5-(adamantine-1-yl)-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-(adamantine-1-yl)-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-(adamantane-1-yl)-1,3,4-oxadiazole-2-thiol；5-(1-adamantyl)-3H-1,3,4-oxadiazole-2-thione
• 化学式: C₁₂H₁₆N₂OS
• mdl: MFCD03819470
• 分子量: 236.338
• InChiKey: QLRSPGHQEPSBOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.833
• 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-(adamantine-1-yl)-1,3,4-oxadiazole-2-thiol 在 copper(l) iodide 、 sodium carbonate 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 15.33h， 生成 2-((3r,5r,7r)-adamantan-1-yl)-5-((4-(4-(3-methoxyphenyl)-2-methylpiperazin-1-yl)but-2-yn-1-yl)thio)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis, anticancer evaluation and docking studies of novel adamantanyl-1,3,4-oxadiazol hybrid compounds as Aurora-A kinase inhibitors

  摘要：

  DOI：

  10.1007/s00044-023-03145-4
• 作为产物：
  描述：

  1-金刚烷甲酸 在 肼 作用下， 以 乙醇 为溶剂， 反应 264.0h， 生成 5-(adamantine-1-yl)-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  新型抗肿瘤金刚烷-吡咯金（I）配合物可能是硫氧还蛋白还原酶的抑制剂

  摘要：

  摘要可以作为抗肿瘤药的金络合物引起了极大的关注。杂环化合物及其金属络合物具有广泛的药理特性。本研究报告了四种含有叔膦和新配体5-金刚烷基-1,3-噻唑烷-2-硫酮，3-甲基金刚烷-1,3,4-恶二唑-2-的新型金（I）配合物的制备和表征。硫酮。光谱数据表明，在所有情况下，金都与环外硫原子配位，这一点已通过对络合物（1），并得到量子力学计算的支持。与顺铂和金诺芬相比，该化合物在三种不同的肿瘤细胞系，结肠癌（CT26WT），转移性皮肤黑素瘤（B16F10），乳腺腺癌（4T1）和肾正常细胞（BHK-21）中的细胞毒性得到了评估。金络合物比它们各自的游离配体更具活性，甚至在白蛋白存在下也能够抑制硫氧还蛋白还原酶（TrxR）酶。进行了分子建模研究，以了解化合物与TrxR酶之间的相互作用，而TrxR酶被认为是治疗癌症中新化合物的潜在靶标。对接结果表明，在与金中心形成共价键之前，金刚烷环对于稳定配体-酶复合物至关重要。

  DOI：

  10.1007/s00775-016-1338-y

文献信息

• Novel antitumor adamantane–azole gold(I) complexes as potential inhibitors of thioredoxin reductase
  作者：Adriana Garcia、Rafael Carvalhaes Machado、Richard Michael Grazul、Miriam Teresa Paz Lopes、Charlane Cimini Corrêa、Hélio F. Dos Santos、Mauro Vieira de Almeida、Heveline Silva

  DOI：10.1007/s00775-016-1338-y

  日期：2016.4

  AbstractGold complexes that could act as antitumor agents have attracted great attention. Heterocyclic compounds and their metal complexes display a broad spectrum of pharmacological properties. The present study reports the preparation and characterization of four novel gold(I) complexes containing tertiary phosphine and new ligands 5-adamantyl-1,3-thiazolidine-2-thione, 3-methyladamantane–1,3,4-oxadiazole-2-thione

  摘要可以作为抗肿瘤药的金络合物引起了极大的关注。杂环化合物及其金属络合物具有广泛的药理特性。本研究报告了四种含有叔膦和新配体5-金刚烷基-1,3-噻唑烷-2-硫酮，3-甲基金刚烷-1,3,4-恶二唑-2-的新型金（I）配合物的制备和表征。硫酮。光谱数据表明，在所有情况下，金都与环外硫原子配位，这一点已通过对络合物（1），并得到量子力学计算的支持。与顺铂和金诺芬相比，该化合物在三种不同的肿瘤细胞系，结肠癌（CT26WT），转移性皮肤黑素瘤（B16F10），乳腺腺癌（4T1）和肾正常细胞（BHK-21）中的细胞毒性得到了评估。金络合物比它们各自的游离配体更具活性，甚至在白蛋白存在下也能够抑制硫氧还蛋白还原酶（TrxR）酶。进行了分子建模研究，以了解化合物与TrxR酶之间的相互作用，而TrxR酶被认为是治疗癌症中新化合物的潜在靶标。对接结果表明，在与金中心形成共价键之前，金刚烷环对于稳定配体-酶复合物至关重要。
• Mono and dinuclear platinum and palladium complexes containing adamantane–azole ligands: DNA and BSA interaction and cytotoxicity
  作者：Ana Luiza de Andrade Querino、Jessika Thayanne da Silva、Josiane Teixeira Silva、Gustavo Miguel Alvarenga、Carolina Hahn da Silveira、Mariana Torquato Quezado de Magalhães、Otávio Augusto Chaves、Bernardo Almeida Iglesias、Renata Diniz、Heveline Silva

  DOI：10.1007/s00775-019-01719-5

  日期：2019.10

  extracellular GSH was also investigated. In general, mononuclear complexes containing thiazolidine–adamantane ligands were more cytotoxic than oxadiazole–adamantane derivatives. PtT complex proved to be as active as cisplatin. Dinuclear compounds were considered inactive to cells in evaluated conditions, due to their high stability with ligands in a chelated and bridged way. Results suggest that GSH cannot

  摘要描述了双核恶二唑-金刚烷铂（II）和钯（II）配合物（PtO，PdO）和单核噻唑烷衍生物配合物（PtT，PdT）的合成。通过元素分析，红外，紫外可见，1 H，13 C，195 Pt NMR光谱，MS光谱和单晶X射线衍射进行表征。还研究了MTT法对有或没有细胞外GSH的肿瘤和正常细胞系的细胞毒性。通常，包含噻唑烷-金刚烷配体的单核复合物比恶二唑-金刚烷衍生物更具细胞毒性。点对点事实证明该复合物与顺铂一样有效。在评估的条件下，双核化合物被认为对细胞无活性，因为它们以螯合和桥接的方式对配体具有很高的稳定性。结果表明，谷胱甘肽不能被视为目标。DNA和BSA的结合相互作用使用紫外可见光谱和荧光光谱，嵌入染料和分子对接进行了评估。与游离的噻唑烷配体相比，与铂（II）配位后，对受试细胞系的细胞毒性作用明显改善。比较噻唑烷衍生物，值得注意的是，活性较低的化合物（PdT）与BSA的相互作用更强，而PtT
• Al-Deeb, Omar A.; Al-Omar, Mohamed A.; El-Brollosy, Nasser R., Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 1, p. 40 - 47
  作者：Al-Deeb, Omar A.、Al-Omar, Mohamed A.、El-Brollosy, Nasser R.、Habib, Elsayed E.、Ibrahim, Tarek M.、El-Emam, Ali A.

  DOI：——

  日期：——
• Vibrational spectroscopic studies (FT-IR, FT-Raman) and quantum chemical calculations on 5-(Adamantan-1-yl)-3-[(4-fluoroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione, a potential chemotherapeutic agent
  作者：Ebtehal S. Al-Abdullah、Sr.S.H.Roseline Sebastian、Reem I. Al-Wabli、Ali A. El-Emam、C.Yohannan Panicker、Christian Van Alsenoy

  DOI：10.1016/j.saa.2014.06.035

  日期：2014.12

  The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 5-(Adamantan-1-yl)-3-[(4-fluoroanilino)methyl]-2,3-dihydro-1,3,4-oxadiazole-2-thione are investigated experimentally and theoretically using Gaussian09 software package. Potential energy distribution of normal modes vibrations was done using GAR2PED program. The HOMO and LUMO analysis are used to determine the charge transfer within the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. The calculated geometrical parameters are in agreement with the XRD data. The calculated first hyperpolarizability is high and the title compound is an attractive candidate for further studies in non-linear optical applications. To estimate the chemical reactivity of the molecule, the molecular electrostatic potential is calculated for the optimized geometry of the molecule. (C) 2014 Elsevier B.V. All rights reserved.
• Spectroscopic investigations, NBO, HOMO–LUMO, NLO analysis and molecular docking of 5-(adamantan-1-yl)-3-anilinomethyl-2,3-dihydro-1,3,4-oxadiazole-2-thione, a potential bioactive agent
  作者：Fatmah A.M. Al-Omary、Y. Sheena Mary、C. Yohannan Panicker、Ali A. El-Emam、Ibrahim A. Al-Swaidan、Abdulaziz A. Al-Saadi、C. Van Alsenoy

  DOI：10.1016/j.molstruc.2015.03.049

  日期：2015.9

  The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 5-(adamantan-1-yl)-3-anilinomethy1-2,3-dihydro-1,3,4-oxadiazole-2-thione have been investigated experimentally and theoretically. The geometrical parameters are in agreement with XRD data. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBC analysis. The frontier molecular orbital analysis is used to determine the charge transfer within the molecule. As can be seen from the MEP map of the title molecule, the negative region are mainly localized over the C=S and the CH2 group attached to the oxadiazole ring and the maximum positive region is localized near the NH group. The first and second order hyperpolarizability values are also calculated theoretically. The title compound forms a stable complex with PPAR alpha as is evident from the binding affinity values and the results suggest that the compound might exhibit inhibitory activity against PPARc( and this may result in development of new anti-diabetic (Type 2) agents. (C) 2015 Published by Elsevier B.V.