共查询到20条相似文献,搜索用时 15 毫秒
1.
Lak Shin Jeong Seung Ah Choe Ae Yil Kim Hea Ok Kim Zhan-Guo Gao Kenneth A. Jacobson 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):717-719
Several N 6 -substituted 3 ′-ureidoadenosine derivatives were efficiently synthesized starting from D-glucose for the development of H272E mutant A 3 adenosine receptor (AR) agonists. Among compounds tested, 3 ′-ureido-N 6 -(3-iodobenzyl)adenosine ( 2c ) exhibited the highest binding affinity (K i = 0.22 μ M) at the H272E mutant A 3 AR without binding to the natural A 3 AR. 相似文献
2.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):923-925
Abstract Synthesis of 3′-deoxy-3′-fluoro-N 6-substituted adenosines as bioisosteres of Cl-IB-MECA and their binding affinities to A3 adenosine receptor are described. 相似文献
3.
S. Van Calenbergh A. Link D. De Keukeleire P. Herdewijn 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):735-736
Abstract Strategies toward the further lead optimization of N 6-cyclopentyl-3′-amido-3′-deoxyxylofuranosyladenosines as adenosine A1 receptor antagonists including the synthesis of the 5′-deoxy-analogues and a practical method for parallel amidation are presented. 相似文献
4.
Abstract 1,2-Di-O-acetyl-3-deoxy-3-trifluoromethyl-5-O-benzoyl-β-D-riboruranose was synthesized from the precursor keto sugar by the use of Ruppert's reagent (CF3SiMe3) as the source of a nucleophilic trifluoromethyl group. Coupling of this trifluoromethyl sugar with nucleobases and elaboration gave novel deoxy and dideoxynucleosides. A single crystal X-ray analysis confirmed the structure and stereochemistry. The deoxynucleosides were converted through an elimination reaction to their dideoxydidehydro derivatives. 相似文献
5.
Lech Celewicz Wojciech Urjasz Krzysztof Golankiewicz 《Nucleosides, nucleotides & nucleic acids》2013,32(9):951-966
Abstract A series of 3′-N-substituted 3′-amino-3′-deoxythymidine derivatives with alkyl, alkenyl and alkylaryl substituents was synthesized by two methods. The first method involved the reaction of 1-(2,3-dideoxy-3-0-mesyl-5-0-trityl-β-D-threo-pentofuranosyl)thymine with an appropriate amine. In the second method, 3′-amino-5′-0-trityl-3′-deoxy-thymidine served as a synthetic precursor which was reacted with an appropiate aldehyde or ketone followed by sodium borohydride reduction. An improved synthesis of 3′-amino-3′-deoxythymidine from 3′ -azido-5′-0-trityl-3′-deoxythymidine using sodium borohydride was also described. 相似文献
6.
Annett Kreimeyer François André Aline Bluzat Catherine Gouyette Tam Huynh-dinh 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):995-999
Abstract The preparation of acyl adenosine 5′-triphosphates as potential membrane permeable prodrugs is presented. The interaction of myristoyl- and cholesteryloxy-carbonyl-ATP with liposomes as model membranes and the release of ATP inside these vesicles was investigated using an enzymatic assay as well as 31P-NMR spectroscopy. 相似文献
7.
Véronique Faivre-Buet Annie Grouiller Gérard Descotes 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1411-1424
Abstract Various routes to the targets 1, 2, 3, 1-deoxy-psicofuranosyl nucleoside analogues related to anti-HIV agents, are reported. Two routes afforded their 6′-benzylated derivatives 9, 10 and 15. Only the epoxide 12 and deoxynucleosides 19 and 22 were able to be deprotected leading in the first case to 16 and its ring opening derivative 17 and in the second case to 20 and to the target 3. 相似文献
8.
Socrates C. H. Cavalcanti Yuejun Xiang M. Gary Newton Raymond F. Schinazi Yung-Chi Cheng Chung K. Chu 《Nucleosides, nucleotides & nucleic acids》2013,32(10):2233-2252
Abstract 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. 相似文献
9.
Ingemar Kvarnström Lars Svansson Carina Svensson Stefan C. T. Svensson Björn Classon 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1367-1370
Abstract Synthesis of 2′,3′-Dideoxy-3′-C-(hydroxymethyl)-α- and β-L-erythro-pentofuranosyl nucleosides of thymine, cytosine and adenine is reported. 相似文献
10.
Biserka Kasnar Dean S. Wise Louis S. Kucera John C. Drach Leroy B. Townsend 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):459-479
Abstract The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-B-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6,19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-B-D-erythro-pentofuranosyl)pyrridazin-6-one (13) in 67% and its α-anomer 14 in 12% yield, respectively. A series of 3′-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1-(3-azido-2,3-dideoxy-B-D-erythro-pentofuranosyl) pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive. 相似文献
11.
L. D. Hawkins J. C. Hanvey F. L. Boyd Jr. David C. Baker H. D. Hollis Showalter 《Nucleosides, nucleotides & nucleic acids》2013,32(5):479-494
Abstract Glycosylation of the heterocycle, 6,7-dihydro-imidazo [4,5-d] [1,3] diazepin-8(3H)-one, with suitably protected sugars under the influence of Lewis acid catalysts gave the β-D-ribo- and 3′-deoxy-β-D-erythropento-furanosyl nucleosides. Deprotection and reduction of the keto nucleosides with sodium borohydride gave the (8R)- and (8S)-3-β-D-glycofuranosyl-3,6,7,8-tetrahydroimidazo [4,5-d]-[1,3] diazepin-8-ols, the (8R)-isomers of which are potent inhibitors of adenosine deaminase. 相似文献
12.
Keykavous Parang Edward E. Knaus Leonard I. Wiebe 《Nucleosides, nucleotides & nucleic acids》2013,32(6):987-1008
Abstract A group of 5′-O-myristoyl analogue derivatives of FLT (2) were evaluated as potential anti-HIV agents that were designed to serve as prodrugs to FLT. 3′-Fluoro-2′,3′-dideoxy-5′-O-(12-methoxydodecanoyl)thymidine (4) (EC50 = 3.8 nM) and 3′-fluoro-2′,3′-dideoxy-5′-O-(12-azidododecanoyl)thymidine (8) (EC50 = 2.8 nM) were the most effective anti-HIV-1 agents. There was a linear correlation between Log P and HPLC Log retention time for the 5 ′-O-FLT esters. The in vitro enzymatic hydrolysis half-life (t½), among the group of esters (3–8) in porcine liver esterase, rat plasma and rat brain homogenate was longer for 3′-fluoro-2′,3′-dideoxy-5 ′-O-(myristoyl)thymidine (7), with t½ values of 20.3, 4.6 and 17.5 min, respectively. 相似文献
13.
Antonella Leggio Angelo Liguori Antonio Procopio Carlo Siciliano Giovanni Sindona 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1515-1518
Abstract The 1,3 dipolar cycloaddition approach represents the most valuable strategy for the preparation of isoxazolidine nucleosides. The latter posses more conformational degrees of freedom than the corresponding dideoxyribosides. Side reactions due to the presence of formaldehyde in the reaction media can be avoided by proper derivatization of the vinyl-nucleobase. 相似文献
14.
Åsa Lundquist Ingemar Kvarnström Stefan C. T. Svensson Björn Classon Bertil Samuelsson 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1493-1502
Abstract The synthesis of 3′,4′-bishydroxymethyl-2′,3′,4′-trideoxy pentopyranosyl derivatives of thymine, uracil, cytosine, and adenine is described. trans-(3S,4S)-Bis(methoxycarbonyl)cyclopentanone (3) was converted to 1-O-acetyl-3,4-C-bis[(tert-butyldiphenylsiloxy)methyl]-2,3,4-trideoxy-α,β-L-threo-pentopyranose (6), which was subsequently condensed with the silylated purine and pyrimidine bases. 相似文献
15.
Abstract The synthesis of several new 5′-deoxy-5′-nucleosideacetic acid derivatives by the reactions of alkoxycarbonylmethylene triphenylphosphoranes with nucleoside 5′-aldehydes is described. 相似文献
16.
Sammy R. Shaver William Pendergast Suhaib M. Siddiqi Benjamin R. Yerxa Dallas K. Croom Robert W. Dougherty 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1099-1102
Abstract Uridine 5′-O-triphosphate (UTP) is a potent agonist of the purinergic receptor designated P2Y2. UTP is rapidly metabolized in human tissue. To find a compound with similar activity that may be more slowly metabolized, a series of 4-substituted uridine 5′-triphosphates were prepared and evaluated in a P2Y2 receptor second messenger assay. 相似文献
17.
G. Cristalli S. Vittori A. Eleuteri R. Volpini E. Camaioni G. Lupidi 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):835-848
Abstract 5, 7-Dichloro-3H-imidazo[4, 5-b]pyridine (4) is a versatile base which can be coupled with a variety of sugar moieties and transformed in a series of 7-alkyl(aryl)amino-derivatives by reacting with the corresponding amines. In this paper synthesis, structure elucidation and ADA inhibitory activity of 2′-deoxyribonucleoside derivatives of N6-substituted 1-deazaapurines are described. 相似文献
18.
Pavel N. Solyev Maxim V. Jasko Inna L. Karpenko Yury A. Sharkin Alexander V. Shipitsyn Marina K. Kukhanova 《Nucleosides, nucleotides & nucleic acids》2013,32(2):64-79
New phosphonate homodimers of 3′-azido-3′-deoxythymidine (AZT) and a phosphonate heterodimer of β-L-2′,3′-dideoxy-3′-thiacytidine (3TC) and AZT were synthesized. The compounds demonstrated moderate anti-HIV activity. Stability of the compounds in human blood serum was studied. A correlation between anti-HIV activity and stability was defined. 相似文献
19.
Andre Rosowsky Ruth M. Ruprecht Vishnu C. Solan 《Nucleosides, nucleotides & nucleic acids》2013,32(4):491-497
Abstract 3′-O-Propargylthymidinc, which may be viewed as a stnictural analogue of the potent antiretroviral agent 3′-azido-3′-deoxythymidine (AZT), was synthesized from 5′-O-(4,4′-dimethoxytritylthymidine by reaction with propargyl bromide followed by gentle acidolysis. The 3′-O-propargyl derivative was tested for antiretroviral activity in SC-1 mouse fibroblasts infected with Rauscher murine leukemia virus (MuLV). No inhibition of MuLV proliferation was observed at concentrations of 3′-O-propargylthymidine from 0.001 to 100 μM. whereas the IC50 against the host cells was 30 μM. By comparison, AZT had an IC50 for MuLV growth of 0.01 μM and an IC50 for cell growth of >100 μM. Thus, replacement of the 3′-N-N≡N group in AZT by a 3′-OCH2C≡CH group increased cytotoxicity but decreased antiretroviral activity relative to AZT. 相似文献
20.
《Bioorganic & medicinal chemistry》2014,22(21):5747-5756
A series of bis(sulfonylethyl) and mono(sulfonylethyl) phenyl phosphotriesters of zidovudine (3′-azido-3′-deoxythymidine, AZT) were synthesized as potential anticancer prodrugs that liberate AZT monophosphate via nonenzymatic β-elimination mechanism. Stability studies demonstrated that all the synthesized prodrugs spontaneously liberate AZT monophosphate with half-lives in the range of 0.07–278.8 h under model physiological conditions in 0.1 M phosphate buffer at pH 7.4 and 37 °C. Analogous to aldophosphamide, the elimination rates were accelerated in the presence of reconstituted human plasma under the same conditions. Among the compounds, 3, 4, 8, and 10 were comparable or superior to AZT against five established human cancerous cell lines in vitro. Moreover, the selected compounds were equally sensitive to both the wild-type osteosarcoma 143B and the thymidine kinase-deficient 143B/TK− cell lines. The findings are consistent with that these compounds deliver AZT monophosphate intracellularly. 相似文献