Solid-phase synthesis of backbone-modified DNA analogs by the boranophosphotriester method using new protecting groups for nucleobases.


:Backbone-modified DNA analogs were synthesized in good yields by the boranophosphotriester method on a solid support. The oligodeoxyribonucleoside boranophosphates, protected with 2-(azidomethyl)benzoyl groups for nucleobases, were converted into DNA and its backbone-modified analogs via the corresponding H-phosphonate intermediates. A new protecting group for the O6 position of 2'-deoxyguanosine, 4-azidobenzyl (ABn) group, was also developed. The ABn group can be quickly removed by treatment with MePPh2 and H2O in the presence of 2-mercaptoethanol.


Bioorg Med Chem Lett


Kawanaka T,Shimizu M,Shintani N,Wada T




Has Abstract


2008-07-01 00:00:00














  • New triple-helix DNA stabilizing agents.

    abstract::Several substituted quinolin-4-amines and heteroaromatic analogs were synthesized and evaluated for interaction with triplex polydA.2polydT and duplex polydA.polydT by using UV-thermal melting experiments. Excellent triple-helix DNA ligands with high affinity toward T.A.T triplets and triple/duplex selectivity were de...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Strekowski L,Hojjat M,Wolinska E,Parker AN,Paliakov E,Gorecki T,Tanious FA,Wilson WD

    更新日期:2005-02-15 00:00:00

  • Synthesis of novel lignan-like compounds and their antimicrobial activity.

    abstract::Herein we report the preparation of 3,4-dibenzylfurans and some oxidized derivatives with lignan backbone. The compounds were prepared using the Friedel-Crafts reaction with BF3 etherate as catalyst, demethylation with iodocyclohexane, acetylation and oxidation reactions. The antimicrobial activity was evaluated throu...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Tufano I,Buommino E,Iesce MR,De Filippis A,Grieco P,Lembo F,DellaGreca M

    更新日期:2020-09-01 00:00:00

  • Antihypertensive activity of substituted 2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridinedicarboxylate enantiomers.

    abstract::The synthesis and antihypertensive activity of racemates and enantiomers of substituted 2,3,8,8a-tetrahydro-7H-oxazolo[3,2-a]pyridinedicarboxylates have been reported. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Martín E,Morán A,Martín ML,San Román L,Puebla P,Medarde M,Caballero E,San Feliciano A

    更新日期:2000-02-21 00:00:00

  • Synthesis of betulinic acid derivatives with activity against human melanoma.

    abstract::Betulinic acid has been modified at C-3, C-20, and C-28 positions and the toxicity of the derivatives has been evaluated against cultured human melanoma (MEL-2) and human epidermoid carcinoma of the mouth (KB) cell lines. This preliminary investigation demonstrates that simple modifications of the parent structure of ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kim DS,Pezzuto JM,Pisha E

    更新日期:1998-07-07 00:00:00

  • Discovery of N-(piperidin-3-yl)-N-(pyridin-2-yl)piperidine/piperazine-1-carboxamides as small molecule inhibitors of PCSK9.

    abstract::A series of N-(piperidin-3-yl)-N-(pyridin-2-yl)piperidine/piperazine-1-carboxamides were identified as small molecule PCSK9 mRNA translation inhibitors. Analogues from this new chemical series, such as 4d and 4g, exhibited improved PCSK9 potency, ADME properties, and in vitro safety profiles when compared to earlier l...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Londregan AT,Aspnes G,Limberakis C,Loria PM,McClure KF,Petersen DN,Raymer B,Ruggeri RB,Wei L,Xiao J,Piotrowski DW

    更新日期:2018-12-15 00:00:00

  • Unique spirocyclopiperazinium salt. Part 4: modification of dispirocyclopiperazinium (DSPZ) salts as analgesics.

    abstract::In order to improve the analgesic activity of lead compound 7a, two series of dispirocyclopiperazinium (DSPZ) salts 9a-h, 10a-e and compounds 14, 15 were synthesized and evaluated for their in vivo analgesic activity both by acetic acid induced writhing test and hot plate test. Compounds 9h, 14, and 15 exhibited bette...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Li A,Wang X,Yue CQ,Ye J,Li CL,Li RT

    更新日期:2007-09-15 00:00:00

  • Thieno[2,3-b]pyridines as negative allosteric modulators of metabotropic GluR5 receptors: hit-to-lead optimization.

    abstract::An HTS campaign of our corporate compound library resulted in thieno[2,3-b]pyridines derivative hits with mGluR5 negative allosteric modulator effects. During the hit-to-lead development our objective was to improve affinity, and to keep the ligand efficiency values at an acceptable level. After different modification...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Nógrádi K,Wágner G,Domány G,Bobok A,Magdó I,Kiss B,Kolok S,Fónagy K,Gyertyán I,Háda V,Kóti J,Gál K,Farkas S,Keserű GM,Greiner I,Szombathelyi Z

    更新日期:2014-08-15 00:00:00

  • New merosesquiterpenes from a Vietnamese marine sponge of Spongia sp. and their biological activities.

    abstract::The investigation of the Vietnamese marine sponge Spongia sp. led to the isolation of three new sesquiterpene phenols, langconols A-C (1-3), and one new sesquiterpene hydroxyquinone, langcoquinone C (4), together with two known meroterpenoids (5 and 6). Their structures were determined on the basis of spectroscopic an...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Nguyen HM,Ito T,Kurimoto SI,Ogawa M,Win NN,Hung VQ,Nguyen HT,Kubota T,Kobayashi J,Morita H

    更新日期:2017-07-15 00:00:00

  • Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione.

    abstract::The reactivity of 4-[13C]- and 5-[13C]-5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) towards a model peptide and glutathione was followed by 13C and 1H[13C] NMR spectroscopy. Both molecules were found to react with GSH but in addition MCI was found to react with histidine and lysine to form...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Alvarez-Sánchez R,Basketter D,Pease C,Lepoittevin JP

    更新日期:2004-01-19 00:00:00

  • Synthesis of N-arylindazole-3-carboxamide and N-benzoylindazole derivatives and their evaluation against α-MSH-stimulated melanogenesis.

    abstract::We have designed and synthesized twenty-six N-arylindazole-3-carboxamide (3a-p) and N-benzoylindazole (6a-j) derivatives to discover with excellent inhibition activities of α-MSH-stimulated melanogenesis. In the bio evaluation studies of these compounds, we discovered eighteen compounds, out of twenty-six exhibited mo...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Arepalli SK,Lee C,Jung JK,Kim Y,Lee K,Lee H

    更新日期:2019-09-15 00:00:00

  • Heterocyclic substituted anthralin derivatives as inhibitors of keratinocyte growth and inducers of differentiation.

    abstract::Heterocyclic substituted derivatives of the antipsoriatic anthralin were synthesized and evaluated in vitro for their antiproliferative action against keratinocytes and their ability to induce keratinocyte differentiation. The indole-2-carboxylic acid analogue 2e exhibited the same excellent antiproliferative activity...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Müller K,Reindl H,Breu K

    更新日期:2001-01-08 00:00:00

  • The synthesis of xanthones, xanthenediones, and spirobenzofurans: their antibacterial and antifungal activity.

    abstract::Exposure of the phenol, (5-bromo-2-hydroxyphenyl)(2,4,5-trimethoxyphenyl)methanone 18 to ceric ammonium nitrate (CAN) resulted in the formation of 7-bromo-3,4a-dimethoxy-2H-xanthene-2,9(4aH)-dione 19 and 5-bromo-2',5'-dimethoxy-3H-spiro[benzofuran-2,1'-cyclohexa[2,5]diene]-3,4'-dione 20. The brominated spirobenzofuran...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Omolo JJ,Johnson MM,van Vuuren SF,de Koning CB

    更新日期:2011-12-01 00:00:00

  • Synthesis and thrombolytic activity of fibrinogen fragment related cyclopeptides.

    abstract::In the modification of the fibrinogen fragment related sequences ARPAK, QRPAK GRPAK and KRPAK, the corresponding cyclo-ARPAK, cyclo-QRPAK, cyclo-GRPAK, and cyclo-KRPAK were prepared in the diluted solution. The bioassay in vivo indicated that the thrombolytic potencies of cyclo-ARPAK, cyclo-GRPAK, cyclo-QRPAK, and cyc...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zhao M,Lin N,Wang C,Peng S

    更新日期:2003-03-10 00:00:00

  • Synthesis and immobilization of ceramide analogs on silica particles.

    abstract::Ceramides are the major lipid components of the stratum corneum, the major permeability barrier of the skin. Here we report a chemical synthesis of ceramide analogs covalently bonded on the silica particles, that can be used to predict the skin permeability of chemicals via HPLC methods. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Yin J,Liu H,Pidgeon C

    更新日期:1998-01-20 00:00:00

  • Probing cytochrome P450 bioactivation and fluorescent properties with morpholinyl-tethered anthraquinones.

    abstract::Structural features from the anticancer prodrug nemorubicin (MMDX) and the DNA-binding molecule DRAQ5™ were used to prepare anthraquinone-based compounds, which were assessed for their potential to interrogate cytochrome P450 (CYP) functional activity and localisation. 1,4-disubstituted anthraquinone 8 was shown to be...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Errington RJ,Sadiq M,Cosentino L,Wiltshire M,Sadiq O,Sini M,Lizano E,Pujol MD,Morais GR,Pors K

    更新日期:2018-05-01 00:00:00

  • Development of indole/indazole-aminopyrimidines as inhibitors of c-Jun N-terminal kinase (JNK): optimization for JNK potency and physicochemical properties.

    abstract::A novel series of indole/indazole-aminopyrimidines was designed and synthesized with an aim to achieve optimal potency and selectivity for the c-Jun kinase family or JNKs. Structure guided design was used to optimize the series resulting in a significant potency improvement. The best compound (17) has IC50 of 3 nM for...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 信件


    authors: Gong L,Han X,Silva T,Tan YC,Goyal B,Tivitmahaisoon P,Trejo A,Palmer W,Hogg H,Jahagir A,Alam M,Wagner P,Stein K,Filonova L,Loe B,Makra F,Rotstein D,Rapatova L,Dunn J,Zuo F,Dal Porto J,Wong B,Jin S,Chang A,T

    更新日期:2013-06-15 00:00:00

  • Studies on a series of potent, orally bioavailable, 5-HT(1) receptor ligands--part II.

    abstract::A series of 5-(piperidinylethyloxy)quinoline 5-HT(1) receptor ligands have been studied by elaboration of the series of dual 5-HT(1)-SSRIs reported previously. These new compounds display a different in vitro pharmacological profile with potent affinity across the 5-HT(1A), 5-HT(1B) and 5-HT(1D) receptors and selectiv...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Ward SE,Eddershaw P,Flynn ST,Gordon L,Lovell PJ,Moore SH,Scott CM,Smith PW,Thewlis KM,Wyman PA

    更新日期:2009-01-15 00:00:00

  • Synthesis and biological activity of retinoic acid receptor-alpha specific amides.

    abstract::Retinoids are analogues of all-trans-retinoic acid, a powerful hormone that mediates many fundamental biological processes. Cancer and other serious hyperproliferative diseases are attractive therapeutic targets for retinoids, but the therapeutic use of retinoids is limited due to severe toxicity. We report here the d...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Beard RL,Duong TT,Teng M,Klein ES,Standevan AM,Chandraratna RA

    更新日期:2002-11-04 00:00:00

  • Synthesis and preliminary evaluation of a new fluorine-18 labelled triazine derivative for PET imaging of cannabinoid CB2 receptor.

    abstract::Cannabinoid CB2 PET tracers are considered as a promising alternative to PBR/TSPO tracers for the in-vivo imaging of neuroinflammation. We describe here the synthesis and characterization of compound 3, a new potent and brain penetrating CB2 ligand based on an original triazine template. The PET tracer [(18)F]-dideute...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Hortala L,Arnaud J,Roux P,Oustric D,Boulu L,Oury-Donat F,Avenet P,Rooney T,Alagille D,Barret O,Tamagnan G,Barth F

    更新日期:2014-01-01 00:00:00

  • Bis(aminopyrrolidine)-derived ureas (APUs) as potent MCH1 receptor antagonists.

    abstract::Ureas derived from two substituted 3-aminopyrrolidine subunits were prepared as constrained analogs of a linear lead compound and tested as antagonists of the MCH(1) receptor. The series was optimized for substitution and stereochemistry to generate a functional antagonist with a K(i) of 3.3 nM and IC(50) of 12 nM (GT...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Grey J,Dyck B,Rowbottom MW,Tamiya J,Vickers TD,Zhang M,Zhao L,Heise CE,Schwarz D,Saunders J,Goodfellow VS

    更新日期:2005-02-15 00:00:00

  • Reaction of naphthoquinones with substituted nitromethanes. Facile synthesis and antifungal activity of naphtho[2,3-d]isoxazole-4,9-diones.

    abstract::We report here a simple entry into naphtho[2,3-d]isoxazole-4,9-dione system containing a EWG in position 3 using the readily available 2,3-dichloro-1,4-naphthoquinone and nitromethyl derivatives in the presence of base. Antifungal activity of synthesised naphthoquinones was evaluated against ATCC and PYCC reference st...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Santos MM,Faria N,Iley J,Coles SJ,Hursthouse MB,Martins ML,Moreira R

    更新日期:2010-01-01 00:00:00

  • Inhibition of human cytomegalovirus protease N(o) with monocyclic beta-lactams.

    abstract::Monocyclic beta-lactams have been identified as potent and selective inhibitors of the human cytomegalovirus protease (HCMV) N(o). Two series of these inhibitors are described, a peptidyl series of compounds and non-peptidic molecules featuring lower molecular weights. The SAR work that lead to the discovery of these ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Déziel R,Malenfant E

    更新日期:1998-06-02 00:00:00

  • Discovery of functionalized bisimidazoles bearing cyclic aliphatic-phenyl motifs as HCV NS5A inhibitors.

    abstract::This Letter describes the discovery of a number of functionalized bisimidazoles bearing a cyclohexylphenyl, piperidylphenyl, or bicyclo[2,2,2]octylphenyl motif as HCV NS5A inhibitors. Compounds 2c, 4b and 6 have demonstrated low single-digit nM potency in gt-1a replicon and double-digit pM potency in gt-1b replicon, r...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zhong M,Peng E,Huang N,Huang Q,Huq A,Lau M,Colonno R,Li L

    更新日期:2014-12-15 00:00:00

  • SAR profiles of spirocyclic nicotinamide derived selective HDAC1/HDAC2 inhibitors (SHI-1:2).

    abstract::A potent family of spirocyclic nicotinyl aminobenzamide selective HDAC1/HDAC2 inhibitors (SHI-1:2) is profiled. The incorporation of a biaryl zinc-binding motif into a nicotinyl scaffold resulted in enhanced potency and selectivity versus HDAC3, but also imparted hERG activity. It was discovered that increasing polar ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Methot JL,Hamblett CL,Mampreian DM,Jung J,Harsch A,Szewczak AA,Dahlberg WK,Middleton RE,Hughes B,Fleming JC,Wang H,Kral AM,Ozerova N,Cruz JC,Haines B,Chenard M,Kenific CM,Secrist JP,Miller TA

    更新日期:2008-12-01 00:00:00

  • Discovery, synthesis, and structure-activity studies of tetrazole based growth hormone secretagogues.

    abstract::A novel class of Growth Hormone Secretagogues (GHS), based on a tetrazole template, has been discovered. In vitro SAR and in vivo potency within this new class of GHS are described. The tetrazole 9q exhibits good oral bioavailability in rats and dogs as well as efficacy following an oral 10 mg/kg dose in dogs. Solutio...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Hernández AS,Cheng PT,Musial CM,Swartz SG,George RJ,Grover G,Slusarchyk D,Seethala RK,Smith M,Dickinson K,Giupponi L,Longhi DA,Flynn N,Murphy BJ,Gordon DA,Biller SA,Robl JA,Tino JA

    更新日期:2007-11-01 00:00:00

  • Novel synthetic ligands for targeted PET imaging and radiotherapy of copper.

    abstract::Novel ligands, NBEA, NBPA, NETA, NE3TA, and NE3TA-Bn, were synthesized and evaluated as potential chelators of copper radioisotopes for use in targeted positron emission tomography (PET) imaging or radiation therapy. The new ligands were radiolabeled with (64)Cu, and in vitro stability of the radiolabeled complexes wa...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Chong HS,Mhaske S,Lin M,Bhuniya S,Song HA,Brechbiel MW,Sun X

    更新日期:2007-11-15 00:00:00

  • N-arylaminonitriles as bioavailable peptidomimetic inhibitors of cathepsin B.

    abstract::To improve the pharmacokinetics of a previously reported series of dipeptidyl nitrile cathepsin B inhibitors, the P(2)-P(3) amide group was replaced with an arylamine. Further optimization of this template resulted in highly potent and selective inhibitors with excellent oral availability. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Greenspan PD,Clark KL,Cowen SD,McQuire LW,Tommasi RA,Farley DL,Quadros E,Coppa DE,Du Z,Fang Z,Zhou H,Doughty J,Toscano KT,Wigg AM,Zhou S

    更新日期:2003-11-17 00:00:00

  • Zinc(II)-mediated inhibition of a ribonuclease by an N-hydroxyurea nucleotide.

    abstract::The inhibition of ribonuclease Bi by 3'-N-hydroxyurea-3'-deoxythymidine 5'-phosphate is enhanced by 30-fold in the presence of Zn(2+). Thus, an N-hydroxyurea nucleotide can recruit Zn(2+) to inhibit the enzymatic activity of a ribonuclease. This result engenders a general strategy for the inhibition of non-metalloenzy...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Higgin JJ,Yakovlev GI,Mitkevich VA,Makarov AA,Raines RT

    更新日期:2003-02-10 00:00:00

  • New nemadectin congeners with acaricidal and nematocidal activity from Streptomyces microflavus neau3 Y-3.

    abstract::Two nemadectin congeners 1 and 2 were isolated from the fermentation broth of a mutant strain (Y-3) of Streptomyces microflavus neau3. Their structures were determined on the basis of extensive spectroscopic analysis and comparison with data from the literature. Compound 2 possessed a 5-membered ring lactone that is u...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Yang LY,Wang JD,Zhang J,Xue CY,Zhang H,Wang XJ,Xiang WS

    更新日期:2013-10-15 00:00:00

  • N',2-diphenylquinoline-4-carbohydrazide based NK3 receptor antagonists.

    abstract::A new class of potent NK3R antagonists based on the N',2-diphenylquinoline-4-carbohydrazide core is described. In an ex vivo assay in gerbil, the lead compound 2g occupies receptors within the CNS following oral dosing (Occ(90) 30 mg/kg po; plasma Occ(90) 0.95 microM) and has good selectivity and promising PK properti...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Elliott JM,Carling RW,Chambers M,Chicchi GG,Hutson PH,Jones AB,MacLeod A,Marwood R,Meneses-Lorente G,Mezzogori E,Murray F,Rigby M,Royo I,Russell MG,Sohal B,Tsao KL,Williams B

    更新日期:2006-11-15 00:00:00