2-O-(N-hexanoyl-6-amino-6-deoxy-β-d-glucopyranosyl)-sn-glycerol | 1435740-14-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-O-(N-hexanoyl-6-amino-6-deoxy-β-d-glucopyranosyl)-sn-glycerol
• 英文别名: N-[[(2R,3S,4S,5R,6R)-6-(1,3-dihydroxypropan-2-yloxy)-3,4,5-trihydroxyoxan-2-yl]methyl]hexanamide
• CAS: 1435740-14-9
• 化学式: C₁₅H₂₉NO₈
• 分子量: 351.397
• InChiKey: MUEFABCDUTZDSH-TVKJYDDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoroethyl hexanoate 、 2-O-(N-hexanoyl-6-amino-6-deoxy-β-d-glucopyranosyl)-sn-glycerol 在 吡啶 作用下， 反应 24.0h， 以80%的产率得到1-O-hexanoyl-2-O-(N-hexanoyl-6-amino-6-deoxyb-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  New 6-amino-6-deoxy-glycoglycerolipids derived from 2-O-β-d-glucopyranosylglycerol: insights into the structure–activity relationship of glycoglycerolipids as anti-tumor promoters

  摘要：

  As part of a project aimed at obtaining compounds capable of inhibiting tumor promotion, new 6-amino-6-deoxyglycoglycerolipids (AGGLs) derived from 2-O-beta-D-glucopyranosyl-sn-glycerol were synthesized and tested for their anti-tumor-promoting activity using a short-term in vitro assay of the inhibition of Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The corresponding 6-amino-6-deoxy-beta-D-octylglucosides were also prepared as simplified aminoglycolipid models and tested. Comparison with the activity of a series of previously studied glycoglycerolipids showed that replacing the 6-oxygen of the glucose moiety by a nitrogen atom greatly reduced the in vitro activity of the compounds. A two-stage mouse skin carcinogenesis test of two representative aminoglycoglycerolipids confirmed their reduced activity also in this in vivo model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.007
• 作为产物：
  描述：

  1,3-di-O-benzyl-2-O-(6-amino-6-deoxy-β-D-glucopyranosyl)-sn-glycerol 在 吡啶 、 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 2-O-(N-hexanoyl-6-amino-6-deoxy-β-d-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  New 6-amino-6-deoxy-glycoglycerolipids derived from 2-O-β-d-glucopyranosylglycerol: insights into the structure–activity relationship of glycoglycerolipids as anti-tumor promoters

  摘要：

  As part of a project aimed at obtaining compounds capable of inhibiting tumor promotion, new 6-amino-6-deoxyglycoglycerolipids (AGGLs) derived from 2-O-beta-D-glucopyranosyl-sn-glycerol were synthesized and tested for their anti-tumor-promoting activity using a short-term in vitro assay of the inhibition of Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The corresponding 6-amino-6-deoxy-beta-D-octylglucosides were also prepared as simplified aminoglycolipid models and tested. Comparison with the activity of a series of previously studied glycoglycerolipids showed that replacing the 6-oxygen of the glucose moiety by a nitrogen atom greatly reduced the in vitro activity of the compounds. A two-stage mouse skin carcinogenesis test of two representative aminoglycoglycerolipids confirmed their reduced activity also in this in vivo model. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.03.007

文献信息

• New 6-amino-6-deoxy-glycoglycerolipids derived from 2-O-β-d-glucopyranosylglycerol: insights into the structure–activity relationship of glycoglycerolipids as anti-tumor promoters
  作者：Diego Colombo、Clarissa Gagliardi、Maria Vetro、Fiamma Ronchetti、Midori Takasaki、Takao Konoshima、Nobutaka Suzuki、Harukuni Tokuda

  DOI：10.1016/j.carres.2013.03.007

  日期：2013.5

  As part of a project aimed at obtaining compounds capable of inhibiting tumor promotion, new 6-amino-6-deoxyglycoglycerolipids (AGGLs) derived from 2-O-beta-D-glucopyranosyl-sn-glycerol were synthesized and tested for their anti-tumor-promoting activity using a short-term in vitro assay of the inhibition of Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA). The corresponding 6-amino-6-deoxy-beta-D-octylglucosides were also prepared as simplified aminoglycolipid models and tested. Comparison with the activity of a series of previously studied glycoglycerolipids showed that replacing the 6-oxygen of the glucose moiety by a nitrogen atom greatly reduced the in vitro activity of the compounds. A two-stage mouse skin carcinogenesis test of two representative aminoglycoglycerolipids confirmed their reduced activity also in this in vivo model. (C) 2013 Elsevier Ltd. All rights reserved.