Solid-phase synthesis of pyrido[2,3-d]pyrimidin-7-ones

被引：10

作者：

Angiolini, M ^{[1
]}

Bassini, DF ^{[1
]}

Gude, M ^{[1
]}

Menichincheri, M ^{[1
]}

机构：

[1] Nerviano Med Sci, Discovery Oncol, I-20014 Nerviano, Italy

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 50期

关键词：

pyrido[2,3-d]pyrimidin-7-one; solid-phase; formyl resin; scaffold; library;

D O I：

10.1016/j.tetlet.2005.10.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel solid-phase method for the synthesis of 4-methyl-pyrido[2,3-d]pyrimidin-7-one compounds with two diversity points is described. The polymer supported methylsulfonyl derivatives A(3), achieved by coupling compound G with different resin-bound amines A(1) followed by oxidation with MCPBA, are substituted with several amines R1R2NH. Final cleavage affords 126 compounds having formula H in good yield and purity. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：8749 / 8752

页数：4

共 8 条

[1] Pyrido[2,3-d]pyrimidin-7-one inhibitors of cyclin-dependent kinases [J].

Barvian, M ;

Boschelli, DH ;

Cossrow, J ;

Dobrusin, E ;

Fattaey, A ;

Fritsch, A ;

Fry, D ;

Harvey, P ;

Keller, P ;

Garrett, M ;

La, F ;

Leopold, W ;

McNamara, D ;

Quin, M ;

Trumpp-Kallmeyer, S ;

Toogood, P ;

Wu, ZP ;

Zhang, EL .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (24) :4606-4616

[2] Synthesis and tyrosine kinase inhibitory activity of a series of 2-amino-8H-pyrido[2,3-d]pyrimidines:: Identification of potent, selective platelet-derived growth factor receptor tyrosine kinase inhibitors [J].

Boschelli, DH ;

Wu, ZP ;

Klutchko, SR ;

Showalter, HDH ;

Hamby, JM ;

Lu, GH ;

Major, TC ;

Dahring, TK ;

Batley, B ;

Panek, RL ;

Keiser, J ;

Hartl, BG ;

Kraker, AJ ;

Klohs, WD ;

Roberts, BJ ;

Patmore, S ;

Elliott, WL ;

Steinkampf, R ;

Bradford, LA ;

Hallak, H ;

Doherty, AM .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (22) :4365-4377

[3] Versatile monitoring tools in parallel solid-phase synthesis [J].

Felder, ER ;

Martina, K ;

Scarpella, S ;

Tatò, M .

CHIMIA, 2003, 57 (05) :229-236

[4] A convenient synthesis of trisubstituted pyrido[2,3-d]pyrimidin-7-ones [J].

Kasparec, J ;

Adams, JL ;

Sisko, J ;

Silva, DJ .

TETRAHEDRON LETTERS, 2003, 44 (24) :4567-4570

[5] 2-substituted aminopyrido[2,3-d]pyrimidin-7(8H) ones.: Structure-activity relationships against selected tyrosine kinases and in vitro and in vivo anticancer activity [J].

Klutchko, SR ;

Hamby, JM ;

Boschelli, DH ;

Wu, ZP ;

Kraker, AJ ;

Amar, AM ;

Hartl, BG ;

Shen, C ;

Klohs, WD ;

Steinkampf, RW ;

Driscoll, DL ;

Nelson, JM ;

Elliott, WL ;

Roberts, BJ ;

Stoner, CL ;

Vincent, PW ;

Dykes, DJ ;

Panek, RL ;

Lu, GH ;

Major, TC ;

Dahring, TK ;

Hallak, H ;

Bradford, LA ;

Showalter, HDH ;

Doherty, AM .

JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (17) :3276-3292

[6] Discovery of a potent and selective inhibitor of cyclin-dependent kinase 4/6 [J].

Toogood, PL ;

Harvey, PJ ;

Repine, JT ;

Sheehan, DJ ;

VanderWel, SN ;

Zhou, HR ;

Keller, PR ;

McNamara, DJ ;

Sherry, D ;

Zhu, T ;

Brodfuehrer, J ;

Choi, C ;

Barvian, MR ;

Fry, DW .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (07) :2388-2406

[7] Pyrido[2,3-d]pyrimidin-7-ones as specific inhibitors of cyclin-dependent kinase 4 [J].

VanderWel, SN ;

Harvey, PJ ;

McNamara, DJ ;

Repine, JT ;

Keller, PR ;

Quin, J ;

Booth, RJ ;

Elliott, WL ;

Dobrusin, EM ;

Fry, DW ;

Toogood, PL .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (07) :2371-2387

[8] EFFICIENT METHOD FOR THE SYNTHESIS OF 1,4-DISUBSTITUTED 5-CARBOMETHOXYPYRIMIDIN-6-ONES [J].

VEALE, CA ;

STEELMAN, GB ;

CHOW, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4490-4493

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