Synthesis and antimicrobial evaluation of novel analogues of dehydroabietic acid prepared by C H-Activation

Three series of 2-(4-methylsulfonylphenyl) indole derivatives have been designed and synthesized. The synthesized compounds were assessed for their antimicrobial, COX inhibitory and anti-inflammatory activities. Compound 7g was identified to be the most potent antibacterial candidate against strains of MRSA, E. coli, K. pneumoniae, P. aeruginosa, and A. baumannii, respectively, with safe therapeutic dose. Compounds 7a-k, 8a-c, and 9a-c showed good antiinflammatory activity with excessive selectivity towards COX-2 in comparison with reference drugs indomethacin and celecoxib. Compounds 9a-c were found to release moderate amounts of NO to decrease the side effects associated with selective COX-2 inhibitors. A molecular modeling study for compounds 7b, 7h, and 7i into COX-2 active site was correlated with the results of in vitro COX-2 inhibition assays.

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“…The antimicrobial and antifungal screening was performed according to CO-ADD (The Community for Antimicrobial Drug Discovery) procedures [27].…”

Section: Biological Evaluation Antimicrobial and Antifungal Activitiesmentioning

confidence: 99%

Synthesis and biological evaluation of 2-(4-methylsulfonyl phenyl) indole derivatives: multi-target compounds with dual antimicrobial and anti-inflammatory activities

et al. 2020

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show abstract

“…The antimicrobial and antifungal screening was performed according to CO-ADD (The Community for Antimicrobial Drug Discovery) procedures [26].…”

Section: Antimicrobial and Antifungal Activitiesmentioning

confidence: 99%

Synthesis and biological evaluation of 2-(4-methylsulfonyl phenyl) indole derivatives: Multi-target compounds with dual antimicrobial and anti-inflammatory activities

Shaker

Abdelall

Abdellatif

et al. 2019

Preprint

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Three series of 2-(4-methylsulfonylphenyl) indole derivatives have been designed and synthesized. The synthesized compounds were evaluated for their antimicrobial, COX inhibitory and anti-inflammatory activities. Compound 7g was identified to be the most potent antibacterial candidate against strains of MRSA , E. coli, K. pneumoniae, P. aeruginosa, and A. baumannii , respectively with safe therapeutic dose. Compounds 7a-k, 8a-c and 9a-c showed good anti-inflammatory activity with high selectivity toward COX-2 in comparison with reference drugs indomethacin and celecoxib. Compounds 9a-c were found to release moderate amounts of NO to decrease the side effects associated with selective COX-2 inhibitors. A molecular modeling study for compounds 7b, 7h, and 7i into COX-2 active site correlated with results of in vitro COX-2 inhibition assays.

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“…Abietanes are a family of natural tricyclic diterpenoids with interesting pharmacological activity including antitumor, antimicrobial, antiviral, antiulcer, and anti-inflammatory activities [5,6,7,8,9]. Interestingly, dehydroabietic acid (DHAA) and its derivatives have exhibited a broad spectrum of biological activities including antibacterial [10,11,12,13], antifungal [14], antiprotozoal [15], antiviral [16], antiulcer [17], antiherpetic [18] and anti-aging [19]. Especially, a number of DHAA derivatives have been reported in recent years which showed significant antitumor property through DNA binding, apoptosis or oncosis inducing mechanisms [20,21,22].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antiproliferative Evaluation of Novel Hybrids of Dehydroabietic Acid Bearing 1,2,3-Triazole Moiety

Huang

et al. 2019

Molecules

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To discover novel potent cytotoxic diterpenoids, a series of hybrids of dehydroabietic acid containing 1,2,3-triazole moiety were designed and synthesized. The target compounds were characterized by means of FT-IR, 1H NMR, 13C NMR, ESI-MS and elemental analysis techniques. The in vitro cytotoxicity of these compounds was evaluated by standard MTT (methyl thiazolytetrazolium) assay against CNE-2 (nasopharynx), HepG2 (liver), HeLa (epithelial cervical), BEL-7402 (liver) human carcinoma cell lines and human normal liver cell (HL-7702). The screening results revealed that most of the hybrids showed significantly improved cytotoxicity over parent compound DHAA. Among them, [1-(3-fluorobenzyl)-1H-1,2,3-triazole-4-yl]dehydroabietic acid methyl ester (3c), and [1-(2-nitrobenzyl)-1H-1,2,3-triazole-4-yl]dehydroabietic acid methyl ester (3k) displayed better antiproliferative activity with IC50 (50% inhibitory concentration) values of 5.90 ± 0.41 and 6.25 ± 0.37 µM toward HepG2 cells compared to cisplatin, while they exhibited lower cytotoxicity against HL-7702. Therefore, the 1,2,3-triazole-hybrids could be a promising strategy for the synthesis of antitumor diterpenoids and it also proved the essential role of 1,2,3-triazole moiety of DHAA in the biological activity.

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Synthesis and antimicrobial evaluation of novel analogues of dehydroabietic acid prepared by C H-Activation

Cited by 28 publications

References 34 publications

Synthesis and biological evaluation of 2-(4-methylsulfonyl phenyl) indole derivatives: multi-target compounds with dual antimicrobial and anti-inflammatory activities

Synthesis and biological evaluation of 2-(4-methylsulfonyl phenyl) indole derivatives: multi-target compounds with dual antimicrobial and anti-inflammatory activities

Synthesis and biological evaluation of 2-(4-methylsulfonyl phenyl) indole derivatives: Multi-target compounds with dual antimicrobial and anti-inflammatory activities

Synthesis and Antiproliferative Evaluation of Novel Hybrids of Dehydroabietic Acid Bearing 1,2,3-Triazole Moiety

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