About: Synthesis and Evaluations of “1,4‐Triazolyl Combretacoumarins” and Desmethoxy Analogs

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

About: Synthesis and Evaluations of “1,4‐Triazolyl Combretacoumarins” and Desmethoxy Analogs Goto Sponge NotDistinct Permalink

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

Attributes	Values
type	Academic Article research paper schema:ScholarlyArticle
isDefinedBy	Covid-on-the-Web dataset
has title	Synthesis and Evaluations of “1,4‐Triazolyl Combretacoumarins” and Desmethoxy Analogs
Creator	Schols, Dominique Andrei, Graciela Snoeck, Robert Lakshman, Mahesh Hess, Jessica Aguilera, Renato Khandaker, Tashrique Pradhan, Padmanava
Source	PMC
abstract	1,4‐Triazolyl combretacoumarins have been prepared by linking the trimethoxyarene unit of combretastatin A4 with coumarins, via a 1,2,3‐triazole. For this, 4‐azidocoumarins were accessed by a sequential two‐step, one‐pot reaction of 4‐hydroxycoumarins with (benzotriazol‐1‐yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), followed by reaction with NaN(3). In the reaction with BOP, a coumarin‐derived phosphonium ion intermediate seems to form, leading to an O (4)‐(benzotriazolyl)coumarin derivative. For the CuAAC reaction of azidocoumarins with 5‐ethynyl‐1,2,3‐trimethoxybenzene, catalytic [(MeCN)(4)Cu]PF(6) in CH(2)Cl(2)/MeOH with 2,6‐lutidine, at 50 (o)C, was suitable. The 4‐azidocoumarins were less reactive as compared to PhN(3) and the NBO coefficients of the azido groups were compared by DFT analysis. Compound solubility was a problem in biological assays. On the basis of the biological and solubility data of one 1,4‐triazolyl combretacoumarin, four analogs lacking one or two methoxy groups were synthesized. Reactivity differences among the phenylacetylenes were noted and the NBO coefficients of the alkynes were compared by DFT analysis. In cytotoxicity assays, 1‐phenyl‐4‐(3,4,5‐trimethoxyphenyl)‐1H‐1,2,3‐triazole showed activity in CEM and MDA‐MB‐231 cell lines by apoptosis. The desmethoxy 6‐bromo‐4‐(4‐(4‐methoxyphenyl)‐1H‐1,2,3‐triazol‐1‐yl)‐2H‐chromen‐2‐one also showed cytotoxicity against the two cell lines, but this did not appear to be consistent with apoptosis. The antiviral activity of the compounds was unremarkable.
has issue date	2019-08-07(xsd:dateTime)
bibo:doi	10.1002/ejoc.201900569
bibo:pmid	31579393
has license	no-cc
sha1sum (hex)	0926ed33799458d78b8cc21fa20a8956675a3d71
schema:url	https://doi.org/10.1002/ejoc.201900569
resource representing a document's title	Synthesis and Evaluations of “1,4‐Triazolyl Combretacoumarins” and Desmethoxy Analogs
has PubMed Central identifier	PMC6774347
has PubMed identifier	31579393
schema:publication	European J Org Chem
resource representing a document's body	covid:0926ed33799458d78b8cc21fa20a8956675a3d71#body_text
is schema:about of	named entity 'dimethylamino' named entity 'MeOH' named entity '2,6-lutidine' named entity 'alkynes' named entity 'PhN' named entity 'azide' named entity 'room temperature' named entity 'ion' named entity 'mmol' named entity 'MeCN' named entity 'PhN' named entity 'electronic properties' named entity 'mmol' named entity 'stir bar' named entity 'alkynyl' named entity 'mol-%' named entity 'coumarins' named entity 'coumarins' named entity 'hexanes' named entity 'azidocoumarin' named entity 'mmol' named entity 'copper' named entity 'ppm' named entity 'solubility' named entity '1.2' named entity 'methoxy groups' named entity 'cycloaddition' named entity 'leukemia' named entity 'Phenyl' named entity 'ppm' named entity 'mol-%' named entity 'propidium iodide' named entity 'CuAAC' named entity 'hexafluorophosphate' named entity 'chromatography' named entity 'DMSO' named entity 'mmol' named entity 'ligation reaction' named entity 'fluorescent' named entity 'MeOH' named entity 'azidocoumarin' named entity 'potency' named entity 'alkyne' named entity 'PhN' named entity 'column chromatography' named entity 'HMPA' named entity 'EtOAc' named entity 'round-bottomed flask' named entity 'HMPA' named entity 'azidocoumarin' named entity 'EtOAc' named entity 'depolymerizing' named entity 'DFT' named entity 'hydroxyl group' named entity 'ppm' named entity 'atom' named entity 'HIV1' named entity 'coumarins' named entity 'alkyne' named entity 'hydroxyl' named entity 'flow cytometry' named entity 'negative charge' named entity 'MeOH' named entity 'nitrogen gas' named entity 'nucleoside' named entity '2,6-lutidine' named entity 'mmol' named entity 'negative charge' named entity 'MeOH' named entity 'Combretastatin' named entity 'combretastatin' named entity 'NaN' named entity 'azidocoumarin' named entity 'antiviral activity'

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