3-(furan-2-yl)-4,5,6,7-tetrahydro-1H-indazole-2(3-H)-carbothioamide | 1192372-58-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 3-(furan-2-yl)-4,5,6,7-tetrahydro-1H-indazole-2(3-H)-carbothioamide
• 英文别名: 3-(2-furyl)-2-thiocarbamoyl-2,3,4,5,6,7-hexahydro-1H-indazole；3-(Furan-2-yl)-1,3,4,5,6,7-hexahydroindazole-2-carbothioamide
• CAS: 1192372-58-9
• 化学式: C₁₂H₁₅N₃OS
• 分子量: 249.337
• InChiKey: GXJVURRBUPFKPX-UHFFFAOYSA-N

物化性质

• 熔点：
  184-185 °C(Solvent: Methanol)
• 沸点：
  405.9±55.0 °C(predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  86.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(furan-2-yl)-4,5,6,7-tetrahydro-1H-indazole-2(3-H)-carbothioamide 、 2-溴-4'-氰基苯乙酮 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到4-(2-(3-(furan-2-yl)-4,5,6,7-tetrahydro-1H-indazol-2(3H)-yl)thiazol-4-yl)benzonitrile
  参考文献：
  名称：

  Synthesis and Antimicrobial Activities of (4,5,6,7-Tetrahydro-1H-indazol- 2(3H)-yl)thiazole Derivatives

  摘要：

  本文介绍了十种新型四氢吲达佐里噻唑的合成、表征及其抗菌活性研究。通过1H和13C NMR、FAB(+)-MS和HRMS分析确定了它们的结构。在衍生物中，化合物3f对S. aureus ATCC 43300、S. aureus ATCC 25923和S. epidermidis ATCC 12228表现出强烈的抗菌活性，MIC值为7.81 µg/ml，对S. aureus ATCC 6538也显示出良好的活性，MIC值为31.25 µg/ml。化合物3a-e和3j表现出良好的抗真菌活性，MIC值范围从31.25 µg/ml到250 µg/ml。

  DOI：

  10.2174/1570180811666140516233913
• 作为产物：
  描述：

  环己酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 42.0h， 生成 3-(furan-2-yl)-4,5,6,7-tetrahydro-1H-indazole-2(3-H)-carbothioamide
  参考文献：
  名称：

  Synthesis and Antimicrobial Activities of (4,5,6,7-Tetrahydro-1H-indazol- 2(3H)-yl)thiazole Derivatives

  摘要：

  本文介绍了十种新型四氢吲达佐里噻唑的合成、表征及其抗菌活性研究。通过1H和13C NMR、FAB(+)-MS和HRMS分析确定了它们的结构。在衍生物中，化合物3f对S. aureus ATCC 43300、S. aureus ATCC 25923和S. epidermidis ATCC 12228表现出强烈的抗菌活性，MIC值为7.81 µg/ml，对S. aureus ATCC 6538也显示出良好的活性，MIC值为31.25 µg/ml。化合物3a-e和3j表现出良好的抗真菌活性，MIC值范围从31.25 µg/ml到250 µg/ml。

  DOI：

  10.2174/1570180811666140516233913

文献信息

• Synthesis and molecular modeling of some novel hexahydroindazole derivatives as potent monoamine oxidase inhibitors
  作者：Nesrin Gökhan-Kelekçi、Ö. Özgün Şimşek、Ayşe Ercan、Kemal Yelekçi、Z. Sibel Şahin、Şamil Işık、Gülberk Uçar、A. Altan Bilgin

  DOI：10.1016/j.bmc.2009.07.033

  日期：2009.9

  A novel series of 2-thiocarbamoyl-2,3,4,5,6,7-hexahydro-1H-indazole and 2-substituted thiocarbamoyl-3,3a, 4,5,6,7-hexahydro-2H-indazoles derivatives were synthesized and investigated for the ability to inhibit the activity of the A and B isoforms of monoamine oxidase (MAO). The target molecules were identified on the basis of satisfactory analytical and spectra data (IR, H-1 NMR, C-13 NMR, D-2 NMR, DEPT, EI-MASS techniques and elemental analysis). Synthesized compounds showed high activity against both the MAO-A (compounds 1d, 1e, 2c, 2d, 2e) and the MAO-B (compounds 1a, 1b, 1c, 2a, 2b) isoforms. In the discussion of the results, the influence of the structure on the biological activity of the prepared compounds was delineated. It was suggested that non-substituted and N-methyl/ethyl bearing compounds (except 2c) increased the inhibitory effect and selectivity toward MAO-B. The rest of the compounds, carrying N-allyl and N-phenyl, appeared to select the MAO-A isoform. The inhibition pro. le was found to be competitive and reversible for all compounds. A series of experimentally tested (1a-2e) compounds was docked computationally to the active site of the MAO-A and MAO-B isoenzyme. The AUTODOCK 4.01 program was employed to perform automated molecular docking. In order to see the detailed interactions of the docked poses of the model inhibitors compounds 1a, 1d, 1e and 2e were chosen because of their ability to reversibly inhibit the MAO-B and MAO-A and the availability of experimental inhibition data. The differences in the intermolecular hydrophobic and H-bonding of ligands to the active site of each MAO isoform were correlated to their biological data. Observation of the docked positions of these ligands revealed interactions with many residues previously reported to have an effect on the inhibition of the enzyme. Excellent to good correlations between the calculated and experimental K-i values were obtained. In the docking of the MAO-A complex, the trans configuration of compound 1e made various very close interactions with the residues lining the active site cavity these interactions were much better than those of the other compounds tested in this study. This tight binding observation may be responsible for the nanomolar inhibition of form of MAOA. However, it binds slightly weaker (experimental K-i = 1.23 mu M) to MAO-B than to MAO-A (experimental K-i = 4.22 nM). (C) 2009 Elsevier Ltd. All rights reserved.