Synthesis of New Pseudo‐C‐Nucleosides Containing Pyrazole Rings in their Structure

References

• Ishibuchi , S. , Morimoto , H. , Oe , T. , Ikebe , T. , Inoue , H. , Fukunari , A. , Kamezawa , M. , Yamada , I. and Naka , Y. 2001 . Synthesis and structure‐activity relationships of 1‐phenylpyrazoles as xanthine oxidase inhibitors . Bioorg. Med. Chem. Lett. , 11 ( 7 ) : 879 – 882 .
   PubMedGoogle Scholar
• Jia , Z. Z.J. , Wu , Y. H. , Huang , W. B. , Goldman , E. , Zang , P. L. , Woolfrey , J. , Wong , P. , Huang , B. , Sinha , U. , Park , G. , Reed , A. , Scarborough , R. M. and Zhu , B. Y. 2002 . Design, synthesis and biological activity of novel non‐amidine factor Xa inhibitors. Part 1: P‐1 structure‐activity relationships of the substituted 1‐(2‐naphtyl)‐1H‐pyrazole‐5‐carboxylamides . Bioorg. Med. Chem. Lett. , 12 ( 12 ) : 1651 – 1655 .
   PubMedGoogle Scholar
• Ruiu , S. , Pinna , G. A. , Marchese , G. , Mussinu , J. M. , Saba , P. , Tambaro , S. , Casti , P. , Vargiu , R. and Pani , L. 2003 . Synthesis and characterization of NESS 0327: A novel putative antagonist of the CB1 cannabinoid receptor . J. Pharm. Exp. Ther. , 306 ( 1 ) : 363 – 370 .
   PubMedGoogle Scholar
• Abadi , A. H. , Eissa , A. A.H. and Hassan , G. S. 2003 . Synthesis of novel 1,3,4‐trisubstituted pyrazole derivatives and their evaluation as antitumor and antiangiogenic agents . Chem. Pharm. Bull. , 51 ( 7 ) : 838 – 844 .
   PubMedGoogle Scholar
• Mehta , K. H. and Desai , K. R. 2003 . Synthesis of new heterocyclic thiazolidinone and azetidinone compounds and their antibacterial activity . Asian J. Chem. , 15 ( 1 ) : 459 – 465 .
   Google Scholar
• Ma , J. A. , Huang , R. Q. , Feng , L. , Song , J. and Qiu , D. W. 2003 . Synthesis and biological activity of new pyrethroid acid oxime‐esters containing pyrazole ring . Chem. Res. Chinese Univ. , 19 ( 3 ) : 297 – 301 .
   Google Scholar
• Zhou , Y. H. , Miao , W. R. , Cheng , L. B. , Wang , D. X. and Bai , Z. S. 2003 . Synthesis and herbicidal activity of substituted phenyl pyrazole derivatives . Chem. J. Chinese Univ.‐Chinese , 24 ( 7 ) : 1225 – 1230 .
   Google Scholar
• Shiga , Y. , Okada , I. and Fukuchi , T. 2003 . Synthesis and acaricidal activity of N‐(1,3,4‐thiadiazol‐2‐yl)pyrazole‐5‐carboxamides and N‐(1,3,4‐thiadiazol‐2‐yl)thiazole‐5‐carboxamides . J. Pest. Sci. , 28 ( 3 ) : 310 – 312 .
   Google Scholar
• Hu , L. M. , Li , X. S. , Chen , Z. Y. and Liu , Z. J. 2003 . Synthesis and biological activity of novel bis‐heterocyclic compounds containing 1H‐pyrazole and thiazole . Chinese J. Org. Chem. , 23 ( 10 ) : 1131 – 1134 .
   Google Scholar
• Ren , J. , Zhang , X. H. , Liu , Y. , Chen , W. Q. and Jin , G. Y. 2002 . Regioselective synthesis and base catalysed transacylation of substituted 1H‐pyrazole‐4‐carboxamides . Chinese J. Chem. , 20 ( 1 ) : 96 – 102 .
   Google Scholar
• Nigam , S. , Joshi , Y. C. and Joshi , P. 2003 . Synthesis of novel pyrazole derivatives from diaryl 1,3‐diketones (Part I) . Heterocycl. Commun. , 9 ( 4 ) : 405 – 410 .
   Google Scholar
• Lee , K. Y. , Kim , J. M. and Kin , J. N. 2003 . Regioselective synthesis of 1,3,4,5‐tetrasubstituted pyrazoles from Baylis‐Hillman adducts . Tetrahedron Lett. , 44 ( 35 ) : 6737 – 6740 .
   Google Scholar
• Sridhar , R. and Perumal , P. T. 2003 . Synthesis of novel 1H‐pyrazole‐4‐carboxylic acid esters by conventional and microwave assisted Vilsmeier cyclization of hydrazones . Synth. Commun. , 33 ( 9 ) : 1483 – 1488 .
   Web of Science ®Google Scholar
• De Luca , L. , Giacomelli , G. , Porcheddu , A. , Salaris , M. and Taddei , M. 2003 . Cellulose beads: a new versatile solid support for microwave‐assisted synthesis. Preparation of pyrazole and isoxazole libraries . J. Comb. Chem. , 5 ( 4 ) : 465 – 471 .
   PubMedGoogle Scholar
• Buffel , D. K. , Meerpoel , L. , Toppet , S. M. and Hoornaert , G. J. 1994 . Synthesis of novel isothiazole and isothiazolo[4,5‐d]pyrimidine analogues of the natural C‐nucleosides pyrazofurin and the formycins . Nucleosides & Nucleotides , 13 ( 1–3 ) : 719 – 736 . and references cited therein
   Google Scholar
• Chen , X. and Schneller , S. W. 1993 . Synthesis and antiviral activity of 5′‐deoxypyrazofurin . J. Med. Chem. , 36 : 3727 – 3730 .
   PubMedGoogle Scholar
• Rycroft , A. D. , Singh , G. and Wightman , R. H. 1995 . Stereoselective synthesis of 3‐β‐D‐ribofuranosylpyrazole from 2,3‐O‐isopropylidene‐D‐ribose; a new route to pyrazole C‐nucleosides . J. Chem. Soc. Perkins Trans.I , : 2667 – 2668 .
   Google Scholar
• Erion , M. D. and Rydzewsky , M. 1997 . 4‐Substituted‐5(3)‐carbamoyl‐3(5)‐(2‐deoxy‐β‐D‐ribofuranosyl)pyrazoles. Application of palladium catalysed glycal coupling methodology to the synthesis of pyrazofurin analogs . Nucleosides & Nucleotides , 16 ( 3 ) : 315 – 337 .
   Web of Science ®Google Scholar
• Veronese , A. C. and Morelli , C. F. 1998 . A new and efficient route to the synthesis of pyrazole and pyrimidine C‐nucleoside derivatives . Tetrahedron Lett. , 39 : 3853 – 3856 .
   Google Scholar
• Manferdini , M. , Morelli , C. F. and Veronese , A. C. 2002 . Synthesis of pyrazole C‐nucleosides via Tin(IV) chloride‐promoted reactions of β‐D‐ribofuranosyl cyanide with β‐dicarbonyl compounds . Tetrahedron , 58 ( 5 ) : 1005 – 1010 .
   Google Scholar
• Methling , K. , Kopf , J. , Michalik , M. , Reinke , H. , Burger , C. , Oberender , H. and Peseke , K. 2003 . Synthesis of acyclic C‐nucleoside analogues using (E)‐1,2‐dideoxy‐1‐dimethylamino‐4,5:6,7‐di‐O‐isopropylidene‐D‐arabino‐hept‐1‐en‐3‐ulose . J. Carbohydr. Chem. , 22 ( 7–8 ) : 537 – 548 .
   Web of Science ®Google Scholar
• Rauter , A. P. , Figueiredo , J. A. , Ismael , M. I. , Padilha , M. , Justino , J. , Ferreira , H. , Ferreira , M. J. , Rajendran , C. and Wilkins , R. Unpublished results
   Google Scholar
• Rauter , A. P. , Figueiredo , J. A. and Ismael , M. I. 1989 . Synthesis of pseudo‐C‐nucleosides . Carbohydr. Res. , 188 : 19 – 24 .
   PubMed Web of Science ®Google Scholar
• Gateau‐Olesker , A. , Castellanos , L. , Panne‐Jacolot , F. , Cleophax , J. and Gero , S. D. 1981 . Ouverture régiospécifique d'un oxirane preparé à partir du D‐xylose par dês carbanions soufrés. Synthèse de C‐nucleosides branches . Tetrahedron , 37 : 1685 – 1690 .
   Google Scholar
• Rauter , A. P. , Fernandes , A. C. , Czernecki , S. and Valery , J. M. 1996 . Deoxygenation at C‐4 and stereospecific branched‐chain construction at C‐3 of a methyl hexopyranuloside. Synthetic approach to the amipurimycin sugar moiety . J. Org. Chem. , 61 : 3594 – 3598 .
   PubMed Web of Science ®Google Scholar
• Popsavin , M. , Torovic , L. , Spaic , S. , Stantov , S. , Kapor , A. , Tomic , Z. and Popsavin , V. 2002 . Synthesis and biological evaluation of new pyrazole‐ and tetrazole‐related C‐nucleosides with modified sugar moieties . Tetrahedron , 58 ( 3 ) : 569 – 580 .
   Google Scholar
• Barton , D. H.R. and Stick , R. V. 1975 . The reaction of diol thiocarbonates with methyl iodide: a synthesis of 6‐deoxy sugars . J. Chem. Soc. Perkin Trans. I , : 1773 – 1776 .
   Google Scholar
• Barton , D. H.R. and Subramanian , R. 1977 . Synthesis of Deoxysugars and of deoxynucleosides from diol thiocarbonates . J. Chem. Soc. Perkin Trans. I , : 1718 – 1723 .
   PubMedGoogle Scholar
• Rauter , A. P. , Figueiredo , J. A. and Ismael , M. I. Unpublished results
   Google Scholar