2-cyano-N-(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)acetamide | 901373-59-9

• 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: 2-cyano-N-(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)acetamide
• 英文别名: 2-cyano-N-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]acetamide
• CAS: 901373-59-9
• 化学式: C₁₃H₁₂N₄O₄S
• 分子量: 320.329
• InChiKey: UHGINHJJCOYCCX-UHFFFAOYSA-N

物化性质

• 密度：
  1.498±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-cyano-N-(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)acetamide 在 吡啶 、 溶剂黄146 作用下， 反应 24.5h， 生成 4-[6-cyano-2-(4-methoxyphenyl)-3,5-dioxo-2,5-dihydro-1,2,4-triazin-4(3H)-yl]-N-(5-methylisoxazol-3-yl)benzenesulfonamide
  参考文献：
  名称：

  一些异恶唑基杂环化合物的合成及抗菌评价

  摘要：

  迄今为止未报道的多功能 2-氰基-N-(4-{[(5-甲基异恶唑 3-基)氨基]磺酰基}苯基)乙酰胺 (3) 被用于合成各种含有氨磺酰基部分的杂环。2-吡啶酮衍生物是通过氰基乙酰胺与戊烷-2,4-二酮、亚芳基丙二腈或对苯二甲醛和丙二腈在催化剂存在下加热回流得到的。氰基乙酰胺 3 与水杨醛缩合得到相应的色烯衍生物。3 与芳烃重氮氯化物偶联得到腙衍生物 13a-c，其在用水合肼和氯甲酸乙酯处理后分别得到相应的吡唑和三嗪衍生物。3 与二硫化碳和 1,2-二溴乙烷 1 的反应，3-二溴丙烷或硫酸二甲酯得到 2-氰基-2-(1,3-dithiolan-2-ylidene)-N-(4-{[(5-methylisoxazol-3yl)amino]sulfonyl}phenyl)acetamide (18)， 2-cyano-2-(1,3-dithian-2-ylidene)-N4-{[(5-methyl

  DOI：

  10.3987/com-14-12954
• 作为产物：
  描述：

  磺胺甲恶唑 、 1-氰基乙酰-3,5-二甲基吡唑 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以80%的产率得到2-cyano-N-(4-{[(5-methylisoxazol-3-yl)amino]sulfonyl}phenyl)acetamide
  参考文献：
  名称：

  一些异恶唑基杂环化合物的合成及抗菌评价

  摘要：

  迄今为止未报道的多功能 2-氰基-N-(4-{[(5-甲基异恶唑 3-基)氨基]磺酰基}苯基)乙酰胺 (3) 被用于合成各种含有氨磺酰基部分的杂环。2-吡啶酮衍生物是通过氰基乙酰胺与戊烷-2,4-二酮、亚芳基丙二腈或对苯二甲醛和丙二腈在催化剂存在下加热回流得到的。氰基乙酰胺 3 与水杨醛缩合得到相应的色烯衍生物。3 与芳烃重氮氯化物偶联得到腙衍生物 13a-c，其在用水合肼和氯甲酸乙酯处理后分别得到相应的吡唑和三嗪衍生物。3 与二硫化碳和 1,2-二溴乙烷 1 的反应，3-二溴丙烷或硫酸二甲酯得到 2-氰基-2-(1,3-dithiolan-2-ylidene)-N-(4-{[(5-methylisoxazol-3yl)amino]sulfonyl}phenyl)acetamide (18)， 2-cyano-2-(1,3-dithian-2-ylidene)-N4-{[(5-methyl

  DOI：

  10.3987/com-14-12954

文献信息

• Computational studies and sever apoptotic bioactivity of new heterocyclic cyanoacrylamide based p-fluorophenyl and p-phenolic compounds against liver carcinoma (Hepg2)
  作者：Magda F. Mohamed、Amna A. Saddiq、Turki M. Al-Shaikh、Nada S. Ibrahim、Ismail A. Abdelhamid

  DOI：10.1016/j.bioorg.2021.105147

  日期：2021.9

  efficient route for the preparation of new heterocyclic cyanoacrylamides based p-fluorophenyl and p-phenolic compounds was depicted. All structures were confirmed based on the different spectral tools and elemental analyses. MTT assay for the novel synthesized series was performed against four different cell lines (A549, MCF7, Hepg2, and Wi38). Among all tested groups, the p-phenolic compound 10 (207.1 µg/ml)

  描述了制备基于对氟苯基和对酚类化合物的新型杂环氰基丙烯酰胺的有效途径。所有结构均基于不同的光谱工具和元素分析得到确认。针对四种不同的细胞系（A549、MCF7、Hepg2 和 Wi38）对新型合成系列进行 MTT 测定。在所有测试组中，选择对酚类化合物10 (207.1 µg/ml) 和相应的对氟苯基衍生物6 (325.7 µg/ml) 进行进一步的模拟和分子研究，以对抗肝癌。化合物6和10从理论上对不同的蛋白质组（cdk2、Bcl2-xl、cIAP1-BIR3 和 MDM2）进行了研究，它们说明了不同的结合亲和力。本报告使用了计算研究和不同的分子技术（例如细胞周期分析、DPA 分析、相关基因表达和 ELISA 分析）。
• Synthesis of novel hexahydroquinolines and 6‐amino‐2‐oxopyridine‐3,5‐dicarbonitriles incorporating sulfamethoxazole via [3 + 3] annulation
  作者：Amr M. Abdelmoniem、Mohamed Gamal Mohamed Abdelrahman、Said Ahmed Soliman Ghozlan、Ismail A. Abdelhamid

  DOI：10.1002/jhet.3737

  日期：2019.12

  incorporated sulfamethoxazole moiety were prepared. Their reactions with arylidenemalononitrile derivatives in ethanol or pyridine/piperidine at reflux yielded the corresponding hexahydroquinoline and 6‐amino‐2‐oxopyridine‐3,5‐dicarbonitrile derivatives incorporating sulfamethoxazole. The mechanism and structural elucidation of products were discussed.

  制备了结合了磺胺甲恶唑部分的环烯胺和氰基乙酰胺衍生物。他们与芳基丙二腈衍生物在乙醇或吡啶/哌啶中的反应在回流下产生相应的六氢喹啉和含有磺胺甲恶唑的6-氨基-2-氧代吡啶-3,5-二碳腈衍生物。讨论了产品的机理和结构说明。
• Novel Bis(2‐cyanoacrylamide) Linked to Sulphamethoxazole: Synthesis, DNA Interaction, Anticancer, ADMET, Molecular Docking, and DFT Studies
  作者：Mohamed A. Ragheb、Fatma G. Mohamed、Hadeer M. Diab、Mona S. Ragab、Marwan Emara、Ahmed H. M. Elwahy、Ismail A. Abdelhamid、Marwa H. Soliman

  DOI：10.1002/cbdv.202301341

  日期：2024.4

  In the light of advancement and potential extensive use of medication design and therapy, new bis(cyanoacrylamides) incorporating sulphamethoxazole derivatives (7 a–7 f) were synthesized and confirmed by different spectral tools. In vitro anticancer activity towards different human cancer cells (HCT116, MDA‐MB‐231 and A549) was assessed using MTT assay. Among all derivatives, 4C‐ and 6C‐spacer derivatives (7 e and 7 f) had the most potent growth inhibitory activities against HCT116 cells with IC50 values of 39.7 and 28.5 μM, respectively. 7 e and 7 f induced apoptosis and suppressed migration of HCT116 cells. These compounds also induced a significant increase in caspase‐3 and CDH1 activities, and a downregulation of Bcl2 using ELISA. pBR322 DNA cleavage activities of cyanoacrylamides were determined using agarose gel electrophoresis. Furthermore, 7 e and 7 f showed good DNA and BSA binding affinities using different spectroscopic techniques. Furthermore, molecular docking for 7 e and 7 f was performed to anticipate their binding capabilities toward various proteins (Bcl2, CDH1 and BSA). The docking results were well correlated with those of experimental results. Additionally, density functional theory and ADMET study were performed to evaluate the molecular and pharmacokinetic features of 7 e and 7 f, respectively. Thus, this work reveals promising antitumor lead compounds that merit future research and activity enhancement.