N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine | 177898-40-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine
• 英文别名: N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hexo-5(5a)-enopyranosylamine
• CAS: 177898-40-7
• 化学式: C₂₁H₃₇NO₄
• 分子量: 367.529
• InChiKey: RLSMFOUBFQRHNY-YRXWBPOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  48.95
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine 在 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.5h， 生成 N-octyl-N-tert-butoxycarbonyl-2,3-di-O-methoxymethyl-6-O-tert-butyldimethylsilyl-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine
  参考文献：
  名称：

  Chemical Modification of the β-Glucocerebrosidase Inhibitor N-Octyl-β-valienamine: Synthesis and Biological Evaluation of 4-Epimeric and 4-O-(β-?-Galactopyranosyl) Derivatives

  摘要：

  N-Octyl-beta-valienemine (1), a potent beta-glucocerebrosidase inhibitor, was chemically transformed into two biologically interesting compounds: the 4-epimer 2, beta-galacto-type N-octyl-valienamine, and the 4-O-(beta-D-galactopyranosyl) derivative 3, a carba-lactosylceramide analogue. The former, interestingly, could be demonstrated to act as a very effective inhibitor (IC50=0.3 muM) of human beta-galactosidase. The latter exhibited moderate inhibitory activity (IC50=20 muM) against beta-glucocerebrosidase (mouse liver). (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00005-6
• 作为产物：
  描述：

  Octanoic acid ((3aS,4R,9aR,9bS)-2,2,8,8-tetramethyl-4,6,9a,9b-tetrahydro-3aH-[1,3]dioxolo[4',5':3,4]benzo[1,2-d][1,3]dioxin-4-yl)-amide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以85%的产率得到N-octyl-2,3:4,6-di-O-isopropylidene-5a-carba-β-D-xylo-hex-5(5a)-enopyranosylamine
  参考文献：
  名称：

  Synthesis of potent β-D-glucocerebrosidase inhibitors: N-alkyl-β-valienamines

  摘要：

  Six homologous derivatives (N-butyl 3a, hexyl 3b, octyl 3c, decyl 3d, tetradecyl 3e and stearyl 3f) of beta-valienamine were synthesized. All have been shown to be potent and specific inhibitors of beta-glucocerebrosidase, and to have no potency against glucosylceramide synthase (mouse liver microsomes). Among them, the N-octyl derivative possesses the strongest activity (IC50 3 x 10(-8) M), being almost 10-fold more potent compared to the unsaturated 5a-carba-glucosylceramide 1. Compounds 3b and 3e are also moderate inhibitors of alpha-glucosidase (Baker's yeast). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00146-1

文献信息

• CARBA-SUGAR AMINE DERIVATIVES AND TREATMENTS FOR DISORDER OF GLYCOLIPID METABOLISM CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：SEIKAGAKU CORPORATION

  公开号：EP1433776B1

  公开（公告）日：2011-01-19
• Chemical modification of β-glucocerebrosidase inhibitor N -octyl-β-valienamine: synthesis and biological evaluation of N -alkanoyl and N -alkyl derivatives
  作者：Seiichiro Ogawa、Yuko Kobayashi、Kazuya Kabayama、Masayuki Jimbo、Jin-ichi Inokuchi

  DOI：10.1016/s0968-0896(98)00143-6

  日期：1998.10

  Several N-alkanoyl 4a-d and N-alkyl derivatives 5a-g of the potent beta-glucocerebrosidase inhibitor N-octyl beta-valienamine (3) were synthesized in order to elucidate a role of hydrophobic portion in the inhibitory action. Although the former lacked inhibitory potency, the latter were strong beta-glucocerebrosidase inhibitors (cf N-decyl-N-octyl-beta-valienamine 5d: K-i 6.6 x 10(-8) M). Furthermore, when being prescribed into mouse-derived B16 melanoma cells, N-butyl-N-octyl-beta-valienamine 5a and 5d were shown to change the amount of GlcCer and GM3, which suggests that they are possibly introduced into cells and influence glycolipids biosynthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.