Bioorganic and Medicinal Chemistry p. 1857 - 1865 (1996)
Update date:2022-08-22
Topics:
Godskesen, Michael
Lundt, Inge
Madsen, Robert
Winchester, Bryan
The four stereoisomeric 1,5-dideoxy-1,5-iminopentitols with D-arabino - (D-lyxo-) (3), ribo- (9), L-lyxo- (L-arabino-) (13) and xylo- (18) configurations were synthesized. The corresponding aldonolactones (1, 7 and 11) or aldonic acid ester (15b) having a leaving group at C-5 gave by reaction with aqueous ammonia, the 5-amino-5-deoxy-1,5-lactams, 2, 8, 12 and 17, respectively. Reduction of the lactam function using sodium borohydride/acetic or trifluoroacetic acid, or borane dimethyl sulfide complex yielded the iminopentitols. The compounds 3, 9, 13 and 18, together with the three 1,5-dideoxy-1,5-iminoheptitols 19, 20 and 21 were tested for inhibition of the glycosidase activities present in an extract from human liver. Compound 18 was a potent and 19 a moderately good inhibitor of β-glucosidase. Compound 3 together with 19, 20 and 21, all having D-arabino-configuration at the hydroxy-substituted carbon atoms, were good inhibitors of α-L-fucosidase.
View MoreContact:+86-512-56795332
Address:No227 Shuanglong Rd, Fenghuang, Zhangjiagang
TAIXING BEST NEW MATERIALS CO., LTD
Contact:0523-87998158;
Address:No.18 Zhonggang Road,Taixing City ,Jiangsu , China
LIAOYANG WANRONG CHEMICALS COMPANY LIMITED
Contact:86-419-2390789
Address:XINLI VILLAGE , DONG NINGWEI COUNTY,TAIZIHE DISTRICT, LIAOYANG , LIAONING
TIANJIN NORTH JINHENG CHEMICAL PLANT.
Contact:0086-22-59952083
Address:DongShigu Country In JiXian TianJin China
taicang liyuan chemical co,.ltd
website:http://www.tcliyuanchem.com/productse.php
Contact:86-512-53539583
Address:Room 804,Huaxu Building,No.95,Renmin South Road,Taicang city,Jiangsu Province,China
Doi:10.1016/j.catcom.2013.07.029
(2014)Doi:10.1039/c4ra10325d
(2014)Doi:10.1039/J29710002006
(1971)Doi:10.1002/hlca.19730560747
(1973)Doi:10.1021/jo00405a046
(1978)Doi:10.1021/jo01366a004
(1954)