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- W2135147260 abstract "Acyclo-7-desazaguanosin (2), ein Strukturanalogon des antiviral hochwirksamen Acycloguanosins (1), wurde synthetisiert. Bei der Phasentransfermethylierung von 2-Amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidin (4c), die ausschließlich zum N-7-Methylderivat 5 führt, konnte Regiospezifität des elektrophilen Angriffs an 4c nachgewiesen werden. Die Konstitutionsermittlung von 5a erfolgte durch Umwandlung in 3,7-Dihydro-7-methyl-4H-pyrrolo[2,3-d]pyrimidin-4-on (5d) über die Zwischenprodukte 5b und 5c. Die Anwendung der Methylierungsbedingungen auf die Reaktion von 4c mit (2-Acetoxyethoxy)methylbromid führte zu 6a, das zu 6b entacetyliert wurde. Für das Acyclonucleosid 2 wird aufgrund der mit 1 identische Seitenkette selektive Phoshorylierung durch Thymidinkinasen und damit antivirale Aktivität erwartet. Synthesis of Acyclo-7-desazaguanosin by Regiospecific Phase-Transfer Alkylation of 2-Amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidineAcyclo-7-deazaguanosine (2), a structural analogue of the antiviral highly active acycloguanosine (1), has been synthesized. Regiospecificity of the electrophilic attack was shown by phase-transfer methylation of 2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine (4c) yielding the N-7 methyl derivative 5a exclusively. Elucidation of the structure of 5a resulted from its conversion into 3,7-dihydro-7-methyl-4H-pyrrolo[2,3-d]pyrimidin-4-one via the intermediates 5b and 5c. By applying the methylation conditions on the reaction of 4c with (2-acetoxyethoxy)methyl bromide the protected compound 6a was obtained which was deacetylated to give 6b. The acyclonucleoside 2 is expected to be phosphorylated by thymidine kinases because of the identical side chain compared with 1. Therefore, antiviral activity can be anticipated" @default.
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- W2135147260 date "1983-01-13" @default.
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- W2135147260 title "Synthese von Acyclo-7-desazaguanosin durch regiospezifische Phasentransferalkylierung von 2-Amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidin" @default.
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- W2135147260 doi "https://doi.org/10.1002/jlac.198319830113" @default.
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