1-(3-phenylpropylidene)thiosemicarbazide | 56967-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-phenylpropylidene)thiosemicarbazide
• 英文别名: 3-phenyl-propionaldehyde-thiosemicarbazone；3-Phenyl-propionaldehyd-thiosemicarbazon；3-Phenylpropionaldehyde-thiosemicarbazone；(3-phenylpropylideneamino)thiourea
• CAS: 56967-43-2
• 化学式: C₁₀H₁₃N₃S
• 分子量: 207.299
• InChiKey: PWBORPXUUJFWAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3-phenylpropylidene)thiosemicarbazide 在 cetyltrimethylammonium peroxodisulphate 作用下， 以 乙腈 为溶剂， 反应 0.67h， 以80%的产率得到苯丙醛
  参考文献：
  名称：

  使用十六烷基三甲基过二硫酸铵作为新的选择性氧化剂对肟、苯腙、缩氨基脲和氨基硫脲对相应羰基化合物的脱保护

  摘要：

  定量制备十六烷基三甲基过氧二硫酸铵 (CTA)2S2O8 并将其用于在乙腈中将肟、苯腙、缩氨基脲和氨基硫脲脱保护为相应的羰基化合物。其试剂效率更高，与同类试剂相比具有氧化剂用量少、反应时间短、后处理简单、收率高等优点。

  DOI：

  10.1002/jccs.200800074
• 作为产物：
  描述：

  4-phenyl-2-thiosemicarbazido-butyric acid 在 碘 、 sodium carbonate 、 potassium iodide 作用下， 生成 1-(3-phenylpropylidene)thiosemicarbazide
  参考文献：
  名称：

  Popovici, Annales de Chimie (Cachan, France), 1932, vol. <10> 18, p. 183 (189), 228

  摘要：

  DOI：

文献信息

• Structure–activity relationship study of thiosemicarbazones on an African trypanosome: Trypanosoma brucei brucei
  作者：Houssou Raymond Fatondji、Salomé Kpoviessi、Fernand Gbaguidi、Joanne Bero、Veronique Hannaert、Joëlle Quetin-Leclercq、Jacques Poupaert、Mansourou Moudachirou、Georges Coffi Accrombessi

  DOI：10.1007/s00044-012-0208-6

  日期：2013.5

  structures. This study that was done using acetophenone thiosemicarbazone (1) as basic model, showed that: (a) the presence of lipophilic substituents in para position on benzene ring, (b) substitution of benzene ring and (c) substitution of hydrogen of thioamide function by a phenyl, strongly influence trypanocidal activity. The various modifications to basic structure (1) allowed the synthesis of 1-(4-chlorophenyl)

  探索非洲锥虫缩氨基硫脲的结构-活性关系：布氏锥虫布氏，一系列的35缩氨基硫脲（1 - 35）已被合成和表征可以通过1 H NMR，13 C NMR，和FT-IR光谱。使用“ Lilit alamar blue”方法测试所有化合物的杀锥虫活性。考虑到它们的结构，比较了硫半脲的锥虫杀菌能力。该研究结果表明，使用苯乙酮缩氨基硫脲进行（1）作为基本模型，表明：（a）中的亲脂性的取代基的存在对在苯环上的位置，（b）苯环的取代和（c）硫代酰胺官能团的氢被苯基取代，强烈影响锥虫活性。对基本结构（1）的各种修饰允许合成1-（4-氯苯基）亚乙基-4-苯基-硫代氨基脲（34）。该化合物具有3.97μM的锥虫杀灭活性，是该系列中最活跃的。
• Studies toward the structural optimization of novel thiazolylhydrazone-based potent antitrypanosomal agents
  作者：Marcelo Zaldini Hernandes、Marcelo Montenegro Rabello、Ana Cristina Lima Leite、Marcos Veríssimo Oliveira Cardoso、Diogo Rodrigo Magalhaes Moreira、Dalci José Brondani、Carlos Alberto Simone、Luiza Campos Reis、Marina Assis Souza、Valéria Rego Alves Pereira、Rafaela Salgado Ferreira、James Hobson McKerrow

  DOI：10.1016/j.bmc.2010.09.056

  日期：2010.11

  In previous studies, we identified promising anti-Trypanosoma cruzi cruzain inhibitors based on thiazolylhydrazones. To optimize this series, a number of medicinal chemistry directions were explored and new thiazolylhydrazones and thiosemicarbazones were thus synthesized. Potent cruzain inhibitors were identified, such as thiazolylhydrazones 3b and 3j, which exhibited IC50 of 200–400 nM. Furthermore

  在以前的研究中，我们确定了基于噻唑基肼唑酮的有前途的抗克氏锥虫锥虫抑制剂。为了优化该系列，探索了许多药物化学方向，并由此合成了新的噻唑基hydr唑酮和硫代半咔唑酮。已鉴定出强效的克鲁萨因抑制剂，例如噻唑基肼唑3b和3j，其IC 50为200–400 nM。此外，分子对接研究表明与实验得出的结构-活性关系（SAR）数据一致。在这项工作的过程中，先导化合物对克氏锥虫的表鞭毛纲和锥鞭毛纲均表现出体外活性进行鉴定，随后进行体内一般毒性分析。记录了新的SAR，包括连接到噻唑基环上的硫代羰基碳的重要性以及硫代半咔唑酮和噻唑基hydr唑酮之间的直接比较。
• Refinement of arylthiosemicarbazone pharmacophore in inhibition of mushroom tyrosinase
  作者：Wei Yi、Carole Dubois、Samir Yahiaoui、Romain Haudecoeur、Catherine Belle、Huacan Song、Renaud Hardré、Marius Réglier、Ahcène Boumendjel

  DOI：10.1016/j.ejmech.2011.07.003

  日期：2011.9

  Melanin play a major role in human skin protection and their biosynthesis is vital. Due to their color, they contribute to the skin pigmentation. Tyrosinase is a key enzyme involved in the first stage of melanin biosynthesis, it catalyzes the transformation of tyrosine into L-dopaquinone. The aim of the present study was to study molecules able to inhibit tyrosinase to be used in treating depigmentation-related disorders. In this study, we targeted arylthiosemicarbazone analogs with the aim to contribute to the identification of the optimal aryl ring to be linked to the thiosemicarbazone moiety. The biological activity was evaluated on commercial mushroom tyrosinase which was purified prior use. The results demonstrated that several of our compounds (1a-h, 1j, 1r and 5) had more potent inhibitory activities than kojic acid which was used as the reference inhibitor. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Mayer,K.H.; Lauerer,D., Justus Liebigs Annalen der Chemie, 1970, vol. 731, p. 142 - 151
  作者：Mayer,K.H.、Lauerer,D.

  DOI：——

  日期：——
• Deprotection of Oximes, Phenylhydrazones, Semicarbazones and Thiosemicarbazones to the Corresponding Carbonyl Compounds Using Cetyltrimethylammonium Peroxodisulfate as a New and Selective Oxidizing Agent
  作者：Mohammad Norouzi、Mahmood Tajbakhsh、Heshmatollah Alinezhad、Azade Geran Urimi

  DOI：10.1002/jccs.200800074

  日期：2008.6

  Cetyltrimethylammonium peroxodisulfate (CTA)2S2O8 was quantitatively prepared and used for the deprotection of oximes, phenylhydrazones, semicarbazones and thiosemicarbazones to the corresponding carbonyl compounds in acetonitrile. Its agent is more efficient and has advantages over similar reagents in terms of the amount of oxidant, short reaction time, simple work up, and high yield.

  定量制备十六烷基三甲基过氧二硫酸铵 (CTA)2S2O8 并将其用于在乙腈中将肟、苯腙、缩氨基脲和氨基硫脲脱保护为相应的羰基化合物。其试剂效率更高，与同类试剂相比具有氧化剂用量少、反应时间短、后处理简单、收率高等优点。