2-(anthracen-9-ylmethylene)-N-ethyl-hydrazinecarbothioamide | 503133-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-(anthracen-9-ylmethylene)-N-ethyl-hydrazinecarbothioamide
• 英文别名: EtATSC；9-anthraldehyde-N(4)-ethylthiosemicarbazone；1-(Anthracen-9-ylmethylideneamino)-3-ethylthiourea
• CAS: 503133-48-0
• 化学式: C₁₈H₁₇N₃S
• 分子量: 307.419
• InChiKey: PPVXQFXSZITMGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(anthracen-9-ylmethylene)-N-ethyl-hydrazinecarbothioamide 在 羟胺 作用下， 以 甲醇 为溶剂， 反应 6.71h， 生成 1-(anthracen-9-ylmethylideneamino)-2-ethyl-3-hydroxyguanidine
  参考文献：
  名称：

  Effect of substitution at N″-position of N′-hydroxy-N-amino guanidines on tumor cell growth

  摘要：

  Structural modification of one of our earlier reported lead molecule (ABNM13) has been carried out to study the effect of different substituents at the N ''-position of N-hydroxy-N'-amino guanidines (HAGs) on their anticancer activity. Compounds with electron donating substituents were found to be less active. In contrast, those with electron withdrawing groups were found favorable for anticancer activity. The obtained results provide significant SAR information that may be useful for further drug designing with HAGs. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.048
• 作为产物：
  描述：

  methyl N-(anthracen-9-ylmethylideneamino)carbamodithioate 、 乙胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.25h， 以45%的产率得到2-(anthracen-9-ylmethylene)-N-ethyl-hydrazinecarbothioamide
  参考文献：
  名称：

  Effect of substitution at N″-position of N′-hydroxy-N-amino guanidines on tumor cell growth

  摘要：

  Structural modification of one of our earlier reported lead molecule (ABNM13) has been carried out to study the effect of different substituents at the N ''-position of N-hydroxy-N'-amino guanidines (HAGs) on their anticancer activity. Compounds with electron donating substituents were found to be less active. In contrast, those with electron withdrawing groups were found favorable for anticancer activity. The obtained results provide significant SAR information that may be useful for further drug designing with HAGs. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.06.048

文献信息

• Microwave synthesis of mixed ligand diimine–thiosemicarbazone complexes of ruthenium(ii): biophysical reactivity and cytotoxicity
  作者：Floyd A. Beckford、Michael Shaloski, Jr.、Gabriel Leblanc、Jeffrey Thessing、Lesley C. Lewis-Alleyne、Alvin A. Holder、Liya Li、Navindra P. Seeram

  DOI：10.1039/b915081a

  日期：——

  are best formulated as [(phen)(2)Ru(thiosemicarbazone)](PF(6))(2) and [(phen)(2)Ru(thiosemicarbazone)](PF(6))(2) where thiosemicarbazone = 9-anthraldehydethiosemicarbazone, 9-anthraldehyde-N(4)-methylthiosemicarbazone, and 9-anthraldehyde-N(4)-ethylthiosemicarbazone. Fluorescence competition studies with ethidium bromide, along with viscometric measurements suggests that the complexes bind calf thymus

  一种新型的微波辅助合成方法已被用于合成一系列含有二亚胺和双齿缩氨基硫脲配体的混合配体钌 (II) 化合物。该化合物含有二亚胺 1,10-菲咯啉 (phen) 或 2,2'-联吡啶 (bpy)，而缩氨基硫脲衍生自 9-蒽醛。根据元素分析和光谱数据，这些化合物最好配制成 [(phen)(2)Ru(缩氨基硫脲)](PF(6))(2) 和 [(phen)(2)Ru(缩氨基硫脲)](PF (6))(2) 其中缩氨基硫腙= 9-蒽醛缩氨基硫脲、9-蒽醛-N(4)-甲基缩氨基硫脲和9-蒽醛-N(4)-乙缩氨基硫脲。与溴化乙锭的荧光竞争研究，与粘度测量一起表明，复合物通过可能涉及二亚胺配体的芳环的嵌入模式相对强烈地结合小牛胸腺 DNA (CTDNA)。该复合物对 MCF-7 和 MDA-MB-231（乳腺腺癌）以及 HCT 116 和 HT-29（结肠直肠癌）细胞系显示出良好的细胞毒性特征。
• Novel microwave synthesis of half-sandwich [(η⁶ -C₆ H₆ )Ru] complexes and an evaluation of the biological activity and biochemical reactivity
  作者：Floyd A. Beckford、Alyssa Stott、Antonio Gonzalez-Sarrías、Navindra P. Seeram

  DOI：10.1002/aoc.3007

  日期：2013.7

  We have used a novel microwave‐assisted method to synthesize a pair of half‐sandwich ruthenium–arene–thiosemicarbazone complexes of the type [(η6‐C6H6Ru(TSC)Cl]PF6. The thiosemicarbazone (TSC) ligands are 2‐(anthracen‐9‐ylmethylene)hydrazinecarbothioamide and 2‐(anthracen‐9‐ylmethylene)‐N‐ethylhydrazinecarbothioamide derived from 9‐anthraldehyde. The complexes are moderately strong binders of DNA,

  我们已经使用了新颖的微波辅助的方法合成的一对半夹心钌-芳烃-缩氨基硫脲的类型的配合物[（η的6 -C 6 H ^ 6的Ru（TSC）CL] PF 6。该缩氨基硫脲（TSC）的配体分别是衍生自9乙醛的2-（蒽-9-基亚甲基）肼甲硫酰胺和2-（蒽-9-基亚甲基）-N-乙基肼甲硫酰胺，该络合物是中等强度的DNA结合剂，结合常数为10 4 m -1。它们也是人血清白蛋白的强粘合剂，具有10的顺序的结合常数5 米-1。该复合物显示出一些在体外对人类结肠癌细胞Caco-2和HCT-116的抗癌活性具有积极的治疗指数。他们没有表现出对所研究生物的任何抗菌活性。版权所有©2013 John Wiley＆Sons，Ltd.
• Cytotoxic gallium complexes containing thiosemicarbazones derived from 9-anthraldehyde: Molecular docking with biomolecules
  作者：Floyd A. Beckford、Alyssa Brock、Antonio Gonzalez-Sarrías、Navindra P. Seeram

  DOI：10.1016/j.molstruc.2016.05.075

  日期：2016.10

  We have synthesized a trio of gallium complexes bearing 9-anthraldehyde thiosemicarbazones. The complexes were assessed for their anticancer activity and their biophysical reactivity was also investigated. The three complexes displayed good cytotoxic profiles against two human colon cancer cell lines, HCT-116 and Caco-2. The IC50 ranged from 4.7 - 44.1 μM with the complex having an unsubstituted amino

  我们已经合成了三种带有 9-蒽醛缩氨基硫脲的镓配合物。评估了复合物的抗癌活性，并研究了它们的生物物理反应性。这三种复合物对两种人结肠癌细胞系 HCT-116 和 Caco-2 显示出良好的细胞毒性特征。IC50 范围为 4.7 - 44.1 μM，其中在缩氨基硫脲上具有未取代氨基的复合物活性最高。这种特殊的复合物还显示出高治疗指数。所有三种复合物都通过嵌入与 DNA 强结合，结合常数范围从 7.46 × 104 M-1 到 3.25 × 105 M-1。结合强度不能与抗癌活性水平直接相关。该复合物还与人血清白蛋白强烈结合，结合常数也为 104 - 105 M-1。这些复合物作为化学核酸酶发挥作用，其切割 pBR322 质粒 DNA 的能力证明了这一点。结合常数和切割结果可能表明 DNA 相互作用的程度与抗癌活性不直接相关。然而，与DNA、核糖核苷酸还原酶和人血清白蛋白对接研究的结果表明，生
• Emissive Pd(II) thiosemicarbazones bearing anthracene: New complexes with unusual coordination mode
  作者：Minh-Hai Nguyen、Thi-Thuy-Ha Khuat、Hung-Huy Nguyen、Quan-Manh Phung、Thi-Hien Dinh

  DOI：10.1016/j.inoche.2019.02.028

  日期：2019.4

  Abstract New emissive Pd(II) complexes with anthracene-based thiosemicarbazones have been readily prepared in high yields. X-ray crystallographic analysis reveals that N(4)-substituted groups of thiosemicarbazone ligands exert marked effect on coordination mode of Pd(II) central ion. Rare asymmetric chelation based on monothiosemicarbazone is found with small N(4)-substituted groups such as methyl

  摘要 已经很容易以高产率制备了具有蒽基缩氨基硫脲的新型发光 Pd(II) 配合物。X 射线晶体学分析表明，缩氨基硫脲配体的 N(4)-取代组对 Pd(II) 中心离子的配位模式产生显着影响。罕见的基于单缩氨基硫脲的不对称螯合与小的 N(4)-取代基团，如甲基或乙基。TD-DFT 计算部分支持这种不寻常排列的优先形成。这些配合物显示出以配体为中心的荧光发射，这与 Pd(II) 的配位模式无关。
• Anthracene-based Ni(II) thiosemicarbazones with novel intramolecular π–π stackings
  作者：Minh-Hai Nguyen、Thi-Thuy-Ha Khuat、Danh-Quang Do、Hung-Huy Nguyen、Thi-Hien Dinh

  DOI：10.1016/j.inoche.2020.107994

  日期：2020.8

  Four new Ni(II) complexes were obtained from the reaction between anthracene-based thiosemicarbazones and inorganic metal salt. Structural investigation of the complexes using X-ray crystallography reveals unusual cis geometries driven by intramolecular pi-pi stackings between anthracenyl rings. Due to the novel interactions, the anthracenyl protons H-1,H-8,H-2,H-7 are not observed and the imine proton is largely shifted in H-1 NMR spectra. The UV-Vis and photoluminescent data clearly indicate strong perturbation of intramolecular pi-pi stackings on electronic structure of anthracenyl cores, namely broadening of absorption and emission bands.