2-(5-mercaptopentyl)isoindoline-1,3-dione | 522607-46-1

• 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-(5-mercaptopentyl)isoindoline-1,3-dione
• 英文别名: N-(5-mercapto-pentyl)-phthalimide；N-(5-Mercapto-pentyl)-phthalimid；2-(5-Mercaptopentyl)isoindoline-1,3-dione；2-(5-sulfanylpentyl)isoindole-1,3-dione
• CAS: 522607-46-1
• 化学式: C₁₃H₁₅NO₂S
• 分子量: 249.334
• InChiKey: ZPKDSHNYTKSTHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(5-mercaptopentyl)isoindoline-1,3-dione 在 sodium hydride 、 一水合肼 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 5-Propan-2-ylsulfanylpentan-1-amine
  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
• 作为产物：
  描述：

  N-(5-溴戊基)邻苯二甲酰亚胺 在 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 生成 2-(5-mercaptopentyl)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

• Structure-based molecular hybridization design of Keap1-Nrf2 inhibitors as novel protective agents of acute lung injury
  作者：Le Zhang、Lijuan Xu、Haihu Chen、Wannian Zhang、Chengguo Xing、Zhuo Qu、Jianqiang Yu、Chunlin Zhuang

  DOI：10.1016/j.ejmech.2021.113599

  日期：2021.10

  and related-inflammation, including acute lung injury (ALI). NXPZ-2, a naphthalensulfonamide derivative, was previously reported to effectively inhibit the Keap1-Nrf2 protein-protein interaction (PPI) by our group. In the present work, a series of novel isothiocyanate-containing naphthalensulfonamides with the thioether, sulfoxide and sulfone moieties were designed by a structure-based molecular hybridization

  阻断 Kelch 样表氯醇相关蛋白 1 (Keap1)-核因子-红细胞 2 相关因子 2 (Nrf2) 通路是减少氧化应激和相关炎症，包括急性肺损伤 (ALI) 的一种有前景的策略。NXPZ-2是一种萘磺酰胺衍生物，我们团队先前曾报道它可有效抑制 Keap1-Nrf2 蛋白-蛋白相互作用 (PPI)。在目前的工作中，使用NXPZ-2通过基于结构的分子杂交策略设计了一系列具有硫醚、亚砜和砜部分的新型含异硫氰酸酯萘磺酰胺。和 Nrf2 激活剂萝卜硫素。它们具有良好的 Keap1-Nrf2 PPI 抑制活性和低细胞毒性。进行分子对接研究以进一步解释含硫醚、亚砜和砜的萘磺酰胺的不同活性。在这些新衍生物中，2-((N-(4-((N-(2-amino-2-oxoethyl)-4-((3-isothiocyanatopropyl)sulfinyl)phenyl)sulfonamido)naphthalen-1-yl)-4
• Manasse, Chemische Berichte, 1902, vol. 35, p. 1371
  作者：Manasse

  DOI：——

  日期：——
• Synthesis and biological evaluation of sulforaphane derivatives as potential antitumor agents
  作者：Kun Hu、Yan-jie Qi、Juan Zhao、He-fei Jiang、Xin Chen、Jie Ren

  DOI：10.1016/j.ejmech.2013.03.045

  日期：2013.6

  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.
• Novel CDKs inhibitors for the treatment of solid tumour by simultaneously regulating the cell cycle and transcription control
  作者：Xin Wang、Kaiyuan Deng、Cheng Wang、Yao Li、Tianqi Wang、Zhi Huang、Yakun Ma、Peiqing Sun、Yi Shi、Shengyong Yang、Yan Fan、Rong Xiang

  DOI：10.1080/14756366.2019.1705290

  日期：2020.1.1

  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.