[(3-Methylcyclopentylidene)amino]thiourea | 100959-70-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [(3-Methylcyclopentylidene)amino]thiourea
• 英文别名: [(3-methylcyclopentylidene)amino]thiourea
• CAS: 100959-70-4
• 化学式: C₇H₁₃N₃S
• 分子量: 171.266
• InChiKey: XONTWAUKHIVGCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  [(3-Methylcyclopentylidene)amino]thiourea 在 α-halo-4'-fluoroacetophenone, halo= Cl, Br 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以89%的产率得到1-(4-(4-fluorophenyl)thiazol-2-yl)-2-(3-methylcyclopentylidene)hydrazine
  参考文献：
  名称：

  确定用于选择人单胺氧化酶B抑制剂的4-芳基-2-环亚烷基肼基噻唑构架中的立体化学要求

  摘要：

  探索脂环族环上的取代基对一系列4-芳基-2-环烷基亚烷基肼基噻唑对人单胺氧化酶B的抑制活性的影响，导致合成了一系列新的2-甲基环戊基和3-甲基环戊基衍生物，并进行了测试在体外作为非对映异构体的混合物。实际上，由于在脂环族环上存在手性中心和三取代的C N键，它们以四种非对映异构体（（E）-（R），（E）-（S），（Z）-（R），（Z）-（S））。选择4-（2,4-二氟苯基）-2-（2-（3-甲基环亚戊基）肼基）噻唑作为模型，研究立体化学要求对立体保守合成后这些衍生物对hMAO-B抑制活性的影响和半制备HPLC非对映体分离。该化合物的（R）-（Z）异构体具有比参比药物更高的有效和选择性hMAO-B抑制作用，这也得到了分子模型研究的证实。

  DOI：

  10.1016/j.bmc.2014.03.042
• 作为产物：
  描述：

  DL-3-甲基环戊酮 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 [(3-Methylcyclopentylidene)amino]thiourea
  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

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 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）。
• 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。
• Anti-Candida activity and cytotoxicity of a large library of new N-substituted-1,3-thiazolidin-4-one derivatives
  作者：Celeste De Monte、Simone Carradori、Bruna Bizzarri、Adriana Bolasco、Federica Caprara、Adriano Mollica、Daniela Rivanera、Emanuela Mari、Alessandra Zicari、Atilla Akdemir、Daniela Secci

  DOI：10.1016/j.ejmech.2015.10.048

  日期：2016.1

  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.
• Synthesis, anti-Candida activity, and cytotoxicity of new (4-(4-iodophenyl)thiazol-2-yl)hydrazine derivatives
  作者：Daniela Secci、Bruna Bizzarri、Adriana Bolasco、Simone Carradori、Melissa D'Ascenzio、Daniela Rivanera、Emanuela Mari、Lucia Polletta、Alessandra Zicari

  DOI：10.1016/j.ejmech.2012.04.006

  日期：2012.7

  Novel (4-(4-iodophenyl)-thiazol-2-yl)hydrazine derivatives were assayed for their in vitro anti-Candida activity, compared to topical and systemic antifungal drugs, against twenty-seven clinical isolates. The presence of aliphatic chains or specific heteroaromatic rings on hydrazone moiety at position C2 and a 4-iodophenyl at C4 of the thiazole ring gave a promising inhibitory activity especially against Candida albicans and Candida krusei. The most active compounds have been also evaluated for their cytotoxicity and in association with clotrimazole for anti-Candida activity. (C) 2012 Elsevier Masson SAS. All rights reserved.