p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-deoxy-2-fluoro-β-D-mannopyranoside | 359687-48-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-deoxy-2-fluoro-β-D-mannopyranoside
• 英文别名: N-[(4-ethenylphenyl)methyl]-3-[4-[(2S,3S,4S,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]propanamide
• CAS: 359687-48-2
• 化学式: C₂₄H₂₈FNO₆
• 分子量: 445.488
• InChiKey: UEANSFQSNSZEFY-DXVXXHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  p-[2-(benzyloxycarbonyl)ethyl]phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 palladium dihydroxide 吡啶 、 18-冠醚-6 、 氢气 、 sodium methylate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 苯甲醇钠 、 三丁基氧化锡 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 甲苯 、 苯甲醇 、 苯 为溶剂， 反应 96.33h， 生成 p-[2-[N-(p-vinylbenzyl)carbamoyl]ethyl]phenyl 2-deoxy-2-fluoro-β-D-mannopyranoside
  参考文献：
  名称：

  SYNTHESIS OF NEW GLYCOPOLYMERS CONTAINING β-D-MANNOPYRANOSE, ANDC-2-SUBSTITUTED β-D-MANNOPYRANOSE RESIDUES AS A NEW CLASS OF INHIBITOR

  摘要：

  New styryl monomers containing beta -D-mannopyranose, 2-acetamido-2-deoxy-beta -D-mannopyranose, 2-deoxy-2-fluoro-beta -D-mannopyranose, and 2-deoxy-beta -D-arabino-hexopyranose on their side chains, were efficiently synthesized as a new class of a potent inhibitor resistant to exo-or-mannosidase digestion. The binding affinity of the carbohydrate polymers obtained from those mannopyranosyl styryl monomers by radical polymerization with Concanavalin A were evaluated. A binding assay indicated that the multivalency effect and the affinity enhancement attained by modification at the C-2 position of the beta -D-mannopyranoside residue resulted in the beta -D-mannopyranosyl polymer which has the same affinity as that of the alpha -D-mannopyranosyl polymer.

  DOI：

  10.1081/car-100103953

文献信息

• [EN] STABLE PROTEIN LIGANDS AS ANTI-INFECTIVE AGENTS<br/>[FR] LIGANDS PROTÉIQUES STABLES UTILISÉS EN TANT QU'AGENTS ANTI-INFECTIEUX
  申请人：UNIV MONASH

  公开号：WO2019227173A1

  公开（公告）日：2019-12-05

  The present invention relates to compounds that inhibit the interaction between the SPRY-domain containing SOCS box protein and inducible nitric oxide synthase (iNOS). In particular, the present invention relates to compounds of Formula (I) and their use as anti- infective agents. (I)

  本发明涉及抑制SPRY域含SOCS盒蛋白与诱导型一氧化氮合酶（iNOS）相互作用的化合物。特别地，本发明涉及公式（I）的化合物及其作为抗感染剂的用途。(I)
• SYNTHESIS OF NEW GLYCOPOLYMERS CONTAINING β-<scp>D</scp>-MANNOPYRANOSE, AND<i>C</i>-2-SUBSTITUTED β-<scp>D</scp>-MANNOPYRANOSE RESIDUES AS A NEW CLASS OF INHIBITOR
  作者：Shoji Akai、Yasuhiro Kajihara、Yasuhiko Nagashima、Masugu Kamei、Junko Arai、Masami Bito、Ken-ichi Sato

  DOI：10.1081/car-100103953

  日期：2001.3.31

  New styryl monomers containing beta -D-mannopyranose, 2-acetamido-2-deoxy-beta -D-mannopyranose, 2-deoxy-2-fluoro-beta -D-mannopyranose, and 2-deoxy-beta -D-arabino-hexopyranose on their side chains, were efficiently synthesized as a new class of a potent inhibitor resistant to exo-or-mannosidase digestion. The binding affinity of the carbohydrate polymers obtained from those mannopyranosyl styryl monomers by radical polymerization with Concanavalin A were evaluated. A binding assay indicated that the multivalency effect and the affinity enhancement attained by modification at the C-2 position of the beta -D-mannopyranoside residue resulted in the beta -D-mannopyranosyl polymer which has the same affinity as that of the alpha -D-mannopyranosyl polymer.