1,3,4-噁二唑-2(3H)-硫酮,5-[(1-萘氧基)甲基]- | 139764-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1,3,4-噁二唑-2(3H)-硫酮,5-[(1-萘氧基)甲基]-
• 英文名称: 5-[(naphthalen-1-yloxy)methyl]-1,3,4-oxadiazole-2-thiol
• 英文别名: 5-(naphthalen-1-yloxymethyl)-3H-1,3,4-oxadiazole-2-thione
• CAS: 139764-54-8
• 化学式: C₁₃H₁₀N₂O₂S
• 分子量: 258.301
• InChiKey: WCPWXKGQTRLLRU-UHFFFAOYSA-N

物化性质

• 熔点：
  203 °C(Solv: ethanol (64-17-5))
• 沸点：
  405.5±47.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

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：

  1,3,4-噁二唑-2(3H)-硫酮,5-[(1-萘氧基)甲基]- 在 potassium carbonate 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 5-[[5-[(naphthalen-1-yloxy)methyl]-1,3,4-oxadiazol-2-ylthio]methyl]-1,3,4-oxadiazole-2-thiol
  参考文献：
  名称：

  Synthesis and antiviral evaluation of new 2,5-disubstituted 1,3,4-oxadiazole derivatives and their acyclic nucleoside analogues

  摘要：

  A number of new 5-[(naphthalen-1-yloxy)-methyl]-1,3,4-oxadiazole derivatives were synthesized. Sugar 2-[5-[(naphthalen-1-yloxy)methyl]-1,3,4-oxadiazol-2-ylthio]acetohydrazones were prepared by condensation of the hydrazide with the corresponding monosaccharides. Cyclization of the sugar hydrazones with acetic anhydride afforded the substituted oxadiazoline derivatives. The synthesized compounds displayed different degrees of antiviral activities or inhibitory actions against HCV and HIV viruses.

  DOI：

  10.1007/s00706-010-0360-y
• 作为产物：
  描述：

  2-(萘-1-基氧基)乙酸乙酯 在 氢氧化钾 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 1,3,4-噁二唑-2(3H)-硫酮,5-[(1-萘氧基)甲基]-
  参考文献：
  名称：

  Oxadiazole mannich bases: Synthesis and antimycobacterial activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2007.04.004

文献信息

• 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.
• Synthesis and antiviral evaluation of new 2,5-disubstituted 1,3,4-oxadiazole derivatives and their acyclic nucleoside analogues
  作者：Wael A. El-Sayed、Farag A. El-Essawy、Omar M. Ali、Barsis S. Nasr、Mohamed M. Abdalla、Adel A.-H. Abdel-Rahman

  DOI：10.1007/s00706-010-0360-y

  日期：2010.9

  A number of new 5-[(naphthalen-1-yloxy)-methyl]-1,3,4-oxadiazole derivatives were synthesized. Sugar 2-[5-[(naphthalen-1-yloxy)methyl]-1,3,4-oxadiazol-2-ylthio]acetohydrazones were prepared by condensation of the hydrazide with the corresponding monosaccharides. Cyclization of the sugar hydrazones with acetic anhydride afforded the substituted oxadiazoline derivatives. The synthesized compounds displayed different degrees of antiviral activities or inhibitory actions against HCV and HIV viruses.