N-[(1S,6S,7R,8R,8aR)-1,7,8-三羟基辛氢-6-吲哚嗪基]乙酰胺 | 134100-29-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 中文名称: N-[(1S,6S,7R,8R,8aR)-1,7,8-三羟基辛氢-6-吲哚嗪基]乙酰胺
• 中文别名: 十六烷基硼酸
• 英文名称: 6-acetamido-6-deoxy-castanospermine
• 英文别名: 6-acetamido-6-deoxycastanospermine；NHAc-CAS；[1S-(1α,6β,7α,8β,8aβ)]-6-acetamidooctahydro-1,7,8-indolizinetriol；N-((1S,6S,7R,8R,8aR)-1,7,8-trihydroxy-octahydroindolizin-6-yl)acetamide；N-[(1S,6S,7R,8R,8aR)-1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl]acetamide
• CAS: 134100-29-1
• 化学式: C₁₀H₁₈N₂O₄
• 分子量: 230.264
• InChiKey: IHKWXDCSAKJQKM-SRQGCSHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  93
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,7,8-tri-O-acetyl-6-O-mesylcastanospermine 在 palladium on activated charcoal 吡啶 、 sodium azide 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 、 甲苯 为溶剂， 反应 25.0h， 生成 N-[(1S,6S,7R,8R,8aR)-1,7,8-三羟基辛氢-6-吲哚嗪基]乙酰胺
  参考文献：
  名称：

  粟精胺的化学，第一部分：C-6的合成修饰

  摘要：

  概述了粟精胺的选择性功能化的方法学，该方法学允许合成许多在C-6处选择性修饰的类似物。还从粟精胺合成了Australine和一些australine类似物。

  DOI：

  10.1016/s0040-4020(01)85075-4

文献信息

• Derivatives of 6-aminooctahydroindolizinetriol
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05079254A1

  公开（公告）日：1992-01-07

  Amide and ester derivatives of 6-amino-octahydro-1,7,8-indolizinetriol are described herein. The compounds are prepared from castanospermine by replacing the appropriate hydroxy function with an amino function while protecting the other hydroxy groups in the meantime. The compounds are useful as hexosaminidase inhibitors.

  本文描述了6-氨基-八氢-1,7,8-吲哚啉三醇的酰胺和酯衍生物。这些化合物是通过用氨基功能替换卡斯坦松霉素中的适当羟基功能来制备的，同时保护其他羟基团。这些化合物可用作己糖氨基酸酶抑制剂。
• A potent inhibitor of β--acetylglucosaminidases: 6-acetamido-6-deoxycastanospermine
  作者：Paul S. Liu、Mohinder S. Kang、Prasad S. Sunkara

  DOI：10.1016/s0040-4039(00)74866-0

  日期：1991.2

  A facile synthesis of 6-acetamido-6-deoxycastanospermine (4) is described. The target compound inhibits mammalian beta-N-acetylglucosaminidases at or below 1-mu-M.
• N-(1,7,8-trihydroxy-octahydroindolizin-6-yl)carboxylic acid amide derivatives as glycosidase inhibitors (O-GlcNAcse) for the treatment of allergy and asthma
  申请人：Simon Fraser University

  公开号：EP2340250B1

  公开（公告）日：2019-06-26
• Selective Glycosidase Inhibitors and Uses Thereof
  申请人：Vocadlo David Jaro

  公开号：US20120095033A1

  公开（公告）日：2012-04-19

  The invention provides compounds of Formula (I) for selectively inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds. The invention also provides methods of treating diseases and disorders related to deficiency or overexpression of O-GlcNAcase, accumulation or deficiency of O-GlcNAc.
• MRNA BASED ENZYME REPLACEMENT THERAPY COMBINED WITH A PHARMACOLOGICAL CHAPERONE FOR THE TREATMENT OF LYSOSOMAL STORAGE DISORDERS
  申请人：ModernaTX, Inc.

  公开号：US20220184185A1

  公开（公告）日：2022-06-16

  This disclosure relates to treatment of lysosomal storage disorders, such as Fabry disease or Gaucher disease, with a combination treatment containing (i) an mRNA encoding a lysosomal enzyme deficient in the lysosomal storage disorder, and (ii) a compound that is a glucosylceramide synthase inhibitor or a pharmacological chaperone of the lysosomal enzyme. mRNAs for use in the invention, when administered in vivo, encode the enzyme that is deficient in the lysosomal storage disorder, functional fragments thereof (e.g., those comprising the catalytic domain), or fusion proteins containing the enzyme that is deficient in the lysosomal storage disorder. mRNA therapies can be used to increase and/or restore deficient levels of a lysosomal enzyme's expression and/or activity in subjects.