{"title":"Stereoselective synthesis of beta-L-2',3'-dideoxy- and L-2',3'-didehydro-2',3'-dideoxy purine nucleosides.","authors":"P Wang, P J Bolon, M G Newton, C K Chua","doi":"10.1080/07328319908044642","DOIUrl":"https://doi.org/10.1080/07328319908044642","url":null,"abstract":"<p><p>beta-L-2',3'-Dideoxy- and L-2',3'-didehydro-2',3'-dideoxy purine nucleosides have been synthesized via a highly stereoselective method of glycosylation by the condensation of L-2-(phenylselenyl)-2,3-dideoxyribose derivative with silylated heterocyclic base.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2819-35"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044642","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495974","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
D R Borcherding, N L Lentz, P M Weintraub, M W Dudley, R Secrest, P R Kastner, N P Peet
{"title":"The synthesis and biological activity of a highly selective adenosine A2a receptor agonist.","authors":"D R Borcherding, N L Lentz, P M Weintraub, M W Dudley, R Secrest, P R Kastner, N P Peet","doi":"10.1080/07328319908044874","DOIUrl":"https://doi.org/10.1080/07328319908044874","url":null,"abstract":"<p><p>Three novel nucleosides 1, 2, and 3 were prepared that contained side chains at the 2-position of adenosine. Compound 1 was shown to be the most selective A2a receptor agonist reported to date having an A1/A2 ratio of 2400. In addition, compound 1 was shown to reduce blood pressure in rats and dogs with only minimal effects on heart rate.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 10","pages":"2175-91"},"PeriodicalIF":0.0,"publicationDate":"1999-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044874","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21472546","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis and biological activity of modified thiopyrimidine nucleosides.","authors":"A M Attia, M A Sallam, A A Almehdi, M M Abbasi","doi":"10.1080/07328319908044883","DOIUrl":"https://doi.org/10.1080/07328319908044883","url":null,"abstract":"<p><p>N3-beta-D-glucopyranosyl, galactopyranosyl and xylopyranosyl 6-methyl-2-methylthiouracil and their 5-bromo derivatives have been synthesized by coupling an alpha-acetobromosugar with the corresponding thiouracil. The new modified thiouridine analogues were evaluated for their inhibitory activity against Human Immunodeficiency Virus (HIV) replication in MT-4 cells as well as for their cytotoxicity.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 10","pages":"2307-15"},"PeriodicalIF":0.0,"publicationDate":"1999-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044883","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21472554","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of some pyridine ribosides and their biological activity.","authors":"A M Attia, H A Mansour, A A Almehdi, M M Abbasi","doi":"10.1080/07328319908044882","DOIUrl":"https://doi.org/10.1080/07328319908044882","url":null,"abstract":"<p><p>A synthesis of 1-(beta-D-ribofuranosyl)-pyridin-2-thiones via reaction of 3-cyanopyridin-2(1H)-thiones with 2,3,5-tri-O-benzoyl-D-ribofuranosyl bromide under basic conditions, followed by hydrolysis with methanolic ammonia is reported.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 10","pages":"2301-6"},"PeriodicalIF":0.0,"publicationDate":"1999-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044882","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21472553","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
I Kers, J Stawiński, J L Girardet, J L Imbach, C Périgaud, G Gosselin, A M Aubertin
{"title":"Synthesis and anti-retroviral activity of O,O'-bis(3'-azido-2',3'-dideoxythymidin-5'-yl) phosphoramidate derivatives.","authors":"I Kers, J Stawiński, J L Girardet, J L Imbach, C Périgaud, G Gosselin, A M Aubertin","doi":"10.1080/07328319908044884","DOIUrl":"https://doi.org/10.1080/07328319908044884","url":null,"abstract":"<p><p>A simple and efficient protocol for the preparation of various symmetrical dinucleoside phosphoramidates derived from AZT, is presented. It consists of the phosphonylation of AZT with phosphonic acid in the presence of DCC to produce the symmetrical H-phosphonate diester, followed by its oxidative conversion to various phosphoramidate analogues. The synthesized compounds were evaluated for their anti-HIV activity in different cell cultures.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 10","pages":"2317-25"},"PeriodicalIF":0.0,"publicationDate":"1999-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044884","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21472555","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Isolation and characterization of 5-carbamoylmethyluridine and 5-carbamoylmethyl-2-thiouridine from human urine.","authors":"G B Chheda, H B Patrzyc, H A Tworek, S P Dutta","doi":"10.1080/07328319908044873","DOIUrl":"https://doi.org/10.1080/07328319908044873","url":null,"abstract":"<p><p>Two new modified uracil nucleosides, 5-carbamoylmethyuridine (ncm5U, I) and 5-carbamoylmethyl-2-thiouridine (ncm5s2U, II) were isolated from a 24 hr collection of a normal human urine. The structures were assigned on the basis of UV, NMR and mass spectral data and confirmed by comparison of the spectral data and HPLC mobilities with those of authentic samples. On the basis of experimental data it appears possible that 5-carbamoylmethyl-2-thio-uridine (ncm5s2U, II) may be a degradation product produced from a labile precursor by the chemical treatments during the isolation procedure. However, the other nucleoside (ncm5U,I) certainly appears to be of metabolic origin and was also found in the urines of one chronic myelogenous leukemia and one lung carcinoma patient. Abbreviations used are: tRNA-transfer ribonucleic acid, TMS-trimethylsilyl, RP-HPLC--reverse phase high performance liquid chromatography, EI--electron impact, cm5U-5-carboxymethyluridine, mcm5U-5-methoxycarbonylmethyluridine, cm5s2U-5-carboxymethyl-2-thiouridine, mcm5s2U-5-methoxycarbonylmethyl-2-thiouridine, t6A-9-beta-D-ribofuranosyl-[N(purin-6-yl)carbamoyl]-1-threonine, C-cytidine, acp3u-3-(3-amino-3-carboxypropyl)uridine, AICR-aminoimidazole carboxamide riboside, alpha-4-PCNR & beta-4-PCNR-9-alpha-D-(or beta-D)-ribofuranosyl-pyridin-4-one-3-carboxamide, H x 7R-7-beta-D-ribofuranosyl hypoxanthine, m3U-3-methyluridine, m1I-1-methylinosine, m1G-1-methylguanosine, DI-5'-deoxyinosine, dms5OA-5'-deoxy-5'-methylthioadenosine sulfoxide, m2(2)G-N2-dimethylguanosine, psi-psi-uridine, A-adenosine, I-inosine, CML-chronic myelogenous leukemia mam5s2U-5-methylaminomethyl-2-thiouridine, ncm5U-5-carbamoylmethyluridine, ncm5s2U-5-carbamoylmethyl-2-thiouridine, UV-ultraviolet, NMR-nuclear magnetic resonance, HPLC-high performance liquid chromatography, GC-MS-gas chromatography-mass spectrometry.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 10","pages":"2155-73"},"PeriodicalIF":0.0,"publicationDate":"1999-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044873","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21473334","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
V Gurvich, H Y Kim, R P Hodge, C M Harris, T M Harris
{"title":"Utilization of tetrabutylammonium triphenyldifluorosilicate (TBAT) in the synthesis of 6-fluoropurine nucleosides.","authors":"V Gurvich, H Y Kim, R P Hodge, C M Harris, T M Harris","doi":"10.1080/07328319908044885","DOIUrl":"https://doi.org/10.1080/07328319908044885","url":null,"abstract":"<p><p>Tetrabutylammonium triphenydifluorosilicate (TBAT) has been found to be a useful reagent for the conversion of 6-chloropurine nucleosides to 6-fluoropurine derivatives. The 6-chloropurine nucleosides were reacted with trimethylamine to form quaternary trimethylammonium salts which were treated in situ with TBAT in DMF to effect conversion to the 6-fluoro derivatives in yields of 59-72%.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 10","pages":"2327-33"},"PeriodicalIF":0.0,"publicationDate":"1999-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044885","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21472556","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
S C Cavalcanti, Y Xiang, M G Newton, R F Schinazi, Y C Cheng, C K Chu
{"title":"Synthesis of 2',3'-dideoxy-2'-fluoro-L-threo-pentofuranosyl nucleosides as potential antiviral agents.","authors":"S C Cavalcanti, Y Xiang, M G Newton, R F Schinazi, Y C Cheng, C K Chu","doi":"10.1080/07328319908044878","DOIUrl":"https://doi.org/10.1080/07328319908044878","url":null,"abstract":"<p><p>A series of 2',3'-dideoxy-2'-fluoro-L-threo-pentofuranosyl nucleosides has been synthesized as potential antiviral agents. The synthesized compounds were evaluated against HIV-1, HBV, HSV-1, and HSV-2. Among the synthesized analogues, only the cytosine derivative showed moderate antiviral activity against HIV and HBV.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 10","pages":"2233-52"},"PeriodicalIF":0.0,"publicationDate":"1999-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044878","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21472550","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
M Isabel Nieto, J Manuel Blanco, O Caamaño, F Fernández, X García-Mera, C López, J Balzarini, E De Clercq
{"title":"Synthesis and antiviral activity of carbocyclic nucleosides incorporating a modified cyclopentane ring. Part 3: Adenosine and uridine analogues.","authors":"M Isabel Nieto, J Manuel Blanco, O Caamaño, F Fernández, X García-Mera, C López, J Balzarini, E De Clercq","doi":"10.1080/07328319908044879","DOIUrl":"https://doi.org/10.1080/07328319908044879","url":null,"abstract":"<p><p>Six new carbocyclic nucleosides were prepared by mounting a purine (compounds 4-6), 8-azapurine (7 and 8) or uridine (9) base on the amino group of (1S,3R)-3-amino-2,2,3-trimethylcyclopentylmethanol (10). At subtoxic concentrations, compounds 5-9 showed at best marginal antiviral activity.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 10","pages":"2253-63"},"PeriodicalIF":0.0,"publicationDate":"1999-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044879","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21472551","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Sensitivity of bacteriophage RB69 DNA polymerase to N2-(p-n-butylphenyl)-2'-deoxyguanosine nucleotides.","authors":"J M Stattel, G E Wright","doi":"10.1080/07328319908044875","DOIUrl":"https://doi.org/10.1080/07328319908044875","url":null,"abstract":"<p><p>The response of bacteriophage RB69 DNA polymerase to N2-(p-n-butylphenyl)-2'-deoxyguanosine 5'-triphosphate (BuPdGTP), related nucleotides and non-nucleoside inhibitors was measured and compared to values obtained for the closely related DNA polymerase from bacteriophage T4. Both enzymes showed similar responses to inhibitors in terms of Ki values and the ability to utilize BuPdGTP as a substrate. These results provide the relevance of using the recent crystal structure of RB69 DNA polymerase for analysis of BuPdGTP/B family DNA polymerase interactions.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 10","pages":"2193-9"},"PeriodicalIF":0.0,"publicationDate":"1999-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044875","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21472547","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}