4-[(2-oxo-1,2-dihydro-3H-indol-3-ylidene)amino]benzenesulfonamide | 83088-99-7

• 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-oxo-1,2-dihydro-3H-indol-3-ylidene)amino]benzenesulfonamide
• 英文别名: 4-[(2-Oxoindol-3-yl)amino]benzenesulfonamide；4-[(2-oxo-1H-indol-3-ylidene)amino]benzenesulfonamide
• CAS: 83088-99-7
• 化学式: C₁₄H₁₁N₃O₃S
• 分子量: 301.326
• InChiKey: FXNKQWYBLXKGFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-hydroxy-1,3,2-benzodioxaphosphole 、 4-[(2-oxo-1,2-dihydro-3H-indol-3-ylidene)amino]benzenesulfonamide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以72%的产率得到4'-{[3-(N-pyrocatecholophosphoryl)-2-oxo-2,3-dihydro-1H-indolyl]amino}benzenesulfamide
  参考文献：
  名称：

  Muzafarova; Akhmetova; Gurevich, Russian Journal of General Chemistry, 2000, vol. 70, # 8, p. 1308 - 1309

  摘要：

  DOI：
• 作为产物：
  描述：

  靛红 、 磺胺 在 溶剂黄146 作用下， 反应 3.0h， 生成 4-[(2-oxo-1,2-dihydro-3H-indol-3-ylidene)amino]benzenesulfonamide
  参考文献：
  名称：

  一些 2-羟吲哚苯磺酰胺缀合物的合成和对人碳酸酐酶亚型 CA I、CA II、CA IX 和 CAXII 的选择性抑制作用。

  摘要：

  通过靛红衍生物1a-e与不同苯磺酰胺的缩合反应制备了三个系列具有不同连接基的2-羟吲哚苯磺酰胺缀合物。筛选了它们抑制人(h)碳酸酐酶(CA，EC 4.2.1.1)亚型hCA I、hCA II、hCA IX和hCA XII的能力。与乙酰唑酰胺 (AAZ) 相比，许多化合物对 CAI、CAII 和 CAIX 表现出良好的活性和选择性，尤其是化合物 2b（分别针对 hCA I、hCA II，KI = 97.6、8.0 nM）和 3a（针对 hCA I、hCA II，KI = 90.2、6.5 和 21.4 nM）分别为 hCA I、hCA II 和 hCA IX）相对于 AAZ（KI = 250、12 和 25 nM）。此外，化合物 4a 显示出针对 hCA II 和 hCA IX 的最高活性，KI 分别为 3.0 和 13.9 nM。将 2b、3a 和 4a 对接至 CA I、II、IX 和 XII

  DOI：

  10.1016/j.bioorg.2019.103514

文献信息

• 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。
• Discovery of novel isatin-based sulfonamides with potent and selective inhibition of the tumor-associated carbonic anhydrase isoforms IX and XII
  作者：Özlen Güzel-Akdemir、Atilla Akdemir、Nilgün Karalı、Claudiu T. Supuran

  DOI：10.1039/c5ob00688k

  日期：——

  A series of 2/3/4-[(2-oxo-1,2-dihydro-3H-indol-3-ylidene)amino]benzenesulfonamides, obtained from substituted isatins and 2-, 3- or 4-aminobenzenesulfonamide, showed low nanomolar inhibitory activity against the tumor associated carbonic anhydrases IX and XII.

  一系列2/3/4-[(2-氧代-1,2-二氢-3H-吲哚-3-基)氨基]苯磺酰胺，由取代异香草酮和2-、3-或4-氨基苯磺酰胺得到，表现出对肿瘤相关的碳酸酐酶IX和XII的低纳摩尔抑制活性。
• Synthesis of a New Series of<i>N-</i>Mannich Bases and Polyhydroxy Mannich Bases of Pharmaceutical Interest Related to Isatin and Its Schiff Bases
  作者：Elsayed M. Afsah、Ahmad A. Fadda、Ahlam H. Hanash

  DOI：10.1002/jhet.3097

  日期：2018.3

  appropriate aldimine afforded the N‐Mannich bases 2–3 and the bis‐base 4. Treatment of 1 with glutaric dialdehyde and morpholine gave the bis‐base 5. Mannich reaction of the Schiff bases 6a–f derived from 1, led to the new Mannich bases and bis‐bases 7–9. The use of N‐methyl‐D‐glucamine as the amine component in the Mannich reaction with 6b–f led to the polyhydroxy Mannich bases 11–13.

  靛红的反应1与苯甲醛和仲胺或得到相应的醛亚胺Ñ -Mannich立足2 - 3和双-基4。用戊二醛和吗啉处理1得到双碱基5。源自1的席夫碱6a – f的曼尼希反应导致了新的曼尼希碱和双碱7 – 9。使用Ñ甲基d -glucamine为与曼尼希反应胺组分6B - ˚F导致多羟基曼尼期碱11 - 13。
• Heterocyclic semicarbazones and thiosemicarbazones. XLIX. Antiinflammatory activity of isatin thiosemicarbazones and their cyclization products
  作者：A. B. Tomchin、I. L. Zhmykhova、M. M. Ponomareva、L. G. Pastushenkov、É. G. Gromova

  DOI：10.1007/bf01148635

  日期：1986.9
• Isatin analogs as novel inhibitors of Candida spp. β-carbonic anhydrase enzymes
  作者：Atilla Akdemir、Özlen Güzel-Akdemir、Nilgün Karalı、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2016.02.036

  日期：2016.4

  Enzyme inhibition data of structurally novel isatin-containing sulfonamides were determined for two carbonic anhydrases (CAs, EC 4.2.1.1) from pathogenic Candida species (CaNce103 from C. albicans and CgNce103 from C. glabrata). The compounds show K-I values in the low nanomolar range for the fungal CAs, while they have significantly higher K-I values for the human CAs. Homology models were constructed for the CaNce103 and CgNce103 and subsequently the ligands were docked into these models to rationalize their enzyme inhibitory properties. (C) 2016 Elsevier Ltd. All rights reserved.