2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)hydrazinecarbothioamide | 6532-26-9

• 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: 2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
• 英文别名: N¹-(diethylamino)methylindole-2,3-dione 3-thiosemicarbazone；N¹-diethylaminomethyl-indole-2,3-dione-3-thiosemicarbazone；N1-diethylaminomethyl-indole-2,3-dione-3-thiosemicarbazone；[[1-(diethylaminomethyl)-2-oxoindol-3-ylidene]amino]thiourea
• CAS: 6532-26-9
• 化学式: C₁₄H₁₉N₅OS
• 分子量: 305.404
• InChiKey: UIOZUNJOVSPBME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  73.96
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  苯胺 在 硫酸 、 溶剂黄146 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 反应 0.4h， 生成 2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-(5-substituted-1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-N-substituted-hydrazinecarbothioamides

  摘要：

  Various 5-substituted-2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (4a, b) and 5-substituted-2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-N-(phenyl-4-substituted)hydrazinecarbothioamide (5a-h) derivatives were synthesized. The compounds were screened for cytotoxicity against human HeLa and CEM T-lymphocytes as well as murine L1210 cells. The compounds were also screened for beta-lactamase inhibitory activity, antiviral, antibacterial, and antifungal activity against various strains of microorganisms. Several of these compounds were endowed with low micromolar 50 %-cytostatic concentration (IC50) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells (L1210) were also the most inhibitory against human T-lymphocyte (CEM) tumor cells. Derivative 2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-N-(4-methoxyphenyl)hydrazinecarbothioamide 5c emerged as the most potent cytostatic compound among the tested compounds. Derivatives 4b, 5a, 5b, and 5d showed antiviral activity against HEL cell cultures (IC50 11-20 mu M). Moderate antimicrobial activity was observed for all derivatives. The encouraging cytostatic and antiviral activity data provide an adequate rationale for further modification of these molecular scaffolds.Derivative 5c (1.9-4.4 mu M) emerged as the most potent cytostatic compound among the tested compounds. Derivatives 4b, 5a, 5b, and 5d showed antiviral activity against HEL cell cultures (IC50 11-20 mu M).

  DOI：

  10.1007/s00044-012-0184-x

文献信息

• Solvent-free microwave-assisted synthesis of 1<i>H</i>-indole-2, 3-dione derivatives
  作者：Ashish Kumar Singh、Sudhish Kumar Shukla、Ishtiaque Ahamad、M. A. Quraishi

  DOI：10.1002/jhet.131

  日期：2009.5

  Microwave-assisted synthesis has been found to increase both reaction rates and yields via more efficient heating compared with standard thermal conduction. Dry reaction of isatins with thiosemicarbazide and their thiosemicarbazone with secondary amine on acid—washed K10 in microwave oven afforded isatin-3-thiosemicarbazones and N-Mannich bases in reasonably good yield. The chemical structures were

  已经发现，与标准的热传导相比，微波辅助合成通过更有效的加热可以提高反应速率和产率。Isatin与thiosemicarbazide以及它们的thiosemicarbazone与仲胺在酸上的干反应-在微波炉中洗涤K10，可以得到相当好的产率的isatin-3-thiosemicarbazones和N-Mannich碱。化学结构通过1 H NMR，IR光谱数据和元素分析得到确认。J.杂环化​​学。，46，571（2009）。
• Microwave-Assisted Synthesis of Some Novel Thiazolidinone and Thiohydantoin Derivatives of Isatins
  作者：Dushyant Singh Raghuvanshi、Krishna Nand Singh

  DOI：10.1080/10426500903567554

  日期：2010.10.28

  A simple, rapid, and efficient method for the synthesis of some new thiazolidinone and thiohydantoin derivatives of isatins along with some Mannich bases has been achieved in excellent yield from indole-2,3-dione-3-thiosemicarbazone employing microwave irradiation.

  一种简单、快速和有效的方法，用于合成一些新的靛红噻唑烷酮和硫代乙内酰脲衍生物以及一些曼尼希碱，使用微波辐射从 indole-2,3-dione-3-thiosemicarbazone 中获得了极好的收率。
• Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives
  作者：Idan Chiyanzu、Cailean Clarkson、Peter J. Smith、Julie Lehman、Jiri Gut、Philip J. Rosenthal、Kelly Chibale

  DOI：10.1016/j.bmc.2005.02.037

  日期：2005.5

  A new class of 4-aminoquinoline derivatives based on the natural product isatin scaffold were designed and synthesized for biological evaluation against three strains of the malaria parasite Plasmodium falciparum. These derivatives showed anti-plasmodial IC50 values in the ranges of 1.3-0.079 and 2.0-0.050 mu M against a chloroquine-sensitive (D10) and two resistant (K1 and W2) strains of P. falciparum, respectively. In order to determine potential targets for this class of compounds in P. falciparum, selected compounds were also tested against the parasitic cysteine protease falcipain-2. In terms of further development of this class of isatin derivatives, two of the compounds based on a flexible alkyl chain linker and a thiosemicarbazone moiety warrant further investigation as potential anti-plasmodial leads. These two derivatives showed good in vitro activity against K1 and W2 with IC50 values of 51 and 54 nM, respectively, while retaining potency against the D10 strain with IC50 values of 79 and 95 nM, respectively. Generally speaking, the inhibitory potency of all compounds in the series against the parasites did not strongly correlate with inhibitory potency against falcipain-2 for selected compounds tested, which at best was weak to moderate, suggesting other mechanisms of inhibition may also be involved or compounds may be selectively taken up by Plasmodium falciparum. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of 2-(5-substituted-1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-N-substituted-hydrazinecarbothioamides
  作者：Subhas S. Karki、Amol A. Kulkarni、Sujeet Kumar、Suresh Kumar Veliyath、Erik De Clercq、Jan Balzarini

  DOI：10.1007/s00044-012-0184-x

  日期：2013.4

  Various 5-substituted-2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)hydrazinecarbothioamide (4a, b) and 5-substituted-2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-N-(phenyl-4-substituted)hydrazinecarbothioamide (5a-h) derivatives were synthesized. The compounds were screened for cytotoxicity against human HeLa and CEM T-lymphocytes as well as murine L1210 cells. The compounds were also screened for beta-lactamase inhibitory activity, antiviral, antibacterial, and antifungal activity against various strains of microorganisms. Several of these compounds were endowed with low micromolar 50 %-cytostatic concentration (IC50) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells (L1210) were also the most inhibitory against human T-lymphocyte (CEM) tumor cells. Derivative 2-(1-((diethylamino)methyl)-2-oxoindolin-3-ylidene)-N-(4-methoxyphenyl)hydrazinecarbothioamide 5c emerged as the most potent cytostatic compound among the tested compounds. Derivatives 4b, 5a, 5b, and 5d showed antiviral activity against HEL cell cultures (IC50 11-20 mu M). Moderate antimicrobial activity was observed for all derivatives. The encouraging cytostatic and antiviral activity data provide an adequate rationale for further modification of these molecular scaffolds.Derivative 5c (1.9-4.4 mu M) emerged as the most potent cytostatic compound among the tested compounds. Derivatives 4b, 5a, 5b, and 5d showed antiviral activity against HEL cell cultures (IC50 11-20 mu M).