1-(4-morpholinobenzylidene)thiosemicarbazide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 1-(4-morpholinobenzylidene)thiosemicarbazide
• 英文别名: thiosemicarbazone；[(4-Morpholin-4-ylphenyl)methylideneamino]thiourea
• 化学式: C₁₂H₁₆N₄OS
• 分子量: 264.351
• InChiKey: QNXVGQNACGSIOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-4'-氰基苯乙酮 、 1-(4-morpholinobenzylidene)thiosemicarbazide 以 乙醇 为溶剂， 反应 4.0h， 以84%的产率得到4-(2-(2-(4-morpholinobenzylidene)hydrazineyl)thiazol-4-yl)benzonitrile
  参考文献：
  名称：

  Design, synthesis and biological assessment of new thiazolylhydrazine derivatives as selective and reversible h MAO-A inhibitors

  摘要：

  In the recent works, it was shown that numerous thiazolylhydrazine derivatives display hMAO inhibitory activity in the range of micromolar concentration. Hence, in the present study a new series of new thiazole-hydrazines (3a-3n) were designed, synthesized, characterized and screened for their hMAO-A and hMAO-B inhibitory activity by an in vitro flurometric method. The enzyme inhibition assay revealed that most of the synthesized compounds have selective inhibition potency against hMAO-A. The compounds 3f and 3h showed promising hMAO-A inhibition with an IC50 values of 0.012 mu M and 0.011 mu M and significant selectivity indexes of 1214 and 1601 towards hMAO-A, respectively. The mechanism of hMAO-A inhibition of compounds 3f and 3h was investigated by Lineweaver-Burk graphics and reversible-competitive inhibition of hMAO-A was determined. Cytotoxicity and genotoxicity studies were carried out and the compound 3h was found as non-cytotoxic and non-genotoxic. Theoretical calculation of ADME properties suggested that synthesized compounds may have a good pharmacokinetic profile. The docking study of compound 3f and 3h revealed that there is a strong interaction between the active sites of hMAO-A and analyzed compound. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.12.013
• 作为产物：
  描述：

  对氟苯甲醛 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 14.0h， 生成 1-(4-morpholinobenzylidene)thiosemicarbazide
  参考文献：
  名称：

  一系列噻唑-2-基con凝聚物的生物学评估和计算机分子对接研究

  摘要：

  摘要 设计，合成了一系列具有不同取代基的杂杂噻唑-2-基hybrid衍生物，并通过角叉菜胶诱导的爪水肿方法筛选了它们的抗炎特性。与双氯芬酸钠相比，化合物 11a，11b，11c，11d，11e，11g，11m 和 11p表现 出显着的抑制作用。随后，两种高效化合物（ 11d 和 11e 评估了它们对肿瘤细胞系的细胞毒性作用。噻唑-2-基-与环氧合酶2（COX-2）蛋白（PDB：3LN1）的结合相互作用表现出与Arg-120，Tyr-385和Tyr-355氨基酸的有效相互作用，这是该酶的主要标准COX-2抑制剂。此外，所有化合物均显示出中等至良好的体外抗菌活性。还测试了大多数活性苄氧基衍生物，以通过2，2-二苯基-1-吡啶并肼基方法了解自由基清除功效。 图形概要

  DOI：

  10.1007/s11164-018-3261-z

文献信息

• Biological evaluation and in silico molecular docking study of a new series of thiazol-2-yl-hydrazone conglomerates
  作者：Mahima Bhat、P. M. Gurubasavaraja Swamy、Boja Poojary、B. C. Revanasiddappa、M. Vijay Kumar、Vasantha Kumar

  DOI：10.1007/s11164-018-3261-z

  日期：2018.4

  Abstract A new series of hybridized thiazol-2-yl-hydrazone derivatives having diverse substituents were designed, synthesized, and screened for their anti-inflammatory property by a carrageenan-induced paw edema method. The compounds 11a, 11b, 11c, 11d, 11e, 11g, 11m and 11p revealed significant inhibition when compared to Diclofenac sodium. Subsequently, two highly potent compounds ( 11d and 11e )

  摘要 设计，合成了一系列具有不同取代基的杂杂噻唑-2-基hybrid衍生物，并通过角叉菜胶诱导的爪水肿方法筛选了它们的抗炎特性。与双氯芬酸钠相比，化合物 11a，11b，11c，11d，11e，11g，11m 和 11p表现 出显着的抑制作用。随后，两种高效化合物（ 11d 和 11e 评估了它们对肿瘤细胞系的细胞毒性作用。噻唑-2-基-与环氧合酶2（COX-2）蛋白（PDB：3LN1）的结合相互作用表现出与Arg-120，Tyr-385和Tyr-355氨基酸的有效相互作用，这是该酶的主要标准COX-2抑制剂。此外，所有化合物均显示出中等至良好的体外抗菌活性。还测试了大多数活性苄氧基衍生物，以通过2，2-二苯基-1-吡啶并肼基方法了解自由基清除功效。 图形概要
• Synthesis, characterization, antimicrobial activity and molecular docking study of transition metal complexes based on azo coumarin and thiosemicarbazone derivative
  作者：Shobha S. Borhade、Pravin T. Tryambake

  DOI：10.1007/s13738-023-02953-0

  日期：2024.3

  complexes were studied for antimicrobial potential against various bacterial and fungal pathogens. Further, the antioxidant potential screening was done using 1,1-diphenyl-2-picrylhydrazyl. Synthesized metal complexes displayed modest to excellent antimicrobial potential. The topoisomerase II receptor protein was used for molecular docking of the extraordinary antimicrobial Co and Zn-complex.

  合成了Co(II)、Fe(III)、Cu(II)、Zn(II)、Cd(II)和Hg(II)金属离子与偶氮香豆素和缩氨基硫脲衍生物的混合配体金属配合物。合成的配体通过 IR、1 HNMR、13 CNMR 和质量分析等光谱技术得到支持，同时通过 FTIR、元素分析、摩尔电导、质谱、热重分析 (TG) 和电子光谱探索金属螯合物的结构和可能的几何形状（紫外线）。根据热研究，还报告了复合物的活化能和动力学参数（ΔG、ΔH、ΔS）。研究了合成配体及其金属配合物对各种细菌和真菌病原体的抗菌潜力。此外，使用1,1-二苯基-2-三硝基苯肼进行抗氧化潜力筛选。合成的金属配合物表现出中等至优异的抗菌潜力。拓扑异构酶 II 受体蛋白用于非凡抗菌 Co 和 Zn 复合物的分子对接。
• Design, synthesis and biological assessment of new thiazolylhydrazine derivatives as selective and reversible h MAO-A inhibitors
  作者：Nafiz Öncü Can、Derya Osmaniye、Serkan Levent、Begüm Nurpelin Sağlık、Büşra Korkut、Özlem Atlı、Yusuf Özkay、Zafer Asım Kaplancıklı

  DOI：10.1016/j.ejmech.2017.12.013

  日期：2018.1

  In the recent works, it was shown that numerous thiazolylhydrazine derivatives display hMAO inhibitory activity in the range of micromolar concentration. Hence, in the present study a new series of new thiazole-hydrazines (3a-3n) were designed, synthesized, characterized and screened for their hMAO-A and hMAO-B inhibitory activity by an in vitro flurometric method. The enzyme inhibition assay revealed that most of the synthesized compounds have selective inhibition potency against hMAO-A. The compounds 3f and 3h showed promising hMAO-A inhibition with an IC50 values of 0.012 mu M and 0.011 mu M and significant selectivity indexes of 1214 and 1601 towards hMAO-A, respectively. The mechanism of hMAO-A inhibition of compounds 3f and 3h was investigated by Lineweaver-Burk graphics and reversible-competitive inhibition of hMAO-A was determined. Cytotoxicity and genotoxicity studies were carried out and the compound 3h was found as non-cytotoxic and non-genotoxic. Theoretical calculation of ADME properties suggested that synthesized compounds may have a good pharmacokinetic profile. The docking study of compound 3f and 3h revealed that there is a strong interaction between the active sites of hMAO-A and analyzed compound. (C) 2017 Elsevier Masson SAS. All rights reserved.