Synthesis and bioactivity of novel methyl 6-deoxy-6(N′-alkyl/aryl-N"-benzothiazol-2-yl)guanidino-α-D-glucopyranosides

被引:14
作者
Liu, Yong-Hua [1 ]
Cao, Ling-Hua [1 ]
机构
[1] Xinjiang Univ, Coll Chem & Chem Engn, Urumqi 830046, Peoples R China
基金
中国国家自然科学基金;
关键词
sugar isothiocyanate; sugar-thiourea; guanidinoglucoside; 2-aminobenzothiazole; anti-influenza activity;
D O I
10.1016/j.carres.2007.12.001
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A series of new methyl 6-deoxy-6-[N'-alkyl/aryl-N"-(benzothiazol-2-yl)]guanidino-alpha-D-glucopyranosides were obtained from the reaction of an alkyl/aryl amine in the presence of HgCl2 and sugar-thiourea derivatives, followed by the removal of protecting groups. The sugar-thiourea derivatives were obtained from the treatment of 2-aminobenzothiazole derivatives with methyl 2,3,4-tri-O-acetyl-6-deoxy-6-isothiocyanato-alpha-D-glucopyranoside in dry pyridine. Some of the synthesized guanidines displayed anti-influenza activity. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:615 / 625
页数:11
相关论文
共 33 条
[1]  
[Anonymous], 1990, CHEM J CHINESE U
[2]  
Babiano R., 1986, CARBOHYD RES, V154, P280
[3]   Urea-, thiourea-, and guanidine-linked glycooligomers as phosphate binders in water [J].
Blanco, Jose L. Jimenez ;
Bootello, Purificacion ;
Benito, Juan M. ;
Mellet, Carmen Ortiz ;
Fernandez, Jose M. Garcia .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14) :5136-5143
[4]   Synthesis, hypotensive and antiarrhythmic activities of 3-alkyl-1-(2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydro-3-naphthalenyl)ureas or thioureas and their guanidine analogues [J].
Chalina, EG ;
Chakarova, L .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (12) :975-983
[5]   A practical entry to the crambescidin family of guanidine alkaloids. Enantioselective total syntheses of ptilomycalin A, crambescidin 657 and its methyl ester (neofolitispates 2), and crambescidin 800 [J].
Coffey, DS ;
McDonald, AI ;
Overman, LE ;
Rabinowitz, MH ;
Renhowe, PA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (20) :4893-4903
[6]   The first bismuth(III)-catalyzed guanylation of thioureas [J].
Cunha, Silvio ;
Rodrigues, Manoel T., Jr. .
TETRAHEDRON LETTERS, 2006, 47 (39) :6955-6956
[7]   A novel solid-phase synthesis of highly diverse guanidines:: Reactions of primary amines attached to the T2*linker [J].
Dahmen, S ;
Bräse, S .
ORGANIC LETTERS, 2000, 2 (23) :3563-3565
[8]   AMINOGLYCOSIDE ANTIBIOTICS .7. DIHYDROSTREPTOMYCIN ANALOGS [J].
DELAWARE, DL ;
SHARMA, MS ;
IYENGAR, BS ;
REMERS, WA ;
PURSIANO, TA .
JOURNAL OF ANTIBIOTICS, 1986, 39 (02) :251-258
[9]  
ERIJMAN EAJ, 1991, J ORG CHEM, V56, P5712
[10]   Conformational energetics of sugar thioureas and synthesis of glycosyl thioureido sugars [J].
Garcia, Fernandez, J. M. ;
Ortiz Mellet, C. ;
Diaz Perez, V. M. ;
Jimenez Blanco, J. L. .
1996, (52)