N-(7-(((2R,3R,4S,5R)-4-amino-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzamide | 1446752-53-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(7-(((2R,3R,4S,5R)-4-amino-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzamide
• 英文别名: N-[7-[(2R,3R,4S,5R)-4-amino-3-hydroxy-5-methoxy-6,6-dimethyloxan-2-yl]oxy-8-methyl-2-oxochromen-3-yl]benzamide
• CAS: 1446752-53-9
• 化学式: C₂₅H₂₈N₂O₇
• 分子量: 468.507
• InChiKey: YNKNJJNPCVGIPT-YWQGAKJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (3R,4S)-4-amino-3-methoxy-2-methylhept-6-en-2-ol 在 吡啶 、 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 、 苯磺酰氯 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 水 、 甲苯 为溶剂， 反应 40.5h， 生成 N-(7-(((2R,3R,4S,5R)-4-amino-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-8-methyl-2-oxo-2H-chromen-3-yl)benzamide
  参考文献：
  名称：

  Simplified aminocoumarin analogues as anticancer agents: Amino isosteric replacement in the noviose moiety resulted in substantial enhancement of antiproliferative activity

  摘要：

  Simplified aminocoumarin analogues, either noviosylated or simple basic heterocycle attached 3-amidocoumarin compounds, are known to be promising anticancer agents targeting the C-terminal ATP-binding site of Hsp90. In this study, 3'-amino isosteric replacement in the noviose moiety of two known noviose containing Hsp90 C-terminal inhibitors was synthetically realized for the first time. In vitro evaluation of these compounds suggested that the introduction of a basic amino group into the noviose subunit resulted in significant improvement of their cytotoxicities. (C) 2013 Yun-Feng Li and Nan Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.04.046

文献信息

• Simplified aminocoumarin analogues as anticancer agents: Amino isosteric replacement in the noviose moiety resulted in substantial enhancement of antiproliferative activity
  作者：Ting Zhang、Zheng Yan、Yun-Feng Li、Nan Wang

  DOI：10.1016/j.cclet.2013.04.046

  日期：2013.8

  Simplified aminocoumarin analogues, either noviosylated or simple basic heterocycle attached 3-amidocoumarin compounds, are known to be promising anticancer agents targeting the C-terminal ATP-binding site of Hsp90. In this study, 3'-amino isosteric replacement in the noviose moiety of two known noviose containing Hsp90 C-terminal inhibitors was synthetically realized for the first time. In vitro evaluation of these compounds suggested that the introduction of a basic amino group into the noviose subunit resulted in significant improvement of their cytotoxicities. (C) 2013 Yun-Feng Li and Nan Wang. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.