3-(5-Mercapto-1,3,4-oxadiazol-2-yl)benzonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(5-Mercapto-1,3,4-oxadiazol-2-yl)benzonitrile
• 英文别名: 3-(2-sulfanylidene-3H-1,3,4-oxadiazol-5-yl)benzonitrile
• 化学式: C₉H₅N₃OS
• 分子量: 203.224
• InChiKey: WGDXWQZBXRKGBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(5-Mercapto-1,3,4-oxadiazol-2-yl)benzonitrile 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 2-(2,4-difluorophenyl)-1-(4-(3-((5-(3-cyanophenyl)-1,3,4-oxadiazol-2-yl)thio)propyl)piperazin-1-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol
  参考文献：
  名称：

  Synthesis and evaluation of novel azoles as potent antifungal agents

  摘要：

  Using a rational approach to the design of antifungal agents, a series of azole agents with 1,3,4-oxadiazole side chains were designed and synthesized. The results of preliminary in vitro antifungal tests with eight human pathogenic compounds showed that all of the title compounds exhibited excellent activities against all of the tested fungi except Aspergillus fumigatus. Compounds 11e and 11f were found to be the most effective, with a minimum inhibitory concentration of 0.0039 mu g/mL, followed by voriconazole, which has a MIC of 0.0625 mu g/mL. The 1,3,4-oxadiazole side chain is not the major contributor but plays a role in eliciting the observed antifungal activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.037
• 作为产物：
  描述：

  3-氰基苯甲酸甲酯 在 盐酸 、 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 3-(5-Mercapto-1,3,4-oxadiazol-2-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and evaluation of novel azoles as potent antifungal agents

  摘要：

  Using a rational approach to the design of antifungal agents, a series of azole agents with 1,3,4-oxadiazole side chains were designed and synthesized. The results of preliminary in vitro antifungal tests with eight human pathogenic compounds showed that all of the title compounds exhibited excellent activities against all of the tested fungi except Aspergillus fumigatus. Compounds 11e and 11f were found to be the most effective, with a minimum inhibitory concentration of 0.0039 mu g/mL, followed by voriconazole, which has a MIC of 0.0625 mu g/mL. The 1,3,4-oxadiazole side chain is not the major contributor but plays a role in eliciting the observed antifungal activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.11.037

文献信息

• Synthesis and a UV and IR spectral study of some 2-aryl-Δ-²-1,3,4-oxadiazoline-5-thiones
  作者：D. A. Charistos、G. V. Vagenas、L. C. Tzavellas、C. A. Tsoleridis、N. A. Rodios

  DOI：10.1002/jhet.5570310653

  日期：1994.11

  2-Aryl-Δ-2-1,3,4-oxadiazoline-5-thione derivatives 2 were synthesized and their uv and ir spectra were studied. Correlation between σ-Hammett constants of aryl substituents and the differences in absorption maxima (Δv = v1-v2 in kK) of the electronic spectra of the deprotonated species were also evaluated. A new method for the synthesis of the 2-(amino)aryl derivatives 2v,w,x is also reported.

  二十四2-芳基Δ- 2 -1,3,4-恶二唑啉-5-硫酮衍生物2的合成和它们的UV和IR光谱进行了研究。还评估了芳基取代基的σ-Hammett常数与去质子化物种的电子光谱的吸收最大值差异（Δv= v 1 -v 2以kK为单位）之间的相关性。还报道了合成2-（氨基）芳基衍生物2v，w，x的新方法。
• 一类含腈基苯的噁二唑亚砜化合物、其制备方 法和用途
  申请人：佛山市赛维斯医药科技有限公司

  公开号：CN104529930B

  公开（公告）日：2016-03-09

  本发明涉及与血栓性疾病相关的药物领域。具体而言，本发明涉及一类含腈基取代苯的恶二唑亚砜结构的PAR-1拮抗剂、其制备方法、及含有它们的药物组合物以及它们在制备治疗血栓性疾病药物中的应用。其中，R选自-CN。
• Design, Synthesis, and Biological Evaluation of Piperazine and <i>N</i>-Benzylpiperidine Hybrids of 5-Phenyl-1,3,4-oxadiazol-2-thiol as Potential Multitargeted Ligands for Alzheimer’s Disease Therapy
  作者：Digambar Kumar Waiker、Akash Verma、Akhilesh、Gajendra T. A、Namrata Singh、Anima Roy、Hagera Dilnashin、Vinod Tiwari、Surendra Kumar Trigun、Surya P. Singh、Sairam Krishnamurthy、Prem Lama、Vincent Jo Davisson、Sushant Kumar Shrivastava

  DOI：10.1021/acschemneuro.3c00245

  日期：2023.6.7

  Our present work demonstrates the successful design and synthesis of a new class of compounds based upon a multitargeted directed ligand design approach to discover new agents for use in Alzheimer’s disease (AD). All the compounds were tested for their in vitro inhibitory potential against human acetylcholinesterase (hAChE), human butylcholinesterase (hBChE), β-secretase-1 (hBACE-1), and amyloid β

  我们目前的工作展示了基于多目标定向配体设计方法成功设计和合成一类新化合物，以发现用于阿尔茨海默氏病 (AD) 的新药物。测试了所有化合物对人乙酰胆碱酯酶 (hAChE)、人丁基胆碱酯酶 (hBChE)、β-分泌酶-1 (hBACE-1) 和淀粉样蛋白 β (Aβ) 聚集的体外抑制潜力。化合物5d和5f显示出与多奈哌齐相当的 hAChE 和 hBACE-1 抑制作用，而 hBChE 抑制作用与卡巴拉汀相当。化合物5d和5f还证明通过硫黄素 T 测定和共聚焦、原子力和扫描电子显微镜研究显着减少了 Aβ 聚集体的形成，并显着取代了总碘化丙啶，即在 50 μM 浓度下分别为 54% 和 51%。化合物5d和5f在 10–80 μM 浓度下对 RA/BDNF（RA = 视黄酸；BDNF = 脑源性神经营养因子）分化的 SH-SY5Y 神经母细胞瘤细胞系没有神经毒性。在东莨菪碱和 Aβ 诱导的 AD