acetophenone-4(N)-methylthiosemicarbazone | 27421-65-4

• 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: acetophenone-4(N)-methylthiosemicarbazone
• 英文别名: 2-acetophenone-N-methylthiosemicarbazone；acetophenone-N-methylthiosemicarbazone；acetophenone-(4-methyl thiosemicarbazone)；Acetophenon-(4-methyl-thiosemicarbazon)；acetophenone 4-methylthiosemicarbazone；acetophenone-4-methylthiosemicarbazone；1-Methyl-3-(1-phenylethylideneamino)thiourea
• CAS: 27421-65-4
• 化学式: C₁₀H₁₃N₃S
• mdl: MFCD02165221
• 分子量: 207.299
• InChiKey: OBIGTWHPKCCAQH-UHFFFAOYSA-N

物化性质

• 熔点：
  135 °C
• 沸点：
  306.6±25.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  acetophenone-4(N)-methylthiosemicarbazone 在 sodium tetrahydroborate 作用下， 生成 1,3-dimethyl-1-[5-oxo-4-(1-phenyl-ethyl)-4,5-dihydro-[1,3,4]thiadiazol-2-yl]-urea
  参考文献：
  名称：

  Sasse,K., Justus Liebigs Annalen der Chemie, 1970, vol. 735, p. 158 - 188

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯基乙烷-1-酮腙 以 乙醚 为溶剂， 生成 acetophenone-4(N)-methylthiosemicarbazone
  参考文献：
  名称：

  N-异硫氰酸根合亚胺的便捷合成

  摘要：

  已经开发出一种新的N-异硫氰酸根合亚胺的合成方法，该方法涉及使3-亚烷基二烯基二硫代氨基甲酸三乙铵与硫光气反应。

  DOI：

  10.1039/c39740000122

文献信息

• The Structure of Isothiosemicarbazones
  作者：Chiji Yamazaki

  DOI：10.1139/v75-085

  日期：1975.2.15

  Isothiosemicarbazones, except N²-substituted ones, were found to exist exclusively in the amino structure by means of i.r. and n.m.r. spectroscopy. The cis configuration (N¹cis to N⁴ about the N²=C bond) with intramolecular hydrogen bonding was proposed as the predominant structure for N⁴-unsubstituted isothiosemicarbazones on the basis of the i.r. spectra from the partially deuterated compounds. The trans configuration (N¹trans to N⁴ about the N²=C bond) was identified in all N⁴-monsubstituted and in a few N⁴-unsubstituted isothiosemicarbazones. The cis/trans ratios for the former varied depending on the solvent used.

  异硫脲肼除N²取代的化合物外，通过红外和核磁共振光谱学手段发现仅存在于氨基结构中。基于部分氘代化合物的红外光谱，提出了具有分子内氢键的顺式构型（N¹cis到N⁴关于N²=C键）作为N⁴-未取代的异硫脲肼的主要结构。所有N⁴-单取代和少量N⁴-未取代的异硫脲肼中鉴定出反式构型（N¹trans到N⁴关于N²=C键）。前者的顺/反比取决于所使用的溶剂。
• Organometallic ruthenium(II) complexes containing NS donor Schiff bases: Synthesis, structure, electrochemistry, DNA/BSA binding, DNA cleavage, radical scavenging and antibacterial activities
  作者：G. Devagi、F. Dallemer、P. Kalaivani、R. Prabhakaran

  DOI：10.1016/j.jorganchem.2017.10.036

  日期：2018.1

  confirmed by single crystal X-Ray diffraction technique. The binding ability of complexes (1–4) to calf-thymus DNA (CT DNA) and Bovine Serum Albumin (BSA) has been explored by absorption and emission titration methods. Based on the observations, an electrostatic and an intercalative binding mode have been proposed for the complexes with CT-DNA. The BSA protein binding studies have been monitored by

  四个新cyclopentadienylruthenium（II） -苯乙酮- 4（Ñ） -取代thiosemi-卡巴腙络合物，与通式的[Ru（ƞ 5 -C 5 H ^ 5）（H-Aptsc）PPH 3 ] .CL（1），[的Ru（ƞ 5 -C 5 H ^ 5）（H-Apmtsc）PPH 3 ] .CL（2），的[Ru（ƞ 5 -C 5 H ^ 5）（H-AP-ETSC）PPH 3 ] .CL（3）和的[Ru（ƞ 5 -C 5 H ^ 5）（H-AP-PTSC）PPH 3 ] .CL（4合成并表征（1 H NMR，13 C NMR，IR和电子光谱）。代表性配合物2和3的分子结构通过单晶X射线衍射技术确认。复合物（结合的能力1 - 4），以小牛胸腺DNA（CT DNA）与牛血清白蛋白（BSA）已经通过吸收和发射滴定法探讨。基于这些观察，已经提出了具有CT-DNA的复合物的静电和插入结合模式。通
• In vitro anti-proliferative, and in silico ribonucleotide reductase and pharmacokinetics studies of heteroleptic silver(I), nickel(II) and copper(II) complexes of 4-methyl-3-thiosemicarbazones and ibuprofen
  作者：Sundaram Bharathi、Dharmasivam Mahendiran、Sumeer Ahmed、Aziz Kalilur Rahiman

  DOI：10.1016/j.jtemb.2023.127211

  日期：2023.9

  reducing ability of the complexes. In vitro anti-proliferative studies by MTT assay, apoptotic behaviour and cellular uptake studies were investigated followed by the in silico interaction with ribonucleotide reductase (RNR) enzyme. Results The spectral studies predicted distorted tetrahedral geometry around silver(I) ion and distorted octahedral geometry around nickel(II) and copper(II) ions. The reducing

  目标 目前的研究重点是通式[ Ag (L 1−4 )(ibu)] ( 1 – 4 ) 和 [M( L 1−4 )(ibu) 2 ] ( 5 – 12 )，其中 L 1−4 = 2-(1-(4-取代苯基)亚乙基)- N-甲基肼硫甲酰胺，ibu = 非甾体类抗炎药（布洛芬） )，M = Cu(II) 和 Ni(II)。 方法 使用各种光谱技术来验证合成复合物的结构。采用紫外-可见光和循环伏安技术分析了配合物的稳定性和还原能力。通过 MTT 测定、细胞凋亡行为和细胞摄取研究进行体外抗增殖研究，然后研究与核糖核苷酸还原酶 (RNR) 的计算机相互作用。 结果 光谱研究预测了银（I）离子周围的扭曲四面体几何形状以及镍（II）和铜（II）离子周围的扭曲八面体几何形状。使用抗坏血酸，通过紫外-可见光和循环伏安技术分析铜(II)络合物的还原能力，验证了络合物的还原能力以及细胞内可能的相互作用。合成复合物对
• Synthesis, Characterization, and Anticancer Activity of a Series of Ketone-N⁴-Substituted Thiosemicarbazones and Their Ruthenium(II) Arene Complexes
  作者：Wei Su、Quanquan Qian、Peiyuan Li、Xiaolin Lei、Qi Xiao、Shan Huang、Chusheng Huang、Jianguo Cui

  DOI：10.1021/ic401362s

  日期：2013.11.4

  A series of ketone-N-4-substituted thiosemicarbazone (TSC) compounds (L1-L9) and their corresponding [(eta(6)-p-cymene)Ru-II(TSC)Cl](+/0) complexes (1-9) were synthesized and characterized by NMR, IR, elemental analysis, and HR-ESI-mass spectrometry. The molecular structures of L4, L9, 1-6, and 9 were determined by single-crystal X-ray diffraction analysis. The compounds were further evaluated for their in vitro antiproliferative activities against the SGC-7901 human gastric cancer, BEL-7404 human liver cancer, and HEK-293T noncancerous cell lines. Furthermore, the interactions of the compounds with DNA were followed by electrophoretic mobility spectrometry studies.
• M-STAGE KINESIN INHIBITOR
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP1616866B1

  公开（公告）日：2011-12-14