About: Asymmetric Primaquine and Halogenaniline Fumardiamides as Novel Biologically Active Michael Acceptors

Facets (new session)
Description
Metadata
Settings
- owl:sameAs
- Inference Rule:

About: Asymmetric Primaquine and Halogenaniline Fumardiamides as Novel Biologically Active Michael Acceptors Goto Sponge NotDistinct Permalink

An Entity of Type : schema:ScholarlyArticle, within Data Space : covidontheweb.inria.fr associated with source document(s)

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
has title	Asymmetric Primaquine and Halogenaniline Fumardiamides as Novel Biologically Active Michael Acceptors
Creator	Beus, Maja Rajić, Zrinka Zorc, Branka Persoons, Leentje Keser, Toma Kosalec, Ivan Michnová, Hana Vlainić, Josipa Id, Dominique Id, Josef Jampílek, Schols,
Source	Medline; PMC
abstract	Novel primaquine (PQ) and halogenaniline asymmetric fumardiamides 4a–f, potential Michael acceptors, and their reduced analogues succindiamides 5a–f were prepared by simple three-step reactions: coupling reaction between PQ and mono-ethyl fumarate (1a) or mono-methyl succinate (1b), hydrolysis of PQ-dicarboxylic acid mono-ester conjugates 2a,b to corresponding acids 3a,b, and a coupling reaction with halogenanilines. 1-[bis(Dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) was used as a coupling reagent along with Hünig′s base. Compounds 4 and 5 were evaluated against a panel of bacteria, several Mycobacterium strains, fungi, a set of viruses, and nine different human tumor cell lines. p-Chlorofumardiamide 4d showed significant activity against Staphylococcus aureus, Streptococcus pneumoniae and Acinetobacter baumannii, but also against Candida albicans (minimum inhibitory concentration (MIC) 6.1–12.5 µg/mL). Together with p-fluoro and p-CF(3) fumardiamides 4b,f, compound 4d showed activity against Mycobacterium marinum and 4b,f against M. tuberculosis. In biofilm eradication assay, most of the bacteria, particularly S. aureus, showed susceptibility to fumardiamides. m-CF(3) and m-chloroaniline fumardiamides 4e and 4c showed significant antiviral activity against reovirus-1, sindbis virus and Punta Toro virus (EC(50) = 3.1–5.5 µM), while 4e was active against coxsackie virus B4 (EC(50) = 3.1 µM). m-Fluoro derivative 4a exerted significant cytostatic activity (IC(50) = 5.7–31.2 μM). Acute lymphoblastic leukemia cells were highly susceptible towards m-substituted derivatives 4a,c,e (IC(50) = 6.7–8.9 μM). Biological evaluations revealed that fumardiamides 4 were more active than succindiamides 5 indicating importance of Michael conjugated system.
has issue date	2018-07-14(xsd:dateTime)
bibo:doi	10.3390/molecules23071724
bibo:pmid	30011922
has license	cc-by
sha1sum (hex)	ff81f65bce47ed0a1a6e586dc196c6543e97d861
schema:url	https://doi.org/10.3390/molecules23071724
resource representing a document's title	Asymmetric Primaquine and Halogenaniline Fumardiamides as Novel Biologically Active Michael Acceptors
has PubMed Central identifier	PMC6100582
has PubMed identifier	30011922
schema:publication	Molecules
resource representing a document's body	covid:ff81f65bce47ed0a1a6e586dc196c6543e97d861#body_text
is schema:about of	named entity 'antiviral' named entity 'evaluations' named entity 'primaquine' named entity 'bacteria' named entity 'acid' named entity 'lines' named entity 'Candida' named entity 'Asymmetric' covid:arg/ff81f65bce47ed0a1a6e586dc196c6543e97d861 named entity 'coupling' named entity 'potential' named entity 'reactions' named entity 'bacteria' named entity 'highly' named entity 'coxsackie virus' named entity 'susceptible' named entity 'simple' named entity 'eradication' named entity 'fumarate' named entity 'bis' named entity 'reduced' named entity 'activity' named entity 'Michael Acceptors' named entity 'dicarboxylic acid' named entity 'Fluoro' named entity '5.7' named entity 'biofilm' named entity 'sindbis virus' named entity 'ethyl' named entity 'hexafluorophosphate' named entity 'primaquine' named entity 'reovirus' named entity 'Streptococcus pneumoniae' named entity '5.5' named entity 'Punta Toro virus' named entity 'carboxylic acid' named entity 'antibacterial' named entity 'drug development' named entity 'extracellular matrix' named entity 'DMSO' named entity 'succinate' named entity 'E. faecalis' named entity 'parafilm' named entity 'trans' named entity 'solid tumor' named entity 'cell lines' named entity 'helenalin' named entity 'primary amino group' named entity 'lithium hydroxide' named entity '3, 4' named entity 'α,β-unsaturated' named entity 'ammonium formate' named entity 'anilines' named entity 'amide' named entity '4a-f' named entity 'mycobactin' named entity 'mammalian cells' named entity 'Capan' named entity 'clinical trials' named entity 'conjugated' named entity '4a-f' named entity 'spectroscopic methods' named entity '5.7' named entity 'condensation' named entity '4a-f' named entity 'cysteine' named entity '4a-f' named entity 'Merck' named entity 'CH-15' named entity 'silica gel'

Faceted Search & Find service v1.13.91 as of Mar 24 2020

Alternative Linked Data Documents: Sponger | ODE Content Formats:

RDF

ODATA

Microdata

About

OpenLink Virtuoso version 07.20.3229 as of Jul 10 2020, on Linux (x86_64-pc-linux-gnu), Single-Server Edition (94 GB total memory)
Data on this page belongs to its respective rights holders.
Virtuoso Faceted Browser Copyright © 2009-2024 OpenLink Software