Fatma Allouche

Synthesis of aminocyanopyrazoles via a multi-component reaction and anti-carbonic anhydrase inhibitory activity of their sulfamide derivatives against cytosolic and transmembrane isoforms.

A convenient protocol for the multicomponent reaction (MCRs) between malononitrile with an orthoester and hydrazine derivatives, under acid catalyst is described. A series of aminocyanopyrazoles 4 was prepared, isolated and characterized. These pyrazoles reacted with sodium nitrite followed by secondary amine reagent and with formic acid to lead pyrazolotriazines 6 and pyrazolopyrimidinones 7. Some of the aminopyrazoles were converted to the corresponding sulfamides by reaction with sulfamoyl chloride. The aminopyrazoles incorporating phenyl and tosyl moieties were tested as inhibitors of four carbonic anhydrase (CA, EC 4.2.1.1) isoforms, the human (h) hCA I, II, IX and XII. Many of them showed low micromolar or submicromolar inhibition of these enzymes. The corresponding sulfamides were low nanomolar CA inhibitors.

Synthesis of New Pyrazolopyrimidinedithiones and Pyrazolopyrimidinephosphines from Aminocyanopyrazoles

Abstract A general, high-yielding synthetic protocol for the expedited synthesis of functionalized pyrazolopyrimidine dithione 2 and pyrazolodiazaphosphininethione 3 from amino-cyano pyrazole 1 precursors is presented.

Synthesis, antibacterial, and antifungal activities of new pyrimidinone derivatives

Abstract An efficient synthesis of new pyrrolopyrimidinones 3a-d and isoxazolopyrimidinones 4a-c from the respective aminocyanopyrroles 1a-d and aminocyanoisoxazoles 2a-c is presented. The synthesized compounds were screened for antimicrobial activity against a panel of bacteria and fungi. Compound 4c exhibits remarkable activity against a broad spectrum of Gram-positive and Gram-negative bacteria and pathogenic fungi.

Synthesis and Biological Activities of Novel 1,7-dihydropyrazolo[3,4-d]imidazo[1,2-f]pyrimidines

A straightforward method has been developed for the synthesis of new anti-inflammatory 1,7-dihydropyrazolo[3,4-d]imidazo[1,2-f]pyrimidine 5 from aminocyanopyrazole. These compounds were screened for their anti-inflammatory, gastroprotective, analgesic, antioxidant and anticandidal activities. Studies of structure-activity relationships have led to selection of compound 6-(4-methoxyphenyl)-3-methyl-1,7-dihydropyrazolo[3,4-d]imidazo[1,2-f]pyrimidine, 5a which exhibited the most potent activities. The structures of all new compounds were elucidated using IR, 1H NMR, 13C NMR and HRMS.

Design, Microwave-Assisted Synthesis and Biological Activities of1,2,4-Triazol-3-Yl-Thiazolidin-4-Ones

A new 3-(5-alkyl-2-phenyl-2H-1,2,4-triazol-3-yl)thiazolidin-4-ones derivatives were obtained by condensation of 5-amino-1,2,4-triazoles, mercaptoacetic acid with aromatic aldehydes and catalyzed by Sm(SO3CF3)3 using microwave irradiation. The prepared compounds were tested for their antioxidant, antibacterial and antifungal proprieties. Some of these compounds displayed significant activities. Among them, compound 2e exhibited remarkable activity against a broad spectrum of Gram positive, negative bacteria and pathogenic fungal strains with low MIC values. The investigation of the mode of action of the most potent antifungal compounds on the fungus Pythium phanidermatum showed a membrane alteration and distortions of hyphal morphology. The newly synthesized compounds exhibited also promising radical scavenging activity.

Synthesis, Antibacterial, and Antifungal Activities of Imidazo[2,1-c][1,2,4]triazoles and 1,2,4-Triazolo[4,3-a]pyrimidinones

Abstract A straightforward method has been developed for the synthesis of 1-phenyl-imidazo [2,1-c][1,2,4]triazole derivatives 5a–j and 1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidinones derivatives 6a–g starting from 5-amino-1-phenyl[1,2,4]triazole and p-toluenesulfonic acid (PTSA). This methodology affords a number of 1-phenyl-imidazo [2,1-c][1,2,4]triazoles 5a–j and 1-phenyl-[1,2,4]triazolo[4,3-a]pyrimidinones 6a–g in reasonable yields and short reaction times. The structures of all new compounds were elucidated using infrared, 1H and 13C NMR, and high-resolution mass spectrometry. Some of the newly synthesized compounds were screened for their antimicrobial activity. [Supplementary materials are available for this article. Go to the publishers online edition of Synthetic Communications ® for the following free supplemental resource(s): Full experimental and spectral details.] GRAPHICAL ABSTRACT