3-nitro-N-(2-phenylethyl)benzenesulfonamide | 35763-22-5

• 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: 3-nitro-N-(2-phenylethyl)benzenesulfonamide
• 英文别名: N-(2-phenylethyl)-3-nitrobenzenesulfonamide；3-nitro-N-phenethylbenzenesulfonamide
• CAS: 35763-22-5
• 化学式: C₁₄H₁₄N₂O₄S
• 分子量: 306.342
• InChiKey: BCJUSNQGZOVQHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-nitro-N-(2-phenylethyl)benzenesulfonamide 在 盐酸 作用下， 以 乙醇 、 水 、 三氟乙酸 为溶剂， 反应 4.0h， 生成 1-acetyl-N-3-nitrobenzenesulfonyl-1,2,3,4-tetrahydroisoquinoline thiosemicarbazone
  参考文献：
  名称：

  新型N-磺酰基-1,2,3,4-四氢异喹啉硫代半碳酰胺衍生物的合成及细胞毒性

  摘要：

  据报道，苯乙苯磺酰胺与市售的乙二醛经改进的Pictet-Spengler反应，可构建1-苯甲酰基和1-乙酰基1,2,3,4-四氢异喹啉9a – n。无论芳环上的氧化方式如何，均可完成该反应，从而得到N-磺酰基四氢异喹啉类似物，其是用于合成1,2,3,4-四氢异喹啉的新的硫半脲酮类似物的通用中间体。生物活性测试表明，大多数硫代半脲类化合物对MOLT-3细胞系均具有细胞毒性，IC 50值小于20μg/ mL。值得注意的是，1-乙酰基四氢异喹啉9j的硫半脲类类似物是对HuCCA-1，HepG2和MOLT-3细胞最有效的细胞毒性化合物。这项研究为进一步发展提供了新颖的先导分子。

  DOI：

  10.1007/s00044-012-0025-y
• 作为产物：
  描述：

  2-苯乙胺 、 3-硝基苯磺酰氯 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到3-nitro-N-(2-phenylethyl)benzenesulfonamide
  参考文献：
  名称：

  新型N-磺酰基-1,2,3,4-四氢异喹啉硫代半碳酰胺衍生物的合成及细胞毒性

  摘要：

  据报道，苯乙苯磺酰胺与市售的乙二醛经改进的Pictet-Spengler反应，可构建1-苯甲酰基和1-乙酰基1,2,3,4-四氢异喹啉9a – n。无论芳环上的氧化方式如何，均可完成该反应，从而得到N-磺酰基四氢异喹啉类似物，其是用于合成1,2,3,4-四氢异喹啉的新的硫半脲酮类似物的通用中间体。生物活性测试表明，大多数硫代半脲类化合物对MOLT-3细胞系均具有细胞毒性，IC 50值小于20μg/ mL。值得注意的是，1-乙酰基四氢异喹啉9j的硫半脲类类似物是对HuCCA-1，HepG2和MOLT-3细胞最有效的细胞毒性化合物。这项研究为进一步发展提供了新颖的先导分子。

  DOI：

  10.1007/s00044-012-0025-y

文献信息

• Progresses in the pursuit of aldose reductase inhibitors: The structure-based lead optimization step
  作者：Anna Ramunno、Sandro Cosconati、Stefania Sartini、Vita Maglio、Sara Angiuoli、Valeria La Pietra、Salvatore Di Maro、Mariateresa Giustiniano、Concettina La Motta、Federico Da Settimo、Luciana Marinelli、Ettore Novellino

  DOI：10.1016/j.ejmech.2012.02.045

  日期：2012.5

  Aldose reductase (ALR2) is a crucial enzyme in the development of the major complications of diabetes mellitus. Very recently it has been demonstrated that the ARL2 inhibitor, fidarestat, significantly prevents inflammatory signals (TNF-alpha, LPS) that cause cancer (colon, breast, prostate and lung), metastasis, asthma, and other inflammatory diseases. Currently, fidarestat is in phase Ill clinical trial for diabetic neuropathy and was found to be safe. Thus the finding of novel, potent ARL2 inhibitors is today more than in the past in great demand as they can pave the way for a novel therapeutic approach for a number of diseases besides the diabetes. Herein, starting from the virtual screening-derived ALR2 inhibitor S12728 (1), a rational receptor-based lead optimization has been undertaken. The design and synthetic efforts here reported led to the discovery of several new compounds endowed with low micromolar/submicromolar activities. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Design, synthesis and early structure–activity relationship of farnesyltransferase inhibitors which mimic both the peptidic and the prenylic substrate
  作者：Martin Schlitzer、Markus Böhm、Isabel Sattler、Hans-Martin Dahse

  DOI：10.1016/s0968-0896(00)00138-3

  日期：2000.8

  Inhibition of the farnesylation of ras proteins has been identified as a promising target in tumor therapy. Only a few farnesyltransferase inhibitors are bisubstrate analogues displaying features of both substrates, the farnesylpyrophosphate and the C-terminal CAAX-tetrapeptide sequence of the res protein. These known bisubstrate analogues consist of an AAX-tripeptide and a farnesyl residue connected through various linkers. We have developed a class of novel compounds that mimic a bisubstrate inhibitor structure and that differ from the known ones by lacking peptidic or farnesylic substructures. Long chain fatty acids and aryl-substituted carboxylic acids were used as farnesyl surrogates. These structures were linked to isoleucine amide, benzoic acid amide, N-substituted aminobenzenesulfonamides and N-alpha-aryl-substituted methionine derivatives, respectively, which function as AA- or AAX-mimetics. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors
  作者：Ratchanok Pingaew、Veda Prachayasittikul、Prasit Mandi、Chanin Nantasenamat、Supaluk Prachayasittikul、Somsak Ruchirawat、Virapong Prachayasittikul

  DOI：10.1016/j.bmc.2015.04.036

  日期：2015.7

  A series of 1,4-disubstituted-1,2,3-triazoles (13-35) containing sulfonamide moiety were synthesized and evaluated for their aromatase inhibitory effects. Most triazoles with open-chain sulfonamide showed significant aromatase inhibitory activity (IC50 = 1.3-9.4 mu M). Interestingly, the meta analog of triazole-benzene-sulfonamide (34) bearing 6,7-dimethoxy substituents on the isoquinoline ring displayed the most potent aromatase inhibitory activity (IC50 = 0.2 mu M) without affecting normal cell. Molecular docking of these triazoles against aromatase revealed that the compounds could snugly occupy the active site of the enzyme through hydrophobic, pi-pi stacking, and hydrogen bonding interactions. The potent compound 34 was able to form hydrogen bonds with Met374 and Ser478 which were suggested to be the essential residues for the promising inhibition. The study provides compound 34 as a potential lead molecule of anti-aromatase agent for further development. (C) 2015 Elsevier Ltd. All rights reserved.
• Novel 1,4-naphthoquinone-based sulfonamides: Synthesis, QSAR, anticancer and antimalarial studies
  作者：Ratchanok Pingaew、Veda Prachayasittikul、Apilak Worachartcheewan、Chanin Nantasenamat、Supaluk Prachayasittikul、Somsak Ruchirawat、Virapong Prachayasittikul

  DOI：10.1016/j.ejmech.2015.09.001

  日期：2015.10

  A novel series of 1,4-naphthoquinones (33-44) tethered by open and closed chain sulfonamide moieties were designed, synthesized and evaluated for their cytotoxic and antimalarial activities. All quinone-sulfonamide derivatives displayed a broad spectrum of cytotoxic activities against all of the tested cancer cell lines including HuCCA-1, HepG2, A549 and MOLT-3. Most quinones (33-36 and 38-43) exerted higher anticancer activity against HepG2 cell than that of the etoposide. The open chain analogs 36 and 42 were shown to be the most potent compounds. Notably, the restricted sulfonamide analog 38 with 6,7-dimethoxy groups exhibited the most potent antimalarial activity (IC50 = 2.8 mu M). Quantitative structure activity relationships (QSAR) study was performed to reveal important chemical features governing the biological activities. Five constructed QSAR models provided acceptable predictive performance (R-cv, 0.5647-0.9317 and RMSEcv 0.1231-0.2825). Four additional sets of structurally modified compounds were generated in silico (34a-34d, 36a-36k, 40a-40d and 42a-42k) in which their activities were predicted using the constructed QSAR models. A comprehensive discussion of the structure activity relationships was made and a set of promising compounds (i.e., 33, 36, 38, 42, 36d, 36f, 42e, 42g and 42f) was suggested for further development as anticancer and antimalarial agents. (C) 2015 Elsevier Masson SAS. All rights reserved.