1-(1-adamantylcarbonyl)-4-methylthiosemicarbazide | 139158-41-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(1-adamantylcarbonyl)-4-methylthiosemicarbazide
• 英文别名: adamantanyl-N-{[(methylamino)thioxomethyl]amino}carboxamide；1-(adamantane-1-carbonylamino)-3-methylthiourea
• CAS: 139158-41-1
• 化学式: C₁₃H₂₁N₃OS
• 分子量: 267.395
• InChiKey: AWNHRGHEAZBLCK-UHFFFAOYSA-N

物化性质

• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-adamantylcarbonyl)-4-methylthiosemicarbazide 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.25h， 生成 5-(1-Adamantyl)-2-[(4-ethoxyanilino)methyl]-4-methyl-1,2,4-triazole-3-thione
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel 5-(1-adamantyl)-2-aminomethyl-4-substituted-1,2,4-triazoline-3-thiones

  摘要：

  The reaction of 5-(1-adamantyl)-4-substituted-1,2,4-triazoline-3-thione 5a,b and 10a,b with formaldehyde solution and various primary aromatic amines or 1-substituted piperazines yielded the corresponding N-Mannich bases 6a-o, 7a-g and 11a-i. The newly synthesized N-Mannich bases 6a-o, 7a-o and 11a-i were tested for in vitro inhibitory activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. The compounds 6j, 6l, 6m, 7a, 7b, 7c, 7d, 7f, 11a, 11b, 11c, 11d, lie, 11f, 11h and 11i displayed moderate to good activity against the tested Gram-positive bacteria, while compounds 7c,11c,11d,11f and 11h showed potent broad spectrum antibacterial activity. None of the newly synthesized compounds were proved to possess marked activity against C albicans. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.024
• 作为产物：
  描述：

  1-金刚烷甲酸甲酯 在 肼 作用下， 以 乙醇 为溶剂， 生成 1-(1-adamantylcarbonyl)-4-methylthiosemicarbazide
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel 5-(1-adamantyl)-2-aminomethyl-4-substituted-1,2,4-triazoline-3-thiones

  摘要：

  The reaction of 5-(1-adamantyl)-4-substituted-1,2,4-triazoline-3-thione 5a,b and 10a,b with formaldehyde solution and various primary aromatic amines or 1-substituted piperazines yielded the corresponding N-Mannich bases 6a-o, 7a-g and 11a-i. The newly synthesized N-Mannich bases 6a-o, 7a-o and 11a-i were tested for in vitro inhibitory activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. The compounds 6j, 6l, 6m, 7a, 7b, 7c, 7d, 7f, 11a, 11b, 11c, 11d, lie, 11f, 11h and 11i displayed moderate to good activity against the tested Gram-positive bacteria, while compounds 7c,11c,11d,11f and 11h showed potent broad spectrum antibacterial activity. None of the newly synthesized compounds were proved to possess marked activity against C albicans. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.024

文献信息

• Theoretical and experimental spectroscopic studies, XPS analysis, dimer interaction energies and molecular docking study of 5-(adamantan-1-yl)-N-methyl-1,3,4-thiadiazol-2-amine
  作者：Lamya H. Al-Wahaibi、Yusuf Sert、Fatih Ucun、Nora H. Al-Shaalan、Aisha Alsfouk、Ali A. El-Emam、Mustafa Karakaya

  DOI：10.1016/j.jpcs.2019.109091

  日期：2019.12

  of the dimer structure were more effectively obtained with the M062X functional. This assured us a test of the efficiency of M06-Class functional calculations on intermolecular interactions of strongly bound systems. Additionally, the molecular docking study was done between our molecule (ligand) and the previously studied and known as cortisone reductase 11β-Hydroxysteroid dehydrogenase type 1 (receptor

  摘要 本研究涉及潜在化疗药物 5-(adamantan-1-yl)-N-methyl-1,3,4-thiadiazol-2-amine 的分子结构、电子性质以及红外、拉曼和 XPS 分析。 . 另一个目的是探索结构稳定性和一致性，并评估其二聚体结构的稳定相互作用能和分子间氢键几何形状。分子的单体和二聚体优化已通过 DFT 方法计算，使用各种功能，如 B3LYP、B3PW91、mPW1PW91 和 M06-2X。尽管在 B3LYP 泛函处计算了最小能量优化，但使用 M062X 泛函更有效地获得了二聚体结构的 BSSE 校正和未校正的相互作用能。这使我们能够测试 M06 级函数计算对强束缚系统分子间相互作用的效率。此外，分子对接研究是在我们的分子（配体）和先前研究的可的松还原酶 11β-羟基类固醇脱氢酶 1 型（受体，11-β-HSD1：PDB-2ILT）之间进行的。
• El-Emam; Ibrahim, Arzneimittel-Forschung/Drug Research, 1991, vol. 41, # 12, p. 1260 - 1264
  作者：El-Emam、Ibrahim

  DOI：——

  日期：——
• Adamantan Derivate, 4. Mitt.: Unerwartete Debenzylierung bei der Cyclisierung von 1-(1-Adamantylcarbonyl)-4-benzylthiosemicarbazid mit Schwefels�ure
  作者：A. A. El-Emam、J. Lehmann

  DOI：10.1007/bf00811852

  日期：1994.5

  Cyclization of 1-(1-adamantylcarbonyl)-4-substituted thiosemicarbazides 2a-e with sulphuric acid at ambient temperature or by heating with phosphorus oxychloride yielded the corresponding 2-(1-adamantyl)-5-amino-1,3,4-thiadiazoles 3a-e. Cyclization of 1-(1-adamantylcarbonyl)-4-benzylthiosemicarbazide 2f with sulphuric acid gave the debenzylated product 2-(1-adamantyl)-5-amino-1,3,4-thiadiazole 4. On the other hand, cyclization of 2f using phosphorus oxychloride yielded 2-(1-adamantyl)-5-benzylamino-1,3,4-thiadiazole 3f.