1-(4-methyl-2-pentylidene) thiosemicarbazide | 79317-52-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(4-methyl-2-pentylidene) thiosemicarbazide
• 英文别名: 4-methyl-2-pentanone thiosemicarbazone；4-methyl-2-pentylidene aminothiourea；(4-methylpentan-2-ylideneamino)thiourea
• CAS: 79317-52-5
• 化学式: C₇H₁₅N₃S
• mdl: MFCD01043480
• 分子量: 173.282
• InChiKey: GYKIDLIHFHUBMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 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：

  1-(4-methyl-2-pentylidene) thiosemicarbazide 在 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 24.0h， 生成 2-(2-(4-methylpentan-2-ylidene)hydrazono)-3-(naphthalen-1-ylmethyl)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：

  氨基硫脲 、 4-甲基-2-戊酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.09h， 生成 1-(4-methyl-2-pentylidene) thiosemicarbazide
  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 Biologically Active [4-(4-Bromophenyl)-2-thiazolyl]hydrazones and their D-Galactose Derivatives
  作者：El Sayed Ramadan

  DOI：10.1002/cjoc.201090118

  日期：——

  Benzaldehyde [4‐(4‐bromophenyl)thiazol‐2‐yl]hydrazones 5a–5d were prepared by reacting the thiosemicarbazones 2a–2d with 2,4′‐dibromoacetophenone (1) in absolute ethanol. Acetylation of 5a and 5b with Ac2O/Py at room temperature gave the N‐acetyl derivatives 6a and 6b. 4‐Methyl‐2‐pentanone/cyclopentanone [4‐(4‐bromo‐phenyl)thiazol‐2‐yl]hydrazones (8a) and (8b) were similarly obtained from the reaction

  苯甲醛[4-（4-溴苯基）噻唑-2-基]腙5A - 5D是由缩氨基硫脲反应而制备2A - 2d中与2,4'-二溴苯乙酮（1在无水乙醇）。在室温下用Ac 2 O / Py对5a和5b进行乙酰化，得到N乙酰基衍生物6a和6b。4-甲基-2-戊酮/环戊酮[4-（4-溴苯基）噻唑-2-基] hydr唑酮（8a）和（8b）相似地由1与硫代半脲酮7a和分别如图7b所示。的环化d半乳糖缩氨基硫脲（9）及其互变异构体10和11与1，得到非环状2- thiazolylhydrazone的平衡混合物12与其各自的环状半乳糖衍生物，一起13和14，其结构通过使用进行了研究1 H和13 1 H NMR谱。使用琼脂扩散技术在体外评估了合成的噻唑衍生物的抗菌活性，其中一些化合物显示出对白色念珠菌的潜在活性。
• 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。
• TIRE RUBBER COMPOSITION AND MANUFACTURING METHOD THEREFOR
  申请人：Bridgestone Corporation

  公开号：EP3006496A1

  公开（公告）日：2016-04-13

  The present invention provides a tire rubber composition prepared by mixing at least one rubber component selected from natural rubbers and synthetic diene rubbers (A), a filler including an inorganic filler (B), a silane coupling agent (C) and a thiosemicarbazone derivative (D), and provides a production method for a tire rubber composition, wherein the tire rubber composition is kneaded in plural stages, and in the first stage of kneading, the rubber component (A), all or part of the inorganic filler (B), all or part of the silane coupling agent (C), and the thiosemicarbazone derivative (D) are kneaded, therefore providing a tire rubber composition having improved reactivity between the coupling agent and the rubber component and excellent in low-heat-generation property and a production method for the composition.

  本发明提供了一种通过混合至少一种选自天然橡胶和合成二烯橡胶的橡胶组分（A）、包括无机填料（B）在内的填料、硅烷偶联剂（C）和硫代氨基脲衍生物（D）制备的轮胎橡胶组合物，并提供了一种轮胎橡胶组合物的生产方法，其中轮胎橡胶组合物经过多个阶段的捏合、在第一阶段捏合过程中，捏合橡胶成分（A）、全部或部分无机填料（B）、全部或部分硅烷偶联剂（C）和硫代氨基脲衍生物（D），从而提供一种轮胎橡胶组合物，该组合物具有更好的偶联剂与橡胶成分之间的反应性和优异的低发热性能，并提供一种该组合物的生产方法。
• Design, synthesis and biological characterization of thiazolidin-4-one derivatives as promising inhibitors of Toxoplasma gondii
  作者：Melissa D'Ascenzio、Bruna Bizzarri、Celeste De Monte、Simone Carradori、Adriana Bolasco、Daniela Secci、Daniela Rivanera、Nathan Faulhaber、Claudia Bordón、Lorraine Jones-Brando

  DOI：10.1016/j.ejmech.2014.08.046

  日期：2014.10

  We designed and synthesized a large number of novel thiazolidin-4-one derivatives for the evaluation of their anti-Toxoplasma gondii activity. This scaffold was functionalized at the N1-hydrazine portion with aliphatic, cycloaliphatic and (hetero)aromatic moieties. Then, a benzyl pendant was introduced at the lactamic NH of the core nucleus to evaluate the influence of this chemical modification on biological activity. The compounds were subjected to several in vitro assays to assess their anti-parasitic efficacy, cytotoxicity on fibroblasts, inhibition of tachyzoite invasion/attachment and replication after treatment. Results showed that fourteen of these thiazole-based compounds compare favorably to control compound trimethoprim in terms of parasite growth inhibition. (c) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma
  作者：Celeste De Monte、Simone Carradori、Daniela Secci、Melissa D'Ascenzio、Paolo Guglielmi、Adriano Mollica、Stefania Morrone、Susanna Scarpa、Anna Maria Aglianò、Sabrina Giantulli、Ida Silvestri

  DOI：10.1016/j.ejmech.2015.10.023

  日期：2015.11

  Antimitotic agents are widely used in cancer chemotherapy but the numerous side effects and the onset of resistance limit their clinical efficacy. Therefore, with the purpose of discovering more selective and efficient anticancer agents to be administered alone or in combination with traditional drugs, we synthesized a large library of 1,3,4-thiadiazoline analogues, maintaining the pharmacophoric structure of an antiproliferative compound known as K858: this is a new inhibitor of kinesin Eg5, able to induce the mitotic arrest in colorectal cancer cells and in xenograft ovarian cancer cells. We screened 103 compounds to assess their antiproliferative activity on PC3 prostate cancer cell line. Two derivatives, compounds 32 (corresponding to K858) and 33, have shown to be the most effective against prostate tumor cells and also towards two melanoma cell lines (SK-MEL-5 and SK-MEL-28) at low micromolar concentrations, confirming the pharmacological activity of this scaffold and revealing the potential role of 1,3,4-thiadiazolines in the management of cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.