1-((thioureidoimino)methyl)-4-(pyrrolidin-1-yl)benzene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1-((thioureidoimino)methyl)-4-(pyrrolidin-1-yl)benzene
• 英文别名: [(4-Pyrrolidin-1-ylphenyl)methylideneamino]thiourea
• 化学式: C₁₂H₁₆N₄S
• 分子量: 248.352
• InChiKey: AHMCAMFTTZJPKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 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：
  85.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-((thioureidoimino)methyl)-4-(pyrrolidin-1-yl)benzene 在 lithium chloride 作用下， 以 乙醇 为溶剂， 反应 27.0h， 生成 2-(2-(4-(pyrrolidin-1-yl)benzylidene)hydrazinyl)-4-methyl-5-(1-(guanidinoazanylidene)ethyl)-thiazole
  参考文献：
  名称：

  胍基噻唑类化合物及其制备方法和应用

  摘要：

  本发明公开了胍基噻唑类化合物及其制备方法和应用。所述的胍基噻唑类化合物的结构式如式(IV)所示。本发明通过在噻唑环的C2位引入亲脂性侧链和C5位引入亲水性胍基，设计合成了一系列全新结构的噻唑类化合物，其制备方法为：以醛类化合物(I)和氨基硫脲为原料，缩合反应得到第一步产物(II)，第一步产物(II)与3‑氯乙酰丙酮反应，制得第二步产物(III)，第二步产物(III)与氨基胍盐酸盐反应，制得最终产物(IV)。该胍基噻唑类化合物呈现出抗菌活性，尤其是对金黄色葡萄球菌、大肠杆菌、铜绿假单胞菌有很好的抗菌活性，可作为抗菌候选化合物。

  公开号：

  CN113336720B
• 作为产物：
  描述：

  对氟苯甲醛 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 1-((thioureidoimino)methyl)-4-(pyrrolidin-1-yl)benzene
  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

文献信息

• 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.
• 胍基噻唑类化合物及其制备方法和应用
  申请人：广东省科学院微生物研究所（广东省微生物分析检测中心）

  公开号：CN113336720B

  公开（公告）日：2022-03-18

  本发明公开了胍基噻唑类化合物及其制备方法和应用。所述的胍基噻唑类化合物的结构式如式(IV)所示。本发明通过在噻唑环的C2位引入亲脂性侧链和C5位引入亲水性胍基，设计合成了一系列全新结构的噻唑类化合物，其制备方法为：以醛类化合物(I)和氨基硫脲为原料，缩合反应得到第一步产物(II)，第一步产物(II)与3‑氯乙酰丙酮反应，制得第二步产物(III)，第二步产物(III)与氨基胍盐酸盐反应，制得最终产物(IV)。该胍基噻唑类化合物呈现出抗菌活性，尤其是对金黄色葡萄球菌、大肠杆菌、铜绿假单胞菌有很好的抗菌活性，可作为抗菌候选化合物。