Design, synthesis, <i>in silico</i> docking studies and biological evaluation of novel quinoxaline-hydrazide hydrazone-1,2,3-triazole hybrids as α-glucosidase inhibitors and antioxidants

Settypalli, Triloknadh; Rao, C. Venkata; Kumari, Maddineni Aruna; Begari, Nagaraju; Allagadda, Rajasekhar; Kotha, Peddanna; Chippada, Appa Rao

doi:10.1039/c9nj02580d

Cited by 51 publications

(26 citation statements)

References 58 publications

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“…Therefore, special concern should be devoted to the development of new antimicrobial agents, possessing completely different chemical structures, and working with different modes of actions. The Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction offers a versatile synthetic access to the 1,2,3-triazole heterocycle derivatives, which are associated with a wide spectrum of pharmacological activities, including antimycobacterial [18][19][20][21], antitubercular [22][23][24][25], anticancer [26][27][28][29], antiviral [30][31][32][33][34], antidiabetic [35][36][37][38], antifungal [39][40][41][42], anti-HIV [43][44][45][46], anti-inflammatory [47][48][49][50], antimalarial [51][52][53][54], anti-oxidant [55][56][57][58], anti-proliferative [59][60][61][62] properties. The 1...…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers

et al. 2020

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Bacterial resistance remains a significant threat and a leading cause of death worldwide, despite massive attempts to control infections. In an effort to develop biologically active antibacterial and antifungal agents, six novel aryl-substituted-1,2,3-triazoles linked to carbohydrate units were synthesized through the Cu(I)-catalyzed azide-alkyne cycloaddition CuAAC of substituted-arylazides with a selection of alkyne-functionalized sugars. The chemical structures of the new derivatives were verified using different spectroscopic techniques. The novel clicked 1,2,3-triazoles were evaluated for in vitro antibacterial activity against Gram-positive Staphylococcus aureus and Gram-negative Pseudomonas aeruginosa, and the obtained results were compared with the activity of the reference antibiotic “Ampicillin”. Likewise, in vitro antifungal activity of the new 1,2,3-triazoles was investigated against Candida albicans and Aspergillus niger using “Nystatin” as a reference drug. The results of the biological evaluation pointed out that Staphylococcus aureus was more susceptible to all of the tested compounds than other examined microbes. In addition, some tested compounds exhibited promising antifungal activity.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers

et al. 2020

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“…The docking study of the investigated products on β-lactamases TEM-1 (1pzo) was conducted to investigates the affinity toward the TEM-1 β-lactamases to be compared with reference anti β-lactamases of various activities. The docking scores of the binding energies due to the interaction between the active ligands (inhibitors) and the enzymes pockets were chosen with the highest score based on geometric shape complementarity 9 .…”

Section: Docking Study On β-Lactamases Tem-1mentioning

confidence: 99%

“…Depending on the above results, amoxicillin was used in two concentrations in the next step, 1000µg/ml for Gram (+)ve bacteria and 2000µg/ml for Gram (-)ve bacteria Table (9). 1:1 = 1000 µg/ml Amoxicillin : 1000 µg/ml synthesized compound for Gram(+)ve bacteria 1:2 = 1000 µg/ml Amoxicillin : 2000 µg/ml synthesized compound for Gram(+)ve bacteria 1:1/2 = 2000 µg/ml Amoxicillin : 1000 µg/ml synthesized compound for Gram(-)ve bacteria 1:1 = 2000 µg/ml Amoxicillin : 2000 µg/ml synthesized compound for Gram(-)ve bacteria…”

Section: Preparation Of Acid Chloride Derivatives (A5 and A6)mentioning

confidence: 99%

Design, synthesis, and evaluation the anti-β-lactamase activity of new sulphathiazole-derived monobactam compounds

Mahmood¹,

Al-Iraqi²,

Abachi³

2020

IJP

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Objectives: β-Lactams are the most successful antibiotics for the management of infectious diseases. Unfortunately, the bacterial production of β-lactamase that hydrolyzes the β-lactam ring can inactivate these drugs. The use of β-lactamase inhibitors like (clavulanic acid) in combination with the β-lactams may reduce this inactivation. The prevalent β-lactamase phenotype is the TEM-1 of class A released by Gram-positive and Gram-negative bacteria. Methods: The docking study with TEM-1 β-lactamase lead to synthesize of new 5 monobactam compounds as the acid chloride derivatives reacted with the Schiff bases compound forming the monobactam ring. The final 5 synthesized compounds were characterized using physical and spectroscopic methods and tested biologically by evaluating their MIC values against 4 strains of β-lactamase Gram-positive and Gram-negative bacteria. The results were compared with those acquired from using clavulanic acid as a co-inhibiter with amoxicillin against the tested bacteria. Results: The results revealed that 2 synthesized compounds showed an anti βlactamase effect resemble to that of clavulanic acid. Conclusion:As conclusion; the β-lactamase active pocket prefers hydrophobic substituents, as the synthesized products with these groups appeared to have the highest affinity.

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“…The reported activities of N-acylhydrazone-bearing compounds include anti-inflammatory, analgesic, antithrombotic [4], antimicrobial [5,6], and antiproliferative (apoptosis-inducing) [7] properties. Other authors disclosed NAHs that were α-glucosidase inhibitors [8], non-ligand binding pocket androgen receptor antagonists [9], or histone deacetylases and phosphatidylinositol 3-kinases inhibitors [10]. A recent review on the roles of NAHs in modern medicinal chemistry was provided by Thota et al [3].…”

Section: Introductionmentioning

confidence: 99%

Antinociceptive and Cytotoxic Activity of Opioid Peptides with Hydrazone and Hydrazide Moieties at the C-Terminus

et al. 2020

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In the present contribution, we analyze the influence that C-terminal extension of short opioid peptide sequences by organic fragments has on receptor affinity, in vivo analgesic activity, and antimelanoma properties. The considered fragments were based on either N-acylhydrazone (NAH) or N′-acylhydrazide motifs combined with the 3,5-bis(trifluoromethyl)phenyl moiety. Eleven novel compounds were synthesized and subject to biological evaluation. The analyzed compounds exhibit a diversified range of affinities for the µ opioid receptor (MOR), rather low δ opioid receptor (DOR) affinities, and no appreciable neurokinin-1 receptor binding. In three out of four pairs, N-acylhydrazone-based derivatives bind MOR better than their N’-acylhydrazide counterparts. The best of the novel derivatives have similar low nanomolar MOR binding affinity as the reference opioids, such as morphine and biphalin. The obtained order of MOR affinities was compared to the results of molecular docking. In vivo, four tested compounds turned out to be relatively strong analgesics. Finally, the NAH-based analogues reduce the number of melanoma cells in cell culture, while their N′-acylhydrazide counterparts do not. The antimelanoma properties are roughly correlated to the lipophilicity of the compounds.

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Design, synthesis, in silico docking studies and biological evaluation of novel quinoxaline-hydrazide hydrazone-1,2,3-triazole hybrids as α-glucosidase inhibitors and antioxidants

Abstract: Novel quinoxaline-hydrazidehydrazone-1,2,3-triazole hybrids were synthesized, characterized and screened for α-glucosidase inhibitory and antioxidant activities.

Cited by 51 publications

References 58 publications

Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers

Design, Synthesis, and Antimicrobial Activities of 1,2,3-Triazole Glycoside Clickamers

Design, synthesis, and evaluation the anti-β-lactamase activity of new sulphathiazole-derived monobactam compounds

Antinociceptive and Cytotoxic Activity of Opioid Peptides with Hydrazone and Hydrazide Moieties at the C-Terminus

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