O-[(4R,5R,6S)-6-acetamido-4,5-dihydroxy-3-hydroxymethylcyclohex-2-enylidene]amino N-phenylcarbamate | 1091630-16-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: O-[(4R,5R,6S)-6-acetamido-4,5-dihydroxy-3-hydroxymethylcyclohex-2-enylidene]amino N-phenylcarbamate
• 英文别名: [(E)-[(4R,5R,6S)-6-acetamido-4,5-dihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-ylidene]amino] N-phenylcarbamate
• CAS: 1091630-16-8
• 化学式: C₁₆H₁₉N₃O₆
• 分子量: 349.343
• InChiKey: LYBHKGGAIJATIC-HFLWSHMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  141
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  O-[(4R,5R,6S)-6-acetamido-4,5-diacetoxy-3-acetoxymethylcyclohex-2-enylidene]amino N-phenylcarbamate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到O-[(4R,5R,6S)-6-acetamido-4,5-dihydroxy-3-hydroxymethylcyclohex-2-enylidene]amino N-phenylcarbamate
  参考文献：
  名称：

  The synthesis and biological evaluation of some carbocyclic analogues of PUGNAc

  摘要：

  The synthesis of some analogues of O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate, PUGNAc, an inhibitor of beta-N-acetylglucosaminidases, is described. The analogues were tested against a range of beta-N-acetylglucosaminidases to establish any biological activity. As well, the analogues were tested as inhibitors of a uridine diphosphate-N-acetyl-D-glucosamine: polypeptidyl transferase, OGT, a critical protein involved in the post-translational modification of nuclear and cytosolic proteins by N-acetyl-D-glucosamine. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.08.012

文献信息

• US8716333B2
  申请人：——

  公开号：US8716333B2

  公开（公告）日：2014-05-06
• The synthesis and biological evaluation of some carbocyclic analogues of PUGNAc
  作者：Adrian Scaffidi、Keith A. Stubbs、David J. Vocadlo、Robert V. Stick

  DOI：10.1016/j.carres.2008.08.012

  日期：2008.11

  The synthesis of some analogues of O-(2-acetamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate, PUGNAc, an inhibitor of beta-N-acetylglucosaminidases, is described. The analogues were tested against a range of beta-N-acetylglucosaminidases to establish any biological activity. As well, the analogues were tested as inhibitors of a uridine diphosphate-N-acetyl-D-glucosamine: polypeptidyl transferase, OGT, a critical protein involved in the post-translational modification of nuclear and cytosolic proteins by N-acetyl-D-glucosamine. (C) 2008 Elsevier Ltd. All rights reserved.