[(4-丙-2-基苯基)亚甲基氨基]硫脲 | 3811-20-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: [(4-丙-2-基苯基)亚甲基氨基]硫脲
• 英文名称: Cuminaldehyde thiosemicarbazone
• 英文别名: [(E)-{[4-(Propan-2-yl)phenyl]methylidene}amino]thiourea；(E)-2-(4-isopropylbenzylidene)thiosemicarbazone；Cutisone；[(E)-(4-propan-2-ylphenyl)methylideneamino]thiourea
• CAS: 3811-20-9
• 化学式: C₁₁H₁₅N₃S
• 分子量: 221.326
• InChiKey: GCIARVDJUYGSFQ-NTUHNPAUSA-N

物化性质

• 熔点：
  147°

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  [(4-丙-2-基苯基)亚甲基氨基]硫脲 、 2-氯乙酰乙酸乙酯 以 乙醇 为溶剂， 以89%的产率得到ethyl 4-methyl-2-[(E)-2-{[3-(propan-2-yl)phenyl]methylidene}hydrazin-1-yl]-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies

  摘要：

  In an attempt to discover new potent inhibitors for Mycobacterium tuberculosis (Mtb), a series of 2-(2hydrazinyl)thiazole derivatives with a wide range of substitutions at 2-, 4- and 5-positions were designed by considering Lipinski rule. The designed compounds were synthesized, characterized and evaluated for their inhibitory potential against Mtb, H(37)Rv, by in vitro assay. The compounds, ethyl-4methyl-2-[(E)-24]-(pyridin-2-yl)ethylidene]hydrazin-1-yl]-1,3-thiazole-5-carboxylate, 4d, and ethyl-2[(E)-2-[(2-hydroxyphenyl)methylidenelhydrazin-1-yl]-4-methyl-1,3-thiazole-5-carboxylate, 2i showed noticeable inhibitory activity against Mtb, H37Rv with minimum inhibitory concentration (MIC) of 12.5 pM and 25 1.1M respectively. An attempt has been made to understand the mechanism of action by binding interactions of these molecules with 0-ketoacyl-ACP synthase protein through docking studies. The inhibition constants for compounds 4d and 2i were found to be 1.46 pM and 0.177 pM respectively. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.054
• 作为产物：
  描述：

  氨基硫脲 、 4-异丙基苯甲醛 以 乙醇 为溶剂， 反应 1.5h， 生成 [(4-丙-2-基苯基)亚甲基氨基]硫脲
  参考文献：
  名称：

  新型缩氨基硫脲化合物E-2-(4-异丙基亚苄基)缩氨基硫脲的晶体结构和FT-IR光谱的合成、实验和理论研究

  摘要：

  摘要 合成了由 4-异丙基苯甲醛和氨基硫脲在乙醇溶液中反应得到的标题化合物 E-2-(4-异丙基苯亚甲基)氨基硫脲 ( 1 ) ，并通过元素分析、FT-IR 和 1 H NMR 光谱和单-晶体 X 射线衍射。使用密度泛函理论 (DFT) 方法计算了其优化的几何形状以及标题化合物振动频率的理论分配。在气相中发现了标题化合物的四种构象异构体，并且发现构象异构体 Sn1 是最稳定的。标题化合物在单斜空间群 P 2 1 / c 中结晶，晶胞参数：a = 14.4054(4), b = 5.6832(10), c = 14.4337(3) A, β = 93.306(2)°, V = 1179.70(5) A 3 和 Z = 4。

  DOI：

  10.1016/j.molstruc.2013.04.041

文献信息

• Cinnamaldehyde and cuminaldehyde thiosemicarbazones and their copper(II) and nickel(II) complexes: A study to understand their biological activity
  作者：Franco Bisceglie、Silvana Pinelli、Rossella Alinovi、Matteo Goldoni、Antonio Mutti、Alessandro Camerini、Lorenzo Piola、Pieralberto Tarasconi、Giorgio Pelosi

  DOI：10.1016/j.jinorgbio.2014.07.014

  日期：2014.11

  This paper reports the synthesis and characterization of trans-cinnamaldehyde thiosemicarbazone (Htcin), cuminaldehyde thiosemicarbazone (Htcum) and their copper and nickel complexes. All the compounds, which on healthy cells (human fibroblasts) show a neglectable cytotoxicity, were screened in vitro in cell line 13937 for their antileukemic activity. These compounds, in spite of their molecular similarity, present variegated behaviors. Htcin shows no inhibition activity in 13935 cells, while both its metal complexes inhibit proliferation with IC50 at mu M concentrations. The other ligand, Htcum, and its metal complexes, besides inhibiting proliferation, induce apoptosis. The cell cycle analysis highlights a G(2)/M checkpoint stop suggesting a possible direct action on DNA or on topoisomerase IIa. From CD and UV spectroscopy experiments, the DNA results to be not the main target of all these molecules, while both copper complexes are effective topoisomerase Ha inhibitors. All of these molecules activate caspase-9 and caspase-3, while caspase-8 activity is significantly induced by both cinnamaldehyde metal complexes. Tests on PgP and intracellular metal concentrations (determined by mean of atomic absorption spectrometry) show that the compounds tend to accumulate in the cytoplasm and that the cells do not manage to pump out copper and nickel ions. (C) 2014 Elsevier Inc. All rights reserved.
• CHENG, SHIQUAN;BAI, ZAIXIAN;GAO, YUANHONG;WULIJIMUREN, LIU LELE;JIANG, HO+, XUASYUEH SHITSZI, 10,(1988) N, S. 373-375
  作者：CHENG, SHIQUAN、BAI, ZAIXIAN、GAO, YUANHONG、WULIJIMUREN, LIU LELE、JIANG, HO+

  DOI：——

  日期：——
• PHARMACEUTICAL COMPOSITIONS CONTAINING COMPOUNDS WITH ACTIVITY FOR THE ENHANCEMENT OF ABSORPTION OF ACTIVE INGREDIENTS
  申请人：INPHARMA S.A.

  公开号：EP1073470A1

  公开（公告）日：2001-02-07
• METHODS FOR IDENTIFYING MODULATORS OF KINESIN ACTIVITY
  申请人：Rosetta Inpharmatics LLC.

  公开号：EP1629284A2

  公开（公告）日：2006-03-01
• METHODS FOR IDENTIFYING GENES THAT MEDIATE A RESPONSE OF A LIVING CELL TO AN AGENT
  申请人：Rosetta Inpharmatics LLC.

  公开号：EP1735464A2

  公开（公告）日：2006-12-27