1-(2-thiazolyl)ethanone thiosemicarbazone | 546112-24-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(2-thiazolyl)ethanone thiosemicarbazone
• 英文别名: [1-(1,3-Thiazol-2-yl)ethylideneamino]thiourea；[1-(1,3-thiazol-2-yl)ethylideneamino]thiourea
• CAS: 546112-24-7
• 化学式: C₆H₈N₄S₂
• 分子量: 200.288
• InChiKey: REIJRKPVQBDWQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  344.8±25.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-thiazolyl)ethanone thiosemicarbazone 、 3-(溴乙酰基)香豆素 以 乙醇 为溶剂， 反应 4.0h， 以99%的产率得到3-(2-(2-(1-(thiazol-2-yl)ethyliden)hydrazynyl)thiazol-4-yl)-2H-chromen-2-one
  参考文献：
  名称：

  4-（香豆素-3-基）噻唑-2-基hydr衍生物的合成和抗幽门螺杆菌活性

  摘要：

  通过α-溴-3-乙酰香豆素与几种硫半脲中间体之间的Hantzsch缩合反应合成了一类新型的香豆素-噻唑共轭体系（1-31）。还评估了该支架对幽门螺杆菌临床菌株的20种分离株的选择性抗菌活性，其中包括4种对甲硝唑耐药的菌株。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.464
• 作为产物：
  描述：

  2-乙酰基噻唑 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.09h， 生成 1-(2-thiazolyl)ethanone thiosemicarbazone
  参考文献：
  名称：

  评价作为组蛋白乙酰转移酶抑制剂的（噻唑-2-基））酮和类似物的大型文库：酶和细胞研究

  摘要：

  最近，我们描述了一些（噻唑-2-基）azo作为抗原生动物，抗真菌和抗MAO试剂以及Gcn5 HAT抑制剂。在这些最后的化合物中，CPTH2和CPTH6在细胞中显示出HAT抑制作用和广泛的抗癌特性。为了鉴定比两个原型更有效的HAT抑制剂，我们合成了几种新的（噻唑-2-基）azo酮，包括一些相关的噻唑烷和嘧啶4（3 H）-酮，并测试了我们现有的整个文库针对人p300和PCAF HAT酶的实验室。某些化合物（1x，1c '，1d '，1i '和2m）在抑制p300 HAT酶方面比CPTH2和CPTH6更有效。在人白血病U937和结肠癌HCT116细胞（100μM，30小时）中进行测试时，1x，1i '和2m产生的凋亡（U937细胞）或类似细胞（HCT116细胞）高于CPTH6，并且在诱导细胞分化方面比CPTH6更有效（U937细胞）。

  DOI：

  10.1016/j.ejmech.2014.04.042

文献信息

• Synthesis of a novel series of thiazole-based histone acetyltransferase inhibitors
  作者：Daniela Secci、Simone Carradori、Bruna Bizzarri、Adriana Bolasco、Paola Ballario、Zoi Patramani、Paola Fragapane、Stefano Vernarecci、Claudia Canzonetta、Patrizia Filetici

  DOI：10.1016/j.bmc.2014.01.022

  日期：2014.3

  Acetylation, which targets a broad range of histone and non-histone proteins, is a reversible mechanism and plays a critical role in eukaryotic genes activation/deactivation. Acetyltransferases are very well conserved through evolution. This allows the use of a simple model organism, such as budding yeast, for the study of their related processes and to discover specific inhibitors. Following a simple yeast-based chemogenetic approach, we have identified a novel HAT (histone acetyltransferase) inhibitor active both in vitro and in vivo. This new synthetic compound,1-(4-(4-chlorophenyl)thiazol-2-yl)-2-(propan-2-ylidene) hydrazine, named BF1, showed substrate selectivity for histone H3 acetylation and inhibitory activity in vitro on recombinant HAT Gcn5 and p300. Finally, we tested BF1 on human cells, HeLa as control and two aggressive cancer cell lines: a neuroblastoma from neuronal tissue and glioblastoma from brain tumour. Both global acetylation of histone H3 and specific acetylation at lysine 18 (H3AcK18) were lowered by BF1 treatment. Collectively, our results show the efficacy of this novel HAT inhibitor and propose the utilization of BF1 as a new, promising tool for future pharmacological studies. (C) 2014 Elsevier Ltd. All rights reserved.
• Recent advances in the development of selective human MAO-B inhibitors: (Hetero)arylidene-(4-substituted-thiazol-2-yl)hydrazines
  作者：Daniela Secci、Adriana Bolasco、Simone Carradori、Melissa D'Ascenzio、Riccardo Nescatelli、Matilde Yáñez

  DOI：10.1016/j.ejmech.2012.10.032

  日期：2012.12

  A large series of (4-substituted-thiazol-2-yl)hydrazine derivatives was synthesized in good yield and assayed for their in vitro human monoamine oxidase (hMAO) inhibitory activity and selectivity. Most of them showed inhibitory activity in the nanomolar range and hMAO-B selective inhibition higher than reference drugs, demonstrating our interest in this privileged scaffold. The structure activity relationship of the different rings on the N1-hydrazine position indicated that a pyridine ring was preferred with the presence of electron-withdrawing substituents on the aryl group at C4 of the thiazole nucleus. The substituent on the alpha-carbon to the N1-hydrazine moiety (methyl or hydrogen) had a great influence on the activity and hMAO-B selectivity. Moreover, the reversibility of the enzyme inhibition for the best active compound was reported. (C) 2012 Elsevier Masson SAS. All rights reserved.