共查询到20条相似文献,搜索用时 14 毫秒
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A very simple synthetic route for novel cyclopentene phosphonate nucleosides is described. The characteristic cyclopentene moiety 6 was constructed via a ring-closing metathesis of divinyl 5, which could be readily prepared from diethylmalonate. The condensation of the mesylate 11 with nucleobases (A, C, T, U) under nucleophilic substitution conditions (K2CO3, 18-Crown-6, DMF) afforded the target nucleosides 12, 13, 14, and 15. In addition, the antiviral evaluations against various viruses were performed. 相似文献
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Stereospecific synthesis of 1-alpha-d-(2-deuteroribofuranosyl)-2-nitroimidazole (2'-[(2)H]-alpha-AZR) is reported. This, deuteration was independent of the configuration of C-2' -OH group (arabinose or ribose) in sugar moiety of starting molecules. Slightly better yield (>37%) of the deuterated product, 6, from arabinosyl precursor in comparison to corresponding ribose precursor (29%) was obtained which may reflect better stereochemical availability of C-2' -OH in arabinose during oxidation. 相似文献
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Novel acyclic nucleoside analogues were designed and synthesized as open-chain analogues of neplanocin A. The coupling of the allylic bromide with pyrimidine bases using cesium carbonate afforded a series of novel acyclic nucleosides. The synthesized compounds 15-22 were evaluated for their antiviral activity against various viruses such as HIV, HSV-1, HSV-2, and HCMV. 相似文献
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M Yokoyama N Yamada T Ikuma N Obara H Togo T Imamoto 《Nucleic acids symposium series》1989,(21):131-132
A new spironucleoside structural type and two new bicyclic nucleoside structural types were synthesized from the reaction of ribose nitrile oxide with dimethyl acetylenedicarboxylate. Next, a synthetic method for novel meso-ionic nucleoside structual type is presented. 相似文献
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Fardis M Pyun HJ Tario J Jin H Kim CU Ruckman J Lin Y Green L Hicke B 《Bioorganic & medicinal chemistry》2003,11(23):5051-5058
A series of fumagillin analogues targeted at understanding tolerability of MetAP2 toward substitution at C4 and C6 were synthesized. Initially, the C6 side chain was maintained as cinnamoyl ester and C4 was modified. It was concluded that replacing the natural C4 of fumagillin with a benzyl oxime at C4 resulted in moderate loss of activity toward binding to MetAP2. Placement of a primary or secondary carbamate at C6 did not improve the potency of compounds toward inhibition of MetAP2. However, the inhibitory activity against MetAP2 was gained back by placing polar groups such as piperazinyl carbamate at C6. Small alkyl substituents on the amine of piperazinyl carbamate were well tolerated. 相似文献
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A modified nitrogen and sulfur glycosylation reaction involving benzothiazole benzoxazole and pyridine nucleoside bases with furanose and pyranose sugars are described. Conformational analysis has been studied by homo- and heteronuclear two-dimensional NMR methods (2D DFQ-COSY, HMQC and HMBC). The N and S sites of glycosylation were determined from the 1H, 13C heteronuclear multiple-quantum coherence (HMQC) experiments. All the deprotected nucleosides were tested for their potential antitumor activity. 相似文献
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U M Krishna M M Reddy J Xia J R Falck M Balazy 《Bioorganic & medicinal chemistry letters》2001,11(18):2415-2418
An effective synthesis is described for the preparation of all four mono trans isomers of arachidonic acid via deoxidation of epoxide precursors with lithium diphenylphosphide and quaternization with methyl iodide. 相似文献
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Park AY Moon HR Kim KR Chun MW Jeong LS 《Nucleosides, nucleotides & nucleic acids》2007,26(8-9):1001-1004
Pseudo-D-vinylcyclopropyl nucleosides 10-12 bearing a quaternary carbon were designed and synthesized starting from (R)-epichlorohydrin using a tandem reaction of double alkylation and lactonization via oxirane-ring opening reaction, a Wittig reaction, and chemoselective reduction as potential anti-herpesvirus agent. 相似文献
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Richard Caldwell Lesley Liu-Bujalski Hui Qiu Igor Mochalkin Reinaldo Jones Constantin Neagu Andreas Goutopoulos Roland Grenningloh Theresa Johnson Brian Sherer Anna Gardberg Ariele Viacava Follis Federica Morandi Jared Head 《Bioorganic & medicinal chemistry letters》2018,28(21):3419-3424
Btk is an attractive target for the treatment of a range of Bcell malignancies as well as several autoimmune diseases such as murine lupus and rheumatoid arthritis. Several covalent irreversible inhibitors of Btk are currently in development including ibrutinib which was approved for treatment of B-cell malignancies. Herein, we describe our efforts using X-ray guided structure based design (SBD) to identify a novel chemical series of covalent Btk inhibitors. The resulting pyridine carboxamides were potent and selective inhibitors of Btk having excellent enzymatic and cellular inhibitory activity. 相似文献
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Vyakaranam K Rana G Spielvogel BF Maguire JA Hosmane NS 《Nucleosides, nucleotides & nucleic acids》2002,21(8-9):581-598
A number of substituted (borano) nucleic acids, 3'-[diethylphosphite(cyano, carboxy, or carbamoyl) borano] deoxynucleosides (3a-4c) and 5'-[diethylphosphite(cyano or carboxy) borano] deoxynucleosides (6a-7d) were prepared by a variety of synthetic procedures. The syntheses of the pyrophosphates (2a-2c), as precursors for 3a-4c, are also described. 相似文献
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Novel vinyl branched apiosyl nucleosides were synthesized in this study. Apiosyl sugar moiety was constructed by sequential ozonolysis and reductions. The bases (uracil and thymine) were efficiently coupled by glycosyl condensation procedure (persilyated base and TMSOTf). The antiviral activities of the synthesized compounds were evaluated against the HIV-1, HSV-1, HSV-2, and HCMV. Compound 10beta displayed moderate anti-HIV activity (EC50 = 17.3 microg/mL) without exhibiting any cytotoxicity up to 100 microM. 相似文献
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Gu P Morral J Wang J Rozenski J Busson R Van Aerschot A De Clercq E Herdewijn P 《Nucleosides, nucleotides & nucleic acids》2003,22(5-8):845-847
A series of cyclohexenyl nucleosides (1-8) were successfully prepared with moderate yield and their cytotoxicity and antiviral activity were investigated. Among the eight new compounds, only the diaminopurine analogue 8 showed pronounced activity against HSV-1, HSV-2. 相似文献
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E Takashiro Y Nakamura S Miyamoto Y Ozawa A Sugiyama K Fujimoto 《Bioorganic & medicinal chemistry》1999,7(9):2105-2114
The synthesis and the SAR study of novel pseudo symmetric inhibitors of HIV-1 protease are described. Michael addition of amino acid derivatives to vinyl ketones was utilized to derive a potent (nM) series of HIV-1 protease inhibitors. 相似文献
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K Shinozuka N Matsumoto A Nakamura H Hayashi H Sawai 《Nucleic acids symposium series》2000,(44):21-22
A facile stereospecific synthetic method for alpha-anomeric 2'-deoxypyrimidine nucleoside unit utilizing aminooxazoline derivative of ribofuranose was investigated. Thus, easily accessible riboaminooxazoline derivative prepared by ribose and cyanamid was allowed to react with ethyl alpha-bromoethylacrylate to give corresponding adduct. The adduct was cyclized by strong base such as potassium t-butokiside. The resulted 2,2'-cyclonucleoside was then treated with acetyl bromide followed by n-butyltin hydride to give alpha-anomeric 3',5'-di-O-acetylthymidine. 3',5'-Di-O-acety groups of the nucleoside were easily removed by the action of excess of triethyl amine in methanol. Essentially same procedure afforded corresponding 2'-deoxyuridine, which was further, converted to alpha-anomeric 2'-deoxycytidine. 相似文献