1-(1-(naphthalen-8-yl)ethylidene)thiosemicarbazide | 64119-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-(naphthalen-8-yl)ethylidene)thiosemicarbazide
• 英文别名: 1-[1]naphthyl-ethanone thiosemicarbazone；1-[1]Naphthyl-aethanon-thiosemicarbazon；(1-Naphthalen-1-ylethylideneamino)thiourea
• CAS: 64119-03-5
• 化学式: C₁₃H₁₃N₃S
• mdl: MFCD02169135
• 分子量: 243.332
• InChiKey: BIKCNDWSGCWWET-UHFFFAOYSA-N

物化性质

• 沸点：
  422.3±28.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 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-(1-(naphthalen-8-yl)ethylidene)thiosemicarbazide 在 sodium acetate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 2-(2-(1-(naphthalen-1-yl)ethylidene)hydrazono)-3-benzylthiazolidin-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：

  1-萘乙酮 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 1-(1-(naphthalen-8-yl)ethylidene)thiosemicarbazide
  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

• New Compounds: Potential Antituberculous Agents I: Alkylaryl 4-Arylformamidinothiosemicarbazones
  作者：P.K. Srivastava、J.S. Upadhyaya

  DOI：10.1002/jps.2600660653

  日期：1977.6

  A series of alkylaryl 4-arylformamidinothiosemicarbazones was synthesized for evaluation as antituberculous agents. The synthesis was effected by the condensation of different arylcyanamides with various thiosemicarbazones. The required intermediates also are described.

  合成了一系列的烷基芳基4-芳基甲酰胺基硫代半碳唑酮作为抗结核剂进行评估。合成是通过将不同的芳基氰酰胺与各种硫代半氨基甲酮缩合来进行的。还描述了所需的中间体。
• 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.
• Investigations on the 2-thiazolylhydrazyne scaffold: Synthesis and molecular modeling of selective human monoamine oxidase inhibitors
  作者：Franco Chimenti、Adriana Bolasco、Daniela Secci、Paola Chimenti、Arianna Granese、Simone Carradori、Matilde Yáñez、Francisco Orallo、Francesco Ortuso、Stefano Alcaro

  DOI：10.1016/j.bmc.2010.06.007

  日期：2010.8

  A new series of [4-(3-methoxyphenyl)-thiazol-2-yl]hydrazyne derivatives were synthesized in good yield (71-99%) and characterized by elemental analysis and H-1 NMR studies. The compounds were assayed for their in vitro human monoamine oxidase (hMAO) inhibitory activity and selectivity and most of them showed IC50 values in the nanomolar range, thus demonstrating our interest in this privileged scaffold. The most active and selective derivative (20), bearing a pyridine moiety on the C=N, displayed IC50 = 3.81 +/- 0.12 nM and selectivity ratio = 119 toward hMAO-B. Molecular modeling studies were carried out on recent and high resolution hMAO-A and hMAO-B crystallographic structures to better justify the enzyme-inhibitor interaction toward hMAO isoforms and to explain the structure-activity relationship of this kind of inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.
• El-Metwally, Amira M., Egyptian Journal of Chemistry, 2011, vol. 54, # 1, p. 129 - 139
  作者：El-Metwally, Amira M.

  DOI：——

  日期：——
• 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。