4-[(3-methoxybenzylidene)amino]benzenesulfonamide | 385447-18-7

• 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-[(3-methoxybenzylidene)amino]benzenesulfonamide
• 英文别名: 4-[(3-Methoxy-benzylidene)-amino]-benzenesulfonamide；4-[(3-methoxyphenyl)methylideneamino]benzenesulfonamide
• CAS: 385447-18-7
• 化学式: C₁₄H₁₄N₂O₃S
• 分子量: 290.343
• InChiKey: PMXSUWQVMRZMRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  萘丁美酮 、 4-[(3-methoxybenzylidene)amino]benzenesulfonamide 在 盐酸 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 生成 4-(5-(6-methoxynaphthalen-2-yl)-1-(3-methoxyphenyl)-3-oxopentylamino)benzenesulfonamide
  参考文献：
  名称：

  Synthesis and antidiabetic performance of β-amino ketone containing nabumetone moiety

  摘要：

  We wish to report the further design and improved synthesis that resulted in two series of target molecules, TM-1 and TM-2, with remarkably simplified structures containing beta-amino ketone of discrete nabumetone moiety. These were obtained via a 'one-pot, two-step, three-component' protocol of Mannich reaction with yield up to 97%. A total of 28 out of 31 new compounds were characterized using H-1 NMR, C-13 NMR, ESI MS and HRMS techniques. Studies on their antidiabetic activities, screened in vitro at 10 mu g mL (1) level, indicate that TM-2 possesses peroxisome proliferator-activated receptor activation and alpha-glucosidase inhibition activity significantly stronger than that of TM-1, and also that of the series B compounds that were previously synthesized by the group. Analysis of the structure-activity relationship points to the sulfanilamide unit as the most probable potent group of b-amino ketone and, on the basis of which, a tangible strategy is presented for the development of new antidiabetic drugs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.01.028
• 作为产物：
  描述：

  磺胺 、 3-甲氧基苯甲醛 以 乙醇 为溶剂， 以77%的产率得到4-[(3-methoxybenzylidene)amino]benzenesulfonamide
  参考文献：
  名称：

  磺胺-亚胺衍生物作为潜在抗癌剂的设计、合成、分子建模和生物学评价。

  摘要：

  根据考布他汀 A-4 和异喹啉氨基磺酸盐（正在研究的抗有丝分裂剂）的化学结构，一系列磺胺席夫碱衍生物（1 至 15）已被设计为潜在的抗微管蛋白药物。设计的化合物通过微波化学合成合成，其纯度通过熔点和 HPLC 确定，化学结构通过 FT-IR、UV、1H 和 13C-NMR 光谱技术确定。使用分子建模程序将合成的化合物对接在 β-微管蛋白的秋水仙碱结合位点，并通过细胞计数法筛选了对人乳腺癌和肺癌细胞的抗肿瘤活性。一些测试化合物显示出针对乳腺癌 (MCF-7) 的有效和选择性活性，IC50 范围为 90 至 166 μM。关于广谱活动，化合物 4、8 和 13 对人乳腺和人肺细胞显示出有效的抗肿瘤活性，IC50 范围为 96 至 140 μM。所得结果表明磺胺席夫碱衍生物可能构成一类有趣的新型抗癌剂，值得进一步研究。

  DOI：

  10.1007/s00210-013-0883-y

文献信息

• Design, synthesis, molecular modeling, and biological evaluation of sulfanilamide-imines derivatives as potential anticancer agents
  作者：Sofian S. Mohamed、Abdalkarem R. Tamer、Salah M. Bensaber、Mousa I. Jaeda、Nouri B. Ermeli、Aemen Ali Allafi、Ibrahim A. Mrema、Mabrouk Erhuma、Anton Hermann、Abdul M. Gbaj

  DOI：10.1007/s00210-013-0883-y

  日期：2013.9

  A series of sulfanilamide Schiff base derivatives (1 to 15) have been designed as potential antitubulin agents depending on the chemical structures of combretastatine A-4 and isoquinoline sulfamate (antimitotic agents under investigation). The designed compounds were synthesized by microwave chemical synthesis, their purity was confirmed by melting point and HPLC and chemical structures were determined

  根据考布他汀 A-4 和异喹啉氨基磺酸盐（正在研究的抗有丝分裂剂）的化学结构，一系列磺胺席夫碱衍生物（1 至 15）已被设计为潜在的抗微管蛋白药物。设计的化合物通过微波化学合成合成，其纯度通过熔点和 HPLC 确定，化学结构通过 FT-IR、UV、1H 和 13C-NMR 光谱技术确定。使用分子建模程序将合成的化合物对接在 β-微管蛋白的秋水仙碱结合位点，并通过细胞计数法筛选了对人乳腺癌和肺癌细胞的抗肿瘤活性。一些测试化合物显示出针对乳腺癌 (MCF-7) 的有效和选择性活性，IC50 范围为 90 至 166 μM。关于广谱活动，化合物 4、8 和 13 对人乳腺和人肺细胞显示出有效的抗肿瘤活性，IC50 范围为 96 至 140 μM。所得结果表明磺胺席夫碱衍生物可能构成一类有趣的新型抗癌剂，值得进一步研究。
• Synthesis and antidiabetic performance of β-amino ketone containing nabumetone moiety
  作者：Hang Wang、Ju-fang Yan、Xiao-li Song、Li Fan、Jin Xu、Guang-ming Zhou、Li Jiang、Da-cheng Yang

  DOI：10.1016/j.bmc.2012.01.028

  日期：2012.3

  We wish to report the further design and improved synthesis that resulted in two series of target molecules, TM-1 and TM-2, with remarkably simplified structures containing beta-amino ketone of discrete nabumetone moiety. These were obtained via a 'one-pot, two-step, three-component' protocol of Mannich reaction with yield up to 97%. A total of 28 out of 31 new compounds were characterized using H-1 NMR, C-13 NMR, ESI MS and HRMS techniques. Studies on their antidiabetic activities, screened in vitro at 10 mu g mL (1) level, indicate that TM-2 possesses peroxisome proliferator-activated receptor activation and alpha-glucosidase inhibition activity significantly stronger than that of TM-1, and also that of the series B compounds that were previously synthesized by the group. Analysis of the structure-activity relationship points to the sulfanilamide unit as the most probable potent group of b-amino ketone and, on the basis of which, a tangible strategy is presented for the development of new antidiabetic drugs. (C) 2012 Elsevier Ltd. All rights reserved.