(+-)-1-methyl-cyclohexanone-(4)-thiosemicarbazone | 22397-22-4

• 分子结构分类: 有机化合物 - 有机硫化合物
• 英文名称: (+-)-1-methyl-cyclohexanone-(4)-thiosemicarbazone
• 英文别名: (+/-)-1-methyl-cyclohexanone-(4)-thiosemicarbazone；(+/-)-1-Methyl-cyclohexanon-(4)-thiosemicarbazon
• CAS: 22397-22-4
• 化学式: C₈H₁₅N₃S
• 分子量: 185.293
• InChiKey: GRWTYCLFTCPLBX-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  50.41
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (+-)-1-methyl-cyclohexanone-(4)-thiosemicarbazone 在 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 3-benzyl-2-(2-(4-methylcyclohexylidene)hydrazono)thiazolidin-4-one
  参考文献：
  名称：

  1,3-噻唑烷丁-4-酮衍生物的合成，生物学评估和定量构效关系。具有高抗真菌效力和低细胞毒性的有前途的化学支架

  摘要：

  参考有关噻唑烷酮支架各种生物学特性的最新研究报告，我们合成了一百多种化合物，这些化合物的特征是1,2噻唑烷酮-4-酮核在C2处衍生化，并带有与（环）脂族连接的肼桥。或杂（芳基）部分，以及它们的N-苄基衍生物。这些分子被作为潜在的抗念珠菌药物进行了分析，显示它们具有与成熟的局部和全身性抗真菌药物（即克霉唑，氟康唑，酮康唑，咪康唑，噻康唑，两性霉素B）相当的生物活性，在某些情况下具有更高的生物学活性。具有最低MIC的化合物进行了进一步测试，以评估其细胞毒性作用（CC 50）在Hep2细胞上，证明了其相对安全性。最后，使用QSAR和3-D QSAR模型预测1,3-噻唑烷丁-4-酮支架的假定化学修饰，以设计针对念珠菌的新的和潜在的更具活性的化合物。

  DOI：

  10.1016/j.ejmech.2017.09.026
• 作为产物：
  描述：

  氨基硫脲 、 4-甲基环己酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.09h， 生成 (+-)-1-methyl-cyclohexanone-(4)-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

• Design, synthesis and biochemical evaluation of novel multi-target inhibitors as potential anti-Parkinson agents
  作者：Simone Carradori、Francesco Ortuso、Anél Petzer、Donatella Bagetta、Celeste De Monte、Daniela Secci、Daniela De Vita、Paolo Guglielmi、Gokhan Zengin、Abdurrahman Aktumsek、Stefano Alcaro、Jacobus P. Petzer

  DOI：10.1016/j.ejmech.2017.10.050

  日期：2018.1

  acetylcholinesterase (AChE) inhibitors, as well as antioxidant agents, for the treatment of neurodegenerative disorders such as Parkinson's disease. Rational molecular design, target recognition and predicted pharmacokinetic properties have been evaluated by means of molecular modelling. Based on these properties, compounds were synthesized and evaluated in vitro as MAO-B and AChE inhibitors, and compared to

  新型的4-（3-硝基苯基）噻唑-2-基hydr衍生物被提议作为双靶标定向单胺氧化酶B（MAO-B）和乙酰胆碱酯酶（AChE）抑制剂，以及抗氧化剂，用于治疗神经退行性疾病，例如作为帕金森氏病。合理的分子设计，目标识别和预测的药代动力学特性已经通过分子建模进行了评估。基于这些特性，合成了化合物并作为MAO-B和AChE抑制剂进行了体外评估，并与相应的同工酶单胺氧化酶A（MAO-A）和丁酰胆碱酯酶（BuChE）的活性进行了比较。还已经在体外研究了抗氧化特性，这些特性在治疗神经退行性疾病中可能有用。在评估的化合物中，三种抑制剂可以被认为是有希望的体外MAO-B和AChE双重抑制剂。对于化合物19， MAO-B抑制作用也显示出竞争性和可逆性。
• Synthesis and Evaluation of 4-Acyl-2-thiazolylhydrazone Derivatives for Anti-<i>Toxoplasma</i> Efficacy in Vitro
  作者：Franco Chimenti、Bruna Bizzarri、Adriana Bolasco、Daniela Secci、Paola Chimenti、Simone Carradori、Arianna Granese、Daniela Rivanera、Nathan Frishberg、Claudia Bordón、Lorraine Jones-Brando

  DOI：10.1021/jm9005862

  日期：2009.8.13

  A new series of 4-acyl-2-thiazolylhydrazone derivatives was synthesized and screened for its in vitro activity against Toxoplasma gondii. We evaluated parasite growth inhibition and cytotoxicity, inhibition of replication, and inhibition of parasite invasion of host cells. The biological results indicated that some substances had an antiproliferative effect against intracellular T. gondii tachyzoites

  合成了一系列新的4-酰基-2-噻唑基hydr衍生物，并筛选了其对弓形虫的体外活性。我们评估了寄生虫的生长抑制和细胞毒性，复制的抑制，以及宿主细胞的寄生虫入侵的抑制。生物学结果表明，某些物质对体外培养的细胞内弓形虫速殖子具有抗增殖作用。
• Synthesis and biological evaluation of novel conjugated coumarin-thiazole systems
  作者：Franco Chimenti、Simone Carradori、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Bruna Bizzarri

  DOI：10.1002/jhet.110

  日期：2009.5

  Seven new 2,4-disubstituted thiazoles have been synthesized by Hantzsch condensation and assayed for several biological activities for a preliminary screening. They have been fully characterized by elemental analysis, UV–Vis spectroscopy, TG-DTA, IR, and 1H NMR as well. These structures display different pharmacological (antimicrobic activity, citotoxicity, and hMAO inhibition) and industrial properties

  通过Hantzsch缩合反应合成了七种新的2,4-二取代噻唑，并对其几种生物学活性进行了测定，以进行初步筛选。它们已经通过元素分析，UV-Vis光谱，TG-DTA，IR和1 H NMR进行了全面表征。这些结构在其取代基上表现出不同的药理作用（抗微生物活性，细胞毒性和hMAO抑制作用）和工业特性（在465-800 nm之间完全透明，并且具有高的热稳定性），可以被认为是进一步发展的良好先导化合物。J.杂环化​​学，（2009）。
• Synthesis, semipreparative HPLC separation, biological evaluation, and 3D-QSAR of hydrazothiazole derivatives as human monoamine oxidase B inhibitors
  作者：Franco Chimenti、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Simone Carradori、Elias Maccioni、M. Cristina Cardia、Matilde Yáñez、Francisco Orallo、Stefano Alcaro、Francesco Ortuso、Roberto Cirilli、Rosella Ferretti、Simona Distinto、Johannes Kirchmair、Thierry Langer

  DOI：10.1016/j.bmc.2010.05.070

  日期：2010.7

  The present study reports on synthesis in high yields (70-99%), HPLC enantioseparation, inhibitory activity against human monoamino oxidases, and molecular modeling including 3D-QSAR studies, of a large series of (4-aryl-thiazol-2-yl) hydrazones (1-45). Most of the synthesized compounds proved to be potent and selective inhibitors of hMAO-B isoform in the micromolar or nanomolar range, thus demonstrating that hydrazothiazole could be considered a good pharmacophore to design new hMAO-B inhibitors. Due to the presence in some derivatives of a chiral center, we also performed a semipreparative chromatographic enantioseparation of these compounds obtained by a stereoconservative pattern. The separated enantiomers were submitted to in vitro biological evaluation to point out the stereorecognition of the active site of the enzyme towards these structures. Finally, a 3D-QSAR study was carried out using Comparative Molecular Field Analysis (CoMFA), aiming to deduce rational guidelines for the further structural modification of these lead compounds. (C) 2010 Elsevier Ltd. All rights reserved.
• Selective Inhibitory Activity against MAO and Molecular Modeling Studies of 2-Thiazolylhydrazone Derivatives
  作者：Franco Chimenti、Elias Maccioni、Daniela Secci、Adriana Bolasco、Paola Chimenti、Arianna Granese、Olivia Befani、Paola Turini、Stefano Alcaro、Francesco Ortuso、Maria C. Cardia、Simona Distinto

  DOI：10.1021/jm060869d

  日期：2007.2.1

  A series of 2-thiazolylhydrazone derivatives have been investigated for the ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO) selectively. All of the compounds showed high activity against both the MAO-A and the MAO-B isoforms with pK(i) values ranging between 5.92 and 8.14 for the MAO-A and between 4.69 and 9.09 for the MAO-B isoforms. Both the MAO-A and the MAO-B isoforms, deposited in the Protein Data Bank as model 2BXR and 1GOS, respectively, were considered in a computational study performed with docking techniques on the most active and MAO-B-selective inhibitor, 18.