C-1-(2'-aminoethyl) α-glucoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: C-1-(2'-aminoethyl) α-glucoside
• 英文别名: 2-(α-D-glucopyranosyl)ethanamine；(2R,3R,4R,5S,6R)-2-(2-aminoethyl)-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₈H₁₇NO₅
• 分子量: 207.227
• InChiKey: BNFUZESWWRCHFC-JAJWTYFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  116
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  C-1-(2'-aminoethyl) α-glucoside 、 1-萘甲酰氯 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以46%的产率得到N-[2'-(α-D-glucopyranosyl)ethyl]-1-naphthalenecarboxyamide
  参考文献：
  名称：

  Dansyl C-葡糖苷作为抗内毒素休克的新型药物

  摘要：

  丹斯尔跟我来！从甲基α- D-吡喃葡萄糖苷合成了一个小的萘基葡萄糖衍生物文库，没有进行保护/脱保护步骤。一个文库成员Dansyl C- glucoside 5表现出非凡的抗炎活性，以25μgkg -1的剂量保护100％的小鼠免于败血症。

  DOI：

  10.1002/cmdc.201000282
• 作为产物：
  描述：

  (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-propene 生成 C-1-(2'-aminoethyl) α-glucoside
  参考文献：
  名称：

  Fluorescence Anisotropy Assays Reveal Affinities of C- and O-Glycosides for Concanavalin A¹

  摘要：

  The free energies of binding of various C- and O-glycosides to the lectin concanavalin A were measured using fluorescence anisotropy. Fluorescein derivatives of mannose and glucose were synthesized and were shown to bind to concanavalin A with free energies of -5.1 and -4.3 kcal mol(-1), respectively. Competition experiments were performed to determine the binding energies of different nonfluorescent carbohydrates, and the results were in excellent agreement with the binding energies determined by microcalorimetry. The minimum carbohydrate epitope that fills the lectin carbohydrate binding site, methyl 3,6-di-O-(alpha-mannopyranosyl)-alpha-mannopyranoside, competes directly for the site with the fluorescent ligands, indicating that the fluorescent ligands bind specifically. The binding affinities of C-glycosides to concanavalin A were compared with those of O-glycosides. The free energies of binding for corresponding C- and O-glycosides differed by less than 0.5 kcal mol(-1), indicating that recognition properties of C- and O-glycosides are very similar. It was found that for some ligands the use of a carbon linkage rather than an oxygen linkage caused the specificity of binding to decrease slightly.

  DOI：

  10.1021/jo951430o

文献信息

• COMPOUNDS WITH GLYCIDIC STRUCTURE ACTIVE IN THE THERAPY OF SYSTEMIC AND LOCAL INFLAMMATION
  申请人：La Perla Barbara

  公开号：US20110112184A1

  公开（公告）日：2011-05-12

  Compounds of the general formula (I) and (II) (including formulae (III) to (V)), wherein X=—CH 2 —, —O—, —S— n=0-10 Y=—NH—, —NHSO 2 —, —NHSO—, —NHCO—, —S—, —O—, —CH═CH—R 1 -R 7 , equal or different can be hydrogen, alkyl C 1 -C 4 , alkenyl C 2 -C 4 , cycloalkyl C 3 -C 7 , aryl or heteroaryl; may be substituted with one or more alkyl C 1 -C 4 , alkoxyl C 1 -C 4 , alkylthio C 1 -C 4 or halogens; —NR 8 R 9 , where R 8 e R 9 , equal or different, represent hydrogen, alkyl C 1 -C 4 , alkenyl C 2 -C 4 , cycloalkyl C 3 -C 7 , aryl or heteroaryl, may be substituted with one or more C 1 -C 4 , alkoxyl C 1 -C 4 , alkylthio C 1 -C 4 or halogens; —(CH 2 ) n , —COOR 10 , with n′=0-4 and R 3 =hydrogen or alkyl C 1 -C 4 , and their addition salts with organic and inorganic acids, or alkaline and alkaline earth metal or ammonium ions, with the exclusion of the compounds having the following formulae ((VI) to (IX)).

  通式(I)和(II)的化合物（包括式(III)到(V)的化合物），其中X=—CH2—，—O—，—S— n=0-10 Y=—NH—，—NHSO2—，—NHSO—，—NHCO—，—S—，—O—，—CH═CH—R1-R7，相等或不同可以是氢，烷基C1-C4，烯基C2-C4，环烷C3-C7，芳基或杂环烷基；可以用一个或多个烷基C1-C4，烷氧基C1-C4，烷硫基C1-C4或卤素取代；—NR8R9，其中R8和R9，相等或不同，代表氢，烷基C1-C4，烯基C2-C4，环烷C3-C7，芳基或杂环烷基，可以用一个或多个C1-C4，烷氧基C1-C4，烷硫基C1-C4或卤素取代；—(CH2)n，—COOR10，其中n′=0-4，R3=氢或烷基C1-C4，以及它们与有机和无机酸的加合盐，或碱金属和碱土金属或铵离子的盐，但不包括具有以下式（VI）到（IX）的化合物。
• Dansyl C-Glucoside as a Novel Agent Against Endotoxic Shock
  作者：Barbara La Ferla、Valerio Spinosa、Giuseppe D'Orazio、Marco Palazzo、Andrea Balsari、Anastasia A. Foppoli、Cristiano Rumio、Francesco Nicotra

  DOI：10.1002/cmdc.201000282

  日期：——

  Come dansyl with me! A small library of naphthyl gluco derivatives was synthesised from methyl α‐D‐glucopyranoside without protection/deprotection steps. One library member, dansyl C‐glucoside 5, showed an extraordinary anti‐inflammatory activity, protecting 100 % of mice from sepsis at a dose of 25 μg kg−1.

  丹斯尔跟我来！从甲基α- D-吡喃葡萄糖苷合成了一个小的萘基葡萄糖衍生物文库，没有进行保护/脱保护步骤。一个文库成员Dansyl C- glucoside 5表现出非凡的抗炎活性，以25μgkg -1的剂量保护100％的小鼠免于败血症。
• Fluorescence Anisotropy Assays Reveal Affinities of <i>C</i>- and <i>O</i>-Glycosides for Concanavalin A¹
  作者：Ross V. Weatherman、Laura L. Kiessling

  DOI：10.1021/jo951430o

  日期：1996.1.1

  The free energies of binding of various C- and O-glycosides to the lectin concanavalin A were measured using fluorescence anisotropy. Fluorescein derivatives of mannose and glucose were synthesized and were shown to bind to concanavalin A with free energies of -5.1 and -4.3 kcal mol(-1), respectively. Competition experiments were performed to determine the binding energies of different nonfluorescent carbohydrates, and the results were in excellent agreement with the binding energies determined by microcalorimetry. The minimum carbohydrate epitope that fills the lectin carbohydrate binding site, methyl 3,6-di-O-(alpha-mannopyranosyl)-alpha-mannopyranoside, competes directly for the site with the fluorescent ligands, indicating that the fluorescent ligands bind specifically. The binding affinities of C-glycosides to concanavalin A were compared with those of O-glycosides. The free energies of binding for corresponding C- and O-glycosides differed by less than 0.5 kcal mol(-1), indicating that recognition properties of C- and O-glycosides are very similar. It was found that for some ligands the use of a carbon linkage rather than an oxygen linkage caused the specificity of binding to decrease slightly.