Indole-3-carboxaldehyde 4-methylthiosemicarbazone | 7275-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Indole-3-carboxaldehyde 4-methylthiosemicarbazone
• 英文别名: indole-3-carboxaldehyde 4-methyl-3-thiosemicarbazone；1-(1H-indol-3-ylmethylideneamino)-3-methylthiourea
• CAS: 7275-74-3
• 化学式: C₁₁H₁₂N₄S
• 分子量: 232.309
• InChiKey: CCUSBMJFLRDBDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Indole-3-carboxaldehyde 4-methylthiosemicarbazone 、 zinc(II) chloride 以 甲醇 为溶剂， 反应 7.0h， 以81%的产率得到bis[(E)-2-((1H-indol-3-yl)methylene)-N-methylhydrazinecarbothioamide]Zn(II)
  参考文献：
  名称：

  吲哚硫代半脲酮的锌（II）配合物：DNA /蛋白质结合，分子对接和体外细胞毒性研究

  摘要：

  摘要通过元素分析和各种分光光度法（UV-Vis，FT-IR，1H NMR，13C NMR和质谱），合成并表征了四种具有吲哚硫代半氨基甲酮的Zn（II）配合物（1-4）。单晶X射线晶体学研究揭示了配合物1和3的四面体几何形状。Zn（II）配合物1-4与小牛胸腺DNA（CT DNA）的相互作用通过UV-Vis光谱和粘度测量进行了检查，暗示复合物通过插入与CT DNA结合，复合物4显示出比其他复合物更高的结合亲和力。通过荧光和吸收技术监测复合物的蛋白质结合相互作用，结果表明该复合物可以与牛血清白蛋白（BSA）有效结合，并且猝灭机理是静态的。同步荧光实验显示了蛋白质微区构象的变化。进行分子对接研究是为了更好地了解复合物与分子靶DNA六聚体和BSA的结合情况。使用以下方法评估了该复合物对两种人类癌症（A549和MCF7）细胞系，两种人类非致瘤性（MCF-10A和HEK-293）细胞系以及一种非癌性小

  DOI：

  10.1016/j.poly.2019.05.039
• 作为产物：
  描述：

  3-吲哚甲醛 以 乙醇 为溶剂， 生成 Indole-3-carboxaldehyde 4-methylthiosemicarbazone
  参考文献：
  名称：

  吲哚硫代氨基脲衍生物在无定形粉末，溶液和纳米纤维中的光致变色行为及其机理

  摘要：

  合成了一系列含有吲哚基团的席夫碱。化合物2-[（（1-甲基-1H-吲哚-3-基）亚甲基]肼基甲硫基酰胺（4）在固-固状态和溶液状态下均表现出优异的可逆光致变色特性。此外，含有化合物4的纳米纤维还显示出优异的光致变色性能，优于4的无定形粉末。本身。根据实验结果和理论计算，我们确认光致变色性质源自分子间质子转移，从而导致肼基碳硫代酰胺中的硫酮型和硫醇型异构化。这种独特的光致变色系统显然不同于传统的席夫碱，例如水杨基苯胺。

  DOI：

  10.1016/j.dyepig.2019.04.009

文献信息

• Solvent-Free Synthesis of Indole-Based Thiosemicarbazones under Microwave Irradiation
  作者：Lingling Liu、Jie Yang、Zhigang Zhao、Peiyu Shi、Xingli Liu

  DOI：10.3184/030823410x12628833270368

  日期：2010.1

  A rapid, efficient and environmentally friendly methodology has been developed for the synthesis of indole-3-carboxaldehyde thiosemicarbazones by using aluminum oxide as the solid support under microwave assisted solvent-free conditions. Compared with the conventional heating method, this method gave the target products in good yield.

  开发了一种快速、高效且环保的方法，用于在微波辅助无溶剂条件下以氧化铝为固体载体合成吲哚-3-甲醛缩氨基硫脲。与常规加热方法相比，该方法得到的目标产物收率良好。
• Synthesis, structures and mechanistic pathways of anticancer activity of palladium(<scp>ii</scp>) complexes with indole-3-carbaldehyde thiosemicarbazones
  作者：Jebiti Haribabu、Manoharan Muthu Tamizh、Chandrasekar Balachandran、Yuvaraj Arun、Nattamai S. P. Bhuvanesh、Akira Endo、Ramasamy Karvembu

  DOI：10.1039/c7nj03743k

  日期：——

  spectroscopic techniques. The solid state structures of the ligand (HL3) and complexes (2–5 and 6) were determined by single crystal X-ray diffraction analysis. Spectroscopic and crystallographic studies revealed that thiosemicarbazone is coordinated to the PdII ion as a monobasic bidentate (NS−) ligand by forming a five membered ring. To determine the potential of the PdII complexes towards biomolecular interactions

  新的[PdCl（L）（PPh 3）]（1-5）和[Pd（L）2 ]（6和7）类型的Pd II配合物（HL =吲哚-3-甲醛硫代半氨基甲酮，HL1-HL5）为了确定在硫代半氨基甲酮的末端氮上的取代对它们的Pd II配合物的生物学特性的影响，已合成了碳纳米管。通过元素分析和紫外可见，FT-IR，1 H NMR，13 C NMR，DEPT-135 NMR，31 P NMR，1 H– 1 H COSY，1 H– 13 C HSQC，1 H对化合物进行表征–13 C HMBC， 1 H– 31 P HMBC和质谱技术。配体（HL3）和配合物（ 2-5和6）的固态结构通过单晶X射线衍射分析确定。光谱和晶体学研究显示，缩氨基硫脲配位到钯II离子作为一元二齿（NS - ）配位体通过形成一个五元环。确定Pd II的潜力复杂的生物分子相互作用，涉及与小牛胸腺DNA（CT DNA）和牛血清白蛋白（BSA）相互作用的其他实验。此外，该复合物在pH
• Synthesis and Molecular Structure of the Zinc(II) Complex Bearing an N, S Donor Ligand
  作者：J. Haribabu、S. Priyarega、N. S. P. Bhuvanesh、R. Karvembu

  DOI：10.1134/s0022476620010072

  日期：2020.1

  between zinc(II) acetate dihydrate and ((1H-indol-3-yl)methylene)-N-methylhydrazinecarbothioamide (L) in methanol results in the formation of Zn(II) complex [Zn(C 11 H 11 N 4 S) 2 ] ( 1 ). The complex is characterized by CHNS and various spectroscopic analyses. The structure of the complex is determined by the single crystal X-ray diffraction technique. XRD reveals that the Zn(II) complex crystallizes

  乙酸锌 (II) 二水合物和 ((1H-indol-3-yl)methylene)-N-methylhydrazinecarbothioamide (L) 在甲醇中的反应导致形成 Zn(II) 络合物 [Zn(C 11 H 11 N 4 S) 2 ] ( 1 )。该复合物的特征在于 CHNS 和各种光谱分析。复合物的结构由单晶 X 射线衍射技术确定。XRD 显示 Zn(II) 配合物在具有 P -1 空间群的三斜晶系​​中结晶，并具有扭曲的四面体几何形状。两个配体分子以二齿一元 (NS - ) 方式与 Zn(II) 离子配位。
• Solid-state photochromic properties of indole thiosemicarbazones with aggregation-induced emission
  作者：Ying Cao、Yuanyuan Che、Lang Liu、Yakun Tang、Yuming Yu

  DOI：10.1039/d3nj05828j

  日期：——

  only reversible solid-state photochromic behavior but also aggregation-induced emission (AIE) characteristics. Furthermore, the structure–activity relationships were revealed by experimental studies, and their photochromism and fluorescence emission were enhanced efficiently with the increase of the conjugation. Furthermore, based on the single crystal structure, FT-IR spectra and theoretical calculations

  通过引入具有不同共轭性的取代基（甲基、乙基、环己基、苯基），通过一步反应合成了四种新型吲哚缩氨基硫脲衍生物，1-(吲哚-2-亚甲基)-4-取代的氨基硫脲。与传统的希夫碱光致变色化合物不同，该工作中的这些化合物对紫外光呈现双重响应信号，它们不仅表现出可逆的固态光致变色行为，而且还表现出聚集诱导发射（AIE）特性。此外，实验研究揭示了构效关系，并且随着共轭度的增加，它们的光致变色和荧光发射有效增强。此外，基于单晶结构、FT-IR光谱和理论计算，所提出的光致变色机制源于硫酮和硫烯醇构型之间的分子间质子转移，而AIE性能与分子内质子的限制密切相关。回转。此外，防伪图表明这些化合物的双重响应非常适合多重加密。该工作丰富了AIE体系，为构建优异的多重光响应材料提供了参考。
• Water-Soluble Mono- and Binuclear Ru(η⁶-<i>p</i>-cymene) Complexes Containing Indole Thiosemicarbazones: Synthesis, DFT Modeling, Biomolecular Interactions, and <i>In Vitro</i> Anticancer Activity through Apoptosis
  作者：Jebiti Haribabu、Gopal Sabapathi、Manoharan Muthu Tamizh、Chandrasekar Balachandran、Nattamai S. P. Bhuvanesh、Ponnambalam Venuvanalingam、Ramasamy Karvembu

  DOI：10.1021/acs.organomet.8b00004

  日期：2018.4.23

  Indole thiosemicarbazone ligands were prepared from indole-3-carboxaldehyde and N-(un)substituted thiosemicarbazide. The Ru(eta(6)-p-cymene) complexes [Ru(eta(6)-p-cymene)(HL1)Cl]Cl (1) and [Ru(eta(6)-p-cymene)(L2)](2)Cl-2 (2*) were exclusively synthesized from thiosemicarbazone (TSC) ligands HD and HL2, and [RuCl2(p-cymene)](2). The compounds were characterized by analytical and various spectroscopic (electronic, FT-IR, 1D/2D NMR, and mass) tools. The exact structures of the compounds (HL1, HL2, 1, and 2*) were confirmed by single-crystal X-ray diffraction technique. In complexes 1 and 2*, the ligand coordinated in a bidentate neutral (1)/monobasic (2*) fashion to form a five-membered ring. The complexes showed a piano-stool geometry around the Ru ion. While 2* existed as a dimer, 1 existed as a monomer, and this was well explained through free energy, bond parameter, and charge values computed at the B3LYP/SDD level. The intercalative binding mode of the complexes with calf thymus DNA (CT DNA) was revealed by spectroscopic and viscometric studies. The DNA (pUC19 and pBR322 DNA) cleavage ability of these complexes evaluated by an agarose gel electrophoresis method confirmed significant DNA cleavage activity. Further, the interaction of the complexes with bovine serum albumin (BSA) was investigated using spectroscopic methods, which disclosed that the complexes could bind strongly with BSA. A hemolysis study with human erythrocytes revealed blood biocompatibility of the complexes. The in vitro anticancer activity of the compounds (HL1, HL2, 1, and 2*) was screened against two cancer cell lines (A549 and HepG-2) and one normal cell line (L929). Interestingly, the binuclear complex 2* showed superior activity with IC50 = 11.5 mu M, which was lower than that of cisplatin against the A549 cancer cell line. The activity of the same complex (IC50 = 35.3 mu M) was inferior to that of cisplatin in the HepG-2 cancer cell line. Further, the apoptosis mode of cell death in the cancer cell line was confirmed by using confocal microscopy and DNA fragmentation analysis.