19-[(1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl]-4,5-dihydrogeldanamycin | 1432746-50-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 19-[(1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl]-4,5-dihydrogeldanamycin
• 英文别名: [(4E,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-21-[(1S,4R)-4-hydroxy-1-methoxy-2-oxopentyl]-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18-tetraen-9-yl] carbamate
• CAS: 1432746-50-3
• 化学式: C₃₅H₅₂N₂O₁₂
• 分子量: 692.804
• InChiKey: IWXKDLKUMGGABM-LTNRGABZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  49
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  210
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (S)-(+)-alpha-甲氧基苯乙酸 、 19-[(1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl]-4,5-dihydrogeldanamycin 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 [(2R,5S)-5-[(4E,8S,9S,10E,12S,13R,14S,16R)-9-carbamoyloxy-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,10,18-tetraen-21-yl]-5-methoxy-4-oxopentan-2-yl] (2S)-2-methoxy-2-phenylacetate
  参考文献：
  名称：

  19-[(1′S,4′R)-4′-Hydroxy-1′-methoxy-2′-oxopentyl]geldanamycin, a Natural Geldanamycin Analogue from Streptomyces hygroscopicus 17997

  摘要：

  A novel natural geldanamycin analogue was discovered in Streptomyces hygroscopicus 17997. Its 4,5-dihydro form was also identified in the gdmP gene disruption mutant of Streptomyces hygroscopicus 17997.. The structures of the two compounds were determined to be 194(1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl]geldanamycin (1) and 19-[(1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl]-4,5-dihydrogeldanamycin (2), respectively, by extensive spectroscopic data analysis, including 2D NMR, modified Mosher's method, and electronic circular dichroism. Compared to geldanamycin, 1 and 2. showed increased water solubility and decreased cytotoxicity against HepG2 cells.

  DOI：

  10.1021/np4000679

文献信息

• 19-[(1′<i>S</i>,4′<i>R</i>)-4′-Hydroxy-1′-methoxy-2′-oxopentyl]geldanamycin, a Natural Geldanamycin Analogue from <i>Streptomyces hygroscopicus</i> 17997
  作者：Shufen Li、Siyang Ni、Linzhuan Wu、Li Li、Bingya Jiang、Hongyuan Wang、Guizhi Sun、Maoluo Gan、Jingyan Li、Weiqing He、Ling Lin、Yiguang Wang、Shuoke Bai、Shuyi Si

  DOI：10.1021/np4000679

  日期：2013.5.24

  A novel natural geldanamycin analogue was discovered in Streptomyces hygroscopicus 17997. Its 4,5-dihydro form was also identified in the gdmP gene disruption mutant of Streptomyces hygroscopicus 17997.. The structures of the two compounds were determined to be 194(1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl]geldanamycin (1) and 19-[(1'S,4'R)-4'-hydroxy-1'-methoxy-2'-oxopentyl]-4,5-dihydrogeldanamycin (2), respectively, by extensive spectroscopic data analysis, including 2D NMR, modified Mosher's method, and electronic circular dichroism. Compared to geldanamycin, 1 and 2. showed increased water solubility and decreased cytotoxicity against HepG2 cells.