5-undecyl-1,3,4-oxadiazole-2-thiol

• 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-undecyl-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-undecyl-3H-1,3,4-oxadiazole-2-thione
• 化学式: C₁₃H₂₄N₂OS
• 分子量: 256.412
• InChiKey: BZCITGIHZAQEMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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-undecyl-1,3,4-oxadiazole-2-thiol 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以62%的产率得到4-amino-5-undecyl-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  具有抗微生物和表面活性的丙氧基化脂肪族噻唑，吡唑，三唑和吡咯衍生物

  摘要：

  月桂酸和环氧丙烷用于修饰四种生物活性杂环（噻唑，吡唑，三唑和吡咯）以合成17种新的表面活性剂。这些表面活性剂的化学结构使用红外光谱，1 H和13 C核磁共振（NMR）光谱进行了确认。这些表面活性剂均显示出良好的表面活性，较低的临界胶束浓度（CMC）值，高浊点和紧密的界面堆积。均对细菌和真菌均显示出抗菌活性。此外，生物降解测试显示在7天内有明显的故障。

  DOI：

  10.1007/s11743-015-1684-8
• 作为产物：
  描述：

  月桂酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5-undecyl-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  具有1,3,4-恶二唑-2-硫酮或1,3-噻唑烷-2-硫酮部分的亲脂金（I）配合物：合成及其细胞毒性和抗菌活性

  摘要：

  合成了含有1,3,4-恶二唑-2-硫酮或1,3-噻唑烷-2-硫酮衍生物的新型亲脂金（I）配合物，并通过IR，高分辨率质谱和1 H，13 C 31 P表征NMR。以顺铂和/或金诺芬为参考在不同肿瘤细胞系中评估了化合物的细胞毒性：结肠癌（CT26WT），转移性皮肤黑素瘤（B16F10），乳腺腺癌（MCF-7），宫颈癌（HeLa），胶质母细胞瘤（ M059 J）。还评估了正常人肺成纤维细胞（GM07492-A）和肾正常细胞（BHK-21）。金（I）配合物比其各自的游离配体和顺铂更具活性。此外，评估了对革兰氏阳性细菌的抗菌活性金黄色葡萄球菌ATCC 25213，表皮葡萄球菌ATCC 12228和革兰氏阴性细菌大肠杆菌ATCC 11229和铜绿假单胞菌ATCC 27853，并以最低抑菌浓度（MIC）表示。与配体和氯霉素抗革兰氏阳性菌和革兰氏阴性菌相比，复合物的MIC值较低。大肠杆菌是一种敏感的金（I）配合物的作用。

  DOI：

  10.1007/s10534-017-0046-6

文献信息

• Crystal structure and spectroscopy properties of new PtII complexes containing 5-alkyl-1,3,4-oxadiazol-2-thione derivatives
  作者：Wesley A. Souza、Angelina M. de Almeida、Marcos Pivatto、Mauro V. de Almeida、Guilherme P. Guedes、Jackson Antônio L.C. Resende、Wendell Guerra

  DOI：10.1016/j.molstruc.2020.129250

  日期：2021.2

  4-oxadiazol-2-thione derivatives and PPh3 = triphenylphosphine). These PtII complexes were characterized by elemental analysis, conductivity measurements, mass spectrometry, FT-IR, multinuclear NMR spectroscopy and X-ray diffraction crystallography. According to X-ray diffraction data, all complexes exhibited distorted square-planar geometry, in which two 5-alkyl-1,3,4-oxadiazol-2-thione derivatives coordinate

  摘要 这项工作描述了五种新型反式-[Pt(L)2(PPh3)2] 型 PtII 配合物的合成和总体表征（L = 5-烷基-1,3,4-恶二唑-2-硫酮衍生物和PPh3 = 三苯基膦）。这些 PtII 配合物的特征在于元素分析、电导率测量、质谱、FT-IR、多核 NMR 光谱和 X 射线衍射晶体学。根据 X 射线衍射数据，所有配合物都表现出扭曲的方形平面几何形状，其中两个 5-烷基-1,3,4-恶二唑-2-硫酮衍生物通过硫原子与两个三苯基膦分子配位铂离子，完成了协调领域。还通过 31 P1H} 和 195Pt1H} NMR 光谱研究了在氘化氯仿溶液中铂配合物的异构化。在所有情况下，
• 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。
• 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.
• Development of 3,5-Dinitrobenzylsulfanyl-1,3,4-oxadiazoles and Thiadiazoles as Selective Antitubercular Agents Active Against Replicating and Nonreplicating <i>Mycobacterium tuberculosis</i>
  作者：Galina Karabanovich、Júlia Zemanová、Tomáš Smutný、Rita Székely、Michal Šarkan、Ivana Centárová、Anthony Vocat、Ivona Pávková、Patrik Čonka、Jan Němeček、Jiřina Stolaříková、Marcela Vejsová、Kateřina Vávrová、Věra Klimešová、Alexandr Hrabálek、Petr Pávek、Stewart T. Cole、Katarína Mikušová、Jaroslav Roh

  DOI：10.1021/acs.jmedchem.5b00608

  日期：2016.3.24

  Herein, we report the discovery and structure activity relationships of 5-substituted-2-[(3,5-dinitrobenzyl)-sulfanyl]-1,3,4-oxadiazoles and 1,3,4-thiadiazoles as a new class of antituberculosis agents. The majority of these compounds exhibited outstanding in vitro activity against Mycobacterium tuberculosis CNCTC My 331/88 and six multidrug-resistant clinically isolated strains of M. tuberculosis, with minimum inhibitory concentration values as low as 0.03 mu M (0.011-0.026 mu g/mL). The investigated compounds had a highly selective antimycobacterial effect because they showed no activity against the other bacteria or fungi tested in this study. Furthermore, the investigated compounds exhibited low in vitro toxicities in four proliferating mammalian cell lines and in isolated primary human hepatocytes. Several in vitro genotoxicity assays indicated that the selected compounds have no mutagenic activity. The oxadiazole and thiadiazole derivatives with the most favorable activity/toxicity profiles also showed potency comparable to that of rifampicin against the nonreplicating streptomycin-starved M. tuberculosis 18b-Lux strain, and therefore, these derivatives, are of particular interest.
• Synthesis and Surface Characterization Studies of Polyether-Linked Symmetric Higher Sulfanyl-1,3,4-Oxadiazoles
  作者：A. Yıldırım、S. Öztürk

  DOI：10.1080/10426507.2014.999067

  日期：2015.9.2

  The synthesis and the characterization of a series of novel symmetric double length alkyl-chained sulfanyl-1,3,4-oxadiazoles functionalized with a polyether head group are reported. In addition, surface characterization studies were conducted on the metal surface of these synthesized compounds. The metal surfaces were characterized by contact angle measurements via the sessile-drop method, and 3D images of the metal surface were obtained using an optical profilometer. The surface studies showed that the inhibitor molecule increases the hydrophobic character and decreases the wettability of the metal surface.