(6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)(3,4-dihydroxyphenyl)methanone | 950750-00-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)(3,4-dihydroxyphenyl)methanone
• 英文别名: (6,7-dihydroxy-3,4-dihydro-1H-isoquinolin-2-yl)-(3,4-dihydroxyphenyl)methanone
• CAS: 950750-00-2
• 化学式: C₁₆H₁₅NO₅
• 分子量: 301.299
• InChiKey: YBUITHUFINKGKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)(3,4-dihydroxyphenyl)methanone 在 三甲基铵三氧化硫共聚物 、 三乙胺 作用下， 以 乙腈 为溶剂， 以85%的产率得到
  参考文献：
  名称：

  Rapid and efficient microwave-assisted synthesis of highly sulfated organic scaffolds

  摘要：

  Sulfation of multiple hydroxylated small organic molecules is fraught with problems of poor yield, multitude of products, and long reaction times. We have developed a rapid microwave-based method for synthesis of highly sulfated small organic molecules, which affords the per-sulfated product in moderate to excellent yields and high purity. The method is expected to be of value in the discovery of per-sulfated organic molecules as mimics of glycosaminoglycans, which are being increasingly recognized as modulators of key physiological functions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.100
• 作为产物：
  描述：

  3,4-di(benzyloxy)phenethylamine 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)(3,4-dihydroxyphenyl)methanone
  参考文献：
  名称：

  多巴胺衍生物的合成和SARs作为流感病毒PAN核酸内切酶的潜在抑制剂。

  摘要：

  当前，流感PAN核酸内切酶已成为开发用于治疗流感感染的新药物的有吸引力的靶标。在本文中，我们报道了从螯合剂多巴胺部分衍生的新PAN核酸内切酶抑制剂的发现。精心制作了一系列多巴胺酰胺衍生物及其受构象限制的1,2,3,4-四氢异喹啉-6,7-二醇基类似物，并针对流感病毒A / WSN / 33（H1N1）进行了分析。大多数化合物表现出中度到出色的抗病毒活性，产生初步的SAR。其中，与参考的Peramivir相比，化合物14和19显示出更强的抗IAV活性。此外，基于FRET测定和SPR测定，14和19证明了浓度依赖性抑制PAN核酸内切酶。还进行了对接研究，以阐明14和19与PAN蛋白的结合模式，并鉴定参与其作用机理的氨基酸，这与生物学数据非常一致。这一发现为合理开发更有效的PAN核酸内切酶抑制剂奠定了基础。

  DOI：

  10.1016/j.ejmech.2020.112048

文献信息

• Discovery of novel sulfonated small molecules that inhibit vascular tube formation
  作者：Karthik Raman、Rajesh Karuturi、Vimal P. Swarup、Umesh R. Desai、Balagurunathan Kuberan

  DOI：10.1016/j.bmcl.2012.04.014

  日期：2012.7

  Tumor-associated angiogenesis is a complex process that involves the interplay among several molecular players such as cell-surface heparan sulfate proteoglycans, vascular endothelial growth factors and their cognate receptors. PI-88, a highly sulfonated oligosaccharide, has been shown to have potent anti-angiogenic activity and is currently in clinical trials. However, one of the major drawbacks of large oligosaccharides such as PI-88 is that their synthesis often requires numerous complex synthetic steps. In this study, several novel polysulfonated small molecule carbohydrate mimetics, which can easily be synthesized in fewer steps, are identified as promising inhibitors of angiogenesis in an in vitro tube formation assay. (C) 2012 Elsevier Ltd. All rights reserved.