1-benzylisatin 3-thiosemicarbazone | 112367-62-1

• 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: 1-benzylisatin 3-thiosemicarbazone
• 英文别名: [(1-benzyl-2-oxoindol-3-ylidene)amino]thiourea
• CAS: 112367-62-1
• 化学式: C₁₆H₁₄N₄OS
• 分子量: 310.379
• InChiKey: CFXISAYTAYDGKB-UHFFFAOYSA-N

物化性质

• 熔点：
  262-264 °C
• 沸点：
  513.6±43.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  70.72
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-benzylisatin 3-thiosemicarbazone 在 potassium carbonate 作用下， 反应 0.04h， 生成 3-benzylthio-5-benzyl-1,2,4-triazino[5,6-b]indole
  参考文献：
  名称：

  Microwave Irradiation for Accelerating each Step for the Synthesis of 1,2,4-Triazino[5,6-b]indole-3-thiolsand their Derivatives from Isatin and 5-Chloroisatin

  摘要：

  微波辐射已被用于加速异靛（1）、5-氯异靛（2）和N-苄基异靛（3）转化为其硫脲衍生物，并随后环化为1,2,4-三氮唑[5,6-b]吲哚-3-硫醇7和8，以及N-苄基衍生物9。在微波辐射下，1、7、8和9的选择性和完全烷基化也已实现。

  DOI：

  10.1055/s-2004-815437
• 作为产物：
  描述：

  溴甲苯 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.51h， 生成 1-benzylisatin 3-thiosemicarbazone
  参考文献：
  名称：

  Microwave Synthesis, Characterization, and Antimicrobial Activity of Some Novel Isatin Derivatives

  摘要：

  三系列吲哚啉衍生物[3-肼基，3-硫脲基和3-亚胺羧酸衍生物]利用微波辐射合成。制备的化合物通过FT-IR、NMR、元素分析和X射线晶体学对衍生物5b进行表征。合成的化合物对选定的细菌和真菌进行抗菌活性筛选。结果显示，N-烷基吲哚啉衍生物具有不同谱活性。大多数3-肼基和3-硫脲基吲哚啉衍生物在生物学上无活性，通常活性衍生物对革兰氏阳性细菌表现出弱到中等的活性。亚胺吲哚羧酸衍生物（2-[4-(1-苄基-5-溴-2-氧吲哚-3-基亚胺基)苯基]乙酸，5d）对所有经测试的革兰氏阳性细菌和真菌病原体表现出有希望的活性。

  DOI：

  10.1155/2015/716987

文献信息

• Microwave‐assisted synthesis and antimicrobial activity of novel spiro 1,3,4‐thiadiazolines from isatin derivatives
  作者：Daniel Pereira Costa、Aleff Cruz Castro、Girlyanderson Araújo Silva、Claudio Gabriel Lima‐Junior、Francisco Patricio Andrade Júnior、Edeltrudes Oliveira Lima、Boniek Gontijo Vaz、Lidya Cardoso Silva

  DOI：10.1002/jhet.4213

  日期：2021.3

  This work describes the synthesis of spiro 1,3,4‐thiadiazolines from isatin‐β‐thiosemicarbazone acetylation, using microwave irradiation as a source of heating the reaction medium. N‐substituted isatin derivatives were used as substrates to obtain thiosemicarbazones by adding thiosemicarbazide to the isatin ketone carbonyl. The final synthetic step was the reaction of thiosemicarbazones with acetic

  这项工作描述了由Isatin-β-thiosemicarbazone乙酰化反应合成螺1,3,4-噻二唑啉，利用微波辐射作为加热反应介质的来源。ñ通过将thiosemicarbazide添加到isatin ketone羰基上，使用预先取代的isatin衍生物作为底物来获得thiosemicarbazones。最终的合成步骤是在微波辐射下硫代半氨基甲酮与乙酸酐的反应，得到螺环化合物。反应时间为6至18分钟，收率高达90％。生物学测定显示出有希望的抗菌和抗真菌活性，尤其是衍生自烯丙基化的靛红的螺噻二唑啉。根据计算机研究的结果，所有提出的分子均被证明是潜在的候选药物，并且符合Lipinski规则，具有令人满意的相似性和评分。微波反应器的使用对于合成硫半脲和螺环化合物非常有效，从而大大减少了常规加热的反应时间。考虑到抗药性的威胁，这项工作提出了一系列易于通过微波反应获得的生物活性分子。
• Synthesis, spectroscopic characterization, <i>in vitro</i> cytotoxic and structure activity relationships of some mononuclear Ru(II) complexes
  作者：Sreekanth Thota、Srujana Vallala、Mohammad Imran、Sravani Mekala、Shyam Sunder Anchuri、Subhas Somalingappa Karki、Rajeshwar Yerra、Jan Balzarini、Erik De Clercq

  DOI：10.1080/00958972.2013.773318

  日期：2013.3.1

  New mononuclear Ru(II) complexes [Ru(A)(2)(B)](2+), where A=2,2-bipyridine/1,10-phenanthroline and B=3,4,5-tri-OCH3-DPC, 4-CH3-DPC, 4-N(CH3)(2)-DPC, 4-NO2-DPC, N-BITSZ, PTSZ and PINH, were prepared and characterized by spectroscopic methods. The in vitro cytotoxic activities of the complexes and their corresponding ligands were investigated against the human cancer T-lymphocyte cell lines molt 4/c8 and CEM and the murine tumor leukemia cell line L1210, human promyelocytic leukemia cells (HL-60) and Bel-7402 liver cancer cells by MTT assay. The complexes [Ru(A)(2)(B)](2+) (A=1,10-phenanthroline, B=3,4,5-tri-OCH3-DPC) exerts rather more potent activities against all of these cell lines, especially for CEM and L1210. Ru complexes and structure-activity relationships and anticancer mechanisms are also discussed.
• Microwave Irradiation for Accelerating each Step for the Synthesis of 1,2,4-Triazino[5,6-<i>b</i>]indole-3-thiolsand their Derivatives from Isatin and 5-Chloroisatin
  作者：El Sayed H. El Ashry、El Sayed Ramadan、Hamida M. Hamid、Mohamed Hagar

  DOI：10.1055/s-2004-815437

  日期：——

  Microwave irradiation has been used to accelerate the conversion of isatin (1), 5-chloroisatin (2), and N-benzylisatin (3) to their thiosemicarbazones and their subsequent cyclization into 1,2,4-triazino[5,6-b]indole-3-thiols 7 and 8; and the N-benzyl derivative 9. Selective and complete alkylation of 1, 7, 8, and 9 has also been achieved under microwave irradiation.

  微波辐射已被用于加速异靛（1）、5-氯异靛（2）和N-苄基异靛（3）转化为其硫脲衍生物，并随后环化为1,2,4-三氮唑[5,6-b]吲哚-3-硫醇7和8，以及N-苄基衍生物9。在微波辐射下，1、7、8和9的选择性和完全烷基化也已实现。
• Microwave Synthesis, Characterization, and Antimicrobial Activity of Some Novel Isatin Derivatives
  作者：Ayman El-Faham、Wael N. Hozzein、Mohammad A. M. Wadaan、Sherine N. Khattab、Hazem A. Ghabbour、Hoong-Kun Fun、Mohammed Rafiq Siddiqui

  DOI：10.1155/2015/716987

  日期：——

  Three series of isatin derivatives [3-hydrazino, 3-thiosemicarbazino, and 3-imino carboxylic acid derivatives] were synthesized employing microwave irradiation. The prepared compounds were characterized by FT-IR, NMR, elemental analysis, and X-ray crystallography for derivatives5b. The synthesized compounds were screened for antimicrobial activity against selected bacteria and fungi. The results revealed that theN-alkyl isatin derivatives were biologically active with different spectrums activity. Most of the 3-hydrazino and 3-thiosemicarbazino isatin derivatives were biologically inactive and generally the active derivatives showed weak to moderate activity mainly against Gram-positive bacteria. The imino isatin carboxylic acid derivatives (2-[4-(1-benzyl-5-bromo-2-oxoindolin-3-ylideneamino) phenyl]acetic acid,5d) showed promising activity against all tested Gram-positive bacteria and against fungal pathogens.

  三系列吲哚啉衍生物[3-肼基，3-硫脲基和3-亚胺羧酸衍生物]利用微波辐射合成。制备的化合物通过FT-IR、NMR、元素分析和X射线晶体学对衍生物5b进行表征。合成的化合物对选定的细菌和真菌进行抗菌活性筛选。结果显示，N-烷基吲哚啉衍生物具有不同谱活性。大多数3-肼基和3-硫脲基吲哚啉衍生物在生物学上无活性，通常活性衍生物对革兰氏阳性细菌表现出弱到中等的活性。亚胺吲哚羧酸衍生物（2-[4-(1-苄基-5-溴-2-氧吲哚-3-基亚胺基)苯基]乙酸，5d）对所有经测试的革兰氏阳性细菌和真菌病原体表现出有希望的活性。