Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Design, synthesis, and antiprotozoal evaluation of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives.

ABSTRACT: A series of new 2,4-bis[(substituted-aminomethyl)phenyl]quinoline, 1,3-bis[(substituted-aminomethyl)phenyl]isoquinoline, and 2,4-bis[(substituted-aminomethyl)phenyl]quinazoline derivatives was designed, synthesised, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani, and Trypanosoma brucei brucei). Biological results showed antiprotozoal activity with IC₅₀ values in the µM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The quinoline 1c was identified as the most potent antimalarial candidate with a ratio of cytotoxic to antiparasitic activities of 97 against the P. falciparum CQ-sensitive strain 3D7. The quinazoline 3h was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 43 on T. brucei brucei strain. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma are possible targets of this kind of nitrogen heterocyclic compounds, we have also investigated stabilisation of the Plasmodium and Trypanosoma telomeric G-quadruplexes by our best compounds through FRET melting assays.

SUBMITTER: Guillon J

PROVIDER: S-EPMC6968685 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Design, Synthesis, and Antiprotozoal Evaluation of New Promising 2,9-<i>Bis</i>[(substituted-aminomethyl)]-4,7-phenyl-1,10-phenanthroline Derivatives, a Potential Alternative Scaffold to Drug Efflux.

Project description:A series of novel 2,9-bis[(substituted-aminomethyl)]-4,7-phenyl-1,10-phenanthroline derivatives was designed, synthesized, and evaluated in vitro against three protozoan parasites (Plasmodium falciparum, Leishmania donovani and Trypanosoma brucei brucei). Pharmacological results showed antiprotozoal activity with IC50 values in the sub and μM range. In addition, the in vitro cytotoxicity of these original molecules was assessed with human HepG2 cells. The substituted diphenylphenanthroline 1l was identified as the most potent antimalarial derivative with a ratio of cytotoxic to antiparasitic activities of 505.7 against the P. falciparum CQ-resistant strain W2. Against the promastigote forms of L. donovani, the phenanthrolines 1h, 1j, 1n and 1o were the most active with IC50 from 2.52 to 4.50 μM. The phenanthroline derivative 1o was also identified as the most potent trypanosomal candidate with a selectivity index (SI) of 91 on T. brucei brucei strain. FRET melting and native mass spectrometry experiments evidenced that the nitrogen heterocyclic derivatives bind the telomeric G-quadruplexes of P. falciparum and Trypanosoma. Moreover, as the telomeres of the parasites P. falciparum and Trypanosoma could be considered to be possible targets of this kind of nitrogen heterocyclic derivatives, their potential ability to stabilize the parasitic telomeric G-quadruplexes have been determined through the FRET melting assay and by native mass spectrometry.

| S-EPMC9699089 | biostudies-literature

1,3-Dibenzyl-1,2,3,4-tetra-hydro-quinazoline-2,4-dione.

Project description:The asymmetric unit of the title compound, C(22)H(18)N(2)O(2), contains two independent mol-ecules, which differ in the orientations of the benzyl groups with respect to the planar (r.m.s. deviations of 0.031 and 0.020 Å) quinazoline-2,4-dione skeletons [dihedral angles of 73.97 (4) and 70.07 (4)° in the first mol-ecule and 75.63 (4) and 63.52 (3)° in the second]. The crystal structure is stabilized by weak inter-molecular C-H⋯O and C-H⋯π interactions and aromatic π-π stacking inter-actions [centroid-centroid distance = 3.735 (2) Å].

| S-EPMC3007055 | biostudies-literature

6,7-Dimeth-oxy-2,4-di-phenyl-quinoline.

Project description:In the title structure of the title compound, C23H19NO2, two conformationally similar mol-ecules (A and B) comprise the asymmetric unit. The dihedral angle between phenyl rings bridged by the quinoline moiety are 76.25 (8)° in mol-ecule A and 70.39 (9)° in mol-ecule B. In the crystal, the independent mol-ecules are connected by C-H⋯O hydrogen bonds and the resulting dimeric aggregates are linked by π-π [inter-centroid distance = 3.7370 (8) Å] and C-H⋯π inter-actions, forming a three-dimensional architecture.

| S-EPMC3998322 | biostudies-literature

5-Phenyl-7,8-dihydro-1,3-dioxano[4,5-g]isoquinoline.

Project description:In the title compound, C(16)H(13)NO(2), the two benzene rings make a dihedral angle of 55.5 (2)°. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds and weak π-π stacking inter-actions [centroid-centroid distance = 3.595 (3)Å], linking the mol-ecules into ladders of inversion dimers.

| S-EPMC2959899 | biostudies-literature

2,4-Bis(diphenyl-phosphan-yl)-1,1,2,3,3,4-hexa-phenyl-1,3-diphospha-2,4-dibora-cyclo-butane tetra-hydro-furan sesqui-solvate.

Project description:In the title compound, C(60)H(50)B(2)P(4)·1.5C(4)H(8)O, the diphospha-diborane mol-ecule lies on an inversion centre, whereas the disordered tetra-hydro-furan solvent mol-ecule is in a general position with a partial occupancy of 0.75. The diphosphadiborane mol-ecule consists of an ideal planar four-membered B(2)P(2) ring with an additional phenyl and a -PPh(2) group attached to each B atom.

| S-EPMC3344071 | biostudies-literature

Potassium bis-(1,1,1,5,5,5-hexa-fluoro-pentane-2,4-dionato)bis-(4,4,4-trifluoro-1-phenyl-butane-1,3-dionato)europate(III).

Project description:In the crystal structure of the title complex, K[Eu(C(5)HF(6)O(2))(2)(C(10)H(6)F(3)O(2))(2)], the Eu(III) ion is in a slightly distorted square-anti-prismatic coordination geometry which is defined by eight O atoms of the anionic ?-diketone ligands. The two K(+) ions lie on crystallographic inversion centers. The Eu-O bond distances are in the range 2.294?(5)-2.413?(5)?Å. The crystal used was a non-merohedral twin, the ratio of the twin domains being 0.5236?(5):0.4764?(5).

| S-EPMC3006768 | biostudies-literature

5-[(4-Acetyl-phenyl)-aminomethyl-ene]-2,2-dimethyl-1,3-dioxane-4,6-dione.

Project description:In the title compound, C(15)H(15)NO(5), the six-membered dioxane ring assumes an envelope conformation with the dimethyl substituted C atom as the flap atom. An intra-molecular N-H⋯O inter-action is also present. In the crystal structure the mol-ecules are linked via C-H⋯O hydrogen bonds into supra-molecular chains along the b axis.

| S-EPMC2969769 | biostudies-literature

Synthesis of Bis(1,2,3-Triazole) Functionalized Quinoline-2,4-Diones.

Project description:Derivatives of 3-(1H-1,2,3-triazol-1-yl)quinoline-2,4(1H,3H)-dione unsubstituted on quinolone nitrogen atom, which are available by the previously described four step synthesis starting from aniline, were exploited as intermediates in obtaining the title compounds. The procedure involves the introduction of propargyl group onto the quinolone nitrogen atom of mentioned intermediates by the reaction of them with propargyl bromide in N,N-dimethylformamide (DMF) in presence of a potassium carbonate and the subsequent formation of a second triazole ring by copper catalyzed cyclisation reaction with azido compounds. The products were characterized by ¹H, 13C and 15N NMR spectroscopy. The corresponding resonances were assigned on the basis of the standard 1D and gradient selected 2D NMR experiments (¹H⁻¹H gs-COSY, ¹H⁻13C gs-HSQC, ¹H⁻13C gs-HMBC) with ¹H⁻15N gs-HMBC as a practical tool to determine 15N NMR chemical shifts at the natural abundance level of 15N isotope.

| S-EPMC6225383 | biostudies-literature

(4,6-Diamino-1,3-phenyl-ene)bis-(phenyl-methanone).

Project description:In the mol-ecule of the title compound, C(20)H(16)N(2)O(2), two intra-molecular N-H?O inter-actions occur. The mol-ecular chains are linked by N-H?? and C-H?? inter-actions into a three-dimensional network, which seems to be very effective in the stabilization of the crystal structure.

| S-EPMC3201319 | biostudies-literature

1,3-Bis(phenyl-sufanylmeth-yl)benzene.

Project description:The complete mol-ecule of the title compound, C(20)H(18)S(2), is generated by crystallographic mirror symmetry, with two C atoms lying on the mirror plane. All of the independent atoms are contained within two planes defined by the thio-phenyl rings (C(6)S) and the central phenyl ring with the methyl-ene bridge; the r.m.s deviations of these planes are 0.012 and 0.025?Å, respectively. The two planes are almost perpendicular to one another at a dihedral angle of 80.24?(10)°. Inter-molecular C-H-? inter-actions are present in the crystal structure.

| S-EPMC2983717 | biostudies-literature

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