Methylpropylketon-thiosemicarbazon | 1752-39-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Methylpropylketon-thiosemicarbazon
• 英文别名: 2-Pentanone thiosemicarbazone；(pentan-2-ylideneamino)thiourea
• CAS: 1752-39-2
• 化学式: C₆H₁₃N₃S
• mdl: MFCD21101374
• 分子量: 159.255
• InChiKey: ATFQXYQKXBTCBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methylpropylketon-thiosemicarbazon 在 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 24.0h， 生成 3-(naphthalen-1-ylmethyl)-2-(2-(pentan-2-ylidene)hydrazono)thiazolidin-4-one
  参考文献：
  名称：

  Anti-Candida activity and cytotoxicity of a large library of new N-substituted-1,3-thiazolidin-4-one derivatives

  摘要：

  On the basis of the recent findings about the biological properties of thiazolidinones and taking into account the encouraging results about the antifungal activity of some (thiazol-2-yl)hydrazines, new N-substituted heterocyclic derivatives were designed combining the thiazolidinone nucleus with the hydrazonic portion. In details, 1,3-thiazolidin-4-ones bearing (cyclo)aliphatic or (hetero)aromatic moieties linked to the N1-hydrazine at C2 were synthesized and classified into three series according to the aromatic or bicyclic rings connected to the lactam nitrogen of the thiazolidinone. These molecules were assayed for their anti-Candida effects in reference to the biological activity of the conventional topic (clotrimazole, miconazole, tioconazole) and systemic drugs (fluconazole, ketoconazole, amphotericin B). Finally, we investigated the selectivity against fungal cells by testing the compounds endowed with the best MICs on Hep2 cells in order to assess their cell toxicity (CC50) and we noticed that two derivatives were less cytotoxic than the reference drug clotrimazole. Moreover, a preliminary molecular modelling approach has been performed against lanosterol 14-alpha demethylase (CYP51A1) to rationalize the activity of the tested compounds and to specify the target protein or enzyme. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.048
• 作为产物：
  描述：

  2-戊酮 生成 Methylpropylketon-thiosemicarbazon
  参考文献：
  名称：

  Shenton; Smith, Chemistry and industry, 1958, p. 1510

  摘要：

  DOI：

文献信息

• Evaluation of a large library of (thiazol-2-yl)hydrazones and analogues as histone acetyltransferase inhibitors: Enzyme and cellular studies
  作者：Simone Carradori、Dante Rotili、Celeste De Monte、Alessia Lenoci、Melissa D'Ascenzio、Veronica Rodriguez、Patrizia Filetici、Marco Miceli、Angela Nebbioso、Lucia Altucci、Daniela Secci、Antonello Mai

  DOI：10.1016/j.ejmech.2014.04.042

  日期：2014.6

  thiazolidines and pyrimidin-4(3H)-ones, and we tested the whole library existing in our lab against human p300 and PCAF HAT enzymes. Some compounds (1x, 1c', 1d', 1i' and 2m) were more efficient than CPTH2 and CPTH6 in inhibiting the p300 HAT enzyme. When tested in human leukemia U937 and colon carcinoma HCT116 cells (100 μM, 30 h), 1x, 1i' and 2m gave higher (U937 cells) or similar (HCT116 cells) apoptosis

  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）。
• Synthesis, biological evaluation and quantitative structure-active relationships of 1,3-thiazolidin-4-one derivatives. A promising chemical scaffold endowed with high antifungal potency and low cytotoxicity
  作者：Simone Carradori、Bruna Bizzarri、Melissa D'Ascenzio、Celeste De Monte、Rossella Grande、Daniela Rivanera、Alessanda Zicari、Emanuela Mari、Manuela Sabatino、Alexandros Patsilinakos、Rino Ragno、Daniela Secci

  DOI：10.1016/j.ejmech.2017.09.026

  日期：2017.11

  hundred compounds characterized by a 1,3-thiazolidin-4-one nucleus derivatised at the C2 with a hydrazine bridge linked to (cyclo)aliphatic or hetero(aryl) moieties, and their N-benzylated derivatives. These molecules were assayed as potential anti-Candida agents and they were shown to possess comparable, and in some cases higher biological activity than well-established topical and systemic antimycotic drugs

  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。
• Synthesis and anti-Helicobacter pylori activity of 4-(coumarin-3-yl)thiazol-2-ylhydrazone derivatives
  作者：Franco Chimenti、Bruna Bizzarri、Adriana Bolasco、Daniela Secci、Paola Chimenti、Arianna Granese、Simone Carradori、Melissa D'Ascenzio、M. Maddalena Scaltrito、Francesca Sisto

  DOI：10.1002/jhet.464

  日期：2010.11

  A novel class of coumarin‐thiazole conjugated systems (1‐31) were synthesized by Hantzsch condensation between α‐bromo‐3‐acetyl coumarin and several thiosemicarbazone intermediates. This scaffold was also evaluated for selective antibacterial activity against 20 isolates of H. pylori clinical strains, including four metronidazole resistant ones. J. Heterocyclic Chem., (2010).

  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）。
• The reactions of the bis(but-2-yne) complex [WI2(CO)(NCMe)(η2-MeC2Me)2] with benzaldehydesemicarbazone and thiosemicarbazones
  作者：Paul K. Baker、Stephen D. Ridyard

  DOI：10.1016/s0277-5387(00)84372-7

  日期：1993.9

  Abstract Reaction of equimolar quantities of [WI2(CO)(NCMe)(η2-MeC2Me)2] and Ph(H)CNNHCONH2 or R(R1)CNNHCSNH2 (R = R1 = Me, Et; R = H, R1 = Ph; R = Me, R1 = Et, Prn, But, Ph) in CH2Cl2 at room temperature gave the cationic bis(but-2-yne) complexes [WI(CO)Ph(H)CNNHCONH2}(η2-MeC2Me)2]I or [WI(CO)R(R1) CNNHCSNH2}(η2-MeC2Me)2]I in good yield. The cationic nature of these complexes was confirmed by reaction

  摘要等摩尔量的[WI2（CO）（NCMe）（η2-MeC2Me）2]与Ph（H）CNNHCONH2或R（R1）CNNHCSNH2（R = R1 = Me，Et; R = H，R1 = Ph; R = Me，R1 = Et，Prn，但是在室温下于CH2Cl2中的Ph生成了阳离子双（丁-2-炔）配合物[WI（CO）Ph（H）CNNHCONH2}（η2-MeC2Me）2] I或[WI（CO）R（R1）CNNHCSNH2}（η2-MeC2Me）2] I收率良好。这些配合物的阳离子性质通过[WI（CO）Me（Ph）CNNHCSNH2}（η2-MeC2Me）2] I与Na [BPh4]在乙腈中的反应得到证实，得到四苯硼酸酯交换产物[WI（CO） Me（Ph）CNNHCSNH2}（η2-MeC2Me）2] [BPh4]。将[WI（CO）Et2CNNHCSNH2}（η2-MeC2Me）2] I的
• EPR, mass, IR, electronic, and magnetic studies on copper(II) complexes of semicarbazones and thiosemicarbazones
  作者：Sulekh Chandra、Lokesh Kumar Gupta

  DOI：10.1016/j.saa.2004.03.040

  日期：2005.1

  Cu(L)(2)X(2) [where L = isopropyl methyl ketone semicarbazone (LLA), isopropyl methyl ketone thiosemicarbazone (LLB), 4-aminoacetophenone semicarbazone (LLC), and 4-aminoacetophenone thiosemicarbazone (LLD) and X = Cl(-), 1/2SO(4)(2-)] have been synthesized. All the Cu(II) complexes reported here have been characterized by elemental analyses, molar conductance, magnetic moment susceptibility, EI mass

  铜（II）配合物，其一般成分为Cu（L）（2）X（2）[其中L =异丙基甲基酮缩氨基脲（LLA），异丙基甲基酮缩酮氨基脲（LLB），4-氨基苯乙酮缩氨基脲（LLC）和4 -氨基苯乙酮硫半碳酮（LLD）和X = Cl（-），1 / 2SO（4）（2-）]已合成。本文报道的所有Cu（II）配合物均已通过元素分析，摩尔电导，磁矩磁化率，EI质量，（1）H NMR，IR，EPR和电子光谱研究进行了表征。发现所有配合物具有对应于一个不成对电子的磁矩。根据EPR，电子和红外光谱研究确定了配合物的可能几何形状。