4-(2-Adamantyl)thiosemicarbazide | 92882-06-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(2-Adamantyl)thiosemicarbazide
• 英文别名: 1-(2-Adamantyl)-3-aminothiourea
• CAS: 92882-06-9
• 化学式: C₁₁H₁₉N₃S
• 分子量: 225.358
• InChiKey: LHRCPALSVQKJEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-chlorobenzoyl)-N,N-dimethylethylamine hydrochloride 、 4-(2-Adamantyl)thiosemicarbazide 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以9%的产率得到N-(2-adamantyl)-3-(3-chlorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide
  参考文献：
  名称：

  Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines

  摘要：

  Thirty new pyrazoline derivatives were synthesized by cyclization of Mannich bases with thiosemicarbazides being substituted by different cyclic and aromatic amines. The structures of the compounds were elucidated by elemental analyses, UV, IR, H-1 and C-13 NMR and ESI-MS spectral data. The in vitro antiamoebic activity was evaluated against Entamoeba histolytica in comparison with metronidazole used as reference substance. Out of the 30 compounds screened for antiamoebic activity, 10 (5, 6, 15, 18, 25-30) were found to be better inhibitors of E. histolytica since they showed lesser IC50 values than metronidazole. The preliminary results indicated that the presence of 3-chloro or 3-bromo substituent on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity as compared to unsubstituted phenyl ring. The study suggests that the preliminary activity of these compounds may further be explored for the development of new targets for amoebiasis. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.032
• 作为产物：
  描述：

  2-氨基金刚烷 以 乙醇 为溶剂， 反应 17.5h， 生成 4-(2-Adamantyl)thiosemicarbazide
  参考文献：
  名称：

  4-（2-金刚烷基）缩氨基硫脲

  摘要：

  4-(2-金刚烷基)缩氨基硫脲(1)与羰基化合物2a-d反应生成4-(2-金刚烷基)缩氨基硫脲3a-d。起始组分 1 可从 2-氨基金刚烷 (4) 经由 (2- 金刚烷基) 异硫氰酸酯 (5) 获得。化合物 5 和结构类型 3 的代表能够发挥抗病毒、抗真菌和解热作用。

  DOI：

  10.1002/ardp.19843170907

文献信息

• 4-(2-Adamantyl)thiosemicarbazone
  作者：Alfred Kreutzberger、Hans-Helmut Schröders、Jörg Stratmann

  DOI：10.1002/ardp.19843170907

  日期：——

  Aus der Umsetzung von 4‐(2‐Adamantyl)thiosemicarbazid (1) mit den Carbonylverbindungen 2a‐d gehen die 4‐(2‐Adamantyl)thiosemicarbazone 3a‐d hervor. Die Startkomponente 1 ist aus 2‐Aminoadamantan (4) über das (2‐Adamantyl)‐isothiocyanat (5) zugänglich. Verbindung 5 und Vertreter des Strukturtyps 3 vermögen antivirale, antimykotische und antipyretische Wirkung auszuüben.

  4-(2-金刚烷基)缩氨基硫脲(1)与羰基化合物2a-d反应生成4-(2-金刚烷基)缩氨基硫脲3a-d。起始组分 1 可从 2-氨基金刚烷 (4) 经由 (2- 金刚烷基) 异硫氰酸酯 (5) 获得。化合物 5 和结构类型 3 的代表能够发挥抗病毒、抗真菌和解热作用。
• Synthesis and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3,5-diphenyl-2-pyrazoline derivatives and their Pd(II) complexes
  作者：A BUDAKOTI、M ABID、A AZAM

  DOI：10.1016/j.ejmech.2005.06.013

  日期：2006.1

  Some 1-N-substituted thiocarbamoyl-3,5-diphenyl-2-pyrazoline derivatives (L), 1-8 were synthesized by a base-catalyzed Claisen-Schrnidt condensation of benzaldehyde with acetophenone followed by cyclization with various N-4 substituted thiosemicarbazides. The palladium(II) complexes [PdLCl2], 1a-8a of these ligands were obtained by reacting them with [Pd(DMSO)2Cl2]. All compounds have been characterized by means of elemental analyses, electronic, IR, 1H NMR and mass spectroscopic data, while the complexes have additionally been characterized by thermogravimetric patterns. The in vitro antiamoebic activity was evaluated against the HM1:1MSS strain of Entamoeba histolytica and the results were compared with the standard drug, metronidazole. The preliminary test results showed that the complexes had better antiamoebic activity than their respective ligands. Moreover, the complexes showed better inhibition of the test organism. The results suggest that the ligands 4, 7 and the complexes 2a-4a, 6a-8a were found with IC50 lower than that of the standard drub metronidazole and thus are better inhibitor of growth of E. histolytica. (c) 2005 Elsevier SAS. All rights reserved.
• Cyclooctadiene Ru(II) complexes of thiophene-2-carboxaldehyde-derived thiosemicarbazones: synthesis, characterization and antiamoebic activity
  作者：Shailendra Singh、Fareeda Athar、Mannar R. Maurya、Amir Azam

  DOI：10.1016/j.ejmech.2006.01.014

  日期：2006.5

  Thiosemicarbazones (TSC) 1-10 were synthesized by condensing substituted thiosemicarbazide with thiophene-2-carboxaldehyde. These thiosemicarbazones were further reacted with [Ru(eta(4)-C8H12)(CH3CN)(2)Cl-2] to forrn complexes of the type [Ru(eta(4) -C8H12)(TSC)Cl-2] 1a-10a. Thiosemicarbazones exhibited antiamoebic activity in the range IC50 = 1.09-5.42 mu M. In vitro assessment of antiamoebic activity indicated that the thiosemicarbazones 3, IC50 = 1.67 mu M, 4, IC50 = 1.11 mu M and 6, IC50 = 1-09 mu M showed substantially less IC50 value than metronidazole (IC50 = 1.87 mu M), a commonly used drug against amoebiasis. Cyclooctadiene Ru(II) complexes of thiosemicarbazones showed significant improvement in antiamoebic activity (IC50 = 0.30-1.39 mu M). All the complexes possess noteworthy potencies and showed less IC50 values than metronidazole against HK-9 strain of Entamoeba histolytica. Among all the complexes, the most promising antiamoebic activities was shown by the complexes 4a and 6a (IC50 = 0.31 mu M of 4a and IC50 = 0.30 mu M of 6a versus metronidazole). (c) 2006 Elsevier SAS. All rights reserved.
• New palladium(II) complexes of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones
  作者：Neelam Bharti、Shailendra、Sangita Sharma、Fehmida Naqvi、Amir Azam

  DOI：10.1016/s0968-0896(03)00213-x

  日期：2003.7

  Thiosemicarbazones (1-7) and their palladium(11) complexes (1a-7a) of the type [Pd(TSCN)Cl-2] (where TSCN = thiosemicarbazone) were prepared from 5-nitro thiophene-2-carboxaldehyde and [Pd(DMSO)(2)Cl-2], respectively. Coordination via the thionic sulphur and the azomethine nitrogen atom of the thiosemicarbazones to the metal ion were confirmed by spectral data. These compounds were screened in vitro against (HK-9) strain of Entamoeba histolytica possess amoebicidal properties. Enhancement of antiamoebic activity resulted due to the introduction of palladium metal in the thiosemicarbazone moiety. The most promising of the group tested are [Pd(5-N-2-TCA-COTSCN)Cl-2] and [Pd(5-N-2-TCA-AdmTSCN)Cl-2] comparable to that of metronidazole. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis, characterization and antiamoebic activity of new indole-3-carboxaldehyde thiosemicarbazones and their Pd(II) complexes
  作者：Kakul Husain、Mohammad Abid、Amir Azam

  DOI：10.1016/j.ejmech.2007.02.012

  日期：2007.10

  In continuation of our research on thiosemicarbazones and their metal complexes as antiamoebic agents, a new series of indole-3-carboxaldehyde thiosemicarbazones (TSC) 1-7 were prepared by condensing indole-3-carboxaldehyde with cycloalkylaminothiocarbonyl hydrazines. Their palladium(H) complexes of the [Pd(TSC)Cl-2] type, were synthesized upon coordination with [Pd(DMSO)(2)Cl-2]. The chemical structures of all the compounds were established by elemental analyses, electronic, IR, H-1 NMR and C-13 NMR spectral data. The structure of the complexes was further established by thermogravimetric analysis and FAB MS. Spectroscopic data revealed that thiosemicarbazones act as bidentate ligands, making use of thione sulphur and azomethine nitrogen atom for coordination to the Pd(II) ion. Among all the compounds evaluated for antiamoebic activity using HM1:IMSS strain of Entamoeba histolytica, all palladium complexes were found to be more active than their respective ligands. Moreover, ligand 5 and complexes 1a-3a, 5a and 7a showed antiamoebic activity, at lower IC50 doses when compared to the reference drug metronidazole with IC50 = 1.81 mu M. (c) 2007 Elsevier Masson SAS. All rights reserved.