(E)-2-(2-ethylbenzylidene)hydrazinecarbothioamide | 1258002-49-1

• 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: (E)-2-(2-ethylbenzylidene)hydrazinecarbothioamide
• 英文别名: 2-(2-Ethylbenzylidene)Hydrazinecarbothioamide；[(E)-(2-ethylphenyl)methylideneamino]thiourea
• CAS: 1258002-49-1
• 化学式: C₁₀H₁₃N₃S
• 分子量: 207.299
• InChiKey: IJILBAJDASPLJK-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 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

• 作为产物：
  描述：

  2-ethylbenzaldehyde 、 氨基硫脲 以 乙醇 、 水 为溶剂， 以94%的产率得到(E)-2-(2-ethylbenzylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis

  摘要：

  A series of thiosemicarbazones 2(e-s) have been synthesized and studied their structure-activity relationship as melanogenesis inhibitor. Among them, (Z)-2-(naphthalen-1-ylmethylene) hydrazinecarbothioamide (2q, >100% inhibition at 10 mu M, IC50 = 1.1 mu M, C log P = 3.039) showed the strongest inhibitory activity. Regarding their structure-activity relationship, the hydrophobic substituents regardless the position on phenyl ring of benzaldehyde thiosemicarbazones enhance the inhibitory activity. Furthermore, the aromatic group of benzaldehydethiosemicarbazones can be replaced with sterically bulky cyclohexyl. Thus, hydrophobicity of the aryl or alkyl group on hydrazine of thiosemicarbazones is determinant factor for their inhibitory activity in melanogenesis rather than planarity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.114

文献信息

• [EN] SEED DRESSING<br/>[FR] ENROBAGE DE GRAINE
  申请人：A & C CHEMICALS PTY LTD

  公开号：WO2007051249A1

  公开（公告）日：2007-05-10

  [EN] An antifungal seed dressing having a formulation (I) in the form of a liquid including a thiosemicarbazone and a solvent having the following general formula HO-[CH(R₄)-CH(R₅)-O]_n-R where R₁ is alkyl or substituted alkyl having 1-6 carbon atoms, R₄ and R₅ is hydrogen or methyl and n=1-4 or having a formulation (II) including a thiosemicarbazone in the form of a suspension concentrate combined with an emulsified oil.
  [FR] La présente invention a pour objet un enrobage de graine antifongique de formule (I) sous forme d'un liquide incluant une thiosemicarbazone et un solvant de formule générale suivante HO-[CH(R₄)-CH(R₅)-O]_n-R où R₁ représente un groupement alkyle éventuellement substitué en C₁-C₆, R₄ et R₅ représentent un atome d'hydrogène ou un groupement méthyle et n=1-4, ou de formule (II) incluant une thiosemicarbazone sous forme d'une suspension concentrée associée à une huile émulsifiée.
• Structural characteristics of thiosemicarbazones as inhibitors of melanogenesis
  作者：Ki-Cheul Lee、Pillaiyar Thanigaimalai、Vinay K. Sharma、Min-Seok Kim、Eunmiri Roh、Bang-Yeon Hwang、Youngsoo Kim、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2010.08.114

  日期：2010.11

  A series of thiosemicarbazones 2(e-s) have been synthesized and studied their structure-activity relationship as melanogenesis inhibitor. Among them, (Z)-2-(naphthalen-1-ylmethylene) hydrazinecarbothioamide (2q, >100% inhibition at 10 mu M, IC50 = 1.1 mu M, C log P = 3.039) showed the strongest inhibitory activity. Regarding their structure-activity relationship, the hydrophobic substituents regardless the position on phenyl ring of benzaldehyde thiosemicarbazones enhance the inhibitory activity. Furthermore, the aromatic group of benzaldehydethiosemicarbazones can be replaced with sterically bulky cyclohexyl. Thus, hydrophobicity of the aryl or alkyl group on hydrazine of thiosemicarbazones is determinant factor for their inhibitory activity in melanogenesis rather than planarity. (C) 2010 Elsevier Ltd. All rights reserved.