Microwave-Assisted Solvent-Free Synthesis of Bis(dihydropyrimidinone)benzenes and Evaluation of their Cytotoxic Activity

被引：42

作者：

Azizian, Javad ^{[2
]}

Mohammadi, Mohammad K. ^{[2
]}

Firuzi, Omidreza ^{[1
]}

Mirza, Behrooz ^{[3
]}

Miri, Ramin ^{[1
]}

机构：

[1] Shiraz Univ Med Sci, Med & Nat Prod Chem Res Ctr, Shiraz, Iran

[2] Islamic Azad Univ, Fac Sci, Dept Chem, Sci & Res Branch, Tehran, Iran

[3] Islamic Azad Univ, Fac Sci, Dept Chem, S Tehran Branch, Tehran, Iran

来源：

CHEMICAL BIOLOGY & DRUG DESIGN | 2010年 / 75卷 / 04期

关键词：

Biginelli reaction; cytotoxicity; dihyropyrimidinone; microwave irradiation; multicomponent; terephthalic aldehyde; TMSCl; BIGINELLI DIHYDROPYRIMIDINE SYNTHESIS; ONE-POT SYNTHESIS; CONDENSATION REACTION; 3-COMPONENT REACTION; EFFICIENT SYNTHESIS; REUSABLE CATALYST; DERIVATIVES; BLOCKERS; ACID; QSAR;

D O I：

10.1111/j.1747-0285.2009.00937.x

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An effective one-pot synthesis of bis(dihydropyrimidinonoe)benzenes using chlorotrimethylsilane (TMSCl) through Biginelli condensation reaction of terephthalic aldehyde, 1,3-dicarbonyl compounds and (thio)urea or guanidine under microwave irradiation conditions is described. Excellent yields of the products and simple work-up are attractive features of this green protocol. Then, the cytotoxic activities of these compounds were evaluated on five different human cancerous cell lines (Raji, HeLa, LS-180, SKOV-3 and MCF7). Their cytotoxic study indicated that they possessed a weak to moderate activity. Furthermore, the higher activity of compound 4b bearing sulfur in C-2 position of pyrimidinone ring showed the importance of this site for cytotoxic activity of these compounds.

引用

页码：375 / 380

页数：6

共 36 条

[21] Biologically active dihydropyrimidones of the Biginelli-type - a literature survey [J].

Kappe, CO .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (12) :1043-1052

[22] Recent advances in the Biginelli dihydropyrimidine synthesis. New tricks from an old dog [J].

Kappe, CO .

ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (12) :879-888

[23] Polyphosphate ester-mediated synthesis of dihydropyrimidines. Improved conditions for the Biginelli reaction [J].

Kappe, CO ;

Falsone, SF .

SYNLETT, 1998, (07) :718-720

[24]

Kumar KA, 2001, TETRAHEDRON LETT, V42, P7873

[25] Dihydropyridine derivatives to overcome atypical multidrug resistance: Design, synthesis, QSAR studies, and evaluation of their cytotoxic and pharmacological activities [J].

Mehdipour, Ahmad R. ;

Javidnia, Katayoun ;

Hemmateenejad, Bahram ;

Amirghofran, Zahra ;

Miri, Ramin .

CHEMICAL BIOLOGY & DRUG DESIGN, 2007, 70 (04) :337-346

[26] Synthesis, cytotoxicity, QSAR, and intercalation study of new diindenopyridine derivatives [J].

Miri, R ;

Javidnia, K ;

Hemmateenejad, B ;

Azarpira, A ;

Amirghofran, Z .

BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (10) :2529-2536

[27]

Obrecht D., 1998, TETR ORG CH

[28] NOVEL ALKALOIDS FROM THE SPONGE BATZELLA SP - INHIBITORS OF HIV GP120-HUMAN CD4 BINDING [J].

PATIL, AD ;

KUMAR, NV ;

KOKKE, WC ;

BEAN, MF ;

FREYER, AJ ;

DEBROSSE, C ;

MAI, S ;

TRUNEH, A ;

FAULKNER, DJ ;

CARTE, B ;

BREEN, AL ;

HERTZBERG, RP ;

JOHNSON, RK ;

WESTLEY, JW ;

POTTS, BCM .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1182-1188

[29] AN ENANTIOSPECIFIC SYNTHESIS OF THE TRICYCLIC GUANIDINE SEGMENT OF THE ANTI-HIV MARINE ALKALOID BATZELLADINE-A [J].

RAO, AVR ;

GURJAR, MK ;

VASUDEVAN, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (13) :1369-1370

[30] CALCIUM-ENTRY BLOCKERS AND ACTIVATORS - CONFORMATIONAL AND STRUCTURAL DETERMINANTS OF DIHYDROPYRIMIDINE CALCIUM-CHANNEL MODULATORS [J].

ROVNYAK, GC ;

KIMBALL, SD ;

BEYER, B ;

CUCINOTTA, G ;

DIMARCO, JD ;

GOUGOUTAS, J ;

HEDBERG, A ;

MALLEY, M ;

MCCARTHY, JP ;

ZHANG, RA ;

MORELAND, S .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (01) :119-129

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