在这些分子中，抑制剂10c，10i，10j和10k对BTK酶显示出高效力，IC50值分别为1.18 nM，0.92 nM，0.42 nM和1.05 nM。特别地，化合物10c可以在6.49μM（Ramos细胞）和13.2μM（Raji细胞）的浓度下显着抑制B淋巴瘤细胞系的增殖，并且比新药斯培鲁替尼更强。另外，对正常PBMC细胞的抑制能力表明抑制剂10c具有低细胞毒性。

  DOI：

  10.1016/j.ejmech.2017.04.037

文献信息

• AROMATIC SULFONE COMPOUND AS ALDOSTERONE RECEPTOR MODULATOR
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1844768A1

  公开（公告）日：2007-10-17

  The present invention provides a compound represented by the following formula (I): [wherein, A represents a group of the following formula (A-1): etc., R1 and R2 each independently represent a hydrogen atom etc., Z represents CR3 etc., W represents CR4 etc., Q represents CR5 etc., R3, R4 and R5 each independently represent a hydrogen atom etc., Y represents an oxygen atom or sulfur atom, X represents an oxygen atom etc. and B represents an optionally substituted aryl group or optionally substituted heteroaryl group], the prodrug thereof or the pharmaceutically acceptable salt thereof for preventing or treating various diseases such as hypertesion, cerebral stroke, cardiac failure, etc.

  本发明提供了以下式（I）所表示的化合物： [其中，A表示以下式（A-1）的基团： 等等，R1和R2分别独立表示氢原子等，Z表示CR3等，W表示CR4等，Q表示CR5等，R3、R4和R5分别独立表示氢原子等，Y表示氧原子或硫原子，X表示氧原子等，B表示可选择地取代的芳基或可选择地取代的杂环基]，其前药或其药学上可接受的盐，用于预防或治疗高血压、脑卒中、心力衰竭等各种疾病。
• Process for preparing 4-amino-3-methyl-N-substituted or unsubstituted
  申请人：Sanko Chemical Company Ltd.

  公开号：US04009205A1

  公开（公告）日：1977-02-22

  A process for the preparation of 4-amino-3-methyl-N-substituted or unsubstituted alkylanilines comprising acylating and/or sulfonylating 4-amino-3-methyl-nitro-benzene having the formula (I) ##STR1## with an acylation or sulfonylation agent to obtain a compound having the general formula (II) ##STR2## wherein R.sub.1 represents a hydrogen atom or an acyl group, R.sub.2 represents an acyl group or a sulfonyl group, or R.sub.1 and R.sub.2 can combine as a difunctional acyl group; reducing the nitro group of the compound having the general formula (II) with hydrogen in the presence of a metal hydrogenation catalyst to obtain a compound having the general formula (III) ##STR3## wherein R.sub.1 and R.sub.2 are as above defined; alkylating the amino group of the compound having the general formula (III) with an alkylation agent selected from the group consisting of an alkyl halide, a substituted alkyl halide and an alkylene oxide to obtain a compound having the general formula (IV) ##STR4## wherein R.sub.1 and R.sub.2 are as above defined, R.sub.3 represents an alkyl group or a substituted alkyl group and R.sub.4 represents a hydrogen atom, an alkyl group or a substituted alkyl group; and hydrolyzing the compound having the general formula (IV) to obtain a compound having the general formula (V) ##STR5## wherein R.sub.3 and R.sub.4 are as above defined.

  一种制备4-氨基-3-甲基-N-取代或未取代烷基苯胺的方法，包括使具有化学式（I）的4-氨基-3-甲基-硝基苯乙酰化和/或磺酰化，其中R.sub.1代表氢原子或酰基，R.sub.2代表酰基或磺酰基，或R.sub.1和R.sub.2可以组合为双官能团酰基；在金属氢化催化剂存在下用氢还原具有化学式（II）的化合物的硝基基团，其中R.sub.1和R.sub.2如上所定义；用从由烷基卤化物、取代烷基卤化物和烷氧基组成的群中选择的烷基化试剂烷基化具有化学式（III）的化合物的氨基团，其中R.sub.1和R.sub.2如上所定义，R.sub.3代表烷基或取代烷基，R.sub.4代表氢原子、烷基或取代烷基；水解具有化学式（IV）的化合物以获得具有化学式（V）的化合物，其中R.sub.3和R.sub.4如上所定义。
• Design, synthesis and biological evaluation of sulfonamide-substituted diphenylpyrimidine derivatives (Sul-DPPYs) as potent focal adhesion kinase (FAK) inhibitors with antitumor activity
  作者：Menghua Qu、Zhihao Liu、Dan Zhao、Changyuan Wang、Jianbin Zhang、Zeyao Tang、Kexin Liu、Xiaohong Shu、Hong Yuan、Xiaodong Ma

  DOI：10.1016/j.bmc.2017.05.044

  日期：2017.8

  A class of sulfonamide-substituted diphenylpyrimidines (Sul-DPPYs) were synthesized to improve activity against the focal adhesion kinase (FAK). Most of these new Sul-DPPYs displayed moderate activity against the FAK enzyme with IC50 values of less than 100 nM; regardless, they could effectively inhibit several classes of refractory cancer cell lines with IC50 values of less than 10 mu M, including the pancreatic cancer cell lines (AsPC-1, Panc-1 and BxPC-3), the NSCLC-resistant H1975 cell line, and the B lymphocyte cell line (Ramos cells). Results of flow cytometry indicated that inhibitor 7e promoted apoptosis of pancreatic cancer cells in a dose-dependent manner. In addition, it almost completely induced the apoptosis at a concentration of 10 mu M. Compound 7e may be selected as a potent FAK inhibitor for the treatment of pancreatic cancer. (C) 2017 Elsevier Ltd. All rights reserved.
• DE160710
  申请人：——

  公开号：——

  公开（公告）日：——
• Light-sensitive material for photomechanical reproduction
  申请人：AZOPLATE CORP

  公开号：US02759817A1

  公开（公告）日：1956-08-21