Synthesis, characterization and biological evaluation of novel 6-ferrocenyl-4-aryl-2-substituted pyrimidine derivatives

被引：72

作者：

Parveen, Humaira ^{[1
]}

Hayat, Faisal ^{[1
]}

Salahuddin, Attar ^{[1
]}

Azam, Amir ^{[1
]}

机构：

[1] Jamia Millia Islamia, Dept Chem, New Delhi 110025, India

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2010年 / 45卷 / 08期

关键词：

Ferrocenyl chalcones; Pyrimidine derivatives; Antiamoebic activity; Entamoeba histolytica; MTT assay; ACTIVITY IN-VITRO; ANTIMALARIAL ACTIVITY; FERROCENYL; ANTICONVULSANT; PYRIDINE; ANALOGS;

D O I：

10.1016/j.ejmech.2010.04.023

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A new series of 6-ferrocenyl-4-aryl-2-substituted pyrimidines were synthesized and evaluated for in vitro antiamoebic activity against HM1:IMSS strain of Entamoeba histolytica. Out of 16 compounds 10 compounds have shown IC50 values in the range of 0.41-1.73 mu M and 1.80 mu M. Pyrimidine derivatives having thiomethyl group, chloro group and mono-, di-, and trimethoxy substitution, exhibited higher antiamoebic activity than the reference drug metronidazole (IC50 = 1.80 mu M). The toxicological studies of these compounds on human kidney epithelial cell line showed that all compounds were non-toxic. 4-(4-Chlorophenyl)-6-ferrocenyl-2-piperidin-1-yl-pyrimidine (4f) was found most active (IC50 = 0.41 mu M) and least toxic among all the compounds. (C) 2010 Elsevier Masson SAS. All rights reserved.

引用

页码：3497 / 3503

页数：7

共 39 条

[1] Synthesis, analgesic, and antiparkinsonian profiles of some pyridine, pyrazoline, and thiopyrimidine derivatives [J].

Abdel-Latif, Nehad A. ;

Sabry, Nermien M. ;

Mohamed, Ashraf M. ;

Abdulla, Mohamed M. .

MONATSHEFTE FUR CHEMIE, 2007, 138 (07) :715-724

[2] Report on the 2nd EMBO workshop on "Pathogenesis of Amoebiasis: From Genomics to Disease" held at Ein Gedi, Israel, November 16-20, 2004 [J].

Ackers, J ;

Mirelman, D .

EXPERIMENTAL PARASITOLOGY, 2005, 110 (03) :170-172

[3]

Ahluwalia VK, 2000, J CHEM RES-S, P162

[4] Synthesis, reactions, and anti-inflammatory activity of heterocyclic systems fused to a thiophene moiety using citrazinic acid as synthon [J].

Amr, Abd El-Galil E. ;

Sabry, Nermien M. ;

Abdulla, Mohamed M. .

MONATSHEFTE FUR CHEMIE, 2007, 138 (07) :699-707

[5] Anticancer activities of some newly synthesized pyridine, pyrane, and pyrimidine derivatives [J].

Amr, Abdel-Galil E. ;

Mohamed, Ashraf M. ;

Mohamed, Salwa F. ;

Abdel-Hafez, Nagla A. ;

Hammam, Abu El-Fotooh G. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (16) :5481-5488

[6]

Amr AEE, 2002, INDIAN J HETEROCY CH, V12, P129

[7] Synthesis and reactions of some new substituted pyridine and pyrimidine derivatives as analgesic, anticonvulsant and antiparkinsonian agents [J].

Amr, AEGE ;

Sayed, HH ;

Abdulla, MM .

ARCHIV DER PHARMAZIE, 2005, 338 (09) :433-440

[8] Synthesis and reactions of some fused oxazinone, pyrimidinone, thiopyrimidinone, and triazinone derivatives with a thiophene ring as analgesic, anticonvulsant, and antiparkinsonian agents [J].

Amr, AGE ;

Hegab, MI ;

Ibrahiem, AA ;

Abdulla, MM .

MONATSHEFTE FUR CHEMIE, 2003, 134 (10) :1395-1409

[9] Synthesis and antimalarial activity in vitro and in vivo of a new ferrocene-chloroquine analogue [J].

Biot, C ;

Glorian, G ;

Maciejewski, LA ;

Brocard, JS ;

Domarle, O ;

Blampain, G ;

Millet, P ;

Georges, AJ ;

Abessolo, H ;

Dive, D ;

Lebibi, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (23) :3715-3718

[10] Synthesis and antimalarial activity in vitro of potential metabolites of ferrochloroquine and related compounds [J].

Biot, C ;

Delhaes, L ;

N'Diaye, CM ;

Maciejewski, LA ;

Camus, D ;

Dive, D ;

Brocard, JS .

BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (12) :2843-2847

← 1 2 3 4 →