About: 6-Alkynylpurines Bearing Electronacceptor Substituents: Preparation, Reactivity in Cycloaddition Reactions and Cytostatic Activity

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About: 6-Alkynylpurines Bearing Electronacceptor Substituents: Preparation, Reactivity in Cycloaddition Reactions and Cytostatic Activity Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	While direct Sonogashira coupling of 6-halopurines with methyl propiolate and with propargyl aldehyde was not successful, the corresponding orthoester and propargyl aldehyde diethylacetal reacted smoothly. Such prepared orthoester was then converted to the desired methylester by methanolysis, the acetal was too stable to be hydrolyzed. The obtained 6-ethynylpurines, bearing orthoester, acetal, methoxycarbonyl and for comparison also the phenyl substituent on the ethynyl group, were subjected to the cycloaddition reaction with cyclopentadiene, diazomethane and phenylazide. Electron deficient alkynylpurines were considerably more reactive in this reaction compared to the not activated phenylethynyl derivative. The prepared alkynylpurines exhibited medium cytostatic activity (IC50 = 2.6-15 mýM), while the cycloadducts were inactive. While direct Sonogashira coupling of 6-halopurines with methyl propiolate and with propargyl aldehyde was not successful, the corresponding orthoester and propargyl aldehyde diethylacetal reacted smoothly. Such prepared orthoester was then converted to the desired methylester by methanolysis, the acetal was too stable to be hydrolyzed. The obtained 6-ethynylpurines, bearing orthoester, acetal, methoxycarbonyl and for comparison also the phenyl substituent on the ethynyl group, were subjected to the cycloaddition reaction with cyclopentadiene, diazomethane and phenylazide. Electron deficient alkynylpurines were considerably more reactive in this reaction compared to the not activated phenylethynyl derivative. The prepared alkynylpurines exhibited medium cytostatic activity (IC50 = 2.6-15 mýM), while the cycloadducts were inactive. (en)
Title	6-Alkynylpurines Bearing Electronacceptor Substituents: Preparation, Reactivity in Cycloaddition Reactions and Cytostatic Activity 6-Alkynylpurines Bearing Electronacceptor Substituents: Preparation, Reactivity in Cycloaddition Reactions and Cytostatic Activity (en)
skos:prefLabel	6-Alkynylpurines Bearing Electronacceptor Substituents: Preparation, Reactivity in Cycloaddition Reactions and Cytostatic Activity 6-Alkynylpurines Bearing Electronacceptor Substituents: Preparation, Reactivity in Cycloaddition Reactions and Cytostatic Activity (en)
skos:notation	RIV/60461373:22810/11:43892735!RIV12-MSM-22810___
http://linked.open...avai/riv/aktivita	I P Z
http://linked.open...avai/riv/aktivity	I, P(GA203/09/1552), P(LC06070), Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika	12
http://linked.open...vai/riv/dodaniDat	2012
http://linked.open...aciTvurceVysledku	Dvořáková, Hana
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Rektorát
http://linked.open...dnocenehoVysledku	244239
http://linked.open...ai/riv/idVysledku	RIV/60461373:22810/11:43892735
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	Cycloaddition reactions; Cytotoxicity; Alkynylpurines (en)
http://linked.open.../riv/klicoveSlovo	Cytotoxicity Alkynylpurines Cycloaddition reactions
http://linked.open...odStatuVydavatele	CZ - Česká republika
http://linked.open...ontrolniKodProRIV	[6D5AF5D4DFAB]
http://linked.open...i/riv/nazevZdroje	Collection of Czechoslovak Chemical Communications
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	1 (xsd:int)
http://linked.open...cetTvurcuVysledku	5 (xsd:int)
http://linked.open...vavai/riv/projekt	Application of 7,8-Dihydropurines in the Synthesis of New Purine Derivatives with Potential Biological Activity The structure and synthetic applications of transition metal complexes
http://linked.open...UplatneniVysledku	2011
http://linked.open...v/svazekPeriodika	76
http://linked.open...iv/tvurceVysledku	Císařová, Ivana Votruba, Ivan Dvořáková, Hana Dvořák, Dalimil Křováček, Martin
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství
issn	0010-0765
number of pages	20 (xsd:int)
http://bibframe.org/vocab/doi	10.1135/cccc2011176
http://localhost/t...ganizacniJednotka	22810

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