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1.
Mol Divers ; 25(2): 861-876, 2021 May.
Article in English | MEDLINE | ID: mdl-32172491

ABSTRACT

In the present investigation, a series of dihydrotriazine derivatives-bearing 5-aryloxypyrazole moieties were synthesized and their structures were confirmed by different spectral tools. The biological evaluation in vitro revealed that some of the target compounds exerted good antibacterial and antifungal activity in comparison with the reference drugs. Among these novel hybrids, compound 10d showed the most potent activity with minimum inhibitory concentration values (MIC) of 0.5 µg/mL against S. aureus 4220, MRSA 3506 and E. coli 1924 strain. The cytotoxic activity of the compounds 6d, 6m, 10d and 10g was assessed in MCF-7 and HeLa cells. Growth kinetics study showed significant inhibition of bacterial growth when treated with different conc. of 10d. In vitro enzyme study implied that compound 10d exerted its antibacterial activity through DHFR inhibition. Moreover, significant inhibition of biofilm formation was observed in bacterial cells treated with MIC conc. of 10d as visualized by SEM micrographs. Twenty-nine target compounds were designed, synthesized and evaluated in terms of their antibacterial and antifungal activities.


Subject(s)
Anti-Bacterial Agents , Triazines , Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Bacteria/drug effects , Bacteria/growth & development , Biofilms/drug effects , Biofilms/growth & development , Cell Survival/drug effects , HeLa Cells , Humans , MCF-7 Cells , Microbial Sensitivity Tests , Molecular Docking Simulation , Structure-Activity Relationship , Tetrahydrofolate Dehydrogenase/chemistry , Triazines/chemical synthesis , Triazines/chemistry , Triazines/pharmacology
2.
Org Lett ; 22(18): 7073-7077, 2020 09 18.
Article in English | MEDLINE | ID: mdl-32886523

ABSTRACT

The development of methods toward the construction of quaternary carbon centers has been a hot topic in recent years. In this work, an Au(I)-catalyzed intramolecular cyclization/semipinacol rearrangement of allene-containing allylic silyl ether was developed to provide a direct strategy for the construction of multisubstituted cyclohexene-type compounds with a quaternary carbon center in moderate to good yields. In particular, this method provides an alternative synthetic strategy for the construction of a multisubstituted spirocyclo[4.5]decane skeleton and may be applied to the synthesis of related bioactive molecules and their derivatives, thus facilitating the corresponding functional studies.

3.
Bioorg Med Chem Lett ; 30(13): 127237, 2020 07 01.
Article in English | MEDLINE | ID: mdl-32386981

ABSTRACT

Twenty benzothiazole derivatives bearing a 1,3,4-oxadiazole moiety were synthesized and evaluated for their anti-oxidant and anti-inflammatory activities. Among these compounds, 8h and 8l were appeared to have high radical scavenging efficacies as 0.05 ± 0.02 and 0.07 ± 0.03 mmol/L of IC50 values in ABTS+ bioassay, respectively. In anti-inflammatory tests, compound 8h displayed good activity with 57.35% inhibition after intraperitoneal administration, which was more potent than the reference drug (indomethacin). Molecular modeling studies were performed to investigate the binding mode of the representative compound 8h into COX-2 enzyme. In vitro enzyme study implied that compound 8h exerted its anti-inflammatory activity through COX-2 inhibition.


Subject(s)
Anti-Inflammatory Agents/therapeutic use , Benzothiazoles/therapeutic use , Free Radical Scavengers/therapeutic use , Inflammation/drug therapy , Oxadiazoles/therapeutic use , Animals , Anti-Inflammatory Agents/chemical synthesis , Anti-Inflammatory Agents/metabolism , Benzothiazoles/chemical synthesis , Benzothiazoles/metabolism , Cyclooxygenase 2/metabolism , Cyclooxygenase 2 Inhibitors/chemical synthesis , Cyclooxygenase 2 Inhibitors/metabolism , Cyclooxygenase 2 Inhibitors/therapeutic use , Free Radical Scavengers/chemical synthesis , Free Radical Scavengers/metabolism , Humans , Mice , Molecular Docking Simulation , Molecular Structure , Oxadiazoles/chemical synthesis , Oxadiazoles/metabolism , Structure-Activity Relationship
4.
Mol Divers ; 24(4): 1165-1176, 2020 Nov.
Article in English | MEDLINE | ID: mdl-31792660

ABSTRACT

The present work describes the in vitro antibacterial evaluation of some new pyrimidine derivatives. Twenty-two target compounds were designed, synthesized and preliminarily explored for their antimicrobial activities. The antimicrobial assay revealed that some target compounds exhibited significantly inhibitory efficiencies toward bacteria and fungal including drug-resistant pathogens. Compound 7c presented the most potent inhibitory activities against Gram-positive bacteria (e.g., Staphylococcus aureus 4220), Gram-negative bacteria (e.g., Escherichia coli 1924) and the fungus Candida albicans 7535, with an MIC of 2.4 µmol/L. Compound 7c was also the most potent, with MICs of 2.4 or 4.8 µmol/L against four multidrug-resistant, Gram-positive bacterial strains. The toxicity evaluation of the compounds 7c, 10a, 19d and 26b was assessed in human normal liver cells (L02 cells). Molecular docking simulation and analysis suggested that compound 7c has a good interaction with the active cavities of dihydrofolate reductase (DHFR). In vitro enzyme study implied that compound 7c also displayed DHFR inhibition.


Subject(s)
Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/chemical synthesis , Pyrimidines/chemistry , Anti-Bacterial Agents/pharmacology , Cell Line , Fungi/drug effects , Gram-Negative Bacteria/drug effects , Gram-Positive Bacteria/drug effects , Humans , Microbial Sensitivity Tests/methods , Molecular Docking Simulation/methods , Structure-Activity Relationship
5.
Planta Med ; 77(7): 705-10, 2011 May.
Article in English | MEDLINE | ID: mdl-20979021

ABSTRACT

Fenugreek seed ( Trigonella foenum-graecum L.) is used as an herbal medicine for treating metabolic and nutritive dysfunctions. To determine if this plant has other beneficial effects, we tested the inhibitory activities of a methanol (MeOH) extract of fenugreek seed on the production of inflammatory cytokines and melanin synthesis in cultured cell lines in vitro. The MeOH extract inhibited the production of phorbol-12-myristate-13-acetate-induced inflammatory cytokines such as tumor necrosis factor (TNF)-α in cultured THP-1 cells, and also restrained the intracellular synthesis of melanin in murine melanoma B16F1 cells. We isolated three active constituents from fenugreek seed extracts. These were identified as the steroidal saponins 26- O-ß-D-glucopyranosyl-(25 R)-furost-5(6)-en-3 ß,22 ß,26-triol-3- O-α-L-rhamno-pyranosyl-(1'' → 2')-O-[ß-D-glucopyranosyl-(1''' → 6')- O]-ß-D-glucopyranoside 1, minutoside B 2, and pseudoprotodioscin 3. Compounds 1 and 2 strongly suppressed the production of inflammatory cytokines, whereas 3 showed a weaker suppressing effect. Melanogenesis in B16F1 cells was significantly suppressed by 1 and 3, and weakly suppressed by 2. All three compounds showed moderate cytotoxicities. These results indicate that fenugreek extract and its active constituents could protect against skin damage.


Subject(s)
Anti-Inflammatory Agents/pharmacology , Melanins/antagonists & inhibitors , Plants, Medicinal/chemistry , Saponins/pharmacology , Trigonella/chemistry , Animals , Anti-Inflammatory Agents/isolation & purification , Antineoplastic Agents/isolation & purification , Antineoplastic Agents/pharmacology , Carbohydrate Sequence , Cell Line, Tumor , Cytokines/antagonists & inhibitors , Cytokines/biosynthesis , Humans , Melanins/biosynthesis , Melanoma, Experimental/metabolism , Mice , Molecular Sequence Data , Molecular Structure , Monocytes/drug effects , Monocytes/immunology , Multiple Myeloma/metabolism , Plant Extracts/pharmacology , Saponins/isolation & purification , Seeds/chemistry , Tumor Necrosis Factor-alpha/antagonists & inhibitors , Tumor Necrosis Factor-alpha/biosynthesis
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