Synthesis and characterization of new N-phenylmaleimide thioglycosides

被引：2

作者：

Salameh, Bader A. ^{[1
]}

Abu-Safieh, Kayed A. ^{[1
]}

Al-Kaabenah, Sanaa R. A. ^{[1
]}

Al-Qawasmeh, Raed A. ^{[2
]}

机构：

[1] Hashemite Univ, Dept Chem, Zarqa 13115, Jordan

[2] Univ Jordan, Dept Chem, Amman 11942, Jordan

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2014年 / 40卷 / 08期

关键词：

Thioglycosides; Sugar thiols; N-phenylmaleimide; PKC-BETA; INHIBITORS; DERIVATIVES; ANTITUMOR; BEARING; POTENT; IMIDE;

D O I：

10.1007/s11164-013-1146-8

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thioglycosides derivatives of N-phenylmaleimide have been prepared by the reaction of derivatives of 1-thio-d-glucopyranose, d-galactopyranose, d-lactose, and d-maltose with 3,4-dichloro-N-phenylmaleimide. The reaction of 3,4-dichloro-N-phenyl maleimide with sugar thiols (protected or unprotected) took place by displacement of both chlorine atoms by sulfide nucleophile giving the corresponding bis-thioglycoside products.

引用

收藏

页码：3001 / 3009

页数：9

相关论文

共 22 条

[1]

ALHOLLY MM, 1979, PHARMAZIE, V34, P645

[2] Syntheses and biological activities (topoisomerase inhibition and antitumor and antimicrobial properties) of rebeccamycin analogues bearing modified sugar moieties and substituted on the imide nitrogen with a methyl group [J].

Anizon, F ;

Belin, L ;

Moreau, P ;

Sancelme, M ;

Voldoire, A ;

Prudhomme, M ;

Ollier, M ;

Severe, D ;

Riou, JF ;

Bailly, C ;

Fabbro, D ;

Meyer, T .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (21) :3456-3465

[3] Granulatimide and isogranulatimide, aromatic alkaloids with G2 checkpoint inhibition activity isolated from the Brazilian ascidian Didemnum granulatum:: Structure elucidation and synthesis [J].

Berlinck, RGS ;

Britton, R ;

Piers, E ;

Lim, L ;

Roberge, M ;

da Rocha, RM ;

Andersen, RJ .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9850-9856

[4] NOVEL PIGMENTS FROM DICHLOROMALEIMIDES [J].

DIMROTH, P ;

REICHENE.F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1969, 8 (10) :751-&

[5] Acyclic N-(azacycloalkyl)bisindolylmaleimides:: Isozyme selective inhibitors of PKCβ [J].

Faul, MM ;

Gillig, JR ;

Jirousek, MR ;

Ballas, LM ;

Schotten, T ;

Kahl, A ;

Mohr, M .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (11) :1857-1859

[6]

FICKENTSCHER K, 1969, TETRAHEDRON LETT, P4273

[7]

Fujiwara A., 1985, CRIT REV BIOTECHNOL, V3, P133, DOI DOI 10.3109/07388558509150782

[8] Some synthetic applications of 2,3-dichloro-N-phenylmaleimide:: A novel synthesis of 2-phenylpyrrolo[3,4-b]quinoxaline-1,3-diones.: I [J].

Hanaineh-Abdelnour, L ;

Bayyuk, S ;

Theodorie, R .

TETRAHEDRON, 1999, 55 (40) :11859-11870

[9] Generality and scope of the synthesis of 2-arylpyrrolo [3,4-b]quinoxaline-1,3-diones from 2,3-dichloro-N-arylmaleimzdes.: II [J].

Hanaineh-Abdelnour, L ;

Salameh, BA .

HETEROCYCLES, 1999, 51 (12) :2931-2940

[10] Synthesis of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones bearing a sugar moiety [J].

Hénon, H ;

Anizon, F ;

Pfeiffer, B ;

Prudhomme, M .

TETRAHEDRON, 2006, 62 (06) :1116-1123