Synthesis and antiviral activity of C-3(C-28)-substituted 2,3-seco-triterpenoids

被引：5

作者：

Tolmacheva, I. A. ^{[1
]}

Igosheva, E. V. ^{[1
]}

Savinova, O. V. ^{[2
]}

Boreko, E. I. ^{[2
]}

Grishko, V. V. ^{[1
]}

机构：

[1] Russian Acad Sci, Inst Tech Chem, Ural Branch, Perm 614013, Russia

[2] Minist Hlth Republ Belarus, RSPC Epidemiol & Microbiol, Minsk 220114, BELARUS

来源：

CHEMISTRY OF NATURAL COMPOUNDS | 2014年 / 49卷 / 06期

关键词：

A-seco-triterpenoids; betulin; betulonic acid; allobetulone; beta-amino alcohols; amides; esters; herpes simplex virus type 1 (HSV-1); ANTI-AIDS AGENTS; BIOLOGICAL-ACTIVITY; ACID-DERIVATIVES; BETULINIC ACID; AMIDES; LUPANE;

D O I：

10.1007/s10600-014-0821-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Amide conjugates with four structural types of beta-amino alcohols were synthesized from 2,3-seco-18 alpha H-oleananoic and 2,3-seco-lupane C-3(C-28) mono- and dicarboxylic acids. Esters were prepared by reaction of C-3-hydroxy derivatives of A-seco-triterpenoids with dicarboxylic acid anhydrides. The antiviral activity of the synthesized compounds was studied against herpes simplex virus type I. The most active amide was 5a (5.7 mu M, MTC/EC50 32.2).

引用

页码：1050 / 1058

页数：9

共 50 条

[41] Synthesis of substituted indole-2-carboxylates: Versatile introduction of a carbamoyl moiety at the C-3 position
Giacobbe, SA
Di Fabio, R
Baraldi, D
Cugola, A
Donati, D
SYNTHETIC COMMUNICATIONS, 1999, 29 (18) : 3125 - 3135
[42] SYNTHESIS AND ANTIVIRAL ACTIVITY OF 3'-C-CYANO-3'-DEOXYNUCLEOSIDES
CAMARASA, MJ
DIAZORTIZ, A
CALVOMATEO, A
DELASHERAS, FG
BALZARINI, J
DECLERCQ, E
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (08) : 1732 - 1738
[43] Synthesis of substituted indole-2-carboxylates: Versatile introduction of a carbamoyl moiety at the C-3 position
Glaxo Wellcome S.p.A., Medicines Research Centre, Via A. Fleming 4, I-37135 Verona, Italy
不详
Synth. Commun., 18 (3125-3135):
[44] THE SYNTHESIS OF SUBSTITUTED [1]BENZOTHIENO[2,3-C]QUINOLINES
MCKENNEY, JD
CASTLE, RN
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 193 : 249 - ORGN
[45] Selective C-3 lithiation of 2,3-dibromo- and 2,3-diiodo-1-methylindoles
Ueda, Ikuko
Nishiura, Mitsuko
Takahashi, Tohru
Eda, Kazuo
Hashimoto, Masao
Yamamura, Kimiaki
TETRAHEDRON LETTERS, 2006, 47 (48) : 8535 - 8537
[46] A rapid synthesis of thieno[2,3-c]pyridine and 2-substituted thieno[2,3-c]pyridines
Graulich, A
Liégeois, JF
SYNTHESIS-STUTTGART, 2004, (12): : 1935 - 1937
[47] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF C-3' ORTHO DIHYDROXYPHTHALIMIDO CEPHALOSPORINS
BAUDART, MG
HENNEQUIN, LF
JOURNAL OF ANTIBIOTICS, 1993, 46 (09): : 1458 - 1470
[48] Synthesis and in vitro antibacterial activity of C-3′ pyridinium cephalosporin derivatives
Chung, IH
Kim, CS
Seo, JH
Chung, BY
ARCHIVES OF PHARMACAL RESEARCH, 1999, 22 (04) : 391 - 397
[49] SYNTHESIS OF SUBSTITUTED THIENO[2,3-C] AND [3,2-D]ISOTHIAZOLES
TORNETTA, B
RONSISVALLE, G
BOUSQUET, E
GUERRERA, F
SIRACUSA, MA
GAZZETTA CHIMICA ITALIANA, 1980, 110 (04): : 233 - 236
[50] A facile synthesis of C2-substituted pyrrolo[2,3-f]quinolines with cytotoxic activity
Tsotinis, A
Vlachou, M
Zouroudis, S
Jeney, A
Timár, F
Thurston, DE
Roussakis, C
LETTERS IN DRUG DESIGN & DISCOVERY, 2005, 2 (03) : 189 - 192

← 1 2 3 4 5 →