Dihydropyrimidinones containing boronic acids

被引：29

作者：

Blacquiere, JM

Sicora, O

Vogels, CM

Cuperlovic-Culf, M

Decken, A

Ouellette, RJ

Westcott, SA ^{[1
]}

机构：

[1] Mt Allison Univ, Dept Chem, Sackville, NB E4L 1G8, Canada

[2] Univ New Brunswick, Dept Chem, Fredericton, NB E3B 5A3, Canada

[3] Inst Rech Med Beausejour, Moncton, NB E1C 8X3, Canada

来源：

CANADIAN JOURNAL OF CHEMISTRY | 2005年 / 83卷 / 12期

关键词：

anticancer; Biginelli compounds; boronic acids; breast cancer; dihydropyrimidinones;

D O I：

10.1139/V05-211

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The addition of formylphenylboronic acid derivatives to urea and ethyl acetoacetate proceeds in the absence of an additional Lewis acid catalyst to give the corresponding dihydropyrimidinones (Biginelli products) in good yields. Novel boron-containing dihydropyrimidinones have been investigated for their ability to act as anticancer agents against the breast cancer cell line MCF7.

引用

页码：2052 / 2059

页数：8

共 78 条

[1]

ARIMORI S, 2004, CHEM COMMUNC AMBRIDG, P1604

[2] In vitro and in vivo evaluation of dihydropyrimidinone C-5 amides as potent and selective α1A receptor antagonists for the treatment of benign prostatic hyperplasia [J].

Barrow, JC ;

Nantermet, PG ;

Selnick, HG ;

Glass, KL ;

Rittle, KE ;

Gilbert, KF ;

Steele, TG ;

Homnick, CF ;

Freidinger, RM ;

Ransom, RW ;

Kling, P ;

Reiss, D ;

Broten, TP ;

Schorn, TW ;

Chang, RSL ;

O'Malley, SS ;

Olah, TV ;

Ellis, JD ;

Barrish, A ;

Kassahun, K ;

Leppert, P ;

Nagarathnam, D ;

Forray, C .

JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (14) :2703-2718

[3] The role of water in the oligomerization equilibria involving bis(pentafluorophenyl)borinic acid in dichloromethane solution [J].

Beringhelli, T ;

D'Alfonso, G ;

Donghi, D ;

Maggioni, D ;

Mercandelli, P ;

Sironi, A .

ORGANOMETALLICS, 2004, 23 (23) :5493-5502

[4]

Biginelli P., 1893, GAZZ CHIM ITAL, V23, P360

[5] Large scale Biginelli reaction via water-based biphasic media: a green chemistry strategy [J].

Bose, AK ;

Manhas, MS ;

Pednekar, S ;

Ganguly, SN ;

Dang, H ;

He, W ;

Mandadi, A .

TETRAHEDRON LETTERS, 2005, 46 (11) :1901-1903

[6]

*BRUK AXS INC, 1997, SAINT 6 02 COMP PROG

[7] Why are B2O2 rings rare? [J].

Burke, JM ;

Fox, MA ;

Goeta, AE ;

Hughes, AK ;

Marder, TB .

CHEMICAL COMMUNICATIONS, 2000, (22) :2217-2218

[8]

Cama E, 2003, BIOCHEMISTRY-US, V42, P8445, DOI 10.1021/bi034340j

[9] Isolation and structural characterization of novel compounds containing B4O2 rings [J].

Carmalt, CJ ;

Clegg, W ;

Cowley, AH ;

Lawlor, FJ ;

Marder, TB ;

Norman, NC ;

Rice, CR ;

Sandoval, OJ ;

Scott, AJ .

POLYHEDRON, 1997, 16 (13) :2325-2328

[10] Ferric chloride/tetraethyl orthosilicate as an efficient system for synthesis of dihydropyrimidinones by Biginelli reaction [J].

Cepanec, I ;

Litvic, M ;

Bartolincic, A ;

Lovric, M .

TETRAHEDRON, 2005, 61 (17) :4275-4280

← 1 2 3 4 5 6 7 8 →