Synthesis, Configuration, and Antimicrobial Properties of Novel Substituted and Cyclized ‘2′,3″‐Thiazachalcones’

Abstract

Nine new thiazachalcone-based drugs, compounds 1 -9, were prepared and fully characterized. The configurations of the photochemical-dimerization products 7 -9 were rationalized by semi-empirical calculations. Both the experimental data and the theoretical calculations showed that the d-truxinic acid type dimer is the most stable isomer of all. All compounds were tested for their antibacterial and antifungal activities. The N-alkylated congeners 4 -6 showed strong antimicrobial activities against various bacteria and a yeast-like fungus. The MIC and MBC values were as low as 0.1 mg/ml. All the compounds were active against the Gram-positive bacterium Staphylococcus aureus.

Thieny/Furanyl-hydroxyphenylpropenones as Inhibitors of LPS-induced ROS and NO Production in RAW 264.7 Macrophages, and Their Structure-Activity Relationship Study

“…Total twelve compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) were synthesized as shown Inhibitory Effects on LPS-induced ROS and NO Production in RAW 264.7 Macrophages. Inhibitory activity of LPS-induced ROS and NO production in RAW 264.7 macrophages of prepared compounds is shown in Table 1.…”

“…Among compounds 8-11, which possess 3-thienyl-phenylpropenone as a basic skeleton without hydroxyl group on phenyl ring (8), and with a single hydroxyl group at ortho, meta or para position on phenyl ring (9, 10, 11, respectively), compound 11 displayed the most significant inhibitory activity of LPSinduced ROS and NO production in RAW 264.7 macrophages (2.2 and 0.70 µM of IC 50 , respectively), which also indicated that para-hydroxyphenyl moiety is important for inhibitory activities on both LPS-induced ROS and NO production. Among compounds 12-15, which possess 2-furanyl-phenylpropenone as a basic skeleton without hydroxyl group on phenyl ring (12), and with a single hydroxyl group at ortho, meta or para position on phenyl ring (13,14,15, respectively), unfortunately compound 15 which possess para-hydroxyphenyl moiety displayed cytotoxicity in RAW 264.7 macrophages on both LPS-induced ROS and NO production.…”

“…Many structural modifications of the chalcone moiety by introducing different substituents in the phenyl rings or replacing the phenyl rings with heterocyclic rings exhibited a wide range of pharmacological activities 5,6 such as antibacterial, 7,8 (Figure 1). In our previous study it has been reported that isosteres of chalcone substituted by aromatic (heteroaromatic) rings of two phenyl moiety of chalcone exhibited considerable COX/5-LOX inhibitory activities for the development of safer antiinflammatory agents.…”

Synthesis and antimicrobial properties of N-substituted derivatives of (E)-2′,3″-thiazachalcones

“…In our previous work, novel substituted (E)-3-, and 4-azachalcones, and their N-alkyl derivatives were synthesized and exhibited very good antimicrobial activities, especially against Gram-positive bacteria [16,17]. In view of continuing interest in new antimicrobial agents, other N-alkyl (C [5][6][7][8][9][10][11][12]14 ) substituted 2′,3″-thiazachalconium bromides have been synthesized with the aim of determining the influence of the length of the carbon chain in the N-alkyl substituent on the antimicrobial activity.…”

“…In past years, the synthesis of azachalcones and their N-alkyl substituted derivatives has been studied. These compounds have been reported to possess several biological activities, such as cytotoxic, antimalarial, antileishmanial, antiinflammatory, anti-HIV, antifungal [9][10][11][12][13][14][15][16][17]. Further, the preparation of furan and thiophene analogues of azachalcones has been described, and some of them have been found to possess a wide variety of biological activities, including antituberculosis, antimicrobial, antioxidant, antiinflammatory and antibacterial properties [15][16][17][18][19][20][21][22][23][24].…”