3-Amino-1-butyl-1-methylthiourea | 6499-18-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-Amino-1-butyl-1-methylthiourea
• CAS: 6499-18-9
• 化学式: C₆H₁₅N₃S
• mdl: MFCD19201353
• 分子量: 161.271
• InChiKey: BNZJEBBFINQRLC-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  231.6±23.0 °C(Predicted)
• 密度：
  1.058±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  73.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Amino-1-butyl-1-methylthiourea 、 2-(3-chlorobenzoyl)-N,N-dimethylethylamine hydrochloride 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 以12%的产率得到N-butyl-5-(3-chlorophenyl)-N-methyl-3,4-dihydropyrazole-2-carbothioamide
  参考文献：
  名称：

  Synthesis and antiamoebic activities of 1-N-substituted cyclised pyrazoline analogues of thiosemicarbazones

  摘要：

  A series of 21 new 1-N-substituted cyclised pyrazoline analogues of thiosemicarbazones were synthesised by cyclisation of Mannich bases with thiosemicarbazides of variegated nature. The chemical structures of the compounds were proved by UV, IR, H-1 NMR, C-13 NMR spectroscopic data and elemental analyses. The antiamoebic activities of these compounds were evaluated by microdilution method against HM1:1MSS strain of Entamoeba histolytica. It was found that 3-chloro and 3-bromo substituents on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity as compared to unsubstituted phenyl ring. Compounds 15, 17, 18, 20 and 21 showed less IC50 value than metronidazole. Moreover, compound 21 have shown the most promising antiamoebic activity (IC50 = 0.6 mu M VS IC50 = 1.8 mu M of metronidazole). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.12.050
• 作为产物：
  描述：

  甲基丁胺 在 一水合肼 、 potassium hydroxide 作用下， 生成 3-Amino-1-butyl-1-methylthiourea
  参考文献：
  名称：

  Synthesis, Characterization and Biological Evaluation of Novel 1-N-Substituted Thiocarbomoyl-3-ferrocenyl-2-pyrazoline Derivatives

  摘要：

  合成了一些新颖的1-N-取代硫代碳酰基-3-二茂铁基-2-吡唑啉衍生物，并评估了它们对Entamoeba histolytica的HM1:IMSS株的体外抗阿米巴活动。结果显示，多数化合物表现出比参考药物甲硝唑（IC50 = 1.78 μM）更有前景的活性（IC50值范围为0.050-1.683 μM）。进一步筛选活性化合物对人类胚胎肾-293（HEK-293）正常细胞系的细胞毒性，以确保其毒性效应，结果显示活性化合物在2.5-50 μM浓度范围内48小时和2.5-25 μM浓度范围内72小时内的毒性最小。在100 μM浓度下48小时和50 μM浓度下72小时，只有四种化合物2c、2h、2k和2l显示出最大的存活率和最小的细胞毒性，结论是所有筛选的化合物在2.5-50和2.5-25 μM浓度范围内对人类胚胎肾-293（HEK-293）正常细胞系的细胞毒性最小。

  DOI：

  10.14233/ajchem.2016.19851

文献信息

• Synthesis and antiamoebic activity of 3,7-dimethyl-pyrazolo[3,4-e][1,2,4] triazin-4-yl thiosemicarbazide derivatives
  作者：Shailendra Singh、Kakul Husain、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejps.2005.02.014

  日期：2005.6

  A series of 3,7-dimethyl-pyrazolo[3,4-e] [ 1,2,4]triazin-4-yl thiosemicarbazide derivatives 3-22 were prepared and evaluated in vitro against HMI:IMSS strain of Entamoeba histolytica, to identify the compounds for antiamoebic activity. They exhibited antiamoebic activity in the range (IC50 = 0.81-7.31 mu M). The results were compared to the activity of known drug metronidazole. It is inferred from the in vitro studies that the compounds 10, 11. 17 and 18 were found to be significantly better inhibitors of E. histolytica since IC50 values in the mu M range elicited by these compounds are much lower than metronidazole. Besides, compounds 11 and 17 have shown the most promising antiamoebic activity (IC50 = 0.81 mu M of 11, IC50 = 0.84 mu M of 17 versus IC50 = 1.81 mu M of metronidazole). The study suggests the possibility of developing triazine analogues as potential drug candidates for antiamoebic activity. (c) 2005 Elsevier B.V. All rights reserved.
• New Pd(II) complexes of the synthesized 1-N-substituted thiosemicarbazones of 3-indole carboxaldehyde: Characterization and antiamoebic assessment against E. histolytica
  作者：Kakul Husain、Abdul Roouf Bhat、Amir Azam

  DOI：10.1016/j.ejmech.2007.12.002

  日期：2008.9

  Reaction of 3-indole carboxaldehyde with aminothiocarbonyl hydrazines resulted in the formation of 3-indole carboxaldehyde thiosemicarbazones (TSCs) 1-13. The synthesized thiosemicarbazones were used as ligands in the formation of [Pd(TSC)Cl-2] complexes with palladium(II) metal ion precursor, [Pd(DMSO)(2)Cl-2]. The chemical structures of all the compounds were established by electronic, IR, H-1 NMR and C-13 NMR spectral data. The structure of the complexes was further established by FABMS and DTA. It is concluded that the thione sulphur and the azomethine nitrogen atom of the ligands are bonded to the metal ion. The testing of the antiamoebic activity of these compounds against the protozoan parasite Entamoeba histolytica suggests that compounds 5, 3a, 5a and 8a-13a might be endowed with important antiamoebic properties since they showed less IC50 values than metronidazole. Moreover, compound 12a displays remarkable antiamoebic activity than metronidazole (IC50 values of 0.29 vs 1.81 mu M, respectively). MTT assay showed that the compounds are non-toxic to human kidney epithelial cell line. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Novel bidentate complexes of Cu(II) derived from 5-nitrofuran-2-carboxaldehyde thiosemicarbazones with antiamoebic activity against E. histolytica
  作者：Sangita Sharma、Fareeda Athar、Mannar R. Maurya、Fehmida Naqvi、Amir Azam

  DOI：10.1016/j.ejmech.2005.01.003

  日期：2005.6

  The novel analogues of 5-nitrofuran-2-carboxaldehyde thiosernicarbazones 1-10 were synthesized and their copper(H) complexes 1a-10a were obtained by means of coordination with cupric chloride. All these compounds have been characterized by elemental analysis, IR, electronic spectra and thermogravimetric patterns while ligands have also been characterized by H-1 NMR spectral studies. These copper complexes are bidentate and possess octahedral geometry around Cu(II) ion. Their antiamoebic activities were carried out to ascertain their effectiveness in comparison to their corresponding thiosemicarbazones. A number of these complexes possess noteworthy potencies towards HK-9 strain of Entainoeba histolytica in vitro. The complexes 2a-7a, 9a and 10a showed less IC50 value than metronidazole, the drug of choice for amoebiasis. Moreover, complexes 2a and 9a have shown the most promising antiamoebic activities (IC50 = 0.38 mu M of 2a and IC50 = 0.34 mu M of 9a versus IC50 = 1.81 mu M of metronidazole). These results indicate that the metallated thiosemicarbazone may be lead molecule to inhibit growth of E. histolytica. (c) 2005 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.