4-(4-methylpiperidine)-3-aminothiourea | 6452-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-(4-methylpiperidine)-3-aminothiourea
• 英文别名: 3-(4-ethylpiperidine)thiosemicarbazide；4-methyl-piperidine-1-carbothioic acid hydrazide；4-Methylpiperidine-1-carbothiohydrazide
• CAS: 6452-01-3
• 化学式: C₇H₁₅N₃S
• mdl: MFCD03819408
• 分子量: 173.282
• InChiKey: CBOSEEGIGVVVQF-UHFFFAOYSA-N

物化性质

• 熔点：
  158 °C
• 沸点：
  266.7±23.0 °C(Predicted)
• 密度：
  1.135±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 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：

  4-(4-methylpiperidine)-3-aminothiourea 、 2-(3-chlorobenzoyl)-N,N-dimethylethylamine hydrochloride 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以15%的产率得到[5-(3-Chlorophenyl)-3,4-dihydropyrazol-2-yl]-(4-methylpiperidin-1-yl)methanethione
  参考文献：
  名称：

  1--Substituted Thiocarbamoyl-3-Phenyl-2-Pyrazolines: Synthesis and In Vitro Antiamoebic Activities

  摘要：

  The title compounds were prepared by reaction of Mannich bases with various N-4 substituted thiosemicarbazides. The chemical structures of the compounds were proved by means of their UV, IR, H-1 NMR, C-13 NMR spectroscopic data and elemental analyses. The in vitro antiamoebic activities of these compounds were evaluated by microdilution method against HM1:IMSS strain of Entamoeba histolytica and compared with the standard drug, metronidazole. It wits concluded that 3-chloro and 3-bromo substituents on the phenyl ring at position 3 of the pyrazoline ring enhanced the antiamoebic activity, Compounds 9, 17, 18, 20 and 21 showed less IC50 value than metronidazole. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.03.015
• 作为产物：
  描述：

  4-甲基哌啶 在 氢氧化钾 、 sodium hydroxide 、 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 4-(4-methylpiperidine)-3-aminothiourea
  参考文献：
  名称：

  Synthesis and antiamoebic activity of 3,7-dimethyl-pyrazolo[3,4-e][1,2,4] triazin-4-yl thiosemicarbazide derivatives

  摘要：

  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.

  DOI：

  10.1016/j.ejps.2005.02.014

文献信息

• Synthesis, Characterization and Biological Evaluation of Novel 1-N-Substituted Thiocarbomoyl-3-ferrocenyl-2-pyrazoline Derivatives
  作者：Humaira Parveen、Raedah Aiyed Suliman Alatawi、Salman Ahmad Khan、Mohammed Issa Al-Ahmdi、Sayeed Mukhtar、Amir Azam、Nadia H. Elsayed

  DOI：10.14233/ajchem.2016.19851

  日期：——

  Some novel 1-N-substituted thiocarbomoyl-3-ferrocenyl-2-pyrazoline derivatives were synthesized and evaluated for in vitro antiamoebic activity against HM1:IMSS strain of Entamoeba histolytica. The results showed that most of the compounds exhibited promising activity (IC50 values in the range of 0.050-1.683 μM) than the reference drug metronidazole (IC50 = 1.78 μM). Active compounds were further screened for cytotoxicity against human embryonic kidney-293 (HEK-293) normal cell lines to ensure their toxic effect and the results revealed that active compounds were least toxic in the concentration range of 2.5-50 μM for 48 h and 2.5-25 μM for 72 h. At 100 μM for 48 h and at 50 μM for 72 h only four compounds 2c, 2h, 2k and 2l showed maximum viability and least cytotoxicity, respectively, concluding that all the screened compounds were least cytotoxic against human embryonic kidney-293 (HEK-293) normal cell lines in the concentration range of 2.5-50 and 2.5-25 μM.

  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。
• 一种以4-（4-甲基哌啶）-3-缩氨基硫脲为配体的金配合物及其合成方法和应用
  申请人：广西师范大学

  公开号：CN109535185A

  公开（公告）日：2019-03-29

  本发明公开了一种以4‑（4‑甲基哌啶）‑3‑缩氨基硫脲为配体的金配合物及其合成方法和应用，该金配合物的合成方法为：将醛类衍生物溶于甲醇，溶解后，加入4‑(4‑甲基哌啶)‑3‑氨基硫脲混合均匀，得到混合溶液，将混合溶液回流、过滤，滤饼用甲醇洗涤2‑3次，得化合物；将得到的化合物溶于甲醇后，再加入Na[AuCl4].2H2O，室温下搅拌12 h，过滤，得黄绿色固体，将固体用正己烷洗涤2‑3次，真空干燥，再用二氯甲烷和正己烷混合液重新结晶得黑色晶体，即为目标配合物。该金配合物具有比顺铂更好的体外抗肿瘤活性，能抑制肿瘤细胞迁移和繁殖，具有高活性低毒性的特点。
• Developing a Novel Anticancer Gold(III) Agent to Integrate Chemotherapy and Immunotherapy
  作者：Juzheng Zhang、Ming Jiang、Shanhe Li、Zhenlei Zhang、Hongbin Sun、Feng Yang、Hong Liang

  DOI：10.1021/acs.jmedchem.1c00050

  日期：2021.5.27

  we innovatively attempted to develop a metal agent to integrate immunotherapy and chemotherapy by dual targeting the cellular components in the tumor microenvironment (TME) based on the specific residue of human serum albumin (HSA) nanoparticles (NPs). We synthesized a series of Au(III) α-N-heterocyclic thiosemicarbazone compounds and obtained a Au agent (5b) with remarkable cytotoxicity to gastric

  为了有效治疗胃癌，我们创新性地尝试通过基于人血清白蛋白（HSA）纳米颗粒（NPs）的特定残基双重靶向肿瘤微环境（TME）中的细胞成分来开发一种将免疫疗法和化学疗法相结合的金属试剂。我们合成了一系列的Au（III）α-N-杂环硫代半碳酰胺化合物，并获得了对胃癌细胞具有明显细胞毒性的Au剂（5b）。此外，我们成功构建了新型的HSA-5b复杂NP递送系统。重要的是，体内结果显示5b / HSA-5b NPs有效抑制胃肿瘤的生长和HSA-5b与单独使用5b相比，NPs增强了治疗效率，生物利用度和靶向能力。此外，体内/体外研究结果表明，5b / HSA-5b NPs可以协同协同攻击TME中的两种不同细胞成分，即极化与肿瘤相关的巨噬细胞极化并诱导胃癌细胞凋亡，从而将化学疗法和免疫疗法整合在一起。细胞。
• Synthesis, characterization and in vitro Antiamoebic Activity of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones and their Palladium (II) and Ruthenium (II) Complexes
  作者：Shailendra Singh、Neelam Bharti、Fehmida Naqvi、Amir Azam

  DOI：10.1016/j.ejmech.2004.02.003

  日期：2004.5

  Synthesis of new Palladium(II) and Ruthenium(II) complexes of the type, [Pd(L)Cl(2)] and [Ru(eta(4)-C(8)H(12))(L)Cl(2)] [where, L = thiosemicarbazones derived from 5-nitrothiophene-2-carboxaldehyde and cycloalkylaminothiocarbonyl hydrazines] have been isolated by the reaction of [Pd(DMSO)(2)Cl(2)] and [Ru(eta(4)-C(8)H(12))(CH(3)CN)(2)Cl(2)] with 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones

  新型[Pd（L）Cl（2）]和[Ru（eta（4）-C（8）H（12））（L）Cl（ 2）] [其中，L =由5-硝基噻吩-2-羧醛和环烷基氨基硫羰基肼衍生的硫代半咔唑]已通过[Pd（DMSO）（2）Cl（2）]和[Ru（eta（4） -C（8）H（12））（CH（3）CN）（2）Cl（2）]与5-硝基噻吩-2-羧醛硫代半脲酮 光谱数据表明，硫代半咔唑类化合物作为二齿配体，利用亚硫磺和偶氮甲碱氮原子与中心金属离子配位。微稀释法用于评估所有化合物对溶组织性变形杆菌的HK-9菌株的抗厌氧活性。在所有的硫代半氨基甲酮中，5-NT-4-BPTSCN（3）表现出显着的抗阿米巴活性（IC（50）-2.56 microM）。通过在硫半脲部分中引入钯和钌金属，可以增强抗厌氧活性。发现所有5-硝基噻吩-2-羧醛硫代半脲酮的Pd（II）和Ru（II）配合物比其各自的配体更具活性。配合物1a-4a，1b和3b显示出抗厌氧活性。
• NITROGEN-CONTAINING HETEROCYCLIC COMPOUND AND THROMBOPOIETIN RECEPTOR ACTIVATOR
  申请人：Miyaji Katsuaki

  公开号：US20090198060A1

  公开（公告）日：2009-08-06

  Compounds effective for preventing, treatment or improving diseases against which activation of the thrombopoietin receptor is effective are provided. A compound represented by the formula (I) (wherein R 1 , R 2 , R 3 , L 1 , L 2 , L 3 , X and Y are defined in the description), a tautomer, prodrug or pharmaceutically acceptable salt of the compound or a solvate thereof.

  本发明提供了一种有效预防、治疗或改善激活血小板生成素受体有效的疾病的化合物。其中化合物由公式(I)表示（其中R1、R2、R3、L1、L2、L3、X和Y在说明中定义），该化合物的互变异构体、前药或药学上可接受的盐或其溶剂化物。