allyl 2-azido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside | 288402-88-0

• 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-azido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
• 英文别名: (4aR,6R,7R,8R,8aS)-7-azido-2,2-dimethyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 288402-88-0
• 化学式: C₁₂H₁₉N₃O₅
• 分子量: 285.3
• InChiKey: ADAPOJCEAJPGDD-ISUQUUIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  105.91
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 2-azido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 在 盐酸 、 4-二甲氨基吡啶 、 [C₈H₁₂Ir(PMePh₂)2]PF₆ 、 氨 、 水 、 氢气 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Synthesis of GLA-60 type pyran carboxylic acids with an alkyl chain instead of an ester chain as LPS-antagonists

  摘要：

  Synthesis of GLA-60 type pyran carboxylic acid analogues with an alkyl chain instead of an ester chain and their LPS-antagonist activity toward human U937 cells are described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00055-6
• 作为产物：
  描述：

  Allyl 2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 triflic azide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 以91%的产率得到allyl 2-azido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of GLA-60 type pyran carboxylic acids with an alkyl chain instead of an ester chain as LPS-antagonists

  摘要：

  Synthesis of GLA-60 type pyran carboxylic acid analogues with an alkyl chain instead of an ester chain and their LPS-antagonist activity toward human U937 cells are described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00055-6

文献信息

• Ether type lipid a 1-carboxylic acid analogs
  申请人：SANKYO COMPANY, LIMITED

  公开号：US20020161221A1

  公开（公告）日：2002-10-31

  A compound of formula (I) below, which exhibits excellent macrophage activity inhibitory action, is useful for the treatment or prophylaxis of inflammatory disorders, autoimmune diseases or septicemia. In a preferred embodiment, R 1 and R 3 each represents a C 1 -C 20 alkanoyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R 2 and R 4 each represents a C 1 -C 20 alkyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R 5 is a hydrogen atom, a halogen atom, a hydroxy group, or a C 1 -C 6 alkoxy group, and substituent group A is a halogen atom, a hydroxy group, an oxo group, a C 1 -C 20 alkoxy group, or a C 1 -C 20 alkanoyloxy group. 1

  以下为化合物式（I），该化合物表现出出色的巨噬细胞活性抑制作用，可用于治疗或预防炎症性疾病、自身免疫性疾病或败血症。在首选实施例中，R1和R3各代表一个C1-C20烷酰基团，该基团可以选择性地被一个或多个取代基团A所取代，R2和R4各代表一个C1-C20烷基团，该基团可以选择性地被一个或多个取代基团A所取代，R5是氢原子、卤素原子、羟基或C1-C6烷氧基团，取代基团A是卤素原子、羟基、氧代基、C1-C20烷氧基团或C1-C20烷酰氧基团。
• Synthesis of Tetrahydropyran-2-carboxylic Acid Derivatives of Lipid A Containing an Olefin in Their Chains and Their LPS-Antagonistic Activities
  作者：Yukiko Watanabe、Masao Shiozaki、Daisuke Tanaka、Takaichi Shimozato、Saori Kanai、Shin-ichi Kurakata

  DOI：10.1246/bcsj.76.2341

  日期：2003.12

  Four tetrahydropyran-2-carboxylic acid derivatives with 3-(tetradec-7-enyloxy)tetradecyl chains instead of 3-(tetradecanoyloxy)tetradecanoyl chains in lipid A were synthesized and their biological activities toward human U937 cells, human whole blood cells and mouse peritoneal resident macrophages were measured. These compounds showed LPS-antagonistic activity toward these three kinds of cells. The IC50 values (nM) (1 M = 1 mol dm−3) of these four compounds (21, 21′, 24 and 24′) toward human monoblastic U937 cells were 2.2, 1.0, 0.017 and 0.055, respectively. However, the LPS-antagonistic activities (IC50 values) of these four compounds toward human whole blood cells were only 0.28, 0.21, 0.81 and 0.58 μM, respectively. The IC50 values (μM) toward mouse peritoneal resident macrophages were 2.49, 0.49, 0.91 and 0.69, respectively.

  合成了四种四氢吡喃-2-羧酸衍生物，其脂质 A 中的 3-(十四烷-7-烯氧基)十四烷基链取代了 3-(十四烷酰氧基)十四烷基链，并测定了它们对人 U937 细胞、人全血细胞和小鼠腹腔巨噬细胞的生物活性。这些化合物对这三种细胞都具有 LPS 拮抗活性。这四种化合物（21、21′、24 和 24′）对人单倍体 U937 细胞的 IC50 值（nM）（1 M = 1 mol dm-3）分别为 2.2、1.0、0.017 和 0.055。然而，这四种化合物对人全血细胞的 LPS 拮抗活性（IC50 值）分别只有 0.28、0.21、0.81 和 0.58 μM。对小鼠腹腔巨噬细胞的 IC50 值（μM）分别为 2.49、0.49、0.91 和 0.69。
• ETHER TYPE LIPID A1-CARBOXYLIC ACID ANALOGUES
  申请人：Sankyo Company, Limited

  公开号：EP1152007A1

  公开（公告）日：2001-11-07

  A compound of formula (I), which exhibits excellent macrophage activity inhibitory action, is useful for the treatment or prophylaxis of inflammatory disorders. autoimmune diseases or septicemia. R1 and R3 each represents a C1-C20 alkanoyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R2 and R4 each represents a C1-C20 alkyl group which may optionally be substituted with one or more substituent groups selected from substituent group A, R5 is a hydrogen atom, a halogen atom, a hydroxy group, or a C1-C6 alkoxy group, and Substituent group A is a halogen atom, a hydroxy group, an oxo group, a C1-C20 alkoxy group, or a C1-C20 alkanoyloxy group.

  式（I）化合物具有出色的巨噬细胞活性抑制作用，可用于治疗或预防炎症性疾病、自身免疫性疾病或败血症。 R1 和 R3 各自代表 C1-C20 烷酰基，可任选被一个或多个选自取代基 A 的取代基取代、 R2 和 R4 各自代表一个 C1-C20 烷基，可任选被一个或多个选自取代基 A 的取代基取代、 R5 是氢原子、卤素原子、羟基或 C1-C6 烷氧基，取代基 A 是卤素原子、羟基、氧代基团、C1-C20 烷氧基或 C1-C20 烷酰氧基。
• US6511965B2
  申请人：——

  公开号：US6511965B2

  公开（公告）日：2003-01-28