5-nonyl-3H-1,3,4-oxadiazole-2-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-nonyl-3H-1,3,4-oxadiazole-2-thione
• 化学式: C₁₁H₂₀N₂OS
• 分子量: 228.359
• InChiKey: SIOPKKJUJKKXPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  2-氨基-5-甲基-1,3,4-噻二唑 、 5-nonyl-3H-1,3,4-oxadiazole-2-thione 在 aluminum oxide 作用下， 反应 0.02h， 以93%的产率得到4-(5-methyl-1,3,4-thiadiazol-2-yl)-3-nonyl-1H-1,2,4-triazole-5-thione
  参考文献：
  名称：

  A Novel Route to 1,2,4-Triazoles

  摘要：

  A novel synthetic method for the synthesis of 1,2,4-triazoles have been described starting from 1,3,4-thiadiazoles by adsorbing on acidic alumina under microwave irradiations (MWI).

  DOI：

  10.1080/00397910008087451
• 作为产物：
  描述：

  癸酸甲酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5-nonyl-3H-1,3,4-oxadiazole-2-thione
  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，
• Preparation, cytotoxic activity and DNA interaction studies of new platinum(II) complexes with 1,10-phenanthroline and 5-alkyl-1,3,4-oxadiazol-2(3H)-thione derivatives
  作者：Wesley A. Souza、Luana M.S. Ramos、Angelina M. de Almeida、Daiane Y. Tezuka、Carla D. Lopes、Mariete B. Moreira、Renan D. Zanetti、Adelino V.G. Netto、Francis B. Ferreira、Ronaldo Junio de Oliveira、Guilherme P. Guedes、Sérgio de Albuquerque、Júlia R.L. Silva、Elene C. Pereira-Maia、Jackson A.L.C. Resende、Mauro V. de Almeida、Wendell Guerra

  DOI：10.1016/j.jinorgbio.2022.111993

  日期：2022.12

  nowadays. DNA binding studies indicated that such complexes are able to bind to ct-DNA with Kb values of 104 M−1. According to data from dichroism circular and fluorescence spectroscopy, these complexes appear to bind to the DNA in a non-intercalative, probably via minor groove. Molecular docking followed by semiempirical simulations indicated that these complexes showed favorable interactions with the

  这项工作描述了 [Pt(L1) 2 (1,10-phen)] 1和 [Pt(L2) 2 (1,10-phen )类型的两种铂 (II) 配合物的合成、表征和体外抗癌活性)] 2，其中 L1 = 5-heptyl-1,3,4-oxadiazole-2-(3H)-thione，L2 = 5-nonyl-1,3,4-oxadiazole-2-(3H)-thione 和 1 ,10-phen = 1,10-菲咯啉。关于这些配合物的结构， 1的X射线结构分析表明铂 (II) 离子周围的几何形状是扭曲的方形平面，其中两个 5-alkyl-1,3,4-oxadiazol-2-thione 衍生物通过硫原子配位铂 (II) 离子。螯合双齿菲咯啉分子完成配位球。我们在两种乳腺癌细胞系中测试了这些复合物，即 MCF-7（一种激素反应性癌细胞）和 MDA-MB-231（三阴性乳腺癌细胞）。在这两种细胞中，亲脂性
• Synthesis and in vitro evaluation of antimycobacterial activity of two palladium(II) complexes based on 5-alkyl-1,3,4-oxadiazol-2(3H)-thione derivatives
  作者：Wesley Almeida Souza、Fernanda Manaia Demarqui、Angelina Maria de Almeida、Raphael Tristão Cruvinel Silva、Douglas Alexsander Alves、Thaise Gonçalves Araújo、Jackson Antonio Lamounier Camargos Resende、Fernando Rogério Pavan、Hélio Ferreira Dos Santos、Mauro Vieira de Almeida、Wendell Guerra

  DOI：10.1016/j.molstruc.2022.133888

  日期：2022.12

  In this work, two palladium(II) complexes, namely, [Pd(L1)2(phen)] 1 and [Pd(L2)2(phen)] 2 (L1 = 5-heptyl-1,3,4-oxadiazole-2-(3H)-thione, L2 = 5-nonyl-1,3,4-oxadiazole-2-(3H)-thione and phen = 1,10-phenanthroline), were prepared and charactherized by conventional techniques. In both complexes, the spectral data indicated that L1 and L2 are coordinated to the metal in a monodentate manner through the

  在这项工作中，两种钯(II)配合物，即[Pd(L 1 ) 2 (phen)] 1和[Pd(L 2 ) 2 (phen)] 2 (L 1  = 5-heptyl-1,3, 4-恶二唑-2-(3H)-硫酮、L 2  = 5-壬基-1,3,4-恶二唑-2-(3H)-硫酮和phen = 1,10-菲咯啉)，采用常规方法制备和表征技巧。在这两种配合物中，光谱数据表明 L 1和 L 2通过硫原子（S -)，而作为双齿配体的菲咯啉分子完成了配位领域。该提议得到了结构和核磁共振谱的 DFT 计算的支持。随后，游离配体及其金属配合物在体外针对人前列腺细胞系 PNT-2（非致瘤性）、LNCaP（雄激素敏感性前列腺癌）和 PC-3（去势抵抗性前列腺癌）进行了测试。如在两种人类乳腺癌细胞系中，MCF7（管腔）和 MDA-MB231（三阴性）。关于细胞毒性，所有化合物都被认为是无活性的，因为发现的 IC 50值高于
• Alumina-supported synthesis of antibacterial quinolines using microwaves
  作者：M. Kidwai、K.R. Bhushan、P. Sapra、R.K. Saxena、R. Gupta

  DOI：10.1016/s0968-0896(99)00256-4

  日期：2000.1

  7-(5'-Alkyl-1',3',4'-thiadiazol/oxadiazol-2'-ylthio)-6-fluoro-2,4-dimethylquinolines and 3-formyl-2-(2'-hydroxy-1',4'-naphthoquinon-3'-yl)-4-melhyl/6-methyl/7 have been synthesised by the reaction of 5-alkyl-1,3,3-thiadiazol/oxadiazol-2-thiols with 7-chloro-6-fluoro-2,4-dimethylquinoline and by the reaction of 2-hydroxy-1,4-naphthoquinone with 2-chloro-3-formyl-4-methyl/6-methyl/7-methyl/8-methylquinoline respectively on basic alumina using microwaves, the reaction time has been brought down from hours to seconds with improved yield as compared to conventional heating. The compounds were tested for their in vitro antibacterial activity. All compounds showed promising antibacterial activity. The best activity was observed by compounds 3a and 3f. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Microwave Assisted Synthesis and Antibacterial Activity of New Quinolone Derivatives
  作者：Mazaahir Kidwai、Preeti Misra、Rajesh Kumar、Rajendra K. Saxena、Rani Gupta、Sapna Bradoo

  DOI：10.1007/pl00013504

  日期：1998.9

  A series of novel 6-fluoro-7-(5-alkyl-1,3,4-thiadiazol/oxadiazol-2-ylsulfanyl)-4-quinolone-3-carboxylic acids were synthesized using microwave irradiation. The compounds were tested for their in vitro antibacterial activity. All compounds containing the 1,3,4-thiadiazole/oxadiazole moiety at position 7 showed promising antibacterial activity.