4-((4-methylbenzylidene)amino)benzenesulfonamide

• 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-((4-methylbenzylidene)amino)benzenesulfonamide
• 英文别名: N-(4-Methylbenzylidene)-4-sulfamoylaniline；4-[(4-methylphenyl)methylideneamino]benzenesulfonamide
• 化学式: C₁₄H₁₄N₂O₂S
• 分子量: 274.343
• InChiKey: SOHFVFXITPDEDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-((4-methylbenzylidene)amino)benzenesulfonamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 25.0h， 以70%的产率得到4-((4-methylbenzyl)amino)benzenesulfonamide
  参考文献：
  名称：

  具有对人碳酸酐酶同工型I，II，IX和XII的抑制活性的4-氨磺酰基苯基-苄胺衍生物的合成

  摘要：

  通过磺胺与取代的芳族醛缩合获得亚胺衍生物。然后用硼氢化钠还原席夫碱，得到相应的胺，即4-氨磺酰基苯基-苄胺的衍生物。研究了这些磺酰胺作为人碳酸酐酶（hCA，EC 4.2.1.1）同工型hCA I和II（胞质同工酶）以及hCA IX和XII（跨膜，肿瘤相关酶）的抑制剂。我们注意到，与相应的席夫碱相比，掺有仲胺部分的化合物对所有CA同工酶表现出更好的抑制活性。检测到低纳摩尔CA II，IX和XII抑制剂，而针对hCA I的活性较低。结合了磺酰胺或类似锌结合基团的仲胺，

  DOI：

  10.1016/j.bmc.2016.01.020
• 作为产物：
  描述：

  对甲基苯甲醛 、 磺胺 在 甲酸 作用下， 以 甲醇 为溶剂， 以85%的产率得到4-((4-methylbenzylidene)amino)benzenesulfonamide
  参考文献：
  名称：

  具有对人碳酸酐酶同工型I，II，IX和XII的抑制活性的4-氨磺酰基苯基-苄胺衍生物的合成

  摘要：

  通过磺胺与取代的芳族醛缩合获得亚胺衍生物。然后用硼氢化钠还原席夫碱，得到相应的胺，即4-氨磺酰基苯基-苄胺的衍生物。研究了这些磺酰胺作为人碳酸酐酶（hCA，EC 4.2.1.1）同工型hCA I和II（胞质同工酶）以及hCA IX和XII（跨膜，肿瘤相关酶）的抑制剂。我们注意到，与相应的席夫碱相比，掺有仲胺部分的化合物对所有CA同工酶表现出更好的抑制活性。检测到低纳摩尔CA II，IX和XII抑制剂，而针对hCA I的活性较低。结合了磺酰胺或类似锌结合基团的仲胺，

  DOI：

  10.1016/j.bmc.2016.01.020

文献信息

• Syntheses of 1-(4-methylsulfonylphenyl)-5-aryl-1,2,3-triazoles and -(4-aminosulfonylphenyl)-5-aryl-1,2,3-triazoles
  作者：F. Johari Daha、H. Matloubi、S. A. Tabatabi、B. Shafii、A. Shafiee

  DOI：10.1002/jhet.5570420106

  日期：2005.1

  permanganate gave 1-(4-methylsulfonylphenyl)-5-aryl-1,2,3-triazoles 5. Similarly, condensation of 4-(N,N-dibenzylaminosulfonyl)aniline with aryl aldehyde followed by 1,3-cycloaddition of diazomethane with the imino compound 11 and the subsequent oxidation of triazoline 12 with potassium permanganate yielded the triazole 13. Debenzylation of compound 13 with sulfuric acid gave the desired compound 1-(4-amino

  4-甲基磺酰基苯胺与芳基醛在乙醇-四氢呋喃中的缩合得到亚氨基化合物3。将重氮甲烷与化合物3进行1,3环加成，然后将三唑啉4用高锰酸钾氧化，得到1-（4-甲基磺酰基苯基）-5-芳基-1,2,3-三唑5。类似地，将4-（N，N-二苄基氨基磺酰基）苯胺与芳基醛缩合，然后将重氮甲烷与亚氨基化合物11进行1,3-环加成，然后将三唑啉12与高锰酸钾氧化，制得三唑13。化合物13的脱苄基作用用硫酸得到所需的化合物1-（4-氨基磺酰基苯基）5-芳基-1,2,3-三唑14。
• 1,2-diphenylpyrrole derivatives, their preparation and their therapeutic
  申请人：Sankyo Company, Limited

  公开号：US05908858A1

  公开（公告）日：1999-06-01

  Compounds of formula (I) and (II): ##STR1## \x9bwherein R is hydrogen, halogen or alkyl; R.sup.1 is alkyl, amino or substituted amino; R.sup.2 is optionally substituted phenyl; R.sup.3 is hydrogen, halogen or optionally substituted alkyl; R.sup.4 is hydrogen, optionally substituted alkyl, cycloalkyl, aryl, or aralkyl! have valuable analgesic, anti-inflammatory, anti-pyretic and anti-allergic activities and have the ability to inhibit the production of leukotrienes and to inhibit bone resorption. They are relatively free from the side effects which generally result from the administration of compounds having these kinds of activities.

  式(I)和(II)的化合物：##STR1## 其中R为氢、卤素或烷基；R.sup.1为烷基、氨基或取代氨基；R.sup.2为可选取代的苯基；R.sup.3为氢、卤素或可选取代的烷基；R.sup.4为氢、可选取代的烷基、环烷基、芳基或芳基烷基！具有有价值的镇痛、抗炎、退烧和抗过敏活性，并具有抑制白三烯产生和抑制骨吸收的能力。它们相对于一般具有这些活性的化合物的副作用较少。
• Synthesis, <i>in vitro</i> enzyme activity and molecular docking studies of new benzylamine-sulfonamide derivatives as selective MAO-B inhibitors
  作者：Begüm Nurpelin Sağlık、Derya Osmaniye、Ulviye Acar Çevik、Serkan Levent、Betül Kaya Çavuşoğlu、Özlem Atlı Eklioğlu、Yusuf Özkay、Ali Savaş Koparal、Zafer Asım Kaplancıklı

  DOI：10.1080/14756366.2020.1784892

  日期：2020.1.1

  Many studies have been conducted on the selective inhibition of human monoamine oxidase B (hMAO-B) enzyme using benzylamine-sulphonamide derivatives. Using various chemical modifications onBB-4h, which was reported previously by our team and showed a significant level of MAO-B inhibition, novel benzylamine-sulphonamide derivatives were designed, synthesised, and their MAO inhibition potentials were evaluated. Among the tested derivatives, compounds4iand4tachieved IC(50)values of 0.041 +/- 0.001 mu M and 0.065 +/- 0.002 mu M, respectively. The mechanism ofhMAO-B inhibition by compounds4iand4twas studied using Lineweaver-Burk plot. The nature of inhibition was also determined to be non-competitive. Cytotoxicity tests were conducted and compounds4iand4twere found to be non-toxic. Molecular docking studies were also carried out for compound4i, which was found as the most potent agent, withinhMAO-B catalytic site.
• Selective inhibition of carbonic anhydrase-IX by sulphonamide derivatives induces pH and reactive oxygen species-mediated apoptosis in cervical cancer HeLa cells
  作者：Ismail Koyuncu、Ataman Gonel、Abdurrahim Kocyigit、Ebru Temiz、Mustafa Durgun、Claudiu T. Supuran

  DOI：10.1080/14756366.2018.1481403

  日期：2018.1.1

  Selective inhibition with sulphonamides of carbonic anhydrase (CA) IX reduces cell proliferation and induces apoptosis in human cancer cells. The effect on CA IX expression of seven previously synthesised sulphonamide inhibitors, with high affinity for CA IX, as well as their effect on the proliferation/apoptosis of cancer/normal cell lines was investigated. Two normal and three human cancer cell lines were used. Treatment resulted in dose- and time-dependent inhibition of the growth of various cancer cell lines. One compound showed remarkably high toxicity towards CA IX-positive HeLa cells. The mechanisms of apoptosis induction were determined with Annexin-V and AO/EB staining, cleaved caspases (caspase-3, caspase-8, caspase-9) and cleaved PARP activation, reactive oxygen species production (ROS), mitochondrial membrane potential (MMP), intracellular pH (pHi), extracellular pH (pHe), lactate level and cell cycle analysis. The autophagy induction mechanisms were also investigated. The modulation of apoptotic and autophagic genes (Bax, Bcl-2, caspase-3, caspase-8, caspase-9, caspase-12, Beclin and LC3) was measured using real time PCR. The positive staining using gamma-H2AX and AO/EB dye, showed increased cleaved caspase-3, caspase-8, caspase-9, increased ROS production, MMP and enhanced mRNA expression of apoptotic genes, suggesting that anticancer effects are also exerted through its apoptosis-inducing properties. Our results show that such sulphonamides might have the potential as new leads for detailed investigations against CA IX-positive cervical cancers.
• USRE039420E1
  申请人：——

  公开号：——

  公开（公告）日：——