3,7-anhydro-6-O-diphenylphosphono-8-fluoro-4-[(R)-3-hydroxytetradecanoylamino]-5-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2,4,8-trideoxy-D-glycero-D-ido-octonic acid | 389087-57-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,7-anhydro-6-O-diphenylphosphono-8-fluoro-4-[(R)-3-hydroxytetradecanoylamino]-5-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2,4,8-trideoxy-D-glycero-D-ido-octonic acid
• 英文别名: 2-[(2R,3S,4R,5S,6S)-6-(fluoromethyl)-3-[[(3R)-3-hydroxytetradecanoyl]amino]-5-[oxido(diphenoxy)phosphaniumyl]oxy-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxyoxan-2-yl]acetic acid
• CAS: 389087-57-4
• 化学式: C₆₂H₁₀₁FNO₁₃P
• 分子量: 1118.46
• InChiKey: KTCKSGAWJGKGPV-NMVJCKELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.3
• 重原子数：
  78
• 可旋转键数：
  50
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  199
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-6-O-diphenylphosphono-8-fluoro-4-[(R)-3-hydroxytetradecanoylamino]-5-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2,4,8-trideoxy-D-glycero-D-ido-octonic acid 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以94.4%的产率得到3,7-anhydro-8-fluoro-4-[(R)-3-hydroxytetradecanoylamino]-6-O-phosphono-5-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2,4,8-trideoxy-D-glycero-D-ido-octonic acid
  参考文献：
  名称：

  Synthesis and Biological Activity of 3,7-Anhydro-2,4-dideoxy-4-[(R)-3-hydroxytetradecanoylamino]-6-O-phosphono-5-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-octonic Acid Derivatives

  摘要：

  合成了d-氨基葡萄糖乙酸衍生物（10、11和12）以研究其对人类单核细胞U937细胞的LPS拮抗活性。化合物10和11表现出弱的LPS拮抗活性，但12表现出LPS的拮抗和激动活性，具体取决于浓度。

  DOI：

  10.1246/bcsj.74.1661
• 作为产物：
  描述：

  3,7-anhydro-4-[(R)-3-benzyloxytetradecanoylamino]-2,4-dideoxy-6-O-diphenylphosphono-5-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-octonic acid benzyl ester 在 palladium hydroxide - carbon (diethylaminato)trifluorosulfur 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 17.5h， 生成 3,7-anhydro-6-O-diphenylphosphono-8-fluoro-4-[(R)-3-hydroxytetradecanoylamino]-5-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2,4,8-trideoxy-D-glycero-D-ido-octonic acid
  参考文献：
  名称：

  Synthesis and Biological Activity of 3,7-Anhydro-2,4-dideoxy-4-[(R)-3-hydroxytetradecanoylamino]-6-O-phosphono-5-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glycero-D-ido-octonic Acid Derivatives

  摘要：

  合成了d-氨基葡萄糖乙酸衍生物（10、11和12）以研究其对人类单核细胞U937细胞的LPS拮抗活性。化合物10和11表现出弱的LPS拮抗活性，但12表现出LPS的拮抗和激动活性，具体取决于浓度。

  DOI：

  10.1246/bcsj.74.1661

文献信息

• Synthesis and Biological Activity of 3,7-Anhydro-2,4-dideoxy-4-[(<i>R</i>)-3-hydroxytetradecanoylamino]-6-<i>O</i>-phosphono-5-<i>O</i>-[(<i>R</i>)-3-(tetradecanoyloxy)tetradecanoyl]-D-<i>glycero</i>-D-<i>ido</i>-octonic Acid Derivatives
  作者：Takanori Wakabayashi、Masao Shiozaki、Saori Kanai、Shin-ichi Kurakata

  DOI：10.1246/bcsj.74.1661

  日期：2001.9

  d-Glucosaminylacetic acid derivatives (10, 11 and 12) of GLA-60 were synthesized to investigate the LPS-antagonistic activity toward human monoblastic U937 cells. Compounds 10 and 11 show weak LPS-antagonistic activity, but 12 shows both LPS-antagonistic and -agonistic activities, depending on the concentration.

  合成了d-氨基葡萄糖乙酸衍生物（10、11和12）以研究其对人类单核细胞U937细胞的LPS拮抗活性。化合物10和11表现出弱的LPS拮抗活性，但12表现出LPS的拮抗和激动活性，具体取决于浓度。