Studies on the Synthesis of N′-Acetyl AZA-Analogues of Ganciclovir—Unexpected Liability of N′-(2-Hydroxyethyl)-Azanucleosides Under Basic Conditions

REFERENCES AND NOTES

• De Clercq , E. 2004 . Antiviral drugs in current clinical use . J. Clin. Virol. , 30 : 115 – 133 .
   PubMed Web of Science ®Google Scholar
• Gawin , R. , De Clercq , E. , Naesens , L. and Koszytkowska-Stawińska , M. 2008 . Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure . Bioorg. Med. Chem. , 16 : 8379 – 8389 .
   PubMedGoogle Scholar
• Koszytkowska-Stawińska , M. , Sas , W. , Kaleta , K. and De Clercq , E. 2007 . Synthesis and antiviral properties of aza–analogues of acyclovir . Nucleos. Nucleot. Nucl. Acids , 26 : 51 – 64 .
   PubMed Web of Science ®Google Scholar
• Koszytkowska-Stawińska , M. , Sas , W. and De Clercq , E. 2006 . Synthesis of aza-analogues of Ganciclovir . Tetrahedron , 62 : 10325 – 10331 .
   Google Scholar
• Koszytkowska-Stawińska , M. , Kołaczkowska , E. , Adamkiewicz , E. and De Clercq , E. 2007 . Synthesis and antiviral properties of aza-analogues of ganciclovir derived from 5,5-bis(hydroxymethyl)pyrrolidin-2-one . Tetrahedron , 63 : 10587 – 10595 .
   Google Scholar
• Myers , A. G. , Yang , B. H. , Chen , H. , McKinstry , L. , Kopecky , D. J. and Gleason , J. L. 1997 . Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantomerically enriched carboxylic acids, alcohols, aldehydes, and ketones . J. Am. Chem. Soc. , 119 : 6496 – 6511 .
   Web of Science ®Google Scholar
• Myers , A. G. and Gleason , J. L. 2004 . Asymetric synthesis of α-amino acids by the alkylation of pseudoephedrine glycinamide: L-allylglycine and N-Boc-L-allylglycine . Org. Synth. , Coll. Voll. 10 : 12
   Google Scholar
• Phillips , A. and Baltzly , R. 1947 . Rearrangements between primary ethanolamides of carboxylic acids and the corresponding aminoethylesters . J. Am. Chem. Soc. , 69 : 200 – 204 .
   PubMedGoogle Scholar
• Markey , S. P. , Dudding , T. and Wang , T-C.L. 2000 . Base- and acid-catalyzed interconversions of O-acyl- and N-acyletanolamines: a cautionary note for lipid analyses . J. Lipid Res. , 41 : 657 – 662 .
   PubMed Web of Science ®Google Scholar
• Van Overloop , H. , Van der Hoeven , G. and Van Veldhoven , P. P. 2005 . N-Acyl migration in ceramides . J. Lipid Res. , 46 : 812 – 816 .
   PubMedGoogle Scholar
• Eberhard , H. and Seitz , O. 2008 . N→O-Acyl migration shift in Fmoc-based synthesis of phosphopeptides . Org. Biomol. Chem. , 6 : 1349 – 1355 .
   PubMedGoogle Scholar
• Hamada , Y. , Ohtake , J. , Sohma , Y. , Kimura , T. , Hayashi , Y. and Kiso , Y. 2002 . New water-soluble prodrugs of HIV protease inhibitors based on O→N intramolecular acyl migration . Bioorg. Med. Chem. , 10 : 4155 – 4167 .
   PubMed Web of Science ®Google Scholar
• Hamada , Y. , Matsumoto , H. , Kimura , T. , Hayashi , Y. and Kiso , Y. 2003 . Effect of the acyl groups on O→N acyl migration in the water-soluble prodrugs of HIV-1 protease inhibitor . Bioorg. Med. Chem. Lett. , 13 : 2727 – 2730 .
   PubMed Web of Science ®Google Scholar
• Hamada , Y. , Matsumoto , H. , Yamaguchi , S. , Kimura , T. and Hayashi , Y. 2004 . Kiso, Water-soluble prodrugs of dipeptide HIV protease inhibitors based on O→N acyl migration: design, synthesis and kinetic study . Bioorg. Med. Chem. , 12 : 159 – 170 .
   PubMed Web of Science ®Google Scholar
• Skwarczynski , M. , Sohma , Y. , Kimura , M. , Hayashi , Y. , Kimura , T. and Kiso , Y. 2003 . O,N intramolecular acyl migration strategy in water-soluble prodrugs of Taxoids . Bioorg. Med. Chem. Lett. , 13 : 4441 – 4444 .
   PubMedGoogle Scholar
• Guarino , V. R. and Stella , V. J. 2007 . “ Prodrugs of amides, imides and other NH acid compounds ” . In Prodrugs: Challenges and Rewards-Part 2 , Edited by: Stella , V. J. , Borchardt , R. T. , Hageman , M. , Oliyai , R. , Maag , H. and Tilley , J. New York : AAPS Press/Springer .
   Google Scholar
• Xiong , J. , Zhu , H.-F. , Zhao , Ya-J. , Lan , Y.-J. , Jiang , Ji-W. , Yang , J.-J. and Zhang , S.-F. 2009 . Synthesis and antitumor activity of amino acid ester derivatives containing 5-fluorouracil . Molecules , 14 : 3142 – 3152 .
   PubMed Web of Science ®Google Scholar
• Madec-Lougerstay , R. , Florent , J.-C. and Monneretm , C. 1999 . Synthesis of self-immolative glucuronide spacers based on aminomethylcarbamate. Application to 5-fluorouracil prodrugs for antibody-directed enzyme prodrug therapy . J. Chem. Soc., Perkin Trans. 1 , : 1369 – 1376 .
   Google Scholar
• Nishitani , T. , Iwasaki , T. , Mushika , Y. and Miyoshi , M. 1979 . Synthesis of 2-(Pyrimidin-l-yl)- and 2-(Purin-9-yl)-2-amino Acids . J. Org. Chem. , 44 : 2019 – 2023 .
   Web of Science ®Google Scholar
• Koszytkowska-Stawińska , M. and Sas , W. 2004 . Facile synthesis of acyclic azanucleosides from N-pivaloyloxymethyl amides and sulfonamides: synthesis of aza-analogues of Ganciclovir . Tetrahedron Lett. , 45 : 5437 – 5440 .
   Google Scholar
• Bordwell , F. R. 1988 . Equilibrium acidities in dimethyl sulfoxide solution . Acc. Chem. Res. , 21 : 456 – 463 .
   Web of Science ®Google Scholar
• Vorbrüggen , H. and Ruh-Pohlenz , C. 2001 . Handbook of Nucleoside Synthesis , New York : John Wiley .
   Google Scholar
• Altmann , K-H. 1993 . Pyrrolidine based analogs of 3′-deoxythymidine . Tetrahedron Lett. , 34 : 7721 – 7724 .
   Google Scholar
• Rassu , G. , Pinna , L. , Ulgheri , F. and Casiraghi , G. 1994 . Total syntheses of N-boc-protected 3′-deoxy-4′-azathymidine and 4′-azauridine . Tetrahedron Lett. , 35 : 4019 – 4022 .
   Google Scholar
• Pickering , L. , Malhi , B. S. , Coe , P. L. and Walker , R. T. 1994 . The synthesis of 4′-t-butylcarbamyl- and 4′-p-toluenesulphonamidyl-2′,3′-dideoxy pyrimidine nucleoside analogues . Nucleosides Nucleotides , 13 : 1493 – 1506 .
   Google Scholar
• Chimishkyan , A. L. , Snagovskii , Yu.S. , Gulyaev , N. D. , Leonova , T. V. and Kusakin , M. S. 1985 . Transamination characteristics of substituted ureas. III. Confirmation of the mechanism via kinetic studies . Zh. Org. Khim. , 21 : 2136 – 2143 .
   Google Scholar
• Murakami , Y. , Kondo , K. , Miki , K. , Akiyama , Y. , Watanabe , T. and Yokoyama , Y. 1997 . The ortho-Substituted N,N-Diacetylaniline as a Selective Acetylating Reagent . Tetrahedron Lett. , 38 : 3751 – 3754 .
   Web of Science ®Google Scholar
• Marvell , E. , Nelson , H. , Joncich , M. , Geiszler , A. and Williams , M. 1957 . Kinetics of the Alcoholysis of o- and p-Nitroacetanilides . J. Am. Chem. Soc. , 79 : 1076 – 1078 .
   Google Scholar
• Verkade , P. E. and Witjens , P. H. 1943 . Deacetylation of acetamino compounds containing a nitro group in the orto or para position . Recl. Trav. Chim. Pay B , 62 : 201 – 204 .
   Google Scholar
• Kawaguchi , S. and Araki , K. 2005 . Mild, rapid and selective alcoholysis of terpyridine-appended amide substrates by Cu2+-catalysis: protonation state and reactivity of the complex . Inorg. Chem. Acta , 358 : 947 – 956 .
   Google Scholar
• Brown , R. S. and Neverov , A. A. 2002 . Acyl and phosphoryl transfer to methanol promoted by metal ions . J. Chem. Soc., Perkin Trans. 2 , : 1039 – 1049 .
   Google Scholar
• Anelli , P. L. , Brocchetta , M. , Canipari , S. , Losi , P. , Manfredi , G. and Tomba , C. 1997 . Synthesis and hydrolytic lability of α-phenoxyacetamides containing hydroxy groups in the N-alkyl residue . Gazz. Chim. Ital. , 127 : 135 – 142 .
   Google Scholar
• Varaprasad , C. V. , Averett , D. and Ramasamy , K. S. 1999 . Synthesis and structural studies of monocyclic 4′-aza-L-nucleosides . Tetrahedron , 55 : 13345 – 13368 .
   Google Scholar
• Fersht , A. R. 1971 . Acyl-transfer reactions of amides and esters with alcohols and thiols. A reference system for the serine and cysteine proteinases. Concerning the N promotion of amides and amide-imidate equilibria . J. Am. Chem. Soc. , 93 : 3504 – 3515 .
   PubMed Web of Science ®Google Scholar
• Carey , F. A. and Sundberg , R. J. 1990 . Advanced Organic Chemistry , 3rd ed. , 439 Plenum Press, New York, Part A .
   Google Scholar
• Hammond , G. S. 1955 . A correlation of reaction rates . J. Am. Chem. Soc. , 77 : 334 – 338 .
   Web of Science ®Google Scholar
• Ruzicka , L. 1935 . The many-membered carbon rings . Chem. Ind. (London) , 13 : 2 – 8 .
   Google Scholar
• “ The ChemBio3D (Ultra 11.0) program was used for the MM2 calculations ” .
   Google Scholar
• In the considered heterocyclic systems C, the total strain order is consisted with that established for the reference hydrocarbons: monocyclic < fused bicyclic < bridged bicyclic , Liebman , J. F. and Greenberg , A. 1976 . A survey of strained organic molecules . Chem. Rev. , 76 : 311 – 365 .
   Google Scholar
• McCasland , G. E. 1955 . N→O Acyl migration in epimeric acetyl inosamines . J. Am. Chem. Soc. , 73 : 2295 – 2297 .
   Google Scholar
• Fodor , G. , Kiss , J. and Sallay , I. 1951 . Configuration Correlation of Chloramphenicol with nor-ψ-ephedrine . J. Chem. Soc. , : 1858 – 1863 .
   Google Scholar
• Bushnev , A. S. , Struchkova , M. I. , Zvonkova , E. N. , Evstigneeva , R. P. and Preobrazhenskii , N. A. 1971 . Infrared absorption spectra and spatial structure of ceramide and its derivatives . Zh. Org. Khim. , 7 : 2132 – 2136 .
   Google Scholar
• Bushnev , A. S. , Zvonkova , E. N. and Evstigneeva , R. P. 1971 . Synthesis of 2-heptadecyl-4-(1-benzoyloxy)hexadecyl-2-oxazoline . Zh. Org. Khim. , 7 : 2313 – 2316 .
   Google Scholar
• Zvonkova , E. N. , Bushnev , A. S. , Mitsner , B. I. and Evstigneeva , R. P. 1973 . Phosphorylation of 3-O-benzoylceramide . Zh. Org. Khim. , 9 : 31 – 35 .
   Google Scholar
• McCarthy , O. , Musso-Buendia , A. , Kaiser , M. , Brun , R. , Ruiz-Perez , L. M. , Johanson , N. G. , Pacanowska , D. G. and Gilbert , I. H. 2009 . Design, synthesis and evaluation of novel uracil acetamide derivatives as potential inhibitors of Plasmodium falciparum dUTP nucleotidohydrolase . Eur. J. Med. Chem. , 44 : 678 – 688 .
   PubMed Web of Science ®Google Scholar
• Eriksson , M. , Christensen , L. , Schmidt , J. , Haaima , G. , Orgel , L. and Nielsen , P. E. 1998 . Sequence dependent N-terminal rearrangement and degradation of peptide nucleic acid (PNA) in aqueous solution . New J. Chem. , 22 : 1055 – 1059 .
   Google Scholar
• Christensen , L. , Fitzpatrick , R. , Gildea , B. , Petersen , K. H. , Hansen , H. F. , Koch , T. , Egholm , M. , Buchardt , O. , Nielsen , P. E. , Coull , J. and Berg , R. H. 1995 . Solid-Phase synthesis of peptide nucleic acids . J. Peptide Sci. , 1 : 175 – 183 .
   PubMedGoogle Scholar
• Hadj-Bouazza , A. , Teste , K. , Colombeau , L. , Chaleix , V. , Zerrouki , R. , Kraemer , M. and Catherine , O. S. 2008 . Synthesis and biological activity of mustard derivatives of thymine . Nucleos. Nucleot. Nucl. Acids , 27 : 439 – 448 .
   PubMed Web of Science ®Google Scholar
• Katritzky , A. R. and Narindoshvili , T. 2008 . Chiral peptide nucleic acid monomers (PNAM) with modified backbones . Org. Biomol. Chem. , 6 : 3171 – 3176 .
   PubMedGoogle Scholar
• Murata , A. and Wada , T. 2006 . Synthesis of a novel ester analog of nucleic acids bearind a serine backbone . Bioorg. Med. Chem. Lett. , 16 : 2933 – 2936 .
   PubMedGoogle Scholar
• Hamzavi , R. , Dolle , F. , Tavitian , B. , Dahl , O. and Nielsen , P. E. 2003 . Modulation of the pharmacokinetic properties of PNA: preparation of galactosyl, mannosyl, fucosyl, N-acetylgalactosaminyl, and N-acetylglucosaminyl derivatives of aminoglycine peptide nucleic acid monomers and their incorporation into PNA oligomers . Bioconiugate Chem. , 14 : 941 – 954 .
   PubMed Web of Science ®Google Scholar
• Bajor , Z. , Sági , G. , Tegyey , Z. and Kraicsovits , F. 2003 . PNA-DNA chimeras containing 5-alkynyl-pyrimidine PNA units. Synthesis, Binding properties, and enzymatic stability . Nucleos. Nucleot. Nucl. Acids , 22 : 1963 – 1983 .
   PubMed Web of Science ®Google Scholar
• Rana , V. S. , Kumar , V. A. and Ganesh , K. N. 2001 . Oligonucleotides with (N-thymin-1-ylacetyl)-1-arylserinol backbone: chiral acyclic analogs with restricted conformational flexibility . Tetrahedron , 57 : 1311 – 1321 .
   Web of Science ®Google Scholar
• Krise , J. P. and Oliyai , R. 2007 . “ Prodrugs of amines ” . In Prodrugs: Challenges and Rewards-Part 2 , Edited by: Stella , V. J. , Borchardt , R. T. , Hageman , M. , Oliyai , R. , Maag , H. and Tilley , J. AAPS Press/Springer .
   Google Scholar
• Harada , M. , Moire , T. , Hirokawa , Y. and Kato , S. 1996 . An efficient synthesis of 6-substituted aminohexahydro-1H-1,4-diazepines from 2-substituted aminopropenals . Chem. Pharm. Bull. , 44 : 2205 – 2212 .
   Google Scholar