Browse
Submit Data
Databases
API
Help

Dataset Information

20 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Synthesis and biofilm inhibition studies of 2-(2-amino-6-arylpyrimidin-4-yl)quinazolin-4(3H)-ones.

ABSTRACT: Synthesis of novel 4(3H)-quinazolinonyl aminopyrimidine derivatives has been achieved via quinazolinonyl enones which in turn were obtained from 2-acyl-4(3H)-quinazolinone. They have been assayed for biofilm inhibition against Gram-positive (methicillin-resistant Staphylococcus aureus (MRSA)) and Gram-negative bacteria (Acinetobacter baumannii). The analogues with 2,4,6-trimethoxy phenyl, 4-methylthio phenyl, and 3-bromo phenyl substituents (5h, 5j & 5k) have been shown to inhibit biofilm formation efficiently in MRSA with IC₅₀ values of 20.7-22.4 μM). The analogues 5h and 5j have demonstrated low toxicity in human cells in vitro and can be investigated further as leads.

SUBMITTER: Rasapalli S

PROVIDER: S-EPMC7704793 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Quinazolin-4(3H)-ones and 5,6-Dihydropyrimidin-4(3H)-ones from β-Aminoamides and Orthoesters.

Project description:Quinazolin-4(3H)-ones have been prepared in one step from 2-aminobenzamides and orthoesters in the presence of acetic acid. Simple 2-aminobenzamides were easily converted to the heterocycles by refluxing in absolute ethanol with 1.5 equivalents of the orthoester and 2 equivalents of acetic acid for 12⁻24 h. Ring-substituted and hindered 2-aminobenzamides as well as cases incorporating an additional basic nitrogen required pressure tube conditions with 3 equivalents each of the orthoester and acetic acid in ethanol at 110 °C for 12⁻72 h. The reaction was tolerant towards functionality on the benzamide and a range of structures was accessible. Workup involved removal of the solvent under vacuum and either recrystallization from ethanol or trituration with ether-pentane. Several 5,6-dihydropyrimidin-4(3H)-ones were also prepared from 3-amino-2,2-dimethylpropionamide. All products were characterized by melting point, FT-IR, ¹H-NMR, 13C-NMR, and HRMS.

| S-EPMC6278269 | biostudies-literature

Synthesis and Evaluation of Antioxidant Properties of 2-Substituted Quinazolin-4(3H)-ones.

Project description:Quinazolinones represent an important scaffold in medicinal chemistry with diverse biological activities. Here, two series of 2-substituted quinazolin-4(3H)-ones were synthesized and evaluated for their antioxidant properties using three different methods, namely DPPH, ABTS and TEACCUPRAC, to obtain key information about the structure-antioxidant activity relationships of a diverse set of substituents at position 2 of the main quinazolinone scaffold. Regarding the antioxidant activity, ABTS and TEACCUPRAC assays were more sensitive and gave more reliable results than the DPPH assay. To obtain antioxidant activity of 2-phenylquinazolin-4(3H)-one, the presence of at least one hydroxyl group in addition to the methoxy substituent or the second hydroxyl on the phenyl ring in the ortho or para positions is required. An additional ethylene linker between quinazolinone ring and phenolic substituent, present in the second series (compounds 25a and 25b), leads to increased antioxidant activity. Furthermore, in addition to antioxidant activity, the derivatives with two hydroxyl groups in the ortho position on the phenyl ring exhibited metal-chelating properties. Our study represents a successful use of three different antioxidant activity evaluation methods to define 2-(2,3-dihydroxyphenyl)quinazolin-4(3H)-one 21e as a potent antioxidant with promising metal-chelating properties.

| S-EPMC8588455 | biostudies-literature

Facile synthesis and herbicidal evaluation of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with 2-phenoxymethyl substituents.

Project description:Series of 4H-3,1-benzoxazin-4-ones and 3H-quinazolin-4-ones with phenoxy-methyl substituents were rationally designed and easily synthesized via one-pot N-acylation/ring closure reactions of anthranilic acids with 2-phenoxyacetyl chlorides to yield the 4H-3,1-benzoxazin-4-ones, and subsequently substituted with amino derivatives to obtain the 3H-quinazolin-4-ones. The herbicidal evaluation was performed on the model plants barnyard grass (a monocotyledon) and rape (a dicotyledon), and most of the title compounds displayed high levels of phytotoxicity. The active substructure and inhibitory phenotype analysis indicated that these compounds could be attributed to the class of plant hormone inhibitors. A docking study of several representative compounds with the hormone receptor TIR1 revealed an appreciable conformational match in the active site, implicating these compounds are potential lead hits targeting this receptor.

| S-EPMC6268642 | biostudies-literature

3-(2-Amino-eth-yl)-2-[4-(trifluoro-meth-oxy)anilino]quinazolin-4(3H)-one.

Project description:In the title compound, C(17)H(15)F(3)N(4)O(2), the dihedral angle between the trifluoro-meth-oxy-substituted benzene ring and the pyrimidinone ring is 45.1?(5)°, while that between the fused benzene ring and the pyrimidinone ring is 0.67?(1)°. Part of one of the benzene rings and its trifluoro-meth-oxy substituent are disordered over two positions of approximately equal occupancy (0.51:0.49). Inter-molecular N-H?O and N-H?N hydrogen bonds contribute to the stability of the crystal structure. A weak intra-molecular C-H?F contact is also found. In addition, ?-? stacking inter-actions, with centroid-centroid distances in the range 3.673?(6)-3.780?(8)?Å, and weak C-H?? inter-actions are also observed.

| S-EPMC3006720 | biostudies-literature

Synthesis, anti-microbial and molecular docking studies of quinazolin-4(3H)-one derivatives.

Project description:In this work, synthesis, antimicrobial activities and molecular docking studies of some new series of substituted quinazolinone 2a-h and 3a-d were described. Starting form 2-aminobenzamide derivatives 1, a new series of quinazolinone derivatives has been synthesized, in high yields, assisted by microwave and classical methods. Some of these substituted quinazolinones were tested for their antimicrobial activity against Gram-negative bacteria (Pseudomonas aeruginosa and Esherichia coli) and Gram-positive bacteria (Staphylococcus aureus, and Bacillus subtilis), and anti-fungal activity against (Aspergillus fumigatus, Saccharomyces cervevisiae, and Candida albicans) using agar well diffusion method. Among the prepared products, 3-benzyl-2-(4-chlorophenyl)quinazolin-4(3H)-one (3a) was found to exhibits the most potent in vitro anti-microbial activity with MICs of 25.6±0.5, 24.3±0.4, 30.1±0.6, and 25.1±0.5 µg/mL against Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa and Esherichia coli, respectively. Compound 3a was found to exhibits the most potent in vitro anti-fungal activity with MICs of 18.3±0.6, 23.1±0.4, and 26.1±0.5 µg/mL against Aspergillus fumigatus, Saccharomyces cervevisiae, and Candidaal bicans, respectively.

| S-EPMC6270882 | biostudies-literature

3-(4-Bromo-phen-yl)quinazolin-4(3H)-one.

Project description:In the title compound, C(14)H(9)BrN(2)O, the quinazoline unit is essentially planar, with a mean deviation of 0.058?(2)?Å from the least-squares plane defined by the ten constituent ring atoms. The dihedral angle between the mean plane of the quinazoline ring system and the 4-bromo-phenyl ring is 47.6?(1)°. In the crystal, mol-ecules are linked by inter-molecular C-H?N and C-H?O hydrogen bonds, forming infinite chains of alternating R(2) (2)(6) dimers and R(2) (2)(14) ring motifs.

| S-EPMC3247341 | biostudies-literature

3-(4-Chloro-phen-yl)quinazolin-4(3H)-one.

Project description:In the title compound, C(14)H(9)ClN(2)O, the quinazoline unit is essentially planar, with a mean deviation from the least-squares plane defined by the ten constituent ring atoms of 0.027 (2) Å. The dihedral angle between the mean plane of the quinazoline ring system and the 4-chloro-phenyl ring is 44.63 (5)°. In the crystal, mol-ecules are linked by inter-molecular C-H⋯N and C-H⋯O hydrogen bonds, forming infinite chains of alternating R(2) (2)(6) dimers and R(2) (2)(14) ring motifs.

| S-EPMC3200588 | biostudies-literature

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones - an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones.

Project description:A regioselective method for the synthesis of 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones - close structural analogs of naturally occurring vasicinone alkaloids - is described. The procedure is based on PIFA-initiated oxidative 5-exo-trig cyclization of 2-(3-butenyl)quinazolin-4(3Н)-ones, in turn prepared by thermal cyclocondensation of the corresponding 2-(pent-4-enamido)benzamides. The products obtained have a good natural product likeness (NPL) score and therefore can be useful for the design of natural product-like compound libraries.

| S-EPMC8630437 | biostudies-literature

Crystal structure of 3-amino-2-propyl-quinazolin-4(3H)-one.

Project description:In the title mol-ecule, C11H13N3O, the propyl group is almost perpendicular to the quinazolin-4(3H)-one mean plane, making a dihedral angle of 88.98 (9)°. In the crystal, mol-ecules related by an inversion centre are paired via π-π overlap, indicated by the short distances of 3.616 (5) and 3.619 (5) Å between the centroids of the aromatic rings of neighbouring mol-ecules. Inter-molecular N-H⋯N and N-H⋯O hydrogen bonds form R 6 (6)(30) rings and C(5) chains, respectively, generating a three-dimensional network. Weak C-H⋯O inter-actions are also observed.

| S-EPMC4571413 | biostudies-literature

Crystal structure of 3-amino-2-ethyl-quinazolin-4(3H)-one.

Project description:The mol-ecule of the title compound, C10H11N3O, is planar, including the ethyl group, as indicated by the N-C-C-C torsion angle of 1.5 (2)°. In the crystal, inversion-related mol-ecules are stacked along the a axis. Mol-ecules are oriented head-to-tail and display π-π inter-actions with a centroid-to-centroid distance of 3.6664 (8) Å. N-H⋯O hydrogen bonds between mol-ecules generate a 'step' structure through formation of an R 2 (2)(10) ring.

| S-EPMC4555403 | 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