Synthesis and biological activities of diflunisal hydrazide–hydrazones
作者： S.Güniz Küçükgüzel , Adil Mazi , Fikrettin Sahin , Suzan Öztürk , James Stables
DOI: 10.1016/J.EJMECH.2003.08.004
关键词: Antibacterial activity 、 Cefepime 、 Diflunisal 、 Pharmacology 、 Stereochemistry 、 Antimicrobial 、 Hydrazide 、 Acinetobacter calcoaceticus 、 Chemistry 、 Antibacterial agent 、 Antimycobacterial
摘要: Abstract Several diflunisal hydrazide–hydrazone derivatives namely 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylic acid [(5-nitro-2-furyl/substitutedphenyl)methylene] hydrazide ( 3a – o ) have been synthesised. Methyl 2′,4′-difluoro-4-hydroxybiphenyl-3-carboxylate 1 and 2 were also synthesised used as intermediate compounds. All compounds screened for their antimycobacterial activity against Mycobacterium tuberculosis H37 Rv, antimicrobial activities various bacteria, fungi yeast species. Compound shown Staphylococcus epidermis HE-5 aureus HE-9 at 18.75 37.5 μg mL −1 , respectively. 3o exhibited Acinetobacter calcoaceticus IO-16 a concentration of whereas Cefepime, the drug standard, found less active microorganisms mentioned above. The to provide 12–34% inhibition mycobacterial growth M. Rv in primary screen 6.25 . Anticonvulsant determined by maximal electroshock (MES) subcutaneous metrazole (scMET) tests mice rats following procedures antiepileptic development (ADD) program National Institutes Health (NIH). 3k showed 25% protection MES induced seizures p.o. rat screening dose level 30 mg kg 3n neurotoxicity after 4 0.5 h 100 300
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sci-hub.se 参考文章(13)
Etienne Szarvasi, Louis Fontaine, Annie Betbeder-Matibet, Antimicrobials. New nitrofuran derivatives. Journal of Medicinal Chemistry. ,vol. 16, pp. 281- 287 ,(1973) , 10.1021/JM00261A027
H TABBA, M ABDELHAMID, M SULEIMAN, M ALARAB, M HASAN, S ABULAFI, N NAJIB, Synthesis, identification and preliminary evaluation of esters and amide derivatives of diflunisal International Journal of Pharmaceutics. ,vol. 54, pp. 57- 63 ,(1989) , 10.1016/0378-5173(89)90165-8
Bilge Çakir, Engin Yildirim, Taner Ercanli, Kevser Erol, M.Fethi Sahin, Synthesis and anticonvulsant activity of some (2/4-substituted)benzaldehyde (2-oxobenzothiazolin-3-yl)acetohydrazones. Farmaco. ,vol. 54, pp. 842- 845 ,(1999) , 10.1016/S0014-827X(99)00110-X
M. A. Khalil, O. A. El-Sayed, H. A. El-Shamy, Synthesis and antimicrobial evaluation of novel oxa(thia)diazolylquinolines and oxa(thia)diazepino[7,6-b] quinolines. Archiv Der Pharmazie. ,vol. 326, pp. 489- 492 ,(1993) , 10.1002/ARDP.19933260812
L.B. Colvin, Metabolic Fate of Hydrazines and Hydrazides Journal of Pharmaceutical Sciences. ,vol. 58, pp. 1433- 1443 ,(1969) , 10.1002/JPS.2600581202
Jonathan R Dimmock, Sarvesh C Vashishtha, James P Stables, Anticonvulsant properties of various acetylhydrazones, oxamoylhydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds. European Journal of Medicinal Chemistry. ,vol. 35, pp. 241- 248 ,(2000) , 10.1016/S0223-5234(00)00123-9
E. M. Bavin, D. J. Drain, M. Seiler, D. E. Seymour, SOME FURTHER STUDIES ON TUBERCULOSTATIC COMPOUNDS Journal of Pharmacy and Pharmacology. ,vol. 4, pp. 844- 855 ,(1952) , 10.1111/J.2042-7158.1952.TB13218.X
L Collins, S G Franzblau, Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrobial Agents and Chemotherapy. ,vol. 41, pp. 1004- 1009 ,(1997) , 10.1128/AAC.41.5.1004
Ş.Güniz Küçükgüzel, Sevim Rollas, Ilkay Küçükgüzel, Muammer Kiraz, Synthesis and antimycobacterial activity of some coupling products from 4-aminobenzoic acid hydrazones European Journal of Medicinal Chemistry. ,vol. 34, pp. 1093- 1100 ,(1999) , 10.1016/S0223-5234(99)00129-4
J.R. Zgoda, J.R. Porter, A Convenient Microdilution Method for Screening Natural Products Against Bacteria and Fungi Pharmaceutical Biology. ,vol. 39, pp. 221- 225 ,(2001) , 10.1076/PHBI.39.3.221.5934