2-(4-((4-nitrobenzyl)thio)butyl)isoindoline-1,3-dione | 1414792-36-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(4-((4-nitrobenzyl)thio)butyl)isoindoline-1,3-dione
• 英文别名: 2-[4-[(4-Nitrophenyl)methylsulfanyl]butyl]isoindole-1,3-dione
• CAS: 1414792-36-1
• 化学式: C₁₉H₁₈N₂O₄S
• 分子量: 370.429
• InChiKey: KTBNDVOUXWRPHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-((4-nitrobenzyl)thio)butyl)isoindoline-1,3-dione 在 间氯过氧苯甲酸 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Novel CDKs inhibitors for the treatment of solid tumour by simultaneously regulating the cell cycle and transcription control

  摘要：

  A novel series of cyclin-dependent kinases (CDKs) inhibitors, which play critical roles in the cell cycle control and regulation of cell transcription, were synthesised. A systematic study of enzymatic and cellular assays led to the identification of compound X22 with a nanomolar potency against CDK4 and CDK9 and potent antiproliferative activities against a panel of tumour cell lines. X22 could induce cell cycle arrest and cell apoptosis in cancer cell lines. X22 dose-dependently inhibits signalling pathways downstream of CDKs in cancer cells. In vivo antitumor activity assays, oral administration of X22 led to significant tumour regression in mouse model without obvious toxicity. Superior anti-cancer efficacy in vitro and in vivo of X22 demonstrated combined depletion of cell cycle and transcriptional CDK all contributed to antitumor activity. Taken together, concomitant inhibition of cell cycle and transcriptional CDK activities provided valuable guide for further structural optimisation.

  DOI：

  10.1080/14756366.2019.1705290
• 作为产物：
  描述：

  S-(4-(1,3-dioxoisoindolin-2-yl)butyl)ethanethioate 在 盐酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 生成 2-(4-((4-nitrobenzyl)thio)butyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of sulforaphane derivatives as potential antitumor agents

  摘要：

  A series of sulforaphane derivatives were synthesized and evaluated in vitro for their cytotoxicity against five cancer cell lines (HepG2, A549, MCF-7, HCT-116 and SH-SY5Y). The pharmacological results showed that many of the derivatives displayed more potent cytotoxicity than sulforaphane (SFN). Furthermore, SFN and derivative 85 could induce cell cycle arrest at S or G2/M phase and cell apoptosis. SFN and 85 exhibited time- and dose-dependent activation on Nrf2 transcription factor, and 85 acted as a more potent Nrf2 inducer than SFN. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.045

文献信息

• Synthesis and Evaluation of Novel Erucin Analogues as Potential Antitumor Compounds
  作者：Yan-Dong Shao、Huang-Wang Song、Wen Feng、Xiang-Hui Wang、Zai-Feng Shi、Lu-Yong Wu、Guang-Ying Chen、Qiang Lin

  DOI：10.2174/1570178614666170710100743

  日期：2018.2.7

  Background：Several studies have shown excellent antitumor activity of erucin, but there are few studies on its analogues. The aim of the study involves the synthesis and the antitumor activities of novel erucin analogues. Ten novel erucin analogues were synthesized and evaluated for their efficacy as antitumor agents. Methods: Ten novel erucin analogues were synthesized by using 1, 4-dibromobutane and

  背景：多项研究表明，芥子油具有优异的抗肿瘤活性，但有关其类似物的研究很少。该研究的目的涉及新型芥酸类似物的合成及其抗肿瘤活性。合成了十种新型芥酸类似物，并评估了其作为抗肿瘤药的功效。 方法：以1，4-二溴丁烷和邻苯二甲酰亚胺钾为起始原料，合成了十种新型芥酸类似物，筛选了针对乳腺癌细胞（MCF-7），宫颈癌细胞（HeLa-229）和肺癌的体外抗肿瘤活性。癌细胞（A549）。 结果：通过1H NMR，13C NMR和元素分析证实了这些新型化合物的结构。初步的生物测定结果表明，所有测试化合物均显示出有效的抗肿瘤活性。在这些化合物中，化合物6b对MCF-7的抑制作用最佳，IC50值为0.46 µM，对A549的抑制作用为IC50值为0.44 µM。化合物6f还显示出对HeLa-229的最佳抑制作用，IC50值为0.32 µM。 结论：合成和筛选了一系列新型芥酸类似物的抗肿瘤活性。所有合成化合物均显