5-(naphthalen-1-ylmethyl)-3H-1,3,4-oxadiazole-2-thione | 80549-59-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(naphthalen-1-ylmethyl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 80549-59-3
• 化学式: C₁₃H₁₀N₂OS
• mdl: MFCD02029663
• 分子量: 242.301
• InChiKey: YLRFXLNGPBLJIH-UHFFFAOYSA-N

物化性质

• 沸点：
  384.2±35.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  65.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(naphthalen-1-ylmethyl)-3H-1,3,4-oxadiazole-2-thione 在 四丁基溴化铵 、 sodium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 (±) 8-cyclopropyl-7-(((5-(naphthalen-1-ylmethyl)-1,3,4-oxadiazol-2-yl)thio)methyl)-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]-pyridine-3-carboxylic acid
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Novel Δ²-Thiazolino 2-Pyridone Derivatives That Potentiate Isoniazid Activity in an Isoniazid-Resistant Mycobacterium tuberculosis Mutant

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c00358
• 作为产物：
  描述：

  1-萘乙酸 在 盐酸 、 硫酸 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 14.0h， 生成 5-(naphthalen-1-ylmethyl)-3H-1,3,4-oxadiazole-2-thione
  参考文献：
  名称：

  Synthesis and effects of oxadiazole derivatives on tyrosinase activity and human SK-MEL-28 malignant melanoma cells

  摘要：

  黑色素是一种给人类皮肤、头发和眼睛着色的色素。

  DOI：

  10.1039/c6ra12754a

文献信息

• Synthesis and pharmacological screening: Sulfa derivatives of 2-pipecoline-bearing 1,3,4-oxadiazole core
  作者：Aziz-ur-Rehman、A. Arif、M. A. Abbasi、S. Z. Siddiqui、S. Rasool、S. A. A. Shah

  DOI：10.1134/s1068162017030025

  日期：2017.5

  in an aprotic medium using LiH as an activator. The structures of all synthesized compounds were corroborated through IR, 1H NMR, and EI-MS techniques. All the compounds were screened for their pharmacological behavior, particularly, antibacterial and enzyme inhibitory activities. Notably efficient results were obtained against both gram-positive and gram-negative bacterial strains. Regarding enzyme

  亲电子试剂，1-（4-（溴甲基苯磺酰基）-2-甲基哌啶，由 2-甲基哌啶（2-哌啶）和 4-溴甲基苯磺酰氯在弱碱性介质中在 pH 控制下反应合成。一系列亲核试剂，5 -芳基/芳烷基-1,3,4-恶二唑-2-硫醇，由相应的羧酸分三步合成。标题分子是通过在非质子介质中使用LiH作为活化剂将亲电试剂与亲核试剂偶联来合成的。结构通过 IR、1H NMR 和 EI-MS 技术证实了所有合成的化合物。筛选了所有化合物的药理行为，特别是抗菌和酶抑制活性。对革兰氏阳性和革兰氏阴性都获得了显着的有效结果细菌菌株。关于酶抑制，化合物对乙酰胆碱酯酶和丁酰胆碱酯酶有效。
• Synthesis & Characterization of 2-(substituted-phenyl)acetohydrazide Analogs, 1,3,4-oxadiazoles, and 1,2,4-triazine Ring Systems: A Novel Class of Potential Analgesic and Anti-Inflammatory Agents
  作者：Prakash S. Nayak、Badiadka Narayana、Jennifer Fernandes、Balladka K. Sarojini、Sana Sheik、Kenkere S. Shashidhara、Konambi R. Chandrashekhar、Kullaiah Byrappa

  DOI：10.2174/1570180812666151003001957

  日期：2016.6.18

  by IR, NMR, mass spectral and elemental analyses. All the synthesized compounds 4(a-d), 5(a-d), 7(a-b), and 8(a-f) are evaluated for their in vitro DPPH scavenging, antimicrobial activity, in vivo analgesic, anti-inflammatory activities. The results of the anti-inflammatory activity are supported by molecular docking study with mouse COX-1 (PDB ID: 2CZT) and COX-2 (PDB ID: 3LN1) enzymes to predict their

  新的2-（取代-苯基）乙酰肼类似物系列，S-烷基化的5-取代的1,3,4-恶二唑-2-硫酮衍生物和5-亚芳基-3-取代的1,2,4-三嗪合成得率很高，并通过IR，NMR，质谱和元素分析进行​​了表征。评价所有合成的化合物4（ad），5（ad），7（ab）和8（af）的体外DPPH清除，抗微生物活性，体内止痛，抗炎活性。抗炎活性的结果得到了与小鼠COX-1（PDB ID：2CZT）和COX-2（PDB ID：3LN1）酶的分子对接研究的支持，以预测其假定的相互作用。在进行的所有测定中，化合物5-（4-溴苯基）-3-（萘-2-基甲基）-1,2,4-三嗪（4d）和2-[5-（二苯甲基）-1,3，
• Synthesis and Characterization of New Schiff Base Containing 1,2,4-Triazole-3-thione Moiety and Its Complexes with Some Transition Metal Ions: Spectroscopic and Computational Studies
  作者：A. A. Ali、K. R. Al-Jorani、M. M. Merza

  DOI：10.1134/s1070363224020221

  日期：2024.2

  and elemental analysis (CHNS) techniques were used to characterize the synthesized complexes. Three complexes of Ni(II), Co(II), and Cu(II), in addition to the ligand LH, were the subject of computational investigations. Benchmark analyses were carried out to determine the best degree of calculation for the complexes under the study. The B3LYP approach was chosen as the computation method. The B3LYP/6-31G

  摘要 合成了具有质子化特定配位化学计量和结构形式的不寻常双齿混合希夫碱基1,2,4-三唑-3-硫酮配体的二价过渡金属离子Co、Ni和Cu配位化合物。配体的结构组成 5-(1-萘甲基)-4-( Z )-[(2E ) -3-苯基-2-丙烯-1-亚基]氨基}-2,4-二氢-3H -1,2,4-三唑-3-硫酮 (LH) 通过1 H 和13 C NMR、FTIR、UV-Vis、质谱以及元素分析得到完全鉴定。使用紫外-可见光、傅立叶变换红外光谱、磁化率测量、摩尔电导、火焰原子吸收和元素分析（CHNS）技术来表征合成的配合物。除了配体 LH 之外，Ni(II)、Co(II) 和 Cu(II) 的三种配合物也是计算研究的主题。进行基准分析以确定研究中复合物的最佳计算程度。选择 B3LYP 方法作为计算方法。 B3LYP/6-31G (d,p) (LANL2DZ) 是最佳计算等级。进行了红外光谱和结构研究
• Nayak, Prakash S.; Narayana, Badiadka; Fernandes, Jennifer, Letters in drug design and discovery, 2016, vol. 13, # 6, p. 547 - 562
  作者：Nayak, Prakash S.、Narayana, Badiadka、Fernandes, Jennifer、Sarojini, Balladka K.、Sheik, Sana、Shashidhara, Kenkere S.、Chandrashekhar, Konambi R.、Byrappa, Kullaiah

  DOI：——

  日期：——
• Synthesis and biological activity of oxadiazole and triazolothiadiazole derivatives as tyrosinase inhibitors
  作者：Kok Wai Lam、Ahmad Syahida、Zaheer Ul-Haq、Mohd. Basyaruddin Abdul Rahman、Nordin H. Lajis

  DOI：10.1016/j.bmcl.2010.04.067

  日期：2010.6

  A series of 16 oxadiazole and triazolothiadiazole derivatives were designed, synthesized and evaluated as mushroom tyrosinase inhibitors. Five derivatives were found to display high inhibition on the tyrosinase activity ranging from 0.87 to 1.49 mu M. Compound 5 exhibited highest tyrosinase inhibitory activity with an IC50 value of 0.87 +/- 0.16 mu M. The in silico protein-ligand docking using AUTODOCK 4.1 was successfully performed on compound 5 with significant binding energy value of -5.58 kcal/mol. The docking results also showed that the tyrosinase inhibition might be due to the metal chelating effect by the presence of thione functionality in compounds 1-5. Further studies revealed that the presence of hydrophobic group such as cycloamine derivatives played a major role in the inhibition. Piperazine moiety in compound 5 appeared to be involved in an extensive hydrophobic contact and a 2.9 angstrom hydrogen bonding with residue Glu 182 in the active site. (C) 2010 Elsevier Ltd. All rights reserved.