Browse
Submit Data
Databases
API
Help

Dataset Information

22 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Discovery of ( ±)-3-(1H-pyrazol-1-yl)-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4] thiadiazine derivatives with promising in vitro anticoronavirus and antitumoral activity.

ABSTRACT: A new series of ( ±)-(3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-phenyl-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-7-yl)(phenyl)methanones were efficiently synthesized starting from 4-amino-5-hydrazinyl-4H-1,2,4-triazole-3-thiol 1, acetyl acetone 2, various aromatic and heterocyclic aldehydes 3 and phenacyl bromides 4. All the newly synthesized compounds were tested for their antiviral and antitumoral activity. It was shown that subtle structural variations on the phenyl moiety allowed to tune biological properties toward antiviral or antitumoral activity. Mode-of-action studies revealed that the antitumoral activity was due to inhibition of tubulin polymerization.

SUBMITTER: Jilloju PC

PROVIDER: S-EPMC8223195 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

9-(2-Chloro-benz-yloxy)-6,7-dihydro-2H-benzo[c][1,2,4]triazolo[4,3-a]azepin-3(5H)-one.

Project description:In the title mol-ecule, C(18)H(16)ClN(3)O(2), the seven-membered ring adopts an envelope conformation with the flap atom deviating by 0.801 (5) Å from the mean plane formed by the remaining non-H atoms. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. The crystal packing also exhibits weak inter-molecular C-H⋯N hydrogen bonds and π-π inter-actions with a short distance of 3.734 (3) Å between the centroids of the aromatic rings of neighbouring mol-ecules.

| S-EPMC3151951 | biostudies-literature

5-Benzyl-2-phenyl-6,8-dihydro-5H-1,2,4-triazolo[3,4-c][1,4]oxazin-2-ium hexa-fluoridophosphate.

Project description:The title compound, C(18)H(18)N(3)O(+)·PF(6) (-), is a chiral bicyclic 1,2,4-triazolium salt which contains four rings, viz. a triazolium, a morpholine and two phenyl rings. Analysis of bond lengths shows that the N-CH-N group in the triazolium ring conforms to a typical three-center/four-electron bond (also known as the Pimentel-Rundle three-center model). The structure is completed by a disordered PF(6) (-) counter-ion [occupancies of F atoms 0.678?(8):0.322?(8)], which inter-acts with the main mol-ecule through weak inter-molecular P-F?? inter-actions.

| S-EPMC2969544 | biostudies-literature

6-Benzyl-6,7-dihydro-5H-pyrrolo-[3,4-b]pyridine-5,7-dione.

Project description:In the title compound, C(14)H(10)N(2)O(2), the dihedral angle between the heterocyclic ring system and the phenyl ring is 45.8?(5)°. Weak inter-molecular C-H?N hydrogen bonding is present in the crystal structure.

| S-EPMC3247312 | biostudies-literature

4-[(3-Benzamido-methyl-6-phenyl-6,7-dihydro-5H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-7-yl)carbon-yl]-3-phenyl-1,2,3-oxadiazol-3-ium-5-olate 0.06-hydrate.

Project description:The asymmetric unit of the title compound, C(27)H(21)N(7)O(4)S·0.06H(2)O, contains four syndone mol-ecules and a water mol-ecule with a site occupancy of 0.25. In two of the syndone mol-ecules, three atoms in a terminal phenyl ring are disordered over two sets of sites, with occupancy ratios of 0.500?(18):0.500?(18) and 0.512?(17):0.488?(17). The dihedral angles between terminal phenyl rings for the syndone mol-ecules are 23.3?(4), 45.57?(16), 68.46?(16) and 56.5?(3)°. In the crystal, mol-ecules are connected via N-H?N, N-H?O, O-H?O, O-H?N and C-H?O hydrogen bonds, forming a three-dimensional network.

| S-EPMC3050302 | biostudies-other

3-Ethyl-6-[3-(4-fluoro-phen-yl)-1H-pyrazol-4-yl]-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the title compound, C(14)H(11)FN(6)S, the 1,2,4-triazolo[3,4-b][1,3,4]thia-diazole ring system is essentially planar [maximum deviation = 0.022?(3)?Å] and is inclined at dihedral angles of 15.00?(18) and 52.82?(16)° with respect to the pyrazole and phenyl rings. In the crystal, mol-ecules are linked into two-dimensional networks parallel to (100) via inter-molecular N-H?N and weak C-H?N hydrogen bonds. The crystal packing is further consolidated by weak ?-? stacking inter-actions, with a centroid-centroid distance of 3.590?(2)?Å. The crystal studied was an inversion twin with a 0.37?(13):0.63?(13) domain ratio.

| S-EPMC3009212 | biostudies-literature

Design, Synthesis, and Biological Evaluation of Novel 7H-[1,2,4]Triazolo[3,4-b][1,3,4]thiadiazine Inhibitors as Antitumor Agents.

Project description:A series of novel anticancer hydrazinotriazolothiadiazine-based derivatives were designed based on the structure-activity relationship of the previously reported anticancer triazolothiadiazines. These derivatives were synthesized and biologically screened against full NCI-60 cancer cell lines revealing compound 5l with a potential antiproliferative effect. 5l was screened over 16 kinases to study its cytotoxic mechanism which showed to inhibit glycogen synthase kinase-3 β (GSK-3β) with IC50 equal to 0.883 μM and 14-fold selectivity over CDK2. Also, 5l increased active caspase-3 levels, induced cell cycle arrest at the G2-M phase, and increased the percentage of Annexin V-fluorescein isothiocyanate-positive apoptotic cells in PC-3 prostate cancer-treated cells. Molecular docking and dynamics were performed to predict the binding mode of 5l in the GSK-3β ATP binding site. 5l can be utilized as a starting scaffold for developing potential GSK-3β inhibitors.

| S-EPMC7439371 | biostudies-literature

Rapid, Microwave Accelerated Synthesis of [1,2,4]Triazolo[3,4-b][1,3,4]oxadiazoles from 4-Acylamino-1,2,4-Triazoles.

Project description:1,2,4-Triazoles and 1,3,4-oxadiazoles are prevalent moieties in pharmaceutical agents, yet fused [1,2,4]-triazolo[3,4-b][1,3,4]oxadiazoles are surprisingly under-represented for both synthesis and biological application. We report a rapid, two-step synthesis of [1,2,4]-triazolo[3,4-b][1,3,4]oxadiazoles from commercial 4-amino-1,2,4-triazoles that is highlighted by a microwave accelerated intramolecular cyclization to generate the fused ring system. Our efforts to optimize reaction conditions and elucidate reaction mechanism are also described.

| S-EPMC5271595 | biostudies-literature

3,6-Bis(3,4,5-trimethoxy-phen-yl)-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the mol-ecule of the title compound, C(21)H(22)N(4)O(6)S, the planar central heterocyclic ring system is oriented with respect to the trimethoxy-phenyl rings at dihedral angles of 2.60 (5) and 3.60 (6)°. Intra-molecular C-H⋯N and C-H⋯S hydrogen bonds result in the formation of planar five- and six-membered rings. In the crystal structure, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules. There is a C-H⋯π contact between a methyl group and a trimethoxy-phenyl ring, and a π-π contact between the central heterocyclic ring system and a trimethoxy-phenyl ring [centroid-centroid distance = 3.640 (1) Å].

| S-EPMC2962044 | biostudies-literature

Synthesis and Anti-Breast Cancer Potency of Mono- and Bis-(pyrazolyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine) Derivatives as EGFR/CDK-2 Target Inhibitors.

Project description:The target mono- and bis-(6-pyrazolyltriazolo-thiadiazine) derivatives 4a-c and 6a-d were synthesized using a straightforward protocol via reaction of 3-bromoacetylpyrazole 2 with 4-amino-s-triazole-3-thiols 3a-c and bis(4-amino-5-mercapto-s-triazol-3-yl)alkanes 5a-d, respectively. The bis(6-pyrazolyl-s-triazolo[3,4-b][1,3,4]thiadiazine) derivatives 8a,b and 10 were also constructed by reaction of the triazolo[3,4-b][1,3,4]thiadiazine-3-thiol 4c with the proper dibromo compounds 7a,b and 9, respectively. Structures of the new substances were determined by spectroscopic and analytical data. Compounds 4b, 4c, and 6a showed potent cytotoxicity against MCF-7 (IC50 = 3.16, 2.74, and 0.39 μM, respectively) and were safe against the MCF-10A cells. Compounds 4b, 4c, and 6a also showed promising dual EGFR and CDK-2 inhibition activities, particularly 6a was the most effective (IC50 = 19.6 and 87.9 nM, respectively), better than Erlotinib and Roscovitine. Compound 6a treatment induced EGFR and CDK-2 enzyme inhibition by 97.18% and 94.11%, respectively, at 10 μM (the highest concentration). Compound 6a notably induced cell apoptosis in MCF-7 cells, increasing the cell population by total apoptosis 43.3% compared to 1.29% for the untreated control group, increasing the cell population at the S-phase by 39.2% compared to 18.6% (control).

| S-EPMC10536063 | biostudies-literature

3-Methyl-6-trichloro-methyl-1,2,4-triazolo[3,4-b][1,3,4]thia-diazole.

Project description:In the crystal structure of the title compound, C(5)H(3)Cl(3)N(4)S, two mol-ecules related by a centre of symmetry demonstrate extremely short inter-molecular S?N contacts of 2.783?(2)?Å. The crystal packing also exhibits ?-? inter-actions indicated by a short distance of 3.340?(1)?Å between the centroids of the triazole rings of neighbouring mol-ecules.

| S-EPMC3089198 | 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