N,N-bis<<(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidinyl>methyl>amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N,N-bis<<(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidinyl>methyl>amine
• 英文别名: N,N-di-{[(2R,3R,4R,5R)-(3,4-hydroxy-5-hydroxymethyl)-pyrrolidine]methyl}amine；(2R,3R,4R,5R)-2-[[[(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-yl]methylamino]methyl]-5-(hydroxymethyl)pyrrolidine-3,4-diol
• 化学式: C₁₂H₂₅N₃O₆
• 分子量: 307.347
• InChiKey: KQFBWVFLBCNIRC-KGQDQTHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  158
• 氢给体数：
  9
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  N-butyloxycarbonyl-N,N-bis<<(2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-<(benzyloxy)methyl>pyrrolidinyl>methyl>amine 在 palladium on activated charcoal 盐酸 、 氢气 、 三氟乙酸 作用下， 生成 N,N-bis<<(2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidinyl>methyl>amine
  参考文献：
  名称：

  A Versatile Synthetic Strategy for the Preparation and Discovery of New Iminocyclitols as Inhibitors of Glycosidases

  摘要：

  A series of iminocyclitols was prepared using a versatile synthetic strategy, and their inhibition of glycosidases was evaluated using capillary electrophoresis. The study has demonstrated that remarkable specificities in enzyme inhibition can be achieved with small modifications on the aglycon side chain and the ring nitrogen. Among the compounds synthesized, (2R,3R,4R,5R)-N-methyl-2-(acetamidomethyl)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidine was found to be very potent; against beta-N-acetylhexosaminidase P with the K-i value of 80 nM.

  DOI：

  10.1021/jo9902446

文献信息

• Iminocyclitol inhibitors of hexoaminidase and glycosidase
  申请人：The Scripps Research Institute

  公开号：US06774140B1

  公开（公告）日：2004-08-10

  Designed iminocylitols that have potent inhibition activity with respect to hexominidases and glycosides are disclosed.

  披露了设计的亚氨基糖醇，它们对己糖苷酶和苷具有强大的抑制活性。
• IMINOCYCLITOL INHIBITORS OF HEXOAMINIDASE AND GLYCOSIDASE
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：EP1181274B1

  公开（公告）日：2010-11-10
• SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
  申请人：Simon Fraser University

  公开号：EP2344452A1

  公开（公告）日：2011-07-20
• Treatment of degenerative cartilage conditions in a mammal with Glycosidasc Inhibitors
  申请人：Ichikawa Yoshitaka

  公开号：US20070197471A1

  公开（公告）日：2007-08-23

  This invention relates to treating, preventing, and lessening the severity of conditions selected from the group consisting of osteoarthritis, rheumatoid arthritis, synovitis, subchondral bone edema, and cartilage degradation with administration of glycosidase inhibitors.
• Selective Glycosidase Inhibitors and Uses Thereof
  申请人：Vocadlo David Jaro

  公开号：US20110301217A1

  公开（公告）日：2011-12-08

  The application relates to an immoalditol compound for selectively inhibiting glycosidases, a prodrug thereof and a pharmaceutical composition comprising the compound or the prodrug The application also relates to the use of the immoalditol compound for treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc Such diseases and disorders include neurodegenerative diseases, tauopathy, cancers, and cardiac disorders