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Nucleosides & nucleotides最新文献

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Synthesis and antiviral studies of unsaturated analogues of isomeric dideoxynucleosides. 二脱氧核苷异构体不饱和类似物的合成及抗病毒研究。
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044614
S Bera, T Mickle, V Nair
{"title":"Synthesis and antiviral studies of unsaturated analogues of isomeric dideoxynucleosides.","authors":"S Bera,&nbsp;T Mickle,&nbsp;V Nair","doi":"10.1080/07328319908044614","DOIUrl":"https://doi.org/10.1080/07328319908044614","url":null,"abstract":"<p><p>Novel isomeric dideoxynucleosides with unsaturation in the carbohydrate moiety have been synthesized. For example, isod4A was synthesized through a rearrangement reaction involving a cyclonucleoside. Support for the structures of both purine and pyrimidine d4 compounds came from UV, NMR, HRMS and single crystal X-ray data. Interestingly, the single crystal X-ray data for isod4C shows that the base is almost orthogonal to the carbon-carbon double bond of the sugar moiety. Consistent with this is the observation that the UV data of this compound does not show a bathochromic shift compared to the saturated compound implying that the pi-bond is not in conjugation with the pyrimidine base.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2379-95"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044614","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495310","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}
引用次数: 9
Oligonucleotide conjugated to linear and branched high molecular weight polyethylene glycol as substrates for RNase H. 作为RNase H底物与线性和支链高分子量聚乙二醇共轭的寡核苷酸。
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044638
P E Vorobjev, V F Zarytova, G M Bonora
{"title":"Oligonucleotide conjugated to linear and branched high molecular weight polyethylene glycol as substrates for RNase H.","authors":"P E Vorobjev,&nbsp;V F Zarytova,&nbsp;G M Bonora","doi":"10.1080/07328319908044638","DOIUrl":"https://doi.org/10.1080/07328319908044638","url":null,"abstract":"<p><p>Two conjugates of an anti-HIV oligonucleotide (ODN) with different high molecular weight monomethoxy polyethylene glycols (MPEGs) have been tested for their activity as substrate towards RNase H. The MPEG does not impede the formation of the regular hybrid duplex with the target RNA sequence as pointed out by the persistence of the RNase H activity; thus, these derivatives stimulate the hydrolysis of RNA by the enzyme at the same site and with the same extent of cleavage as the native sequence.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2745-50"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044638","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495315","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}
引用次数: 7
Synthesis of di- and tri-substituted adenosine derivatives and their affinities at human adenosine receptor subtypes. 二取代和三取代腺苷衍生物的合成及其在人腺苷受体亚型上的亲和力。
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044623
R Volpini, E Camaioni, S Costanzi, S Vittori, K N Klotz, G Cristalli
{"title":"Synthesis of di- and tri-substituted adenosine derivatives and their affinities at human adenosine receptor subtypes.","authors":"R Volpini,&nbsp;E Camaioni,&nbsp;S Costanzi,&nbsp;S Vittori,&nbsp;K N Klotz,&nbsp;G Cristalli","doi":"10.1080/07328319908044623","DOIUrl":"https://doi.org/10.1080/07328319908044623","url":null,"abstract":"<p><p>The synthesis of 2-(hex-1-ynyl)adenosine derivatives substituted at the N6- and/or 5'-position was carried out on the basis that 2-(hex-1-ynyl)adenosine-5'-N-ethyluronamide (HENECA, 2) showed good affinity and different degree of selectivity for rat adenosine receptors. All new compounds were tested in radioligand binding and adenylyl cyclase assays with recently cloned human A1, A2A, A2B, and A3 adenosine receptors.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2511-20"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044623","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495971","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}
引用次数: 9
Synthesis, cytotoxic effect and antiviral activity of 1-(beta-D-arabinofuranosyl)-5-bromo-N4-substituted cytosine and 1-(beta-D-arabinofuranosyl)-5-bromo-4-methoxypyrimidin-2(1H)-one derivatives. 1-（β-D-阿拉伯呋喃糖基）-5-溴-N4-取代胞嘧啶和1-（βD-阿拉伯呋喃糖基-5-溴-4-甲氧基嘧啶-2（1H）-酮衍生物的合成、细胞毒性和抗病毒活性。
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044622
R Saladino, M Mezzetti, E Mincione, A T Palamara, P Savini, S Marini
{"title":"Synthesis, cytotoxic effect and antiviral activity of 1-(beta-D-arabinofuranosyl)-5-bromo-N4-substituted cytosine and 1-(beta-D-arabinofuranosyl)-5-bromo-4-methoxypyrimidin-2(1H)-one derivatives.","authors":"R Saladino,&nbsp;M Mezzetti,&nbsp;E Mincione,&nbsp;A T Palamara,&nbsp;P Savini,&nbsp;S Marini","doi":"10.1080/07328319908044622","DOIUrl":"https://doi.org/10.1080/07328319908044622","url":null,"abstract":"<p><p>A convenient and mild synthesis of 5-bromo-N4-substituted-1-(beta-D-arabinofuranosyl)cytosine and 5-bromo-O4-methyl-1-(beta-D-arabinofuranosyl)pyrimidin-2(1H)-one derivatives by selective oxyfunctionalization of the corresponding 4-thionucleosides with 3,3-dimethyldioxirane is reported. The cytotoxicity and the antiviral activity against parainfluenza 1 (Sendai virus) of all new synthesized products are also reported.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2499-510"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044622","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495311","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}
引用次数: 3
Synthesis and biological evaluation of 9-(beta-L-arabinofuranosyl)adenine. 9-(β - l -阿拉伯糖脲基)腺嘌呤的合成及生物学评价。
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044620
V Boudou, J L Imbach, G Gosselin
{"title":"Synthesis and biological evaluation of 9-(beta-L-arabinofuranosyl)adenine.","authors":"V Boudou,&nbsp;J L Imbach,&nbsp;G Gosselin","doi":"10.1080/07328319908044620","DOIUrl":"https://doi.org/10.1080/07328319908044620","url":null,"abstract":"<p><p>For the first time, the stereospecific synthesis of 9-(beta-L-arabinofuranosyl) adenine was carried out. Unfortunately, and unlike its \"natural\" D-counterpart Vidarabine, this L-enantiomer did not show significant activity when evaluated against a broad range of viruses.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2463-73"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044620","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495313","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}
引用次数: 1
Acyclic sugar analogs of triciribine: lack of antiviral and antiproliferative activity correlate with low intracellular phosphorylation. 曲西瑞滨的无环糖类似物:缺乏抗病毒和抗增殖活性与低细胞内磷酸化相关。
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044621
A R Porcari, K Z Borysko, R G Ptak, J M Breitenbach, L L Wotring, J C Drach, L B Townsend
{"title":"Acyclic sugar analogs of triciribine: lack of antiviral and antiproliferative activity correlate with low intracellular phosphorylation.","authors":"A R Porcari,&nbsp;K Z Borysko,&nbsp;R G Ptak,&nbsp;J M Breitenbach,&nbsp;L L Wotring,&nbsp;J C Drach,&nbsp;L B Townsend","doi":"10.1080/07328319908044621","DOIUrl":"https://doi.org/10.1080/07328319908044621","url":null,"abstract":"<p><p>Triciribine and triciribine monophosphate have antiviral and antiproliferative activity at low or submicromolar concentrations. In an effort to improve and better understand this activity, we have synthesized a series of acyclic analogs and evaluated them for activity against select viruses and cancer cell lines. We conclude that the rigid ribosyl ring system of triciribine must be intact in order to be phosphorylated and to obtain significant antiviral and antiproliferative activity.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2475-97"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044621","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495316","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}
引用次数: 7
Introduction of 6-formylcytidine into a Myb binding sequence. 将6-甲酰基胞苷引入Myb结合序列。
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044640
A Kittaka, T Kuze, M Amano, H Tanaka, T Miyasaka, K Hirose, T Yoshida, A Sarai, T Yasukawa, S Ishii
{"title":"Introduction of 6-formylcytidine into a Myb binding sequence.","authors":"A Kittaka,&nbsp;T Kuze,&nbsp;M Amano,&nbsp;H Tanaka,&nbsp;T Miyasaka,&nbsp;K Hirose,&nbsp;T Yoshida,&nbsp;A Sarai,&nbsp;T Yasukawa,&nbsp;S Ishii","doi":"10.1080/07328319908044640","DOIUrl":"https://doi.org/10.1080/07328319908044640","url":null,"abstract":"<p><p>Single 6-formylcytidine was introduced into a oligonucleotide duplex (23 mers) as a substitute for thymidine in the Myb binding sequence of 3'-TTGAC-5'. The modified duplex showed Tm of 67 degrees C, which was six degrees lower than the Tm of the native duplex. Binding affinity of the 23-mers to the Myb protein was estimated by electrophoretic mobility shift assays, and the binding was almost completely abolished.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2769-83"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044640","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495972","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}
引用次数: 3
Intramolecular glycosylation to form 4-methoxy-2,6-dioxopyrimidine nucleosides via O6,5'-cyclonucleosides. 分子内糖基化通过o6,5 '-环核苷形成4-甲氧基-2,6-二氧嘧啶核苷。
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044616
C Castro, C Chen, M E Jung
{"title":"Intramolecular glycosylation to form 4-methoxy-2,6-dioxopyrimidine nucleosides via O6,5'-cyclonucleosides.","authors":"C Castro,&nbsp;C Chen,&nbsp;M E Jung","doi":"10.1080/07328319908044616","DOIUrl":"https://doi.org/10.1080/07328319908044616","url":null,"abstract":"<p><p>Lewis-acid promoted intramolecular N1 glycosylation to form the novel O6,5'-cyclonucleoside 1a occurs in high yield from the corresponding acyclic thiophenyl-glycoside 12. The relative stability of the O6,5' tether compared with O2,5' and O2,3' tethers is reported. Cleavage of the anhydro bond was effected with aqueous base to yield the 4-methoxybarbituric acid nucleoside analogue 14.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2415-23"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044616","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495312","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}
引用次数: 2
L-nucleoside analogues as potential antimalarials that selectively target Plasmodium falciparum adenosine deaminase. 选择性靶向恶性疟原虫腺苷脱氨酶的l -核苷类似物作为潜在的抗疟药物。
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044624
D M Brown, A G Netting, B K Chun, Y Choi, C K Chu, A M Gero
{"title":"L-nucleoside analogues as potential antimalarials that selectively target Plasmodium falciparum adenosine deaminase.","authors":"D M Brown,&nbsp;A G Netting,&nbsp;B K Chun,&nbsp;Y Choi,&nbsp;C K Chu,&nbsp;A M Gero","doi":"10.1080/07328319908044624","DOIUrl":"https://doi.org/10.1080/07328319908044624","url":null,"abstract":"<p><p>The L-stereoisomer analogues of D-coformycin selectively inhibited P. falciparum adenosine deaminase (ADA) in the picomolar range (L-isocoformycin, Ki 7 pM; L-coformycin, Ki 250 pM). While the L-nucleoside analogues, L-adenosine, 2,6-diamino-9-(L-ribofuranosyl)purine and 4-amino-1-(L-ribofuranosyl)pyrazolo[3,4-d]-pyrimidine were selectively deaminated by P. falciparum ADA, L-thioinosine and L-thioguanosine were not. This is the first example of 'non-physiological' L-nucleosides that serve as either substrates or inhibitors of malarial ADA and are not utilised by mammalian ADA.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2521-32"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044624","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495973","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}
引用次数: 15
Inhibitory potency of 5-benzyluracil, 5-phenylcytosine and 5-phenylpyrimidin-2-one nucleosides against uridine phosphorylase from mouse leukemic L1210 cells. 5-苄基尿嘧啶、5-苯基胞嘧啶和5-苯基嘧啶-2- 1核苷对小鼠白血病L1210细胞尿苷磷酸化酶的抑制作用
Nucleosides & nucleotides Pub Date : 1999-11-01 DOI: 10.1080/07328319908044626
I Votruba, M Krecmerová, H Hrebabecký, A Holý
{"title":"Inhibitory potency of 5-benzyluracil, 5-phenylcytosine and 5-phenylpyrimidin-2-one nucleosides against uridine phosphorylase from mouse leukemic L1210 cells.","authors":"I Votruba,&nbsp;M Krecmerová,&nbsp;H Hrebabecký,&nbsp;A Holý","doi":"10.1080/07328319908044626","DOIUrl":"https://doi.org/10.1080/07328319908044626","url":null,"abstract":"<p><p>The inhibitory activity of a series of novel sugar-modified nucleosides derived from 5-benzyluracil, 5-phenylcytosine and 5-phenylpyrimidin-2-one against uridine phosphorylase purified from mouse leukemic L-1210 cells was investigated. Significant activity was encountered with O2,2'-anhydro-5-benzylcytidine hydrochloride, 2',3'-dideoxy-5-benzyluridine, 2',3'-dideoxy-4-thiouridine and alpha- and beta-anomers of 5-benzyl-1-(2-deoxy-D-arabino-hexopyranosyl)uracil.</p>","PeriodicalId":19222,"journal":{"name":"Nucleosides & nucleotides","volume":"18 11-12","pages":"2551-64"},"PeriodicalIF":0.0,"publicationDate":"1999-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1080/07328319908044626","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21495314","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}
引用次数: 2
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