allyl 2,3-di-O-dodecyl-4,6-isopropylidene-α-D-glucopyranoside | 721455-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: allyl 2,3-di-O-dodecyl-4,6-isopropylidene-α-D-glucopyranoside
• 英文别名: allyl 2,3-di-O-dodecyl-4,6-O-isopropylidene-α-D-glucopyranoside；(4aR,6S,7R,8S,8aR)-7,8-didodecoxy-2,2-dimethyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 721455-99-8
• 化学式: C₃₆H₆₈O₆
• 分子量: 596.932
• InChiKey: POHJRVUTLYSXGC-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.8
• 重原子数：
  42
• 可旋转键数：
  27
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2,3-di-O-dodecyl-4,6-isopropylidene-α-D-glucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 氢氟酸 、 氢气 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 73.84h， 生成 4-O-allyloxycarbonyl-2,3-di-O-dodecyl-6-O-{2-deoxy-4-O-diallylphosphono-3-O-[(R)-3-(methoxy)decyl]-6-O-methyl-2-[(2,2,2-trichloroethoxycarbonyl)amino]-β-D-glucopyranosyl}-D-glucopyranose
  参考文献：
  名称：

  Syntheses of Glucose-Containing Lipid A Analogues and Their LPS-Antagonistic Activities

  摘要：

  合成了三对具有还原端为葡萄糖的脂质A型二糖的异构体，并测量了它们的LPS拮抗活性。这六种化合物（16α、16β、28α、28β、40α和40β）对人全血细胞中LPS诱导的TNFα产生的抑制活性（IC50）分别为0.35、0.42、2.37、1.16、2.89和7.70 nM。

  DOI：

  10.1246/bcsj.78.1091
• 作为产物：
  描述：

  烯丙基-alpha-D-吡喃葡萄糖苷 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 allyl 2,3-di-O-dodecyl-4,6-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of Glucose-Containing Lipid A Analogues and Their LPS-Antagonistic Activities

  摘要：

  合成了三对具有还原端为葡萄糖的脂质A型二糖的异构体，并测量了它们的LPS拮抗活性。这六种化合物（16α、16β、28α、28β、40α和40β）对人全血细胞中LPS诱导的TNFα产生的抑制活性（IC50）分别为0.35、0.42、2.37、1.16、2.89和7.70 nM。

  DOI：

  10.1246/bcsj.78.1091

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。
• LEVULOSE GLUCOSELIPID A ANALOGUE
  申请人：Sankyo Company, Limited

  公开号：EP1702926A1

  公开（公告）日：2006-09-20

  A compound having excellent macrophage activity inhibitory action, which is represented by the general following formula: [wherein Q represents an oxygen atom, a C1-C3 alkylene group, a -O-Alk- group or a -O-Alk-O- group (in which Alk is a C1-C3 alkylene group), R1 represents a C1-C20 alkanoyl group which may be substituted, a C3-C20 alkenoyl group which may be substituted or a C3-C20 alkynoyl group which may be substituted, R2, R3 and R4, which may be the same or different, represent a hydrogen atom, a C1-C20 alkyl group which may be substituted, a C2-C20 alkenyl group which may be substituted, a C2-C20 alkynyl group which may be substituted, a C1-C20 alkanoyl group which may be substituted, a C3-C20 alkenoyl group which may be substituted or a C3-C20 alkynoyl group which may be substituted, R5 represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-C6 alkoxy group which may be substituted, a C2-C6 alkenyloxy group which may be substituted or a C2-C6 alkynyloxy group which may be substituted, and W represents an oxygen atom or a -NH- group], or a pharmacologically acceptable salt thereof.

  一种具有优异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 亚烷基、-O-Alk- 基团或 -O-Alk-O- 基团（其中 Alk 为 C1-C3 亚烷基）、 R1 代表可被取代的 C1-C20 烷酰基、可被取代的 C3-C20 烯酰基或可被取代的 C3-C20 炔酰基、 R2、R3 和 R4（可以相同或不同）代表氢原子、可被取代的 C1-C20 烷基、可被取代的 C2-C20 烯基、可被取代的 C2-C20 烷炔基、可被取代的 C1-C20 烷酰基、可被取代的 C3-C20 烯酰基或可被取代的 C3-C20 烷炔基、 R5 代表氢原子、卤素原子、羟基、可被取代的 C1-C6 烷氧基、可被取代的 C2-C6 烯氧基或可被取代的 C2-C6 烷炔氧基，以及 W 代表氧原子或-NH-基团]，或其药理学上可接受的盐。
• Synthesis of lipid A analogues containing glucose instead of glucosamine and their LPS-antagonistic activities
  作者：Masao Shiozaki、Yukiko Watanabe、Yuji Iwano、Toshio Kaneko、Hiromi Doi、Daisuke Tanaka、Takaichi Shimozato、Shin-ichi Kurakata

  DOI：10.1016/j.tet.2005.03.034

  日期：2005.5

  Lipid A analogues containing glucose in substitution for glucosamine on the reducing end were synthesized, and the inhibitory activities on LPS-induced TNF alpha production (LPS-antagonistic activity) in vitro using human whole blood cells were measured. The IC50 values (nM) of these ten compounds, 8, 14, 21, 31, 40, 51, 57, 62, 67 and 72, were 11.2, 15.4, 2.7, 0.1, 0.4, 1.3, 3.2, 3.2, 1.4 and 14.4, respectively. And also inhibitory activities (ID50) on TNF alpha production toward galactosamine loaded C3H/HeN mice in vivo of compounds 21, 31, 57, 62 and 67 were measured. The values of these compounds were 0.29, 0.50, 0.61, not dose-dependent and 0.33 mg/kg, respectively. (c) 2005 Elsevier Ltd. All rights reserved.
• EP1702926
  申请人：——

  公开号：——

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

  DOI：10.1016/j.carres.2006.02.023

  日期：2006.5

  Glucose analogues 6, 12, 17b, 19a, and 19b of E5564 were synthesized, and their LPS-antagonistic activities were measured. The antagonistic activities (IC50) On LPS-induced TNF alpha production of these five compounds toward human whole blood were 72.8, 3.0, 0.9, 7.5, and 1.4 nM, respectively. Inhibitory doses (ID50) of compounds 12, 17b, 19a, and 19b on TNF alpha. production induced by co-injection of galactosamine and LPS in C3H/HeN mice in vivo were measured. The values of these compounds were 0.9, ND (not determined), 1.6, and 0.9 mg/kg, respectively. (c) 2006 Elsevier Ltd. All rights reserved.