公开(公告)号：WO2004113289A2

公开(公告)日：2004-12-29

申请号：PCT/CA2004/000958

申请日：2004-06-25

Applicant: SIMON FRASER UNIVERSITY ,  PINTO, Brian, Mario ,  JOHNSTON, Blair, D. ,  GHAVAMI, Ahmad ,  SZCZEPINA, Monica, Gabriela ,  LIU, Hui ,  SADALAPURE, Kashinath

Inventor： PINTO, Brian, Mario ,  JOHNSTON, Blair, D. ,  GHAVAMI, Ahmad ,  SZCZEPINA, Monica, Gabriela ,  LIU, Hui ,  SADALAPURE, Kashinath

IPC: C07D207/00

CPC classification number: C07H11/00

Abstract: A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions.

Abstract translation: 合成Salacinol，其立体异构体和类似物的方法，其可能用作乙二醇酶抑制剂的同系物和其它衍生物。 本发明的化合物可以具有通式（I）或（II）：合成方案包括使环硫酸盐与含有杂原子（X）的5元环糖反应。 杂原子优选包含硫，硒或氮。 环状硫酸盐和环糖试剂可以容易地从碳水化合物前体如D-葡萄糖，L-葡萄糖，D-木糖和L-木糖制备。 通过在5元环糖上的杂原子的亲核攻击来打开环状硫酸盐来制备目标化合物。 所得的杂环化合物具有包含杂原子阳离子和硫酸根阴离子的稳定的内盐结构。 合成方案以有限的副反应以中等到良好的产率产生目标化合物的各种立体异构体。

公开(公告)号：WO2004113289A3

公开(公告)日：2004-12-29

申请号：PCT/CA2004/000958

申请日：2004-06-25

Applicant: SIMON FRASER UNIVERSITY ,  PINTO, Brian, Mario ,  JOHNSTON, Blair, D. ,  GHAVAMI, Ahmad ,  SZCZEPINA, Monica, Gabriela ,  LIU, Hui ,  SADALAPURE, Kashinath

Inventor： PINTO, Brian, Mario ,  JOHNSTON, Blair, D. ,  GHAVAMI, Ahmad ,  SZCZEPINA, Monica, Gabriela ,  LIU, Hui ,  SADALAPURE, Kashinath

IPC: A61K31/381

Abstract: A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions.

公开(公告)号：WO2007098597A1

公开(公告)日：2007-09-07

申请号：PCT/CA2007/000330

申请日：2007-03-02

Applicant: SIMON FRASER UNIVERSITY ,  PINTO, Brian Mario ,  JOHNSTON, Blair, D. ,  GHAVAMI, Ahmad ,  SZCZEPINA, Monica Gabriela ,  LIU, Hui ,  SADALAPURE, Kashinath ,  JENSEN, Henrik H. ,  NASI, Ravindranath ,  KUMAR, Nag Sharwan

Inventor： PINTO, Brian Mario ,  JOHNSTON, Blair, D. ,  GHAVAMI, Ahmad ,  SZCZEPINA, Monica Gabriela ,  LIU, Hui ,  SADALAPURE, Kashinath ,  JENSEN, Henrik H. ,  NASI, Ravindranath ,  KUMAR, Nag Sharwan

IPC: C07D333/32 ,  A61K31/095 ,  A61K31/381 ,  A61K31/40 ,  C07C391/00 ,  C07D207/12

CPC classification number: C07D207/12 ,  C07D333/32 ,  C07D335/02 ,  C07D345/00 ,  C07D495/04

Abstract: Methods for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycosidase inhibitors are described. In some embodiments the compounds of the invention may have the general formula (I) or (II). The synthetic schemes may comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions. Chain-extended analogues of Salacinol are also described.

Abstract translation: 描述了可能用作糖苷酶抑制剂的Salacinol，其立体异构体和类似物，同系物和其它衍生物的合成方法。 在一些实施方案中，本发明的化合物可以具有通式（I）或（II）。 合成方案可以包括使环硫酸盐与含有杂原子（X）的5元环糖反应。 杂原子优选包含硫，硒或氮。 环状硫酸盐和环糖试剂可以容易地从碳水化合物前体如D-葡萄糖，L-葡萄糖，D-木糖和L-木糖制备。 通过在5元环糖上的杂原子的亲核攻击来打开环状硫酸盐来制备目标化合物。 所得的杂环化合物具有包含杂原子阳离子和硫酸根阴离子的稳定的内盐结构。 合成方案以有限的副反应以中等到良好的产率产生目标化合物的各种立体异构体。 还描述了Salacinol的链延长类似物。