Synthesis, <i>in Vivo</i> Anti-inflammatory, and <i>in Vitro</i> Antimicrobial Activity of New 5-Benzofuranyl Fused Pyrimidines

Abstract

Chalcone (3) has been synthesized as a new chalcone derivative bearing benzofuran moiety at 1 position. Such chalcone was used as a model dielectrophile applied to react with some nucleophiles such as 5-amino pyrazoles, 5-amino-1,2,4-triazole, 2-aminobenzimidazole, and 6-uraciles under Michael reaction conditions and resulted in a new series of fused pyrimidines such as pyrazolo[1,5-a]pyrimidines 7a-e, [1,2,4]-triazolo[1,5-a]pyrimidine 9, pyrimido[1,2-a]benzimidazole 11, and synthesis of pyrido[2,3-d]pyrimidinones 13a and b. The structures of the synthesized target heterocyclic compounds were confirmed by microanalytical and spectral data such as Fourier transform (FT)-IR, (1)H-NMR, and MS spectra. The newly synthesized compounds were evaluated for their anti-inflammatory and antimicrobial activities; most showed significant activities.

Ultrasonic-induced synthesis of novel diverse arylidenes via Knoevenagel condensation reaction. Antitumor, QSAR, docking and DFT assessment

“…IR spectra (400-4000 cm −1 ) were performed in KBr disc on the Nicolet iS10 FT-IR spectrometer. 1 H NMR (at 400 MHz) and 13 C NMR (at 100 MHz) spectra were recorded on a Varian Gemini spectrometer using tetramethylsilane (TMS) as an internal standard in deuterated dimethylsulphoxide (DMSOd 6 ). Mass spectra were recorded on a Shimadzu GCMS-QP 1000 EX mass spectrometer at 70 eV at the Regional Center for Mycology and Biotechnology of Al-Azhar University.…”

“…40 Accordingly, we utilized an eco-friendly method; ultrasonic waves for synthesis of 2-cyano-N'-(4-(piperidin-1-yl)benzylidene) acetohydrazide 3 as a synthon to synthesize novel arylidenes and heteroarylidenes. The newly synthesized compounds were conrmed via spectral analyses such as FT-IR, 1 H NMR, 13 C NMR, and mass spectra. These compounds were evaluated for their antitumor activity.…”

A new synthetic route for the preparation of 2,2′,5′‐trimethyl‐7‐oxo‐4,7‐dihydro‐[6,7′‐bipyrazolo[1,5‐a]pyrimidine]‐3,3′‐dicarbonitrile, structural elucidation, Hirshfeld surface analysis, energy framework, density functional theory and molecular docking investigations

“…The bicyclic moiety containing N1 is essentially planar as there is only an 0.87 (6) dihedral angle between the constituent planes while that containing N5 is less planar with a corresponding dihedral angle of 1.10 (7) . The dihedral angle between the two 6-membered rings is 73.48 (8) . The N2 C6 and N6 C15 bond distances of 1.325 (3) and 1.331 (4) Å are consistent with largely localized double bonds as is the N5 C12 distance of 1.324 (3) Å.…”

“…Indeed, these heterocycles possess many active sites that make them favorable precursors for the synthesis of novel heterocyclic molecular systems capable of exhibiting a wide spectrum of activity. Moreover, they are used as antibacterial, [3,4] Tropomyosin receptor kinases (Trks), [5] anticancer, [6,7] anti-inflammatory, [8] and antitumor agents. [9] Recently, Das et al synthesized a series of substituted pyrazolo [1,5-a]pyrimidine derivatives via a green synthetic route, which show potential antibacterial activity.…”

Aminouracil and aminothiouracil as versatile precursors for a variety of heterocyclic systems

“…On the other hand, compounds 63 (R 1 = 4-Cl-C6H4, R 2 = 4-H3CO-C6H4), (R 1 = 2-Thienyl, R 2 = 4-F-C6H4) and (R 1 = 2-Thienyl, R 2 = 4-H3CO-C6H4) were reported to have the most active anti-fungal agents against Aspergillus fumigatus. Otherwise, Nassar et al 88 reported that pyrido[2,3-d]pyrimidine 63 (R 1 = 2-Thienyl, R 2 = 4-H3CO-C6H4) showed the most anti-microbial effect against Gram-negative Pseudomonas aeruginosa (Scheme 25, Table 10).…”