naphthalene-1-carbaldehyde (4-oxo-thiazolidin-2-ylidene)-hydrazone | 96954-52-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphthalene-1-carbaldehyde (4-oxo-thiazolidin-2-ylidene)-hydrazone
• 英文别名: 4-Oxo-2--thiazolidin；(2E)-2-(naphthalen-1-ylmethylidenehydrazinylidene)-1,3-thiazolidin-4-one
• CAS: 96954-52-8
• 化学式: C₁₄H₁₁N₃OS
• 分子量: 269.327
• InChiKey: BSMOMGJTALEJMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  79.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (氯甲基)萘 、 naphthalene-1-carbaldehyde (4-oxo-thiazolidin-2-ylidene)-hydrazone 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 3-(naphthalen-1-ylmethyl)-2-(2-(naphthalen-1-ylmethylene)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：

  1-萘甲醛 在 sodium acetate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 naphthalene-1-carbaldehyde (4-oxo-thiazolidin-2-ylidene)-hydrazone
  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

• 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.
• Thiazolylhydrazone dervatives as inhibitors for insect N-acetyl-β-d-hexosaminidase and chitinase
  作者：Huibin Yang、Huitang Qi、Zesheng Hao、Xusheng Shao、Tian Liu、Qing Yang、Xuhong Qian

  DOI：10.1016/j.cclet.2019.11.035

  日期：2020.5

  Insect chitinase and N-acetyl-beta-D-hexosaminidases (Hex) are potential targets for developing new pesticides. Here, a series of thiazolylhydrazones I (with substituted group R(1 )at N3) and II (with substituted group R-1 at N2) were designed, synthesised and evaluated as competitive inhibitors of OfHex1 and OfChi-h, from the agricultural pest Ostrinia furnacalis. Derivatives I-3d and II-3d, with phenoxyethyl group at R-1, demonstrated the best inhibitory activities against OfHex1 and Of Chi-h. Molecular docking analysis indicated that the branched conformation compound II-3d (K-i = 1.5 mu mol/L) formed more hydrogen bonds with OfHex1 than the stretched conformation compound I-3d (K-i = 5.9 mu mol/L). The differences in compounds' binding conformations with OfChi-h explained differences in inhibitory activity of compounds I-3d (K-i =1.9 mu mol/L) and II-3d (K-i = 4.1 mu mol/L). This work suggests a novel scaffold for developing specific Hex and Chi-h inhibitors. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.