3-methyl-2-furoyl isothiocyanate | 856906-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 3-methyl-2-furoyl isothiocyanate
• 英文别名: 3-Methylfuran-2-carbonyl isothiocyanate
• CAS: 856906-98-4
• 化学式: C₇H₅NO₂S
• 分子量: 167.188
• InChiKey: DCVIIOUHSPEJFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methyl-2-furoyl isothiocyanate 、 对三氟甲氧基苯胺 以 乙醚 、 环己烷 为溶剂， 反应 5.0h， 以73%的产率得到1-(3-methylfuran-2-carbonyl)-3-[4-(trifluoromethoxy)phenyl]-thiourea
  参考文献：
  名称：

  Furan derivatives of substituted phenylthiourea: spectral studies, semi-empirical quantum-chemical calculations and X-ray structure analyses

  摘要：

  Fifty new derivatives of 1-(furan-2-carbonyl)- and 1-(furan-3-carbonyl)-3-phenyl substituted thiourea have been synthesised and identified. Intramolecular hydrogen bonds were investigated in detail, using IR spectroscopy. The three-level Fermi resonance effect in the IR spectra was analysed after deconvolution and band separation. Semi-empirical quantum-chemical calculations (AMI and PM3) support the results of the IR spectroscopic studies. X-ray single crystal diffraction analyses of four selected compounds, namely 1-(furan-3-carbonyl)-3(2-trifluoromethyl-phenyl)-thiourea (le), 1-(2-methyl-furan-3-carbonyl)-3-(2-trifluoromethyl-phenyl)-thiourea (2e), 1-(2,6-dichlorophenyl)-3-(2-methyl-furan-3-carbonyl)-thiourea (2n) and 1-(4-methoxyphenyl)-3-(3-methyl-2-furan-carbonyl)-thiourea (3e), corroborated the molecular and crystal structure of these compounds. Relatively strong intramolecular hydrogen bonds of the N-H...O=C type as well as intermolecular two-centred and bifurcated three-centred hydrogen bonds were observed, confirming the results of the IR spectral study and the semi-empirical quantum-chemical calculations. A variety of intermolecular interactions, yielding the supramolecular architectures in the four crystalline compounds, are discussed in detail. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2005.02.014
• 作为产物：
  描述：

  3-甲基呋喃-2-羰酰氯 、 potassium thioacyanate 以 乙腈 为溶剂， 反应 1.0h， 生成 3-methyl-2-furoyl isothiocyanate
  参考文献：
  名称：

  与莫匹罗星协同作用的新型金黄色葡萄球菌RnpA抑制剂

  摘要：

  我们最近发现RnpA是耐甲氧西林金黄色葡萄球菌（MRSA）的有希望的新药物发现靶标。RnpA是一种必需蛋白，被认为可以执行两个必需的细胞过程。作为RNA的一部分，Rnpa介导RNA降解。与rnpB结合可形成tRNA成熟所需的RNase P卤酶。高通量筛选确定RNPA2000是RnpA相关活性的抑制剂，对临床相关金黄色葡萄球菌具有抗菌活性。，包括MRSA。旨在提高效力并取代潜在的代谢毒性呋喃部分的结构活性研究导致鉴定出许多更有效的类似物。许多新的类似物具有明显的细胞毒性，因此不能用作抗生素，但包括衍生物5o在内的两种衍生物与莫匹罗星具有令人印象深刻的协同作用，后者是一种用于MSRA非定殖的抗生素，其有效性最近因细菌耐药性而受到损害。根据我们的研究结果，像5o这样的化合物可能最终可用于使对莫匹罗星耐药的细菌对莫匹罗星重新敏感。

  DOI：

  10.1016/j.bmcl.2018.01.022

文献信息

• Furan derivatives of substituted phenylthiourea: spectral studies, semi-empirical quantum-chemical calculations and X-ray structure analyses
  作者：Ol'ga Hritzová、Juraj Černák、Peter Šafař、Zdenka Frőhlichová、Ingeborg Csőregh

  DOI：10.1016/j.molstruc.2005.02.014

  日期：2005.5

  Fifty new derivatives of 1-(furan-2-carbonyl)- and 1-(furan-3-carbonyl)-3-phenyl substituted thiourea have been synthesised and identified. Intramolecular hydrogen bonds were investigated in detail, using IR spectroscopy. The three-level Fermi resonance effect in the IR spectra was analysed after deconvolution and band separation. Semi-empirical quantum-chemical calculations (AMI and PM3) support the results of the IR spectroscopic studies. X-ray single crystal diffraction analyses of four selected compounds, namely 1-(furan-3-carbonyl)-3(2-trifluoromethyl-phenyl)-thiourea (le), 1-(2-methyl-furan-3-carbonyl)-3-(2-trifluoromethyl-phenyl)-thiourea (2e), 1-(2,6-dichlorophenyl)-3-(2-methyl-furan-3-carbonyl)-thiourea (2n) and 1-(4-methoxyphenyl)-3-(3-methyl-2-furan-carbonyl)-thiourea (3e), corroborated the molecular and crystal structure of these compounds. Relatively strong intramolecular hydrogen bonds of the N-H...O=C type as well as intermolecular two-centred and bifurcated three-centred hydrogen bonds were observed, confirming the results of the IR spectral study and the semi-empirical quantum-chemical calculations. A variety of intermolecular interactions, yielding the supramolecular architectures in the four crystalline compounds, are discussed in detail. (c) 2005 Elsevier B.V. All rights reserved.
• Novel inhibitors of Staphylococcus aureus RnpA that synergize with mupirocin
  作者：Nicole Lounsbury、Tess Eidem、Jennifer Colquhoun、George Mateo、Magid Abou-Gharbia、Paul M. Dunman、Wayne E. Childers

  DOI：10.1016/j.bmcl.2018.01.022

  日期：2018.4

  relevant strains of S. aureus, including MRSA. Structure-activity studies aimed at improving potency and replacing the potentially metabotoxic furan moiety led to the identification of a number of more potent analogs. Many of these new analogs possessed overt cellular toxicity that precluded their use as antibiotics but two derivatives, including compound 5o, displayed an impressive synergy with mupirocin

  我们最近发现RnpA是耐甲氧西林金黄色葡萄球菌（MRSA）的有希望的新药物发现靶标。RnpA是一种必需蛋白，被认为可以执行两个必需的细胞过程。作为RNA的一部分，Rnpa介导RNA降解。与rnpB结合可形成tRNA成熟所需的RNase P卤酶。高通量筛选确定RNPA2000是RnpA相关活性的抑制剂，对临床相关金黄色葡萄球菌具有抗菌活性。，包括MRSA。旨在提高效力并取代潜在的代谢毒性呋喃部分的结构活性研究导致鉴定出许多更有效的类似物。许多新的类似物具有明显的细胞毒性，因此不能用作抗生素，但包括衍生物5o在内的两种衍生物与莫匹罗星具有令人印象深刻的协同作用，后者是一种用于MSRA非定殖的抗生素，其有效性最近因细菌耐药性而受到损害。根据我们的研究结果，像5o这样的化合物可能最终可用于使对莫匹罗星耐药的细菌对莫匹罗星重新敏感。