[5R-(5α,6β,7α,8β,8aα)]-octahydro-6,7,8-trihydroxy-5-hydroxymethylindolizine | 137326-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: [5R-(5α,6β,7α,8β,8aα)]-octahydro-6,7,8-trihydroxy-5-hydroxymethylindolizine
• 英文别名: (5R,6R,7R,8S,8aR)-5-(hydroxymethyl)-1,2,3,5,6,7,8,8a-octahydroindolizine-6,7,8-triol
• CAS: 137326-09-1
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: MWQULCYLMYWIJU-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (5R,6R,7R,8S,8aR)-6,7,8-Tris-benzyloxy-5-benzyloxymethyl-octahydro-indolizine 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以75%的产率得到[5R-(5α,6β,7α,8β,8aα)]-octahydro-6,7,8-trihydroxy-5-hydroxymethylindolizine
  参考文献：
  名称：

  Synthesis of polyhydroxylated indolizidine and quinolizidine compounds--potent inhibitors of α-glucosidase I

  摘要：

  Polyhydroxylated indolizidine 6a and quinolizidine 6b were synthesized from a common precursor, iminoheptitol 8. The target compounds are potent inhibitors of the glycoprotein trimming enzyme--alpha-glucosidase I.

  DOI：

  10.1016/s0040-4039(00)79409-3

文献信息

• Hydroxymethyl-indolizidines and quinolizidines
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0449294A1

  公开（公告）日：1991-10-02

  The present invention describes a group of polyhydroxylated indolizidines and quinolizidines and their esters. These compounds are prepared starting from 2,6-dideoxy-2,6-imino-1,3,4,5-tetrakis-O-(phenylmethyl)-D-glycero-L-gulo-heptitol or a corresponding N-substituted compound. The compounds are useful in the treatment of diabetes and as α-glucosidase I inhibitors.

  本发明描述了一组多羟基化的吲嗪类和醌类化合物及其酯类。这些化合物由 2,6-二脱氧-2,6-亚氨基-1,3,4,5-四-O-(苯基甲基)-D-甘油-L-谷甾醇或相应的 N-取代化合物制备而成。这些化合物可用于治疗糖尿病和作为 α-葡萄糖苷酶 I 抑制剂。
• US5028614A
  申请人：——

  公开号：US5028614A

  公开（公告）日：1991-07-02
• Synthesis of polyhydroxylated indolizidine and quinolizidine compounds--potent inhibitors of α-glucosidase I
  作者：Paul S. Liu、Roland S. Rogers、Mohinder S. Kang、Prasad S. Sunkara

  DOI：10.1016/s0040-4039(00)79409-3

  日期：1991.10

  Polyhydroxylated indolizidine 6a and quinolizidine 6b were synthesized from a common precursor, iminoheptitol 8. The target compounds are potent inhibitors of the glycoprotein trimming enzyme--alpha-glucosidase I.