High Throughput Synthesis of Extended Pyrazolo[3,4-d]dihydropyrimidines

被引：11

作者：

Ryabukhin, Sergey V. ^{[1
,2
]}

Granat, Dmitry S. ^{[2
]}

Plaskon, Andrey S. ^{[2
]}

Shivanyuk, Alexander N. ^{[1
,3
]}

Tolmachev, Andrey A. ^{[4
]}

Volovenko, Yulian M. ^{[2
]}

机构：

[1] Kyiv Natl Taras Shevchenko Univ, Inst High Technol, UA-03187 Kiev, Ukraine

[2] Kyiv Natl Taras Shevchenko Univ, Dept Chem, UA-01601 Kiev, Ukraine

[3] Natl Acad Med Sci, Inst Pharmacol & Toxicol, UA-03680 Kiev, Ukraine

[4] Enamine Ltd, UA-01103 Kiev, Ukraine

来源：

ACS COMBINATORIAL SCIENCE | 2012年 / 14卷 / 08期

关键词：

aldehydes; aminopyrazoles; dihydropyrimidines; chlorotrimethylsilane; high throughput synthesis; BIGINELLI REACTION; PYRAZOLO<3,4-D>PYRIMIDINE DERIVATIVES; CHLOROTRIMETHYLSILANE; INHIBITORS; DISCOVERY; SYNTHONS;

D O I：

10.1021/co300063x

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Thirteen 5-hetarylaminopyrazoles were synthesized in 62-93% yield through the arylation of 1-isopropyl- and 1-phenyl-5-aminopyrazoles with electrophilic hetarylhalides under optimized conditions. Condensation of 5-hetarylaminopyrazoles with carbonyl compounds facilitated by AcOH or Me3SiCl furnished 23 pyrazolo[3,4-d]dihydropyrimidines in 69-86% yield. The target compounds were isolated through simple crystallization. The scope and limitation of the method are discussed.

引用

页码：465 / 470

页数：6

共 24 条

[1]

[Anonymous], 2009, INST JCHEM WAS US PR

[2]

Bacon E., 2007, Substituted pyrazolopyrimidines, Patent No. [20070281949A1, 20070281949, US20070281949]

[3] Pyrazolo-pyrimidines:: A novel heterocyclic scaffold for potent and selective p38α inhibitors [J].

Das, Jagabandhu ;

Moquin, Robert V. ;

Pitt, Sidney ;

Zhang, Rosemary ;

Shen, Ding Ren ;

McIntyre, Kim W. ;

Gillooly, Kathleen ;

Doweyko, Arthur M. ;

Sack, John S. ;

Zhang, Hongjian ;

Kiefer, Susan E. ;

Kish, Kevin ;

McKinnon, Murray ;

Barrish, Joel C. ;

Dodd, John H. ;

Schieven, Gary L. ;

Leftheris, Katerina .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (08) :2652-2657

[4] Generation of a set of simple, interpretable ADMET rules of thumb [J].

Gleeson, M. Paul .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (04) :817-834

[5] ANTI-TUMOR ACTIVITY OF 84 SYNTHESIZED N-HETEROAROMATIC COMPOUNDS [J].

HAYASHI, E ;

HIGASHINO, T ;

IIJIMA, C ;

OISHI, E ;

MAKINO, H ;

IRIE, T ;

YAMAMOTO, F ;

YOKOYAMA, Y ;

IWAI, Y ;

KATO, H ;

SHIMADA, N ;

SUZUKI, S ;

SONE, S ;

MORIKAWA, K ;

MOCHIZUKI, H ;

MIYASHITA, A ;

MORIKAWA, T ;

IINUMA, M ;

TOMITA, E ;

OHKUMA, M ;

SHINODA, H ;

KOHNO, M ;

MIZUNO, D .

YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 1977, 97 (09) :1022-1033

[6]

HIGASHINO T, 1986, CHEM PHARM BULL, V34, P4569

[7]

HIGASHINO T, 1976, CHEM PHARM BULL, V24, P3120

[8]

HIGASHINO T, 1987, CHEM PHARM BULL, V35, P4803

[9]

Holzer P., 2007, [Novartis Pharma GmbH, Int. PCT Pub], Patent No. [WO2007062805A1, 2007062805, 2007/062805 A1]

[10]

ISHIKAWA F, 1980, CHEM PHARM BULL, V28, P3172

← 1 2 3 →