5-(naphthalen-2-yloxymethyl)-3H-[1,3,4]oxadiazole-2-thione | 136414-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(naphthalen-2-yloxymethyl)-3H-[1,3,4]oxadiazole-2-thione
• 英文别名: 5-(naphthalen-2-yloxymethyl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 136414-04-5
• 化学式: C₁₃H₁₀N₂O₂S
• 分子量: 258.301
• InChiKey: UVLSZYZSGRAHRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(naphthalen-2-yloxymethyl)-3H-[1,3,4]oxadiazole-2-thione 、 3-溴丙炔 在 碳酸氢钠 作用下， 以 水 、 甲苯 为溶剂， 反应 10.5h， 以55%的产率得到5-(2-naphthyloxymethyl)-2-prop-2-ynylsulfanyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and in-vitro antioxidant activities of some coumarin derivatives containing 1,2,3-triazole ring

  摘要：

  A new green protocol was developed for the S-alkylation of 2-mercapto-1,3,4-oxadiazole by the reaction of 5-substituted-2-mercapto-1,3,4-oxadiazole with propargyl bromide in sodium bicarbonate in water. The newly synthesized 5-[(substitutedphenoxy)methyl]-2-[(prop-2-yn-1-yl)sulfanyl]-1,3,4-oxadiazole when reacted with azidomethyl coumarins underwent regioselective reaction yielding 4-(((4-((5-((substitutedphenoxy)methyl)-1,3,4-oxadiazol-2-yl)sulfanylmethyl)-1H-1,2,3-triazol-1-yl)methyl)-6-methyl)-2H-chromene-2-one or 1-((4-((5-((substitutedphenoxy)methyl)-1,3,4-oxadiazol-2-yl)sulfanylmethy)-1H-1,2,3-triazol-1-yl-)methyl)-3H-benzo[f]chromene-3-one. Structures of the newly synthesized compounds were confirmed by spectral and analytical data. The compounds were screened for their in-vitro antioxidant property.[GRAPHICS]

  DOI：

  10.1080/10426507.2017.1417293
• 作为产物：
  描述：

  2-萘氧乙酸 在 硫酸 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-(naphthalen-2-yloxymethyl)-3H-[1,3,4]oxadiazole-2-thione
  参考文献：
  名称：

  Design, Synthesis and in vitro Antibacterial Evaluation of Naphthalen-2-yloxy based Oxadiazole-2-thione Derivatives

  摘要：

  一系列新颖的Mannich碱5-(萘-2-氧甲基)-3-(取代)氨甲基-3H-[1,3,4]噁二唑-2-硫酮 (5a-h) 通过将取代-1,3,4-噁二唑-2(3H)-硫酮与等摩尔浓度的一级或二级胺进行氨甲基化合成。合成的化合物通过光谱技术（红外线、1H和13C核磁共振）进行表征，并利用环丙沙星作为标准药物，采用杯-板法评估其对各种革兰氏阳性和革兰氏阴性细菌菌株的抗菌潜力。化合物5a-c和5g表现出对测试细菌菌株的强抗菌活性。化合物5a对枯草芽孢杆菌、痢疾杆菌和霍乱弧菌具有活性；化合物5b对枯草芽孢杆菌和痢疾杆菌具有显著活性；化合物5c对枯草芽孢杆菌和霍乱弧菌具有活性；化合物5g对痢疾波氏杆菌和乙醋杆菌菌株具有活性。结构活性关系研究表明，合成的化合物（5a-h）中具有较小体积基团的化合物表现出良好的抗菌活性。

  DOI：

  10.14233/ajchem.2021.22912

文献信息

• 一种含芳香稠环的噁二唑乙酰胺类神经氨酸酶抑制剂及其制备方法与应用
  申请人：上海应用技术大学

  公开号：CN116120255A

  公开（公告）日：2023-05-16

  本发明涉及一种含芳香稠环的噁二唑乙酰胺类神经氨酸酶抑制剂及其制备方法与应用。抑制剂具有式Ⅴ或式Ⅵ所示的结构： 制备方法具体为：(1)将取代苯胺，氯乙酰氯，在三乙胺催化下经亲核取代反应得到式Ⅱ中间体；(2)取乙酯取代化合物与水合肼在乙醇中经亲核取代得到式Ⅲ(1)或式Ⅲ(2)中间体。(3)取式Ⅲ(1)或式Ⅲ(2)中间体与二硫化碳，在氢氧化钾碱性环境下在乙醇中通过环加成反应得到式Ⅳ(1)或式Ⅳ(2)中间体。(4)取式Ⅱ中间体和式Ⅳ(1)或式Ⅳ(2)中间体溶于有机溶剂中，在碘化钾催化作用下，反应后经取代反应得到。与现有技术相比，本发明的化合物结构新颖，具有良好的神经氨酸酶抑制活性，可用于制备抑制神经氨酸酶活性的药物。
• Synthesis and antimicrobial activity of some 1,3,4-oxadiazole derivatives
  作者：Gülay Şahin、Erhan Palaska、Melike Ekizoğlu、Meral Özalp

  DOI：10.1016/s0014-827x(02)01245-4

  日期：2002.7

  Six new 5-(1-/2-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-thione, 2-amino-5-(1-/2-naphthyloxymethyl)-1,3,4-oxadiazole, 5-(1-/ 2-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-one derivatives have been synthesized from 1-and/or 2-naphthol. The structures,of the compounds were confirmed by IR and H-1 NMR spectral data and microanalysis. The antimicrobial properties of the compounds were investigated against Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, Candida albicans, C. krusei and C. parapsilosis using microbroth dilution method. 2-Amino-5-(2-naphthytoxymethyl)-1,3,4-oxadiazole and 5-(2-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-one show significantly (32 mug/ml), compounds 5-(1-/2-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-thione, 2-amino-5-(1-naphthyloxymethyl)-1,3,4-oxadiazole and 5-(1-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-one moderately (64 mug/ml) active against C. krusei. All the compounds were active against S. a ureus,. coli, P. aeruginosa, C. albicans, and C. parapsilosis at 64-256 mug/ml concentration. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Shahar Yar; Ahmad Siddiqui; Ashraf Ali, Journal of the Chinese Chemical Society, 2007, vol. 54, # 1, p. 5 - 8
  作者：Shahar Yar、Ahmad Siddiqui、Ashraf Ali

  DOI：——

  日期：——
• Kalluraya; Shetty, Journal of the Indian Chemical Society, 1991, vol. 68, # 7, p. 424 - 425
  作者：Kalluraya、Shetty

  DOI：——

  日期：——
• Oxadiazole mannich bases: Synthesis and antimycobacterial activity
  作者：Mohamed Ashraf Ali、Mohammad Shaharyar

  DOI：10.1016/j.bmcl.2007.04.004

  日期：2007.6

  A series of oxadiazole mannich bases were synthesized by reacting oxadiazole derivatives, dapsone and appropriate aldehyde in the presence of methanol. The synthesized compounds were evaluated for antimycobacterial activity against M. tuberculosis H(37)Rv and INH resistant M. tuberculosis. Among the synthesized compounds, compound (4) 3-2-furyl[4-(4-2-furyl [5-(2-naphthyloxymethyl)-2-thioxo-2,3-dihydro-1,3,4-oxadiazol-3-yl]methylamino}phenylsulfonyl)anilino]methyl}-5-(2-naphthyloxymethyl)-2,3 -dihydro-1, 3, 4-oxadiazole-2-thione was found to be the most promising compound active against M. tuberculosis H(37)Rv and isoniazid (INH) resistant M. tuberculosis with Minimum inhibitory concentration (MIC) 0.1 mu M & 1.10 mu M respectively. (c) 2007 Elsevier Ltd. All rights reserved.