1-[[1-adamantyl(pyridin-2-yl)methylidene]amino]-3-aminothiourea | 442157-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-[[1-adamantyl(pyridin-2-yl)methylidene]amino]-3-aminothiourea
• CAS: 442157-61-1
• 化学式: C₁₇H₂₃N₅S
• 分子量: 329.469
• InChiKey: HSXLNDYJUCQYJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  75.33
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,4-二氯苯基异硫氰酸酯 、 1-[[1-adamantyl(pyridin-2-yl)methylidene]amino]-3-aminothiourea 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-[[1-adamantyl(pyridin-2-yl)methylidene]amino]-3-[(2,4-dichlorobenzenecarbothioyl)amino]thiourea
  参考文献：
  名称：

  New 2-(1-adamantylcarbonyl)pyridine and 1-acetyladamantane thiosemicarbazones–thiocarbonohydrazones: cell growth inhibitory, antiviral and antimicrobial activity evaluation

  摘要：

  The new thiosemicarbazones and thiocarbonohydrazones 4a-d, 5a-d derived from 2-(1-adamantylcarbonyl)pyridine and 1-acetyladamantane were synthesized and evaluated for their inhibitory effect on tumor cell proliferation and their antiviral and antimicrobial activity. Thiosemicarbazone 4a inhibited tumor cell proliferation (GI50's range: 2.4-100 muM and mean GI50 43.9 muM against various human leukemic cell lines) while thiosemicarbazone 5a and thiocarbonohydrazone 5d exhibited significant inhibition of tumor cell proliferation (GI50's range 2.3-23.6 muM and mean GI50 7.2 muM for 5a and GI50's range 2.4-32.4 muM and mean GI50 12.8 muM for 5d). These GI50 values are comparable to that of 2-acetylpyridine thiosemicarbazone an important lead in TSCS family. The compounds did not afford specific activity against any of the viruses tested when examined at non-toxic concentrations. A weak activity was found for thiocarbonohydrazones 4d, 5d against Gram-(+) bacteria (MIC50 117.3 and 133 muM, respectively). Using a combination of molecular mechanics calculations and NOE spectroscopy it was shown that the parent compounds 4a and 5a have opposite configuration around C=N bond. Whether this difference in structure can be correlated with the biological activity will be investigated in future studies. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00838-1
• 作为产物：
  描述：

  2-吡啶基锂 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 生成 1-[[1-adamantyl(pyridin-2-yl)methylidene]amino]-3-aminothiourea
  参考文献：
  名称：

  New 2-(1-adamantylcarbonyl)pyridine and 1-acetyladamantane thiosemicarbazones–thiocarbonohydrazones: cell growth inhibitory, antiviral and antimicrobial activity evaluation

  摘要：

  The new thiosemicarbazones and thiocarbonohydrazones 4a-d, 5a-d derived from 2-(1-adamantylcarbonyl)pyridine and 1-acetyladamantane were synthesized and evaluated for their inhibitory effect on tumor cell proliferation and their antiviral and antimicrobial activity. Thiosemicarbazone 4a inhibited tumor cell proliferation (GI50's range: 2.4-100 muM and mean GI50 43.9 muM against various human leukemic cell lines) while thiosemicarbazone 5a and thiocarbonohydrazone 5d exhibited significant inhibition of tumor cell proliferation (GI50's range 2.3-23.6 muM and mean GI50 7.2 muM for 5a and GI50's range 2.4-32.4 muM and mean GI50 12.8 muM for 5d). These GI50 values are comparable to that of 2-acetylpyridine thiosemicarbazone an important lead in TSCS family. The compounds did not afford specific activity against any of the viruses tested when examined at non-toxic concentrations. A weak activity was found for thiocarbonohydrazones 4d, 5d against Gram-(+) bacteria (MIC50 117.3 and 133 muM, respectively). Using a combination of molecular mechanics calculations and NOE spectroscopy it was shown that the parent compounds 4a and 5a have opposite configuration around C=N bond. Whether this difference in structure can be correlated with the biological activity will be investigated in future studies. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00838-1

文献信息

• New 2-(1-adamantylcarbonyl)pyridine and 1-acetyladamantane thiosemicarbazones–thiocarbonohydrazones: cell growth inhibitory, antiviral and antimicrobial activity evaluation
  作者：Antonios Kolocouris、Kostas Dimas、Christophe Pannecouque、Myriam Witvrouw、George B. Foscolos、George Stamatiou、George Fytas、Grigoris Zoidis、Nicolas Kolocouris、Graciela Andrei、Robert Snoeck、Erik De Clercq

  DOI：10.1016/s0960-894x(01)00838-1

  日期：2002.3

  The new thiosemicarbazones and thiocarbonohydrazones 4a-d, 5a-d derived from 2-(1-adamantylcarbonyl)pyridine and 1-acetyladamantane were synthesized and evaluated for their inhibitory effect on tumor cell proliferation and their antiviral and antimicrobial activity. Thiosemicarbazone 4a inhibited tumor cell proliferation (GI50's range: 2.4-100 muM and mean GI50 43.9 muM against various human leukemic cell lines) while thiosemicarbazone 5a and thiocarbonohydrazone 5d exhibited significant inhibition of tumor cell proliferation (GI50's range 2.3-23.6 muM and mean GI50 7.2 muM for 5a and GI50's range 2.4-32.4 muM and mean GI50 12.8 muM for 5d). These GI50 values are comparable to that of 2-acetylpyridine thiosemicarbazone an important lead in TSCS family. The compounds did not afford specific activity against any of the viruses tested when examined at non-toxic concentrations. A weak activity was found for thiocarbonohydrazones 4d, 5d against Gram-(+) bacteria (MIC50 117.3 and 133 muM, respectively). Using a combination of molecular mechanics calculations and NOE spectroscopy it was shown that the parent compounds 4a and 5a have opposite configuration around C=N bond. Whether this difference in structure can be correlated with the biological activity will be investigated in future studies. (C) 2002 Elsevier Science Ltd. All rights reserved.