Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

An Efficient One-Pot Catalyzed Synthesis of 2,4-Disubstituted 5-Nitroimidazoles Displaying Antiparasitic and Antibacterial Activities.

ABSTRACT: A one-pot regioselective bis-Suzuki-Miyaura or Suzuki-Miyaura/Sonogashira reaction on 2,4-dibromo-1-methyl-5-nitro-1H-imidazole under microwave heating was developed. This method is applicable to a wide range of (hetero)arylboronic acids and terminal alkynes. Additionally, this approach provides a simple and efficient way to synthesize 2,4-disubstituted 5-nitroimidazole derivatives with antibacterial and antiparasitic properties.

SUBMITTER: Mathias F

PROVIDER: S-EPMC6152245 | biostudies-literature | 2017 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

An Efficient One-Pot Catalyzed Synthesis of 2,4-Disubstituted 5-Nitroimidazoles Displaying Antiparasitic and Antibacterial Activities.

Mathias Fanny F Kabri Youssef Y Okdah Liliane L Di Giorgio Carole C Rolain Jean-Marc JM Spitz Cédric C Crozet Maxime D MD Vanelle Patrice P

Molecules (Basel, Switzerland) 20170803 8

A one-pot regioselective bis-Suzuki-Miyaura or Suzuki-Miyaura/Sonogashira reaction on 2,4-dibromo-1-methyl-5-nitro-1H-imidazole under microwave heating was developed. This method is applicable to a wide range of (hetero)arylboronic acids and terminal alkynes. Additionally, this approach provides a simple and efficient way to synthesize 2,4-disubstituted 5-nitroimidazole derivatives with antibacterial and antiparasitic properties. ...[more]

PMID: 28771219

Similar Datasets

Copper-catalyzed synthesis of 2,4-disubstituted allenoates from ?-diazoesters.

Project description:A Cu-catalyzed method for coupling ?-substituted-?-diazoesters with terminal alkynes to give substituted allenoates is described. Key to the development of a selective method was the recognition that an adventitous base catalyzes the isomerization to form the allenoate product. A plausible mechanism is proposed, based in part on evidence against a mechanism that involves a Cu(I)-acetylide as a low-valent intermediate.

| S-EPMC3128944 | biostudies-literature

Sequential one-pot synthesis of bis(indolyl)glyoxylamides: Evaluation of antibacterial and anticancer activities.

Project description:A series of bis(indolyl)glyoxylamides 10a-n has been designed and synthesized. In situ generated indole-3-glyoxalylchloride from the reaction of readily available indole 9 with oxalyl chloride was treated with tryptamine to produce bis(indolyl)glyoxylamides 10a-n in 82-93% yields. All the synthesized bis(indolyl)glyoxylamides were well characterized and tested for their antibacterial activity against Gram-positive and Gram-negative bacterial strains. Compounds 10d, 10g and 10i were found to display potent antibacterial activity against Gram-negative strain. Further, the cytotoxicity of bis(indolyl)glyoxylamides 10a-n were evaluated against a panel of human cancer cell lines. Of the screened analogues, compound 10f (IC50=22.34μM; HeLa, 24.05μM; PC-3, 21.13μM; MDA-MB-231 and 29.94μM; BxPC-3) was identified as the most potent analogue of the series. Exposure of PC-3 cells to either 10a or 10f resulted in increased levels of cleaved PARP1, indicating that bis(indolyl)glyoxylamides induce apoptosis in PC-3 cells. Most importantly, compounds 10d, 10g and 10i were completely ineffective in mammalian cells, suggesting that they target bacterial-specific targets and thus will not display any toxicity in host cells.

| S-EPMC4899133 | biostudies-literature

DMAP-Catalyzed One-Pot Synthesis of Quinazoline-2,4-diones from 2-Aminobenzamides and Di-tert-butyl Dicarbonate.

Project description:The one-pot synthesis of quinazoline-2,4-diones was developed in the presence of 4-dimethylaminopyridine (DMAP) by metal-free catalysis. The commercially available (Boc)2O acted as a key precursor in the construction of the 2-position carbonyl of quinazolinediones. The p-methoxybenzyl (PMB)-activated heterocyclization could smoothly proceed at room temperature instead of the microwave condition. This strategy is compatible with a variety of substrates with different functional groups. Furthermore, this protocol was utilized to smoothly prepare Zenarestat with a total yield of 70%.

| S-EPMC7191844 | biostudies-literature

Copper-Catalyzed One-Pot Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from Arylacetic Acids and Hydrazides via Dual Oxidation.

Project description:A simple and efficient protocol has been developed to access symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles from arylacetic acids and hydrazides via copper-catalyzed dual oxidation under an oxygen atmosphere. Oxidative decarboxylation of arylacetic acids and oxidative functionalization of the imine C-H bond are the key steps. This is the first example of the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles through dual oxidation in one-pot. Avoidance of the expensive ligand and high yield of the products are advantageous features of the developed method.

| S-EPMC9366783 | biostudies-literature

Palladium-Catalyzed Three-Component Coupling of 1,1-Dibromoalkenes, Vinylzinc Chloride, and Soft Nucleophiles: One-Pot Synthesis of 1,3-Disubstituted Allenes.

Project description:The three-component coupling reaction of 1,1-dibromoalkenes 1, vinylzinc chloride 2, and carbon soft nucleophiles 3 was realized in the presence of the catalytic palladium/Xantphos species, and 1,3-disubstituted allenic products 5 were obtained in yields of up to 77%. The successive two palladium-catalyzed processes, namely the cross-coupling reaction and the allylic substitution, assembled 5 from the easily accessible starting compounds.

| S-EPMC6868900 | biostudies-literature

Efficient One-Pot, Two-Component Modular Synthesis of 3,5-Disubstituted Pyrazoles.

Project description:The pyrazole scaffold is one of the most prevalent and important tool in medicinal chemistry. Here, we report a method for preparing 3,5-diarylpyrazoles in good to excellent yield by reacting hydrazones of aryl aldehydes with substituted acetophenones in ethanol in the presence of dimethyl sulfoxide/cat. I2/cat. HCl. The reverse process, reacting hydrazones of substituted acetophenones with aryl aldehydes under the same conditions, also provides 3,5-diarylpyrazoles in good to excellent yields. Reaction of hydrazones of aldehydes with 2'-aryloxy ketones in the presence of cat. HCl in ethanol and the catalyst-free reaction of phenacyl bromides with hydrazones of aldehydes in ethanol also gave good to excellent yields of 3,5-diarylpyrazoles.

| S-EPMC6643981 | biostudies-literature

One-pot phosphine-catalyzed syntheses of quinolines.

Project description:In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the β-phosphonium enoate α-vinyl anion generated in situ through nucleophilic addition of PPh(3) to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile N-tosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.

| S-EPMC3459651 | biostudies-literature

Copper-catalyzed in situ oxidative-coupling for one-pot synthesis of 5-aryl-1,4-disubstituted 1,2,3-triazoles under mild conditions.

Project description:A new reaction system with CuCl as catalyst, TEA as base and O2/chloramine-T as oxidant was developed for one-pot in situ oxidative-coupling to synthesize 5-aryl-1,4-disubstituted 1,2,3-triazoles in this paper. A variety of 5-arylated-1,2,3-triazole compounds could be efficiently prepared directly from the readily accessible organic azides, terminal alkynes and arylboronic acids. Advantages of the method include use of low-cost catalyst, clean oxidant, less-toxic additive, and low reaction temperature. Importantly, due to avoiding harsh strong basic reagents and high temperatures, the presented method can offer mild conditions for multi-component synthesis of 5-aryl-1,2,3-triazoles from the designed structurally complicated alkynyl or azide donors bearing natural product motifs and sensitive functional groups.

| S-EPMC9043963 | biostudies-literature

Quercetin- and caffeic acid-functionalized chitosan-capped colloidal silver nanoparticles: one-pot synthesis, characterization, and anticancer and antibacterial activities

Project description:The presented study comprises the one-pot synthesis and the characterization of quercetin- and caffeic acid-functionalized chitosan-capped colloidal silver nanoparticles (Ch/Q- and Ch/CA-Ag NPs), and their antibacterial and anticancer activities. The formation of Ch/Q- and Ch/CA-Ag NPs has been confirmed by ultraviolet–visible (UV–vis) spectroscopy, Fourier-transform infrared (FTIR) spectroscopy, and transmission electron microscopy (TEM). The characteristic surface plasmon resonance (SPR) absorption band has been found at 417 and 424 nm for Ch/Q- and Ch/CA-Ag NPs, respectively. The formation of a chitosan shell comprising quercetin and caffeic acid, which surround the colloidal core Ag NPs, was confirmed by UV–vis, and FTIR analyses, and monitored by TEM microscopy. The size of nanoparticles has been determined as 11.2 and 10.3 nm for Ch/Q- and Ch/CA-Ag, respectively. The anticancer activity of Ch/Q- and Ch/CA-Ag NPs has been evaluated against U-118 MG (human glioblastoma) and ARPE-19 (human retinal pigment epithelium) cells. Both NPs showed anticancer activity, but Ch/Q-Ag NPs seemed to be more effective on cancer cell lines (U-118 MG) in comparison to healthy ones (ARPE-19). Furthermore, the antibacterial activity of Ch/Q- and Ch/CA-Ag NPs against Gram-negative (P. aeruginosa and E. coli) and Gram-positive (S. aureus and S. epidermidis) bacteria was determined, and dose-dependent antibacterial effects were found.

| S-EPMC10043739 | biostudies-literature

One-Pot Modified Madelung Synthesis of 3-Tosyl- and 3-Cyano-1,2-disubstituted Indoles.

Project description:A One-pot, two-step procedure for the synthesis of 1,2-disubstituted-3-tosyl and 1,2-disubstituted-3-cyanoindoles from the corresponding N-(o-tolyl)benzamides is reported. The developed procedure is operationally simple, does not utilize any transition metals, and provides variably substituted indoles in good yields from readily available starting materials.

| S-EPMC9631411 | 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