Browse
Submit Data
Databases
API
Help

Dataset Information

10 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Searching Anti-Zika Virus Activity in 1H-1,2,3-Triazole Based Compounds.

ABSTRACT: Zika virus (ZIKV) is a mosquito-borne virus belonging to the Flaviviridae family and is responsible for an exanthematous disease and severe neurological manifestations, such as microcephaly and Guillain-Barré syndrome. ZIKV has a single strand positive-sense RNA genome that is translated into structural and non-structural (NS) proteins. Although it has become endemic in most parts of the tropical world, Zika still does not have a specific treatment. Thus, in this work we evaluate the cytotoxicity and antiviral activities of 14 hybrid compounds formed by 1H-1,2,3-triazole, naphthoquinone and phthalimide groups. Most compounds showed low cytotoxicity to epithelial cells, specially the 3b compound. After screening with all compounds, 4b was the most active against ZIKV in the post-infection test, obtaining a 50% inhibition concentration (IC₅₀) of 146.0 µM and SI of 2.3. There were no significant results for the pre-treatment test. According to the molecular docking compound, 4b was suggested with significant binding affinity for the NS5 RdRp protein target, which was further corroborated by molecular dynamic simulation studies.

SUBMITTER: Dantas WM

PROVIDER: S-EPMC8510480 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Methyl 1H-1,2,3-triazole-4-carboxyl-ate.

Project description:The title compound, C(4)H(5)N(3)O(2), features an essentially planar mol-ecule (r.m.s. deviation for all non-H atoms = 0.013?Å). The crystal structure is stabilized by inter-molecular N-H?O hydrogen bonds and ?-? stacking inter-actions (centroid-centroid distance 3.882?Å).

| S-EPMC2968371 | biostudies-literature

Regioselective Reduction of 1H-1,2,3-Triazole Diesters.

Project description:Regioselective reactions can play pivotal roles in synthetic organic chemistry. The reduction of several 1-substituted 1,2,3-triazole 4,5-diesters by sodium borohydride has been found to be regioselective, with the C(5) ester groups being more reactive towards reduction than the C(4) ester groups. The amount of sodium borohydride and reaction time required for reduction varied greatly depending on the N(1)-substituent. The presence of a β-hydroxyl group on the N(1)-substituent was seen to have a rate enhancing effect on the reduction of the C(5) ester group. The regioselective reduction was attributed to the lower electron densities of the C(5) and the C(5) ester carbonyl carbon of the 1,2,3-triazole, which were further lowered in cases involving intramolecular hydrogen bonding.

| S-EPMC8469956 | biostudies-literature

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia.

Project description:The enzyme tyrosine kinase BCR-Abl-1 is the main molecular target in the treatment of chronic myeloid leukemia and can be competitively inhibited by tyrosine kinase inhibitors such as imatinib. New potential competitive inhibitors were synthesized using the (phenylamino)pyrimidine-pyridine (PAPP) group as a pharmacophoric fragment, and these compounds were biologically evaluated. The synthesis of twelve new compounds was performed in three steps and assisted by microwave irradiation in a 1,3-dipolar cycloaddition to obtain 1,2,3-triazole derivatives substituted on carbon C-4 of the triazole nucleus. All compounds were evaluated for their inhibitory activities against a chronic myeloid leukemia cell line (K562) that expresses the enzyme tyrosine kinase BCR-Abl-1 and against healthy cells (WSS-1) to observe their selectivity. Three compounds showed promising results, with IC50 values between 1.0 and 7.3 μM, and were subjected to molecular docking studies. The results suggest that such compounds can interact at the same binding site as imatinib, probably sharing a competitive inhibition mechanism. One compound showed the greatest interaction affinity for BCR-Abl-1 in the docking studies.

| S-EPMC8450943 | biostudies-literature

New 1,2,3-Triazole-genipin Analogues and Their Anti-Alzheimer's Activity.

Project description:A novel series of 1,2,3-triazole-genipin analogues were designed, synthesized, and evaluated for neuroprotective activity, acetylcholinesterase (AChE), and butyrylcholinesterase (BuChE) inhibitory activity. The genipin analogues bearing bromoethyl- and diphenylhydroxy-triazole showed in vitro neuroprotective properties against H2O2 toxicity along with potent inhibitory activity on BuChE with IC50 values of 31.77 and 54.33 μM, respectively, compared with galantamine (IC50 = 34.05 μM). The molecular docking studies of these genipin analogues showed good binding energy and interact well with the key amino acids of BuChE via hydrogen-bonding and hydrophobic interactions. Triazole genipins might be promising lead compounds as anti-Alzheimer's agents.

| S-EPMC9301951 | biostudies-literature

Methyl 1-methyl-1H-1,2,3-triazole-4-carboxyl-ate.

Project description:The title mol-ecule, C(5)H(7)N(3)O(2), has an almost planar conformation, with a maximum deviation of 0.043?(3)?Å, except for the methyl H atoms. In the crystal structure, inter-molecular C-H?O hydrogen bonds link the mol-ecules into layers parallel to the bc plane. Inter-molecular ?-? stacking inter-actions [centroid-centroid distances = 3.685?(2) and 3.697?(2)?Å] are observed between the parallel triazole rings.

| S-EPMC2979655 | biostudies-literature

1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole.

Project description:In the title compound, C(19)H(15)N(3), the benzyl group is almost perpendicular to the triazole ring [dihedral angle = 80.64 (8)°], while the napthyl group makes an angle of 30.27 (12)° with the plane of the triazole ring. This conformation is different from the 1-benzyl-4-phenyl-1H-1,2,3-triazole analogue, which has the benzyl ring system at an angle of 87.94° and the phenyl group at an angle of 3.35° to the plane of the triazole ring.

| S-EPMC3151948 | biostudies-literature

Methyl 5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxyl-ate.

Project description:The asymmetric unit of the title compound, C8H9N5O2, contains two independent mol-ecules (A and B) in which the dihedral angles between the triazole and pyrazole rings are 4.80?(14) and 8.45?(16)°. In the crystal, mol-ecules are linked by N-H?N hydrogen bonds into supra-molecular independent A and B chains propagating along the b-axis direction. The crystal structure also features ?-? stacking between the aromatic rings of adjacent chains, the centroid-centroid separations being 3.8001?(15), 3.8078?(17), 3.8190?(14) and 3.8421?(15)?Å.

| S-EPMC4120607 | biostudies-literature

Methyl 1-benzyl-1H-1,2,3-triazole-4-carboxyl-ate.

Project description:In the title compound, C(11)H(11)N(3)O(2), prepared by the [3+2] cycloaddition reaction of benzyl azide with methyl propiolate, the dihedral angle between the ring planes is 67.87?(11)°.

| S-EPMC3006897 | biostudies-other

1-Benzyl-5-methyl-1H-1,2,3-triazole-4-carboxylic acid monohydrate.

Project description:In the title compound, C(11)H(11)N(3)O(2)·H(2)O, the planes of the triazole and phenyl rings are almost perpendicular to each other [dihedral angle 89.5?(3)°]. The crystal packing is stabilized by strong inter-molecular O-H?O and O-H?N hydrogen bonds involving the water mol-ecule as both donor and acceptor.

| S-EPMC2969608 | biostudies-literature

5-Methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid.

Project description:The title compound, C(10)H(9)N(3)O(2), was synthesized from azido-benzene and ethyl acetyl-acetate. A pair of hydrogen bonds [2.617?(2)?Å] inter-connects a pair of the carboxyl groups, forming an R(2) (2)(8) inversion dimer, a frequent motif in carboxylic acids. In the title structure, the bonding H atom in the aforementioned O-H?O hydrogen bond is significantly shifted towards the acceptor O atom [the donor and acceptor O-H distances are 1.25?(4) and 1.38?(4)?Å, respectively]. A plot of the O?O versus O-H distances in compounds with paired carboxyl groups shows that the title structure belongs to the group of structures with abnormally long O-H distances with regard to the O?O contacts. The displacement of the bonding H atom towards the centre of the hydrogen bond is concomitant with more equal C-O bonding distances in the carboxyl group.

| S-EPMC2960561 | biostudies-other

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data