Synthesis and Antimicrobial Evaluation of Some New Cyclooctanones and Cyclooctane‐Based Heterocycles

Abstract

The versatile synthon (E)-2-((dimethyl amino)methylene)cyclooctanone (2) was used as a key intermediate for the synthesis of cyclooctanones and cyclooctane-based heterocycles with pyrazole, isoxazole, pyrimidine, pyrazolopyrimidine, triazolopyrimidine and imidazopyrimidine derivatives via its reactions with several nitrogen nucleophiles. The newly synthesized compounds were screened in vitro for their antimicrobial activity against pathogenic microorganisms (Listeria monocytogenes, methicillin-resistant Staphylococcus aureus (MRSA), Staphylococcus aureus, Pseudomonas aeruginosa and Candida albicans). Most of the tested compounds showed moderate to high antibacterial and antifungal effects against the tested pathogenic microorganisms. Among the synthesized compounds, 2-((p-sulfonamidophenyl)methylene)cyclooctanone (5) showed excellent activity against Listeria monocytogenes.

Reactions of 2,4-diphenyl-butadiene-1,4-sultone with some 1,2- and 1,3-nitrogen bi-nucleophiles

“…[8][9][10][11] They were used as Michael donors in reactions with electrophilic substrates, where the reaction was initiated by the attack of the NH 2 group onto an electron-deficient center followed by cyclization via addition/elimination to give fused heterocycles. 10,11 The behavior of 2,4-diphenylbutadiene-1,4-sultone (1) towards some 1,3-binucleophilic aminoazoles was investigated.…”

“…[5][6][7] To the best of our knowledge, the reactivity of sultones, especially of 2,4-disubstituted butadiene-1,4-sultones, towards 1,2-and 1,3-binucleophiles has not yet been reported. In view of this, and in continuation of our current interest in the chemistry of 1,2-and 1,3-binucleophiles towards various types of dienophile, [8][9][10][11] the goal of the present study was the examination of the reactivity of 2,4-diphenylbutadiene-1,4-sultone towards selected 1,2-and 1,3-binucleophiles.…”

Synthesis of 3,4,5-Trisubstituted Isoxazoles in Water via a [3+2]-Cycloaddition of Nitrile Oxides and 1,3-Diketones, β-Ketoesters, or β-Ketoamides: Base-mediated and Keto-enol-controlled Mechanism

“…Isoxazoles are a privileged class of fivemembered heterocycles, which are found in numerous bioactive natural products 1,2 and synthetic small molecule drugs, 3,4 and are used as important precursors for the synthesis of βhydroxy carbonyls and γ-amino alcohols. 1 Isoxazoles, appearing in 33 patents from the year of 2016 to 2018, 3 is an important drug class due to their wide range of biological activities, such as anticancer, 5 antibiotic, 6,7 antimicrobial, 8 antifungal, 9 and anti-inflammatory. 10 Therefore, new methods to develop efficient, high-yield, and green routes to isoxazoles are always highly desirable.…”

Synthesis and Anticancer Properties of Silver(I) Complexes Containing 2,6-Bis(substituted)pyridine Derivatives

“…On the other hand, functionalized pyridine derivatives are gaining a great deal of interest in medicinal and organic synthesis, where some of pyridine derivatives are used as bactericides [12], fungicides [13], and anticancer agents [14–17]. In view of these observations and in continuation of our current interest in the synthesis of organic compounds for biological evaluations [18–25] and our interest in the chemistry of 2,6-disubstituted pyridine derivatives [26–29], we described herein a facile synthesis of novel silver complex with some of the newly synthesized 2,6-disubstituted pyridine ligands. The newly synthesized compounds were evaluated for their in vitro anticancer activity against four human cancer cell lines including hepatocellular carcinoma (HePG2), lung adenocarcinoma (A549), colon carcinoma (HT29), and breast adenocarcinoma (MCF7).…”