5-heptadecyl-1,3,4-oxadiazole-2(3H)-thione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-heptadecyl-1,3,4-oxadiazole-2(3H)-thione
• 英文别名: 5-heptadecyl-3H-1,3,4-oxadiazole-2-thione
• 化学式: C₁₉H₃₆N₂OS
• 分子量: 340.574
• InChiKey: VYELQOVVWRJRHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  23
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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-heptadecyl-1,3,4-oxadiazole-2(3H)-thione 、 氯乙酸 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以69%的产率得到
  参考文献：
  名称：

  Novel Fatty Acid Analogues as Human Fatty Acid Synthase Thioesterase Domain Inhibitors: Synthesis and their Cytotoxicity Screening

  摘要：

  制备了一类新的1, 3, 4-噁二唑取代的硬脂酸/棕榈酸类似物。对人类脂肪酸合成酶的硫酯酶结构域（2PX6）进行了计算机对接研究，获得了一些关于配体结合相互作用的重要结构信息。残基His 2481、Tyr 2462和Ala 2448与1, 3, 4-噁二唑环形成了氢键。所有目标化合物与活性位点残基表现出良好的结合相互作用。通过SRB法对一些选定化合物在对人类肺癌细胞系（A-549）进行了细胞毒性测试。这些化合物显示出较强的细胞毒性。

  DOI：

  10.2174/1570180812666141216210751
• 作为产物：
  描述：

  油酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 19.0h， 生成 5-heptadecyl-1,3,4-oxadiazole-2(3H)-thione
  参考文献：
  名称：

  Newly Synthesized Oxadiazole Based Mannich Base Derivatives of Fatty Acid: in Silico Study and in Vivo Anti-Hyperglycaemic Estimation

  摘要：

  靶向过氧化物酶体增殖激活受体-γ（PPAR-γ）的一系列新脂肪酸化学实体（M1-M22）被设计、合成并通过光谱分析进行了表征。利用molinspiration在线软件根据利宾斯基五规则计算了代谢物的分子特性。在PPAR γ的共晶蛋白结构PDB-1FM9上进行了分子对接研究，结果显示M15、M17和M8在活性位点定位最佳，得分分别为-10.43、-10.21和-10.00。使用Maestro 9.0（Schrodinger）模型进行了自由结合能估计，其值介于-80.15至-61.26千卡/摩尔之间，与标准值（-48.58千卡/摩尔）相比具有显著性。九个最佳对接衍生物在体内通过链脲佐菌素诱导的糖尿病模型评估了口服葡萄糖耐量及抗高血糖活性，其中M15显示出比标准药物格列本脲更具有前景的抗糖尿病活性。这些有希望的结果鼓励未来对脂肪酸进行深入研究，以开发出活性化合物。

  DOI：

  10.13005/ojc/340505

文献信息

• Synthesis, Evaluation and Molecular Docking Studies of 1,3,4-oxadiazole- 2-thiol Incorporating Fatty Acid Moiety as Antitumor and Antimicrobial Agents
  作者：Fatma Mohamed、Ahmed Hashem、Randa Swellem、Galal Nawwar

  DOI：10.2174/157018081131000072

  日期：2014.2

  A series of 1,3,4-oxadiazole-2-thiol incorporating fatty acid moieties was synthesized. The chemical structure of the synthesized compounds was established by their spectral data, elemental analysis, and their chemical behavior. Their thioglycosides derivatives and the analogous 1,2,4-triazole were also prepared. The in vitro cytotoxicty of the synthesized compounds was screened against two cell lines; breast cell line MCF-7, and liver cell line HepG2. The most potent compound is (E)-5-(heptadec-8-enyl)-1,3,4-oxadiazole-2-thiol 4f with IC50 (2.82 | µg/ml) and (3.87 µg/ml) against breast cell line MCF-7 and liver cell line HepG2 respectively. Molecular Docking study of Bcl-2 was conducted for the most potent compound, its analogues and the lowest cytotoxicty compound. The antimicrobial activity was also screened, compound (E)-5-ethyl-1,3,4-oxadiazole-2-thiol 4a showed a broad spectrum of activity. A relationship between the length of the fatty acid chain and the biological activity was noticed in the tested compounds.

  一系列含有脂肪酸基团的1,3,4-噁二唑-2-硫醇化合物被合成。通过光谱数据、元素分析和化学行为确定了合成分子的化学结构。它们的硫代糖苷衍生物及其类似的1,2,4-三唑化合物也被制备。体外细胞毒性测试对两种细胞系进行了筛选：乳腺癌细胞系MCF-7和肝癌细胞系HepG2。最具活性的化合物是(E)-5-(十七碳-8-烯基)-1,3,4-噁二唑-2-硫醇4f，其对MCF-7细胞系的IC50值为2.82 µg/ml，对HepG2细胞系的IC50值为3.87 µg/ml。对最具活性化合物、其类似物和最低细胞毒性化合物的Bcl-2分子对接研究进行了开展。抗微生物活性也被筛选，化合物(E)-5-乙基-1,3,4-噁二唑-2-硫醇4a显示出广谱活性。在测试的化合物中，注意到脂肪酸链的长度与生物活性之间存在关系。
• Synthesis of 5-heptadecyl- and 5-heptadec-8-enyl substituted 4-amino-1,2,4-triazole-3-thiol and 1,3,4-oxadiazole-2-thione from (Z)-octadec-9-enoic acid: preparation of Palladium(II) complexes and evaluation of their antimicrobial activity
  作者：Manel Chehrouri、Adil A. Othman、Cristina Moreno-Cabrerizo、Mohammad Gholinejad、José M. Sansano

  DOI：10.1007/s00706-019-02540-1

  日期：2020.2

  state), IR, 1H, 13C NMR spectroscopy, XRD, and XPS. These resulting metallic entities are also identified in solution based in mass spectrometry (MS-ESI) experiments. Most compounds and their palladium(II) complexes are tested in vitro against Gram-positive, Gram-negative bacteria, and fungi, some of them showed variable activity. Graphic abstract

  摘要通过常见的合成途径，包括在大气中将（Z）-甲基十八烷基-9-烯酸酯加氢-酰化为十八碳酰肼，可获得两种4-氨基-1,2,4-三唑和两种1,3,4-恶二唑。通过在氩气氛下进行酰化反应来实现七十八碳烯基中烯烃键的保留。烯烃键的消失通过物理数据，IR，1 H和13 C NMR光谱法检测。获得了由4-氨基-5-十七烷基-1,2,4-三唑-3-硫醇和5-十七烷基-1,3,4-恶二唑-2（3 H）-硫酮衍生的新钯配合物，并通过元素鉴定分析（固态），IR，1 H，13C NMR光谱，XRD和XPS。这些生成的金属实体也可以在基于质谱（MS-ESI）实验的溶液中进行鉴定。大多数化合物及其钯（II）配合物均经过体外抗革兰氏阳性，革兰氏阴性细菌和真菌的测试，其中一些具有可变的活性。 图形摘要
• Synthesis and Antimicrobial Studies of 5-N-alkyl-1,3,4-oxadiazole-2-thiol Derivatives from Fatty Acids
  作者：B. Naga Sudha、N. Yella Subbaiah、A.M. Srikanth、C. Venkata Ramana Reddy、M. Sneha Latha、P. Vijaya Lakshmi

  DOI：10.14233/ajchem.2017.20665

  日期：——

  The novel 5-N-alkyl-1,3,4-oxadiazole-2-thiol derivatives have been synthesized by esterification of fatty acid followed by reaction the ester with hydrazine hydrate. The acid hydrazide was converted to 1,3,4-oxadiazole by ring closure mechanism. The synthesized compounds have been characterized by physical (melting point and TLC) and spectral (IR, 1H NMR and mass) data. All the compounds were screened for their antimicrobial activity. The compounds 3F1 & 3F4 showed good inhibition activity against all four types of bacteria; while compound 3F2 & 3F3 shown moderate activity.

  新型5-N-烷基-1,3,4-噁二唑-2-硫醇衍生物通过脂肪酸酯化反应合成，随后将酯与水合肼反应。酸肼通过环闭合机制转化为1,3,4-噁二唑。合成的化合物通过物理（熔点和薄层色谱）和光谱（红外、氢核磁共振和质谱）数据进行表征。所有化合物均进行了抗微生物活性筛选。化合物3F1和3F4对所有四种细菌表现出良好的抑制活性，而化合物3F2和3F3则表现出中等活性。
• Synthesis of Various Nitrogen Heterocycles as Antimicrobial Surface Agents
  作者：Refat El-Sayed、Basim H. Asghar

  DOI：10.1002/jhet.1918

  日期：2014.9

  A number of novel, thiazole 5, oxadiazole 6, thiadiazole 7, triazole 8, 9, and fused triazole derivatives 10, 11, 12 were obtained from a valuable and inexpensive fatty acids (stearic acid). Propoxylation of these compounds using 5 moles of propylene oxide produced nonionic surface active agents (13, 14,15 16, 17,18,19,20). The surface properties and the biodegradability of the latter compounds were

  一些新颖的，噻唑5，恶二唑6，噻二唑7，三唑8，9，和稠合的三唑衍生物10，11，12是从一个有价值的和廉价的脂肪酸得到的（硬脂酸）。用5摩尔环氧丙烷的这些化合物的丙氧基化产生的非离子表面活性剂（13，14,15 16，17,18,19,20）。评价了后一种化合物的表面性质和生物降解性。研究了一些合成的化合物的抗菌活性。
• Improved Protocol Toward 1,3,4-Oxadiazole-2(3H)-thiones and Scale-up Synthesis in the Presence of SDS as a Micelle Promoted Catalyst
  作者：Ayhan YILDIRIM

  DOI：10.17344/acsi.2014.1100

  日期：2015.6.15

  Convenient procedure for in situ cyclization of hydrazinecarbodithioate potassium salts to 1,3,4-oxadiazole-2(3H)-thiones under normal phase micellar media catalysis promoted by sodium dodecyl sulfate (SDS) as an anionic surfactant is reported. The main advantage of this procedure is to provide shorter reaction time for the completion of cyclization; scale-up synthesis is possible and the oxadiazoles were obtained in high to excellent yields (87-100%), making the protocol an attractive alternative to the available methods.