methyl 3-amino-2,3,6-trideoxy-β-D-arabino-hexopyranoside | 116836-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-amino-2,3,6-trideoxy-β-D-arabino-hexopyranoside
• 英文别名: (2R,3S,4R,6R)-4-amino-6-methoxy-2-methyloxan-3-ol
• CAS: 116836-60-3
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: UIWJWFKPPXKEJV-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-amino-2,3,6-trideoxy-β-D-arabino-hexopyranoside 在 sodium nitrite 作用下， 以 甲酸 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 beta-D-arabino-Hexopyranoside, methyl 3-((((2-chloroethyl)nitrosoamino)carbonyl)amino)-2,3,6-trideoxy-
  参考文献：
  名称：

  Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars

  摘要：

  Various new nitrosoureido derivatives of di- or trideoxy sugars were synthesized. The influence of the hydroxyl substitution pattern, the configuration at the anomeric center, and the absolute configuration of the sugar moiety on the antitumor activity of a series of nitrosoureido derivatives of di- and trideoxy sugars was studied. All compounds showed a very significant activity in vivo against L1210 leukemia, B16 melanocarcinoma, and Lewis lung carcinoma. Methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-2,3-dideoxy-alpha-D-arabino- hexopyranoside, 24 (NSC 609224), was found to be the most active compound. When treated with 24 (NSC 609224) at 20 mg/kg on day 1, at least 90% of the L1210 leukemia and B16 melanocarcinoma bearing mice showed a survival of over 60 days for a LD50 value for this compound of 42 mg/kg.

  DOI：

  10.1021/jm00121a005
• 作为产物：
  描述：

  methyl 3-azido-2,3,6-trideoxy-β-D-arabino-hexopyranoside 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 以95%的产率得到methyl 3-amino-2,3,6-trideoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars

  摘要：

  Various new nitrosoureido derivatives of di- or trideoxy sugars were synthesized. The influence of the hydroxyl substitution pattern, the configuration at the anomeric center, and the absolute configuration of the sugar moiety on the antitumor activity of a series of nitrosoureido derivatives of di- and trideoxy sugars was studied. All compounds showed a very significant activity in vivo against L1210 leukemia, B16 melanocarcinoma, and Lewis lung carcinoma. Methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-2,3-dideoxy-alpha-D-arabino- hexopyranoside, 24 (NSC 609224), was found to be the most active compound. When treated with 24 (NSC 609224) at 20 mg/kg on day 1, at least 90% of the L1210 leukemia and B16 melanocarcinoma bearing mice showed a survival of over 60 days for a LD50 value for this compound of 42 mg/kg.

  DOI：

  10.1021/jm00121a005

文献信息

• Rationale for the synthesis and preliminary biological evaluation of highly active new antitumor nitrosoureido sugars
  作者：Pierre Roger、Claude Monneret、Jean Paul Fournier、Patrick Choay、Roselyne Gagnet、Charles Gosse、Yves Letourneux、Ghanem Atassi、Alain Gouyette

  DOI：10.1021/jm00121a005

  日期：1989.1

  Various new nitrosoureido derivatives of di- or trideoxy sugars were synthesized. The influence of the hydroxyl substitution pattern, the configuration at the anomeric center, and the absolute configuration of the sugar moiety on the antitumor activity of a series of nitrosoureido derivatives of di- and trideoxy sugars was studied. All compounds showed a very significant activity in vivo against L1210 leukemia, B16 melanocarcinoma, and Lewis lung carcinoma. Methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-2,3-dideoxy-alpha-D-arabino- hexopyranoside, 24 (NSC 609224), was found to be the most active compound. When treated with 24 (NSC 609224) at 20 mg/kg on day 1, at least 90% of the L1210 leukemia and B16 melanocarcinoma bearing mice showed a survival of over 60 days for a LD50 value for this compound of 42 mg/kg.