(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-2-O-benzoyl-α-D-galactopyranosyloxy]-4-octadecene | 206857-41-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-2-O-benzoyl-α-D-galactopyranosyloxy]-4-octadecene
• 英文别名: (2S,3R 4E)-3-Benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpent-1-yl)-2-O-benzoyl-α-D-galactopyranosyloxy]-4-octadecene
• CAS: 206857-41-2
• 化学式: C₆₉H₁₁₁NO₁₄
• 分子量: 1178.64
• InChiKey: HDDRLMRZBLCNRP-GMCPQRSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.61
• 重原子数：
  84.0
• 可旋转键数：
  45.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  202.45
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-2-O-benzoyl-α-D-galactopyranosyloxy]-4-octadecene 在 三氟乙酸 作用下， 以57%的产率得到(2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-dicarboxypentyl)-2-O-benzoyl-α-D-galactopyranosyloxy]-4-octadecene
  参考文献：
  名称：

  Novel mimics of sialyl Lewis X

  摘要：

  A series of potent inhibitors of P-selectin as potential anti-inflammatory agents is reported. These compounds are derivatives of galactocerebrosides bearing a malonate side chain in positions 2 and 3 of the galactose moiety. Based on the binding mode of sialyl Lewis X, the two acidic groups of the malonate are designed to form ionic interactions with two important lysines in the active site of P-selectin, Lys113 and Lys111. On the other hand, the 4- and 6-hydroxy groups on the galactose ring are arranged to chelate the calcium ion in the P-selectin active site. The synthesis and the biological activity of this series of compounds are described. Lead compounds having a greater potency than sialyl Lewis X are identified. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00015-3
• 作为产物：
  描述：

  1-硫代-Β-D-乙基半乳糖苷 在 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 硫化氢 、 potassium tert-butylate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 34.0h， 生成 (2S,3R,4E)-3-benzoyloxy-2-hexadecanoylamino-1-[3-O-(5,5-di-tert-butyloxycarbonylpentyl)-2-O-benzoyl-α-D-galactopyranosyloxy]-4-octadecene
  参考文献：
  名称：

  Novel mimics of sialyl Lewis X

  摘要：

  A series of potent inhibitors of P-selectin as potential anti-inflammatory agents is reported. These compounds are derivatives of galactocerebrosides bearing a malonate side chain in positions 2 and 3 of the galactose moiety. Based on the binding mode of sialyl Lewis X, the two acidic groups of the malonate are designed to form ionic interactions with two important lysines in the active site of P-selectin, Lys113 and Lys111. On the other hand, the 4- and 6-hydroxy groups on the galactose ring are arranged to chelate the calcium ion in the P-selectin active site. The synthesis and the biological activity of this series of compounds are described. Lead compounds having a greater potency than sialyl Lewis X are identified. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00015-3

文献信息

• Malonate derivatives of glycolipids as cell adhesion inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US05747463A1

  公开（公告）日：1998-05-05

  There is provided a novel series of malonate derivatives of glycolipid compounds of the formula ##STR1## wherein R is an acyl residue of a fatty acid: R.sup.1 is --(CH.dbd.CH).sub.m --(CH.sub.2).sub.n --CH.sub.3 ; R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 each are independently hydrogen, unsubstituted or substituted (lower)alkanoyl, arylalkyl or arylcarbonyl wherein said substituent is selected from the group consisting of halogen, C.sub.1-4 alkyl, trifluoromethyl, hydroxy and C.sub.1-4 alkoxy provided that one of R.sup.2, R.sup.3, R.sup.4 and R.sup.6 substituents is --(CH.sub.2).sub.p --CH(CO.sub.2 R.sup.7).sub.2 ; m is an integer of 0 or 1; n is an integer of from 5 to 14 inclusive; p is an integer of from 2 to 6 inclusive; and R.sup.7 is hydrogen, a hydrolyzable ester group or a cation to form a non-toxic pharmaceutically acceptable salt; or a solvate or hydrate thereof which are inhibitors of selectin-mediated cellular adhesion and are useful in the treatment or prevention of inflammatory diseases and other pathological conditions in mammals.

  提供了一系列新颖的甘油脂衍生物的马隆酸衍生物，其化学式为##STR1##其中，R是脂肪酸的酰基残基：R.sup.1是--(CH.dbd.CH).sub.m--(CH.sub.2).sub.n--CH.sub.3; R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6各自独立地为氢、未取代或取代的(较低)烷酰基、芳基烷基或芳基羰基，其中所述取代基从卤素、C.sub.1-4烷基、三氟甲基、羟基和C.sub.1-4烷氧基的群中选择，前提是R.sup.2、R.sup.3、R.sup.4和R.sup.6中的一个取代基是--(CH.sub.2).sub.p--CH(CO.sub.2R.sup.7).sub.2; m是0或1的整数；n是从5到14的整数，包括14；p是从2到6的整数，包括6；和R.sup.7是氢、可水解酯基或阳离子，以形成非毒性药学可接受盐；或其溶剂化合物或水合物，这些化合物是选择素介导的细胞黏附抑制剂，并且在哺乳动物的炎症性疾病和其他病理条件的治疗或预防中有用。