1H-1,2,3,4-tetrahydroquinoline-1-thiocarboxylic acid hydrazide | 135765-59-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1H-1,2,3,4-tetrahydroquinoline-1-thiocarboxylic acid hydrazide
• 英文别名: 1,2,3,4-tetrahydroquinolinyl-1-carbothiohydrazide；1,2,3,4-tetrahydroquinolinyl-1-thiocarbamoyl hydrazide；3,4-dihydro-2H-quinoline-1-carbothiohydrazide
• CAS: 135765-59-2
• 化学式: C₁₀H₁₃N₃S
• 分子量: 207.299
• InChiKey: BMKMKQVBSVMLON-UHFFFAOYSA-N

物化性质

• 沸点：
  347.3±35.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  1H-1,2,3,4-tetrahydroquinoline-1-thiocarboxylic acid hydrazide 、 乙基磺酰氯 在 吡啶 作用下， 以78%的产率得到
  参考文献：
  名称：

  (1,2,3,4-四氢喹啉-(硫代)羰基)取代磺酰肼类化合物及其制备方法和应用

  摘要：

  本发明公开了(1,2,3,4‑四氢喹啉‑(硫代)羰基)取代磺酰肼类化合物及其制备方法和应用。本发明(1,2,3,4‑四氢喹啉‑(硫代)羰基)取代磺酰肼类化合物的结构式如式I。本发明将磺酰基片段引入到含1,2,3,4‑四氢喹啉片段的取代苯甲醛缩氨基(硫)脲类化合物骨架中，得到N'‑(1,2,3,4‑四氢喹啉‑1‑(硫代)羰基)取代磺酰肼类化合物，其结构新颖，制备方法操作简单、原料易得、不易产生有害副产物；本发明化合物对多种病原真菌表现出抑制作用，尤其对油菜菌核病菌、苹果腐烂病菌具有明显的抑制效果，可以作为农用杀菌剂；本发明化合物对多种农业害虫表现出抑制作用，尤其对小菜蛾、粘虫和草地贪夜蛾具有明显的抑制效果，可以作为农用杀虫剂，具有极大的应用价值。

  公开号：

  CN113698344B
• 作为产物：
  描述：

  2-((1,2,3,4-tetrahydroquinoline-1-carbonothioyl)thio)acetic acid 在 一水合肼 作用下， 生成 1H-1,2,3,4-tetrahydroquinoline-1-thiocarboxylic acid hydrazide
  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

文献信息

• Synthesis, spectral studies and screening for amoebicidal activity of new palladium(II) complexes derived from thiophene-2-carboxaldehyde thiosemicarbazones
  作者：Shailendra, Neelam Bharti、Fehmida Naqvi、Amir Azam

  DOI：10.1016/s0960-894x(02)01005-3

  日期：2003.2

  latter with [Pd(DMSO)(2)Cl(2)] gave requisite palladium thiosemicarbazone complexes of the type [Pd(TSC)Cl(2)] (where TSC=thiosemicarbazones). Screening of antiamoebic activity of these compounds was assayed in vitro against (HM-1:1MSS) strain of E. histolytica. Enhancement of antiamoebic resulted from introducing palladium metal in the thiosemicarbazone moiety. Among the studied compounds, [Pd(2-TCA-1

  鉴于观察到的许多噻吩-2-羧甲醛硫代氨基脲的抗厌氧性能，制备了一系列衍生自噻吩-2-甲醛的N（4）-取代的硫代氨基甲酮金属配合物，以评价抗溶组织剂。噻吩-2-甲醛与具有不同胺的环烷基氨基硫代羰基肼反应，得到相应的硫代半脲。后者与[Pd（DMSO）（2）Cl（2）]的反应产生[Pd（TSC）Cl（2）]类型的必需钯硫代半碳酸盐配合物（其中TSC =硫代半碳氮酮）。在体外针对解组织性大肠杆菌（HM-1：1MSS）菌株对这些化合物的抗厌氧活性进行了筛选。通过在硫半脲部分中引入钯金属，可以增强抗厌氧性。在研究的化合物中，[Pd（2-TCA-1,2,3，
• Design, Synthesis, and Biological Activity of Novel Fungicides Containing a 1,2,3,4-Tetrahydroquinoline Scaffold and Acting as Laccase Inhibitors
  作者：Xiaoming Zhang、Huan Xu、Huifei Su、Xinling Yang、Tengda Sun、Xingxing Lu、Fasheng Shi、Hongxia Duan、Xili Liu、Yun Ling

  DOI：10.1021/acs.jafc.1c06595

  日期：2022.2.16

  it has applications in the discovery of new pesticides. In this work, PMDD-5Y was selected as a lead compound, and we designed and synthesized a series of novel sulfonyl hydrazide derivatives containing the natural product scaffold 1,2,3,4-tetrahydroquinoline. The new compounds had antifungal activities against several fungi, especially Valsa mali and Sclerotinia sclerotiorum. One compound (4bl) displayed

  漆酶是杀菌剂的新靶标。我们之前开发了一种新的杀菌剂，4-氯肉桂醛氨基硫脲 (PMDD-5Y)，作为漆酶抑制剂。将天然产物的活性基团引入农药分子结构框架中，是发现活性先导化合物的有效方法，在新农药的发现中具有应用价值。本工作以PMDD-5Y为先导化合物，设计合成了一系列含有天然产物支架1,2,3,4-四氢喹啉的新型磺酰肼衍生物。新化合物对几种真菌具有抗真菌活性，尤其是Valsa mali和Sclerotinia sclerotiorum。一种化合物 ( 4bl ) 表现非常好对核盘菌和马里弧菌的体外活性，EC 50值分别为 3.32 和 2.78 μg/mL。酶活性测定结果表明，4bh对漆酶的抑制活性最好，EC 50值为14.85 μg/mL。这比先导化合物 PMDD-5Y 和阳性对照半胱氨酸更活跃。使用分子对接方法，我们研究了标题化合物与漆酶的结合模式。这些新型漆酶抑制剂作为杀菌剂的结构特
• N’-取代苯亚甲基-1,2,3,4-四氢喹啉基-1- (硫代)酰肼类化合物及其制备方法和应用
  申请人：中国农业大学

  公开号：CN105037263B

  公开（公告）日：2017-07-18

  本发明属于病原菌控制技术领域，具体涉及N’‑取代苯亚甲基‑1,2,3,4‑四氢喹啉基‑1‑(硫代)酰肼类化合物及其制备方法和应用。本发明将具有优良生物活性的1,2,3,4‑四氢喹啉片段引入到取代苯甲醛缩氨基(硫)脲类化合物中，得到一类结构新颖的N’‑取代苯亚甲基‑1,2,3,4‑四氢喹啉基‑1‑(硫代)酰肼类化合物。所述化合物的结构如式I所示：本发明所述制备方法操作简单、原料易得、不产生有害副产物。所述化合物具有广谱的杀菌活性，尤其对苹果腐烂病菌、水稻纹枯病菌、小麦全蚀病菌具有明显的抑制效果，可以作为杀菌剂用于上述植物病害的防治。
• Synthesis, spectral studies and in vitro assessment for antiamoebic activity of new cyclooctadiene ruthenium(II) complexes with 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones
  作者：Shailendra Singh、Fareeda Athar、Amir Azam

  DOI：10.1016/j.bmcl.2005.08.103

  日期：2005.12

  We report here the synthesis, characterization and in vitro antiamoebic activity of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones (TSC), 1-5, and their bidentate complexes [Ru(eta(4)-C8H12)(TSC)Cl-2] 1a-5a. The biological studies of these compounds were investigated against HK-9 strain of Entamoeba histolytica and the concentration causing 50% cell growth inhibition (IC50) was calculated in the micromotar range. The ligands exhibited antiamoebic activity in the range (2.05-5.29 mu M). Screening results indicated that the potencies of the compounds increased by the incorporation of ruthenium(II) in the thiosemicarbazones. The complexes 1a-5a showed antiamoebic activity with an IC50 of 0.61-1.43 mu M and were better inhibitors of growth of E histolytica, based on IC50 values. The most promising among them is Ru(II) complex 2a having 1,2,3,4-tetrahydroquinoline as N-4 substitution. (c) 2005 Elsevier Ltd. All rights reserved.
• Scovill, John P., Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 61, # 1.2., p. 77 - 82
  作者：Scovill, John P.

  DOI：——

  日期：——