1-萘基 2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷 | 121356-12-5

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-萘基 2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷
• 中文别名: 1-萘基2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷；1-萘基2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-BETA-D-吡喃葡萄糖苷
• 英文名称: [1]naphthyl-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside)
• 英文别名: [1]Naphthyl-(tri-O-acetyl-2-acetylamino-2-desoxy-β-D-glucopyranosid)；[(2R,3S,4R,5R,6S)-5-acetamido-3,4-diacetyloxy-6-naphthalen-1-yloxyoxan-2-yl]methyl acetate
• CAS: 121356-12-5
• 化学式: C₂₄H₂₇NO₉
• 分子量: 473.48
• InChiKey: TWFPJHVIRXYIGJ-MRKXFKPJSA-N

物化性质

• 沸点：
  654.4±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-萘基 2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以99%的产率得到1-萘基-N-乙酰基-beta-D-氨基葡萄糖苷
  参考文献：
  名称：

  Design of N-acetyl-6-sulfo-β-d-glucosaminide-based inhibitors of influenza virus sialidase

  摘要：

  Biological activity of N-acetyl-6-SUIfO-beta-D-glucosaminides (6-sulfo-GlcNAc 1) having a structural homology to N-acetylneuraminic acid (Neu5Ac 2) and 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en 3) was examined in terms of inhibitory activity against influenza virus sialidase (influenza, A/Memphis/l/71 H3N2). pNP 6-Sulfo-GlcNAc la was proved to show substantial activity to inhibit the virus sialidaSe IC50 2.8 mM), though p-nitrophenyl (pNP) GlcNAc without 6-sulfo group and pNP 6-sulfo-GlcNH(3)(+) 1b without 2-NHAc showed little activity IC50 > 50 mM). The activity was enhanced nearly 100-fold when the pNP group of la was converted to p-acetamidophenyl one 5 (IC50 = 30 muM) or replaced with 1-naphthyl 6 IC50 = 10 muM) or n-propyl one 8 (IC50 = 11 muM) (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.01.013
• 作为产物：
  描述：

  β-D-葡萄糖胺五乙酸酯 在 盐酸 、 sodium hydroxide 、 乙酸酐 、 丙酮 作用下， 生成 1-萘基 2-乙酰氨基-3,4,6-O-三乙酰基-2-脱氧-beta-D-吡喃葡萄糖苷
  参考文献：
  名称：

  958. The preparation and properties of acetochloroglucosamine and its use in the synthesis of 2-acetamido-2-deoxy-β-D-glucosides (N-acetyl-β-D-glucosaminides)

  摘要：

  DOI：

  10.1039/jr9570004754

文献信息

• Roy, Rene; Tropper, Francois, Synthetic Communications, 1990, vol. 20, # 14, p. 2097 - 2102
  作者：Roy, Rene、Tropper, Francois

  DOI：——

  日期：——
• Acceptor substrate-based selective inhibition of galactosyltransferases
  作者：Sang J Chung、Shuichi Takayama、Chi-Huey Wong

  DOI：10.1016/s0960-894x(98)00618-0

  日期：1998.12

  This paper describes the discovery of glycosyl acceptor analogs as potent and selective inhibitors of alpha-1,3- and beta-1,4-galactosyltransferases. Incorporation of an appropriate aromatic group to the aglycon position of the enzyme's accepters results in a strong inhibition, representing the first and most potent small uncharged molecules as selective inhibitors of these two enzymes and thus providing a new strategy for the development of selective glycosyltransferase inhibitors. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Fujise; Yokoyama, Nippon Kagaku Zasshi, 1951, vol. 72, p. 728
  作者：Fujise、Yokoyama

  DOI：——

  日期：——
• ROY, RENE;TROPPER, FRANCOIS, SYNTH. COMMUN., 20,(1990) N4, C. 2097-2102
  作者：ROY, RENE、TROPPER, FRANCOIS

  DOI：——

  日期：——
• Design of N-acetyl-6-sulfo-β-d-glucosaminide-based inhibitors of influenza virus sialidase
  作者：Kenji Sasaki、Yoshihiro Nishida、Mikie Kambara、Hirotaka Uzawa、Tadanobu Takahashi、Takashi Suzuki、Yasuo Suzuki、Kazukiyo Kobayashi

  DOI：10.1016/j.bmc.2004.01.013

  日期：2004.3

  Biological activity of N-acetyl-6-SUIfO-beta-D-glucosaminides (6-sulfo-GlcNAc 1) having a structural homology to N-acetylneuraminic acid (Neu5Ac 2) and 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en 3) was examined in terms of inhibitory activity against influenza virus sialidase (influenza, A/Memphis/l/71 H3N2). pNP 6-Sulfo-GlcNAc la was proved to show substantial activity to inhibit the virus sialidaSe IC50 2.8 mM), though p-nitrophenyl (pNP) GlcNAc without 6-sulfo group and pNP 6-sulfo-GlcNH(3)(+) 1b without 2-NHAc showed little activity IC50 > 50 mM). The activity was enhanced nearly 100-fold when the pNP group of la was converted to p-acetamidophenyl one 5 (IC50 = 30 muM) or replaced with 1-naphthyl 6 IC50 = 10 muM) or n-propyl one 8 (IC50 = 11 muM) (C) 2004 Elsevier Ltd. All rights reserved.