6-O-[(2R,S)-N-(2-hydroxyethyl-N-decylamino)propan-2-ol]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-O-[(2R,S)-N-(2-hydroxyethyl-N-decylamino)propan-2-ol]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: 1-[decyl(2-hydroxyethyl)amino]-3-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]propan-2-ol
• 化学式: C₂₇H₅₁NO₈
• 分子量: 517.704
• InChiKey: LXHBTIVQHQXWBT-BPVAZVPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.1
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-氯癸烷 在 四丁基溴化铵 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 6-O-[(2R,S)-N-(2-hydroxyethyl-N-decylamino)propan-2-ol]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis and evaluation of antibacterial and antitumor activities of new galactopyranosylated amino alcohols

  摘要：

  Three series of D-galactose derivatives linked to a lipophilic aminoalcohol moiety were synthesized and their antibacterial activity was evaluated against Mycobacterium tuberculosis and representative species of Gram positive and Gram negative bacteria. Five out of the thirteen tested compounds displayed activity against M. tuberculosis, with a minimal inhibitory concentration (MIC) of 12.5 mu g/mL and seven compounds were active against the four bacterial strains tested. The best results were obtained for amino alcohols 10 and 11 against Staphylococcus epidermidis (MIC = 2 mu g/mL). The antitumor activity was evaluated against three tumor cell lines (MCF-7, HeLa and MO59J) and compared to the normal cell line GM07492A. The results showed that the lowest IC50 values were observed for the amino alcohol 16 against MCF-7 (11.9 mu M) and MO59J (10.0 mu M). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.037

文献信息

• Synthesis and evaluation of antibacterial and antitumor activities of new galactopyranosylated amino alcohols
  作者：Fábio de Souza Fernandes、Tayrine Silva Fernandes、Lígia Souza da Silveira、Wiliam Caneschi、Maria Cristina S. Lourenço、Claudio G. Diniz、Pollyanna Francielli de Oliveira、Sabrina de Paula Lima Martins、Daiane Eleutério Pereira、Denise Crispim Tavares、Mireille Le Hyaric、Mauro V. de Almeida、Mara Rubia C. Couri

  DOI：10.1016/j.ejmech.2015.11.037

  日期：2016.1

  Three series of D-galactose derivatives linked to a lipophilic aminoalcohol moiety were synthesized and their antibacterial activity was evaluated against Mycobacterium tuberculosis and representative species of Gram positive and Gram negative bacteria. Five out of the thirteen tested compounds displayed activity against M. tuberculosis, with a minimal inhibitory concentration (MIC) of 12.5 mu g/mL and seven compounds were active against the four bacterial strains tested. The best results were obtained for amino alcohols 10 and 11 against Staphylococcus epidermidis (MIC = 2 mu g/mL). The antitumor activity was evaluated against three tumor cell lines (MCF-7, HeLa and MO59J) and compared to the normal cell line GM07492A. The results showed that the lowest IC50 values were observed for the amino alcohol 16 against MCF-7 (11.9 mu M) and MO59J (10.0 mu M). (C) 2015 Elsevier Masson SAS. All rights reserved.