Matches in SemOpenAlex for { <https://semopenalex.org/work/W2951362937> ?p ?o ?g. }
- W2951362937 endingPage "2202" @default.
- W2951362937 startingPage "2195" @default.
- W2951362937 abstract "The α-hydroxybenzylphosphonates 1a–1j of the antiviral drug 3′-azido-2′,3′-dideoxythymidine 5 (AZT) as potential lipophilic prodrugs were readily accessible in 49% to 87% yield via a four-step synthetic pathway introducing the modifications in the aromatic ring system in the last step by making use of intermediate 6. All compounds 1a–1j exhibited higher partition coefficients in 1-octanol/water than AZT (5). In hydrolysis studies at pH 7.5 we observed that precursors to bioactive compounds were delivered by simple hydrolysis of the lipophilic precursors 1a–1j via two different mechanisms: the phosphonate-phosphate rearrangement leading to the benzylphosphotriesters 2 and/or the direct cleavage into the di-AZT phosphonate 6. Both compounds 2 and 6 were further degraded yielding the potentially antiviral active compounds 4 and 8, respectively. The hydrolysis pathway could be controlled by the substitution pattern in the benzylic moiety. Identical hydrolytic behavior of 1 was detected in „biological”︁ hydrolysis kinetics by using a RPMI culture medium containing 10% heat-inactivated fetal calf serum (FCS). The title compounds 1a–1j exhibited considerable HIV-1 and HIV-2 activity in wild-type CEM/O cells." @default.
- W2951362937 created "2019-06-27" @default.
- W2951362937 creator A5011995952 @default.
- W2951362937 creator A5038319371 @default.
- W2951362937 creator A5040662398 @default.
- W2951362937 creator A5054321425 @default.
- W2951362937 date "1995-12-01" @default.
- W2951362937 modified "2023-09-23" @default.
- W2951362937 title "Lipophilic α-hydroxybenzylphosphonates as prodrugs of 3′-azido-2′,3′-dideoxythymidine (AZT)" @default.
- W2951362937 cites W1497236662 @default.
- W2951362937 cites W1969604023 @default.
- W2951362937 cites W1969718963 @default.
- W2951362937 cites W1970750348 @default.
- W2951362937 cites W1976580962 @default.
- W2951362937 cites W1979629823 @default.
- W2951362937 cites W1983648839 @default.
- W2951362937 cites W1988771912 @default.
- W2951362937 cites W1989605545 @default.
- W2951362937 cites W1991670386 @default.
- W2951362937 cites W1992132637 @default.
- W2951362937 cites W1998507449 @default.
- W2951362937 cites W1999210337 @default.
- W2951362937 cites W2000654111 @default.
- W2951362937 cites W2003282022 @default.
- W2951362937 cites W2003764499 @default.
- W2951362937 cites W2005199549 @default.
- W2951362937 cites W2007259169 @default.
- W2951362937 cites W2007972675 @default.
- W2951362937 cites W2009824405 @default.
- W2951362937 cites W2013490624 @default.
- W2951362937 cites W2028900503 @default.
- W2951362937 cites W2030164839 @default.
- W2951362937 cites W2036819090 @default.
- W2951362937 cites W2038551100 @default.
- W2951362937 cites W2044929983 @default.
- W2951362937 cites W2049545460 @default.
- W2951362937 cites W2050207842 @default.
- W2951362937 cites W2051318981 @default.
- W2951362937 cites W2062656389 @default.
- W2951362937 cites W2066149756 @default.
- W2951362937 cites W2073517737 @default.
- W2951362937 cites W2075953658 @default.
- W2951362937 cites W2086186867 @default.
- W2951362937 cites W2089928701 @default.
- W2951362937 cites W2090938639 @default.
- W2951362937 cites W2091526158 @default.
- W2951362937 cites W2093001560 @default.
- W2951362937 cites W2095047192 @default.
- W2951362937 cites W2099418931 @default.
- W2951362937 cites W2138206116 @default.
- W2951362937 cites W2143773220 @default.
- W2951362937 cites W2147033389 @default.
- W2951362937 cites W2162658079 @default.
- W2951362937 cites W2315163484 @default.
- W2951362937 cites W2326927314 @default.
- W2951362937 cites W2329990076 @default.
- W2951362937 cites W2950590087 @default.
- W2951362937 cites W2951008375 @default.
- W2951362937 cites W2951776329 @default.
- W2951362937 cites W88512482 @default.
- W2951362937 doi "https://doi.org/10.1002/jlac.1995199512305" @default.
- W2951362937 hasPublicationYear "1995" @default.
- W2951362937 type Work @default.
- W2951362937 sameAs 2951362937 @default.
- W2951362937 citedByCount "14" @default.
- W2951362937 countsByYear W29513629372014 @default.
- W2951362937 countsByYear W29513629372018 @default.
- W2951362937 countsByYear W29513629372020 @default.
- W2951362937 crossrefType "journal-article" @default.
- W2951362937 hasAuthorship W2951362937A5011995952 @default.
- W2951362937 hasAuthorship W2951362937A5038319371 @default.
- W2951362937 hasAuthorship W2951362937A5040662398 @default.
- W2951362937 hasAuthorship W2951362937A5054321425 @default.
- W2951362937 hasConcept C108215921 @default.
- W2951362937 hasConcept C127413603 @default.
- W2951362937 hasConcept C134121241 @default.
- W2951362937 hasConcept C175156509 @default.
- W2951362937 hasConcept C178790620 @default.
- W2951362937 hasConcept C185592680 @default.
- W2951362937 hasConcept C187320778 @default.
- W2951362937 hasConcept C191897082 @default.
- W2951362937 hasConcept C192562407 @default.
- W2951362937 hasConcept C2776568683 @default.
- W2951362937 hasConcept C2777132085 @default.
- W2951362937 hasConcept C2777626080 @default.
- W2951362937 hasConcept C43369102 @default.
- W2951362937 hasConcept C55493867 @default.
- W2951362937 hasConcept C71240020 @default.
- W2951362937 hasConcept C94412978 @default.
- W2951362937 hasConceptScore W2951362937C108215921 @default.
- W2951362937 hasConceptScore W2951362937C127413603 @default.
- W2951362937 hasConceptScore W2951362937C134121241 @default.
- W2951362937 hasConceptScore W2951362937C175156509 @default.
- W2951362937 hasConceptScore W2951362937C178790620 @default.
- W2951362937 hasConceptScore W2951362937C185592680 @default.
- W2951362937 hasConceptScore W2951362937C187320778 @default.
- W2951362937 hasConceptScore W2951362937C191897082 @default.
- W2951362937 hasConceptScore W2951362937C192562407 @default.