Novel and efficient synthesis of 8-oxoadenine derivatives

被引：10

作者：

Hirota, K ^{[1
]}

Kazaoka, K ^{[1
]}

Niimoto, I ^{[1
]}

Sajiki, H ^{[1
]}

机构：

[1] Gifu Pharmaceut Univ, Med Chem Lab, Gifu 5028585, Japan

来源：

HETEROCYCLES | 2001年 / 55卷 / 12期

关键词：

8-oxoadenine; 2-oxoimidazole; synthesis; cyclization; triphosgene;

D O I：

10.3987/COM-01-9356

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel synthetic method of 8-oxoadenine derivatives (3 and 4) is reported. This widely applicable synthetic method was realized through the use of 5-aminlo-4-cyano-2-oxoimidazole derivatives (2) as the key intermediates. A variety of substituents were successfully introduced to the 2- and 9-position of the 8-oxoadenine nucleus.

引用

页码：2279 / 2282

页数：4

共 12 条

[1] Purin-8-ones as corticotropin-releasing hormone (CRH-R1) receptor antagonists [J].

Beck, JP ;

Arvanitis, AG ;

Curry, MA ;

Rescinito, JT ;

Fitzgerald, LW ;

Gilligan, PJ ;

Zaczek, R ;

Trainor, GL .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (07) :967-972

[2] HYDROXYLATING ACTIVITY OF A WATER-SOLUBLE MANGANESE PORPHYRIN ASSOCIATED WITH POTASSIUM HYDROGEN PERSULFATE - FORMATION OF 8-HYDROXYADENOSINE-5'-MONO-PHOSPHATE FROM AMP [J].

BERNADOU, J ;

GELAS, P ;

MEUNIER, B .

TETRAHEDRON LETTERS, 1988, 29 (50) :6615-6618

[3] Repair of oxidative damage to nuclear and mitochondrial DNA in mammalian cells [J].

Croteau, DL ;

Bohr, VA .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (41) :25409-25412

[4]

FRIEDBERG EC, 1995, DNA REPAIR MUTAGENES

[5] SYNTHESIS OF 6-IMINO-1,9-DIMETHYL-8-OXOPURINE, A CONSTITUENT OF THE MARINE SPONGE HYMENIACIDON-SANGUINEA GRANT [J].

FUJII, T ;

SAITO, T ;

MORI, S .

HETEROCYCLES, 1988, 27 (05) :1145-1148

[6]

Itaya T, 1996, CHEM PHARM BULL, V44, P2025

[7]

Itaya T, 1997, CHEM PHARM BULL, V45, P1867

[8]

KAMEYAMA K, 1983, SYNTHESIS-STUTTGART, P849

[9] BENZODIAZEPINE RECEPTOR-BINDING ACTIVITY OF 8-SUBSTITUTED-9-(3-SUBSTITUTED-BENZYL)-6-(DIMETHYLAMINO)-9H-PURINES [J].

KELLEY, JL ;

MCLEAN, EW ;

LINN, JA ;

KROCHMAL, MP ;

FERRIS, RM ;

HOWARD, JL .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :196-202

[10] SYNTHESIS AND ANTIRHINOVIRUS ACTIVITY OF 8-SUBSTITUTED ANALOGS OF 6-(DIMETHYLAMINO)-9-(4-METHYLBENZYL)-2-(TRIFLUOROMETHYL)-9H-PURINE [J].

KELLEY, JL ;

LINN, JA ;

SELWAY, JWT .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :157-160

← 1 2 →