(E)-1-propenyl 4-O-(diallylphosphono)-3-O-[(R)-3-methoxydecyl]-2-O-[(Z)-11-octadecenoyl]-α-D-glucopyranoside | 859508-18-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (E)-1-propenyl 4-O-(diallylphosphono)-3-O-[(R)-3-methoxydecyl]-2-O-[(Z)-11-octadecenoyl]-α-D-glucopyranoside
• 英文别名: (E)-1-propenyl 4-O-diallylphosphono-3-O-[(R)-3-methoxydecyl]-2-O-[(Z)-11-octadecenoyl]-α-D-glucopyranoside；(E)-1-Propenyl 4-O-diallylphosphono-3-O-[(R)-3-methoxydecyl]-2-O-[(Z)-11-octadecenoyl]-alpha-D-glucopyranoside；[(2S,3R,4R,5R,6R)-5-bis(prop-2-enoxy)phosphoryloxy-6-(hydroxymethyl)-4-[(3R)-3-methoxydecoxy]-2-[(E)-prop-1-enoxy]oxan-3-yl] (Z)-octadec-11-enoate
• CAS: 859508-18-2
• 化学式: C₄₄H₇₉O₁₁P
• 分子量: 815.078
• InChiKey: JDOHVLJUIFONGI-NASIFYQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  56
• 可旋转键数：
  39
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (E)-1-propenyl 4-O-(diallylphosphono)-3-O-[(R)-3-methoxydecyl]-2-O-[(Z)-11-octadecenoyl]-α-D-glucopyranoside 、 trimethoxonium tetrafluoroborate 在 2,6-二叔丁基-4-甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到(E)-1-propenyl 4-O-(diallylphosphono)-3-O-[(R)-3-methoxydecyl]-6-O-methyl-2-O-[(Z)-11-octadecenoyl]-α-D-glucopyranoside
  参考文献：
  名称：

  EP1702926

  摘要：

  公开号：
• 作为产物：
  描述：

  十八烷酸 在 四氮唑 、 4-二甲氨基吡啶 、 WSC*HCl 、 硫酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 23.92h， 生成 (E)-1-propenyl 4-O-(diallylphosphono)-3-O-[(R)-3-methoxydecyl]-2-O-[(Z)-11-octadecenoyl]-α-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of glucose-containing E5564 analogues and their LPS-antagonistic activities

  摘要：

  Lipid A analogues containing a glucose moiety on their non-reducing end were synthesized, and their LPS-antagonistic activities were measured. The inhibitory activities (IC50) on LPS-induced TNF alpha production of these six compounds, 26, 33, 440, 520, 59, and 61, toward human whole blood cells were 0.49, 0.65, 0.51, 0.98, 0.46, and 1.11 nM, respectively. Inhibitory doses (ID50) of compounds 26, 33, 440, 59, and 61 on TNF alpha production induced by coinjection of galactosamine and LPS in C3HMeN mice were measured. The ID50 values of these compounds were 0.45, 0.96, < 0.2, 1.08, and < 0.2 mg/kg, respectively. Moreover, C3H/HeN mice preinjected with compounds 26, 33, and 440 were protected from lethality induced by coinjection of galactosamine and LPS. Out of eight mice preinjected with 1 mg/kg of compounds 26, 33, and 440, five, eight and six mice were protected, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.115

文献信息

• Left-Side Glucose Lipid a Analogue
  申请人：Shiozaki Masao

  公开号：US20090062214A1

  公开（公告）日：2009-03-05

  A compound having excellent macrophage activity inhibitory action, which is represented by the general following formula: wherein Q represents an oxygen atom, a C 1 -C 3 alkylene group, a —O-Alk- group or a —O-Alk-O— group (in which Alk is a C 1 -C 3 alkylene group), R 1 represents a C 1 -C 20 alkanoyl group which may be substituted, a C 3 -C 20 alkenoyl group which may be substituted or a C 3 -C 20 alkynoyl group which may be substituted, R 2 , R 3 and R 4 , which may be the same or different, represent a hydrogen atom, a C 1 -C 20 alkyl group which may be substituted, a C 2 -C 20 alkenyl group which may be substituted, a C 2 -C 20 alkynyl group which may be substituted, a C 1 -C 20 alkanoyl group which may be substituted, a C 3 -C 20 alkenoyl group which may be substituted or a C 3 -C 20 alkynoyl group which may be substituted, R 5 represents a hydrogen atom, a halogen atom, a hydroxyl group, a C 1 -C 6 alkoxy group which may be substituted, a C 2 -C 6 alkenyloxy group which may be substituted or a C 2 -C 6 alkynyloxy group which may be substituted, and W represents an oxygen atom or a —NH— group, or a pharmacologically acceptable salt thereof.

  一种具有出色的巨噬细胞活性抑制作用的化合物，其通式如下：其中，Q代表氧原子、C1-C3烷基、—O-Alk-基团或—O-Alk-O—基团（其中，Alk代表C1-C3烷基），R1代表C1-C20烷酰基，可以被取代的C3-C20烯酰基或可以被取代的C3-C20炔酰基，R2、R3和R4，可以相同也可以不同，代表氢原子、可以被取代的C1-C20烷基、可以被取代的C2-C20烯基、可以被取代的C2-C20炔基、可以被取代的C1-C20烷酰基、可以被取代的C3-C20烯酰基或可以被取代的C3-C20炔酰基，R5代表氢原子、卤原子、羟基、可以被取代的C1-C6烷氧基、可以被取代的C2-C6烯氧基或可以被取代的C2-C6炔氧基，W代表氧原子或—NH—基团，或其药学上可接受的盐。
• EP1702926
  申请人：——

  公开号：——

  公开（公告）日：——
• Syntheses of glucose-containing E5564 analogues and their LPS-antagonistic activities
  作者：Masao Shiozaki、Hiromi Doi、Daisuke Tanaka、Takaichi Shimozato、Shin-ichi Kurakata

  DOI：10.1016/j.tet.2005.09.115

  日期：2006.1

  Lipid A analogues containing a glucose moiety on their non-reducing end were synthesized, and their LPS-antagonistic activities were measured. The inhibitory activities (IC50) on LPS-induced TNF alpha production of these six compounds, 26, 33, 440, 520, 59, and 61, toward human whole blood cells were 0.49, 0.65, 0.51, 0.98, 0.46, and 1.11 nM, respectively. Inhibitory doses (ID50) of compounds 26, 33, 440, 59, and 61 on TNF alpha production induced by coinjection of galactosamine and LPS in C3HMeN mice were measured. The ID50 values of these compounds were 0.45, 0.96, < 0.2, 1.08, and < 0.2 mg/kg, respectively. Moreover, C3H/HeN mice preinjected with compounds 26, 33, and 440 were protected from lethality induced by coinjection of galactosamine and LPS. Out of eight mice preinjected with 1 mg/kg of compounds 26, 33, and 440, five, eight and six mice were protected, respectively. (c) 2005 Elsevier Ltd. All rights reserved.