4-(2-oxoindolin-3-ylideneamino)-N-(pyrimidin-2-yl)benzenesulfonamide | 193277-67-7

• 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-(2-oxoindolin-3-ylideneamino)-N-(pyrimidin-2-yl)benzenesulfonamide
• 英文别名: 4-[(2-oxo-1H-indol-3-ylidene)amino]-N-pyrimidin-2-ylbenzenesulfonamide
• CAS: 193277-67-7
• 化学式: C₁₈H₁₃N₅O₃S
• 分子量: 379.399
• InChiKey: IJPATWXVJXJHTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 加替沙星 、 4-(2-oxoindolin-3-ylideneamino)-N-(pyrimidin-2-yl)benzenesulfonamide 以 乙醇 为溶剂， 以71.9%的产率得到1-cyclopropyl-6-fluoro-8-methoxy-7-[3-methyl-4-[[(3Z)-2-oxo-3-[4-(pyrimidin-2-ylsulfamoyl)phenyl]imino-indolin-1-yl]methyl]piperazin-1-yl]-4-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Gatifloxacin derivatives: Synthesis, antimycobacterial activities, and inhibition of Mycobacterium tuberculosis DNA gyrase

  摘要：

  Sixteen 7-substituted gatifloxacin derivatives were synthesized and evaluated for antimycobacterial activity in vitro and in vivo against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB), and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. tuberculosis. Among the synthesized compounds, 1-cyclopropyl-6-fluoro-8-methoxy-7-[[[N-4-[I'-(5-isatinyl-beta-semicarbazo)]methyl]3-methyl]N-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (3d) was found to be the most active compound in vitro with an MIC of 0.0125 mu g/mL against MTB and MTR-TB. In the in vivo animal model 3d decreased the bacterial load in lung and spleen tissues with 3.62- and 3.76-log 10 protections, respectively. Compound 3d was also found to be equally active as gatifloxacin in the inhibition of the supercoiling activity of wild-type M. tuberculosis DNA gyrase with an IC50 of 3.0 mu g/mL. The results demonstrate the potential and importance of developing new quinolone derivatives against mycobacterial infections. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.065
• 作为产物：
  描述：

  磺胺嘧啶 、 靛红 以 乙醇 为溶剂， 以51%的产率得到4-(2-oxoindolin-3-ylideneamino)-N-(pyrimidin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Cytotoxicity of Novel Sulfanilamides Towards Sensitive and Multidrugresistant Leukemia Cells

  摘要：

  新型磺胺Schiff碱通过芳香族磺酰胺与芳香族醛或杂环酮以等摩尔比例反应合成并表征。其细胞毒性通过对人类敏感的CCRF-CEM细胞和多药耐药的CEM/ADR5000白血病细胞进行resazurin测定进行评估。测试的三种化合物，即4-(蒽9-亚甲基氨基)-N-(嘧啶-2-基)苯磺酰胺（4）、4-(蒽9-亚甲基氨基)苯磺酰胺（5）和4-((3-苯基烯丙基)氨基)苯磺酰胺（6）具有细胞毒性（IC50值：5.38-19.96 µM）。CEM/ADR5000细胞对这些化合物没有交叉耐药性，表明其对其他药物耐药肿瘤仍具有活性。化合物6通过增加多柔比星的积累并减少CEM/ADR5000细胞中P-糖蛋白的表达来抑制P-糖蛋白。使用人类P-糖蛋白同源模型进行分子对接研究。化合物6和维拉帕米（一个著名的P-糖蛋白抑制剂）与相同结合口袋的结合能相似。

  DOI：

  10.2174/0929867321666140120120708

文献信息

• Synthesis, antibacterial, antifungal and anti-HIV activities of norfloxacin Mannich bases
  作者：Surendra N Pandeya、Dhamrajan Sriram、Gopal Nath、Erik De Clercq

  DOI：10.1016/s0223-5234(00)00125-2

  日期：2000.2

  Mannich bases of norfloxacin were synthesized by reacting them with formaldehyde and several isatin derivatives. Their chemical structures have been confirmed by means of their IR, H-1-NMR data and by elemental analysis. Investigation of in vitro antimicrobial activity of compounds was done by the agar dilution method against 28 pathogenic bacteria, eight pathogenic fungi and anti-HIV activity against replication of HIV-1 (III B) in MT-4 cells. The in vivo antibacterial efficacy of selected derivatives was determined using a mouse infection model. All the synthesized compounds are more active than norfloxacin against the 13 bacteria tested. The compounds are also more active than the standard drug clotrimazole against Histoplasma capsulatum. Two compounds S-8 and S-9 have shown inhibition against HIV-1 (III B) with EC50 values of 11.3 and 13.9 mu g/mL, respectively. In the mouse protection test, two compounds S-4 (ED50: 1.25 mg/kg) and S-9 (ED50: 1.62 mg/kg) are more active than norfloxacin (ED50: 6mg/kg). Among the compounds tested, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7[[N-4-[5'-bromo-3'-(4'-amino-5'-trimethoxybenzylpyrimidin-2'-yl]-imino-1'-isatinyl]methyl]N-1-piperazinyl]-3-quinoline carboxylicacid (S-9) showed promising activity in all the three tests. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• Cytotoxicity of Novel Sulfanilamides Towards Sensitive and Multidrugresistant Leukemia Cells
  作者：T. AlSalim、M.E.M. Saeed、J.S. Hadi、M. Zeino、R. Gany、O. Kadioglu、S.J.J. Titinchi、H.S. Abbo、T. Efferth

  DOI：10.2174/0929867321666140120120708

  日期：2014.1.20

  Novel sulfa Schiff bases were synthesized and characterized by a reaction between aromatic sulfonamides and aromatic aldehydes or heterocyclic ketones in equimolar ratios. Their cytotoxicity was evaluated by the resazurin assay towards human sensitive CCRF-CEM and multidrug-resistant CEM/ADR5000 leukemia cells. Three of the tested compounds viz., 4-(anthracen-9-ylmethyleneamino)-N-(pyrimidin-2-yl)benzenesulfonamide (4), 4-(anthracen-9- ylmethyleneamino)benzenesulfonamide, (5) and 4-((3-phenylallylidene)amino)benzene-sulfonamide, (6) were cytotoxic (IC50 values: 5.38-19.96 µM). CEM/ADR5000 cells were not cross-resistant to these compounds, indicating activity against otherwise drug-resistant tumors. Compound 6 inhibited P-glycoprotein by increasing doxorubicin accumulation and reducing expression of P-glycoprotein in CEM/ADR5000 cells. A human P-glycoprotein homology model was used for molecular docking studies. Compound 6 and verapamil (a well-known P-glycoprotein inhibitor) docked with similar binding energies to the same binding pocket.

  新型磺胺Schiff碱通过芳香族磺酰胺与芳香族醛或杂环酮以等摩尔比例反应合成并表征。其细胞毒性通过对人类敏感的CCRF-CEM细胞和多药耐药的CEM/ADR5000白血病细胞进行resazurin测定进行评估。测试的三种化合物，即4-(蒽9-亚甲基氨基)-N-(嘧啶-2-基)苯磺酰胺（4）、4-(蒽9-亚甲基氨基)苯磺酰胺（5）和4-((3-苯基烯丙基)氨基)苯磺酰胺（6）具有细胞毒性（IC50值：5.38-19.96 µM）。CEM/ADR5000细胞对这些化合物没有交叉耐药性，表明其对其他药物耐药肿瘤仍具有活性。化合物6通过增加多柔比星的积累并减少CEM/ADR5000细胞中P-糖蛋白的表达来抑制P-糖蛋白。使用人类P-糖蛋白同源模型进行分子对接研究。化合物6和维拉帕米（一个著名的P-糖蛋白抑制剂）与相同结合口袋的结合能相似。
• Gatifloxacin derivatives: Synthesis, antimycobacterial activities, and inhibition of Mycobacterium tuberculosis DNA gyrase
  作者：Dharmarajan Sriram、Alexandra Aubry、Perumal Yogeeswari、L.M. Fisher

  DOI：10.1016/j.bmcl.2006.02.065

  日期：2006.6

  Sixteen 7-substituted gatifloxacin derivatives were synthesized and evaluated for antimycobacterial activity in vitro and in vivo against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB), and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. tuberculosis. Among the synthesized compounds, 1-cyclopropyl-6-fluoro-8-methoxy-7-[[[N-4-[I'-(5-isatinyl-beta-semicarbazo)]methyl]3-methyl]N-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (3d) was found to be the most active compound in vitro with an MIC of 0.0125 mu g/mL against MTB and MTR-TB. In the in vivo animal model 3d decreased the bacterial load in lung and spleen tissues with 3.62- and 3.76-log 10 protections, respectively. Compound 3d was also found to be equally active as gatifloxacin in the inhibition of the supercoiling activity of wild-type M. tuberculosis DNA gyrase with an IC50 of 3.0 mu g/mL. The results demonstrate the potential and importance of developing new quinolone derivatives against mycobacterial infections. (c) 2006 Elsevier Ltd. All rights reserved.