3-氨基-1-苄基-1-甲基硫脲 | 114324-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氨基-1-苄基-1-甲基硫脲
• 英文名称: 4-benzyl-4-methylthiosemicarbazide
• 英文别名: N-benzyl-N-methylhydrazinecarbothioamide；4-Benzyl-4-(methyl)thiosemicarbazid；3-amino-1-benzyl-1-methylthiourea
• CAS: 114324-56-0
• 化学式: C₉H₁₃N₃S
• mdl: MFCD19201321
• 分子量: 195.288
• InChiKey: CCCSKFUQQXLJKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  320.2±35.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 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-氨基-1-苄基-1-甲基硫脲 在 过氧乙酸 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 生成 Isobutyraldehyd<4-benzyl-4-methylthiosemicarbazon-S.S.S-trioxid>
  参考文献：
  名称：

  Walter,W.; Rohloff,C., Justus Liebigs Annalen der Chemie, 1977, p. 447 - 462

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(N-benzyl-N-methylthiocarbamoyl)imidazole 在 一水合肼 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以41%的产率得到3-氨基-1-苄基-1-甲基硫脲
  参考文献：
  名称：

  Activation of dithiocarbamate by 2-halothiazolium salts

  摘要：

  DOI：

  10.1021/jo00245a025

文献信息

• Antiamoebic coumarins from the root bark of Adina cordifolia and their new thiosemicarbazone derivatives
  作者：Prince Firdoos Iqbal、Abdul Roouf Bhat、Amir Azam

  DOI：10.1016/j.ejmech.2008.06.003

  日期：2009.5

  our search for potential antiamoebic agents from folklore Indian medicinal plants, we found that the benzene and ethyl acetate extracts from the root bark of Adina cordifolia exhibited strong antiamoebic activity with IC50 values of 2.92 and 2.50 μg/ml, respectively. Bioassay-guided fractionation of benzene and ethyl acetate extracts led to the isolation of 7-hydroxycoumarin (umbelliferone 1) and

  在我们的用于从民俗印度药用植物潜在antiamoebic剂搜索的继续，我们发现，从根皮苯和乙酸乙酯萃取物阿迪纳茜草表现出很强的活性antiamoebic带IC 50个分别为2.92和2.50微克/毫升，值。苯和乙酸乙酯提取物的生物测定指导分馏分别导致了7-羟基香豆素（伞形酮1）和7-β-D-葡萄糖基香豆素（脱脂蛋白2）的分离。伞形酮1转化为7-乙酰氧基香豆素1a，经氯化铝处理后得到7-羟基-8-乙酰香豆素2a。一系列新的硫半脲3a–合成了具有不同硫代氨基脲的e- 7-羟基-8-乙酰香豆素。伞形酮还被转化为其甲氧基衍生物（7-甲氧基香豆素4）。随后，评估所有化合物对溶组织变形杆菌的HM1：IMMS菌株的抗厌氧活性。发现伞形酮和skimmin具有非常好的活性，IC 50值分别为6.38和4.35μM / ml。将化合物2a转化为其硫代半碳酰胺衍生物3a – e的活性急剧增加，其IC 50值在1
• Bis-pyrazolines: Synthesis, characterization and antiamoebic activity as inhibitors of growth of Entamoeba histolytica
  作者：Abdul R. Bhat、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejmech.2007.11.005

  日期：2009.1

  condition led to the formation of new compounds, thiocarbamoyl bis-pyrazoline derivatives. The structure of the compounds were elucidated by UV, IR, 1H NMR, 13C NMR and ESI-MS spectral data and thermogravimetric analysis, and their purities were confirmed by elemental analyses. The antiamoebic activity of these complexes was evaluated by microdilution method against HM1:IMSS strain of Entamoeba histolytica

  在碱性条件下，用N-4取代的硫代氨基脲将查尔酮环化，导致形成新的化合物硫代氨基甲酰基双吡唑啉衍生物。通过UV，IR，1 H NMR，13 C NMR和ESI-MS光谱数据以及热重分析阐明了化合物的结构，并通过元素分析证实了其纯度。这些复合物的antiamoebic活性通过对微量稀释法评估HM1：IMSS的应变阿米巴并将结果与​​标准药物甲硝唑进行比较。结构-活性关系表明，在硫代氨基甲酰基上具有芳香取代基的化合物比具有环状基团的化合物更具活性。但是，从IC 50值可以清楚地看出，化合物15和20具有更高的活性，并且两者都显示出结构相似性，其中吸电子基团连接在苯环上。MTT分析表明所有化合物对人肾上皮细胞系无毒。
• Preparation of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles via chemoselective сyclocondensation of electrophilically activated nitroalkanes to (thio)semicarbazides or thiohydrazides
  作者：Nicolai A. Aksenov、Nikolai A. Arutiunov、Nikita K. Kirillov、Dmitrii A. Aksenov、Alexander V. Aksenov、Michael Rubin

  DOI：10.1007/s10593-020-02775-5

  日期：2020.8

  Unusual reaction proceeding via the electrophilic activation of nitroalkanes in the presence of polyphosphoric acid has been discovered. Subsequent nucleophilic attack with semicarbazides or thiosemicarbazides allows to access 2-amino-1,3,4-oxadiazoles and 2-amino-1,3,4-thiadiazoles, respectively.

  已经发现在多磷酸存在下经由硝基链烷的亲电活化进行的异常反应。随后用氨基脲或硫代氨基脲的亲核攻击使得可以分别接近2-氨基-1,3,4-恶二唑和2-氨基-1,3,4-噻二唑。
• [EN] THIOSEMICARBAZONES<br/>[FR] THIOSEMICARBAZONES
  申请人：ONCOCHEL THERAPEUTICS LLC

  公开号：WO2017058748A1

  公开（公告）日：2017-04-06

  Described herein are thiosemicarbazone compounds and their use in therapy. More particularly, described herein a selection of dipyridyl thiosemicarbazone compounds, pharmaceutical compositions containing those compounds, and methods of treating cancer comprising administering those compounds and compositions.

  本文描述了硫代半胱氨酸化合物及其在治疗中的应用。更具体地，本文描述了一系列二吡啶硫代半胱氨酮化合物，包含这些化合物的药物组合物，以及通过给予这些化合物和组合物进行治疗的癌症治疗方法。
• Synthesis, spectral studies and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3-phenyl-2-pyrazolines
  作者：Mohammad Abid、Abdul Roouf Bhat、Fareeda Athar、Amir Azam

  DOI：10.1016/j.ejmech.2007.10.032

  日期：2009.1

  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.