2,2-dimethyl-6,7-bis((4-nitrobenzyl)oxy)chroman-4-ol | 131859-43-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2-dimethyl-6,7-bis((4-nitrobenzyl)oxy)chroman-4-ol
• 英文别名: 2,2-Dimethyl-6,7-bis[(4-nitrophenyl)methoxy]-3,4-dihydrochromen-4-ol
• CAS: 131859-43-3
• 化学式: C₂₅H₂₄N₂O₈
• 分子量: 480.474
• InChiKey: SMXZREIVHGBWMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-6,7-bis((4-nitrobenzyl)oxy)chroman-4-ol 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 以96%的产率得到2,2-dimethyl-6,7-bis((4-nitrobenzyl)oxy)-2H-chromene
  参考文献：
  名称：

  Discovery of Small Molecules as Multi-Toll-like Receptor Agonists with Proinflammatory and Anticancer Activities

  摘要：

  Therapies based on activation of multiple Toll-like receptors (TLRs) may offer superior therapeutic profiles than that of single TLR activation. To, discover new small molecules that could activate multiple TLRs, we performed a cell-based high-throughput, screening of a small-molecule library based on TLR3-mediated NF-kappa B activation. Subsequent structural optimization and counterscreening of other TLRs produced the first small molecule 17e (CU-CPT17e), capable of simultaneously activating TLRs 3) 8, and 9. Biochemical studies demonstrated that 17e could induce a strong immune response via the production of various cytokines in human monocytic THP-1 cells. Furthermore, 17e inhibited the proliferation of HeLa cancer cells by triggering apoptosis and arresting the-cell. cycle at the S phase. These results Showcase potential therapeutic applications of 17e it both vaccine adjuvants and anticancer therapies based on multi-TLR activation.

  DOI：

  10.1021/acs.jmedchem.7b00419
• 作为产物：
  描述：

  2,2-dimethyl-6,7-bis((4-nitrobenzyl)oxy)chroman-4-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以81%的产率得到2,2-dimethyl-6,7-bis((4-nitrobenzyl)oxy)chroman-4-ol
  参考文献：
  名称：

  Discovery of Small Molecules as Multi-Toll-like Receptor Agonists with Proinflammatory and Anticancer Activities

  摘要：

  Therapies based on activation of multiple Toll-like receptors (TLRs) may offer superior therapeutic profiles than that of single TLR activation. To, discover new small molecules that could activate multiple TLRs, we performed a cell-based high-throughput, screening of a small-molecule library based on TLR3-mediated NF-kappa B activation. Subsequent structural optimization and counterscreening of other TLRs produced the first small molecule 17e (CU-CPT17e), capable of simultaneously activating TLRs 3) 8, and 9. Biochemical studies demonstrated that 17e could induce a strong immune response via the production of various cytokines in human monocytic THP-1 cells. Furthermore, 17e inhibited the proliferation of HeLa cancer cells by triggering apoptosis and arresting the-cell. cycle at the S phase. These results Showcase potential therapeutic applications of 17e it both vaccine adjuvants and anticancer therapies based on multi-TLR activation.

  DOI：

  10.1021/acs.jmedchem.7b00419

文献信息

• Levai; Timar, Pharmazie, 1990, vol. 45, # 9, p. 660 - 662
  作者：Levai、Timar

  DOI：——

  日期：——
• LEVAI, A.;TIMAR, T., PHARMAZIE, 45,(1990) N, C. 660-662
  作者：LEVAI, A.、TIMAR, T.

  DOI：——

  日期：——