Design and synthesis of an all-in-one 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group for photo-affinity labeling.


:A novel radioisotope-free photo-affinity probe containing the 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group was designed and synthesized. This very compact functionality is envisaged to allow photochemically-induced coupling of a compound to its target followed by click reaction coupling with an azido-biotin reagent in order to facilitate purification of the labeled target. In a proof-of-concept study we have shown that 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group could be photolyzed to efficiently furnish the methanol adduct 23 and that the generated highly unstable carbene does not react with the neighboring acetylene moiety. A subsequent click reaction with the azido-biotin derivative 25 proceeded smoothly to give triazole 26. This chemical probe should thus be of unique value for facilitating identification of the molecular structure of the target of a bioactive compound.


Bioorg Med Chem


Kumar NS,Young RN




Has Abstract


2009-08-01 00:00:00














  • Synthesis of new chemical entities from paracetamol and NSAIDs with improved pharmacodynamic profile.

    abstract::It was envisaged to combine high antipyretic activity of paracetamol into commonly used NSAIDs. To achieve this goal new chemical entities were synthesized by chemically combining paracetamol and NSAIDs, and biologically evaluated for their antipyretic, analgesic, anti-inflammatory and ulcerogenic potential. The acid ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yadav MR,Nimekar DM,Ananthakrishnan A,Brahmkshatriya PS,Shirude ST,Giridhar R,Parmar A,Balaraman R

    更新日期:2006-12-15 00:00:00

  • Design and optimization of aspartate N-acetyltransferase inhibitors for the potential treatment of Canavan disease.

    abstract::Canavan disease is a fatal neurological disorder caused by defects in the metabolism of N-acetyl-l-aspartate (NAA). Recent work has shown that the devastating symptoms of this disorder are correlated with the elevated levels of NAA observed in these patients, caused as a consequence of the inability of mutated forms o...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Thangavelu B,Mutthamsetty V,Wang Q,Viola RE

    更新日期:2017-02-01 00:00:00

  • Inhibition of Helicobacter pylori aminoacyl-tRNA amidotransferase by chloramphenicol analogs.

    abstract::Genomic studies revealed the absence of glutaminyl-tRNA synthetase and/or asparaginyl-tRNA synthetase in many bacteria and all known archaea. In these microorganisms, glutaminyl-tRNA(Gln) (Gln-tRNA(Gln)) and/or asparaginyl-tRNA(Asn) (Asn-tRNA(Asn)) are synthesized via an indirect pathway involving side chain amidation...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Balg C,De Mieri M,Huot JL,Blais SP,Lapointe J,Chênevert R

    更新日期:2010-11-15 00:00:00

  • Efficient one-pot synthesis of biologically active polysubstituted aromatic amines.

    abstract::An efficient and modular one-pot synthesis of polysubstituted aromatic amines by a mild reductive amination procedure is described and the biological potential of these nitrogen-centered compounds is demonstrated by growth inhibition of murine connective tissue cells and microscopy-based morphological studies. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Menche D,Arikan F,Li J,Rudolph S,Sasse F

    更新日期:2007-12-01 00:00:00

  • Synthesis and SAR studies of benzyl ether derivatives as potent orally active S1P₁ agonists.

    abstract::We report herein the synthesis and structure-activity relationships (SAR) of a series of benzyl ether compounds as an S1P₁ receptor modulator. From our SAR studies, the installation of substituents onto the central benzene ring of 2a was revealed to potently influence the S1P₁ and S1P₃ agonistic activities, in particu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Tsuji T,Suzuki K,Nakamura T,Goto T,Sekiguchi Y,Ikeda T,Fukuda T,Takemoto T,Mizuno Y,Kimura T,Kawase Y,Nara F,Kagari T,Shimozato T,Yahara C,Inaba S,Honda T,Izumi T,Tamura M,Nishi T

    更新日期:2014-08-01 00:00:00

  • New 3-methylquinoxaline-2-carboxamide 1,4-di-N-oxide derivatives as anti-Mycobacterium tuberculosis agents.

    abstract::Mycobacterium tuberculosis (M.Tb) is a bacillus capable of causing a chronic and fatal condition in humans known as tuberculosis (TB). It is estimated that there are 8 million new cases of TB per year and 3.1 million infected people die annually. Thirty-six new amide quinoxaline 1,4-di-N-oxide derivatives have been sy...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ancizu S,Moreno E,Solano B,Villar R,Burguete A,Torres E,Pérez-Silanes S,Aldana I,Monge A

    更新日期:2010-04-01 00:00:00

  • Characterization and in vitro activity of a branched peptide boronic acid that interacts with HIV-1 RRE RNA.

    abstract::A branched peptide containing multiple boronic acids was found to bind RRE IIB selectively and inhibit HIV-1 p24 capsid production in a dose-dependent manner. Structure-activity relationship studies revealed that branching in the peptide is crucial for the low micromolar binding towards RRE IIB, and the peptide demons...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wynn JE,Zhang W,Tebit DM,Gray LR,Hammarskjold ML,Rekosh D,Santos WL

    更新日期:2016-09-01 00:00:00

  • Biaryl diacid inhibitors of human s-PLA2 with anti-inflammatory activity.

    abstract::Twenty-four hydrophobic dicarboxylic acids are described which were evaluated as inhibitors of 14 kDa human platelet phospholipase A2 (HP-PLA2). In general, biarylacetic acid derivatives were found to be more active than biaryl acids or biarylpropanoic acids. More potent inhibitors were obtained when hydrophobic group...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Springer DM,Luh BY,Bronson JJ,McElhone KE,Mansuri MM,Gregor KR,Nettleton DO,Stanley PL,Tramposch KM

    更新日期:2000-05-01 00:00:00

  • Kinetic controlled affinity labeling of target enzyme with thioester chemistry.

    abstract::High specificity has been an important feature in affinity labeling for target profiling. Especially, to label targets via rapidly progressing reactions with consumption of ligand (probe), high specificity of reaction with common functional groups of target protein should be achieved without reactions with similar gro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Tomohiro T,Nakabayashi M,Sugita Y,Morimoto S

    更新日期:2016-08-01 00:00:00

  • Synthesis and biological relationships of 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives as antimitotic agents.

    abstract::As part of a continuing search for potential anticancer drug candidates in the 2-phenyl-4-quinolone series, 3',6-substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives and their salts were synthesized and evaluated. Preliminary screening showed that carboxylic acid analogs containing a m-fluoro substituted 2-p...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Lai YY,Huang LJ,Lee KH,Xiao Z,Bastow KF,Yamori T,Kuo SC

    更新日期:2005-01-03 00:00:00

  • Synthesis, structure, and antimycobacterial activity of 6-[1(3H)-isobenzofuranylidenemethyl]purines and analogs.

    abstract::6-Benzofuryl-, styryl, benzyl, and furfurylpurines as well as 6-[1(3H)-isobenzofuranylidenemethyl]purines have been synthesized and their activities against Mycobacterium tuberculosis (Mtb) determined. Several compounds displayed profound antimycobacterial activity in combination with low toxicity towards mammalian ce...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Braendvang M,Bakken V,Gundersen LL

    更新日期:2009-09-15 00:00:00

  • Synthesis and biological evaluation of Aspergillomarasmine A derivatives as novel NDM-1 inhibitor to overcome antibiotics resistance.

    abstract::The β-lactam antibiotic resistance of Gram-negative bacteria has shown to be a critical global health problem. One of the primary reasons for the drug resistance is the existence of β-lactamases especially metallo-β-lactamases such as New Delhi metallo-β-lactamase (NDM-1) and Verona Integron-encoded metallo-β-lactamas...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zhang J,Wang S,Wei Q,Guo Q,Bai Y,Yang S,Song F,Zhang L,Lei X

    更新日期:2017-10-01 00:00:00

  • Selective angiotensin II AT(2) receptor agonists devoid of the imidazole ring system.

    abstract::A versatile parallel synthetic method to obtain three series of non-cyclic analogues of the first drug-like selective angiotensin II AT(2) receptor agonist (1) has been developed. In analogy with the transformation of losartan to valsartan it was demonstrated that a non-cyclic moiety could be employed as an imidazole ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Murugaiah AM,Wallinder C,Mahalingam AK,Wu X,Wan Y,Plouffe B,Botros M,Karlén A,Hallberg M,Gallo-Payet N,Alterman M

    更新日期:2007-11-15 00:00:00

  • Structure-activity relationship of human GLO I inhibitory natural flavonoids and their growth inhibitory effects.

    abstract::Glyoxalase I (GLO I) is the rate-limiting enzyme for detoxification of methylglyoxal (MG), a side product of glycolysis, which is able to induce apoptosis. Since GLO I is known to be highly expressed in the most tumor cells and little in normal cells, specific inhibitors of this enzyme have been expected as effective ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Takasawa R,Takahashi S,Saeki K,Sunaga S,Yoshimori A,Tanuma S

    更新日期:2008-04-01 00:00:00

  • TRH mimetics: differentiation of antiamnesic potency from antidepressant effect.

    abstract::For the purpose of rational modification of the TRH molecule, we were pursuing an approach that consists of two steps: (1) 'obligatory' replacement of histidine with glutamine in TRH and (2) the application of conformational constraints for putative bioactive conformation I stabilized by an intramolecular hydrogen bon...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Mazurov AA,Andronati SA,Korotenko TI,Sokolenko NI,Dyadenko AI,Shapiro YE,Gorbatyuk VYa,Voronina TA

    更新日期:1997-11-01 00:00:00

  • NMR determination of Electrophorus electricus acetylcholinesterase inhibition and reactivation by neutral oximes.

    abstract::Neurotoxic organophosphorus compounds (OPs), which are used as pesticides and chemical warfare agents lead to more than 700,000 intoxications worldwide every year. The main target of OPs is the inhibition of acetylcholinesterase (AChE), an enzyme necessary for the control of the neurotransmitter acetylcholine (ACh). T...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: da Cunha Xavier Soares SF,Vieira AA,Delfino RT,Figueroa-Villar JD

    更新日期:2013-09-15 00:00:00

  • Synthesis and evaluation of amino-threoses in D- and L-series: are five membered ring amino-sugars more potent glycosidase inhibitors than the six membered ones?

    abstract::Cyclic D- and L-4-aminothreose were synthesised from ethyl D- and L-tartrate, respectively. D-aminothreose was a potent inhibitor of alpha-glucosidase and of alpha-mannosidase. From the glycosidase inhibition potencies of the four 4-amino-4-deoxy-tetroses, the contribution of binding of each functionality of the 5 and...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Chevrier C,Defoin A,Tarnus C

    更新日期:2007-06-15 00:00:00

  • Antioxidant activity of benzoxazolinonic and benzothiazolinonic derivatives in the LDL oxidation model.

    abstract::A series of benzazolone compounds were synthesized utilizing benzoxazolinonic and benzothiazolinonic heterocycles as the building unit. The antioxidant activity of these compounds was determined by inhibition of lipid peroxidation. The oxidation of LDL was induced in the presence of CuSO(4) or 2,2'-azobis(2-amidinopro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yekini I,Hammoudi F,Martin-Nizard F,Yous S,Lebegue N,Berthelot P,Carato P

    更新日期:2009-11-15 00:00:00

  • Carbonic anhydrases of anaerobic microbes.

    abstract::Carbonic anhydrases (CAs) catalyze the reversible hydration of carbon dioxide to bicarbonate and are abundantly distributed in prokaryotes and eukaryotes. There are five classes (α,β,γ,δ,ζ) with no significant sequence or structural identity among them, a remarkable example of convergent evolution. The β and γ classes...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ferry JG

    更新日期:2013-03-15 00:00:00

  • Complex molecules, clever solutions - Enzymatic approaches towards natural product and active agent syntheses.

    abstract::Natural compounds are often structurally complex and their synthesis is still highly challenging. The review intends to give an overview on developments in biotechnology and their role for the production of natural products and active agents. In vitro and in vivo methods are presented side by side beginning with rathe...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Classen T,Pietruszka J

    更新日期:2018-04-01 00:00:00

  • Synthesis and evaluation of water-soluble docetaxel prodrugs-docetaxel esters of malic acid.

    abstract::The synthesis of docetaxel esters of malic acid is described. These compounds were found to have greatly improved water solubility and are stable in solution at neutral pH. The C2' modified compounds 2a-c and 3a-c behave as prodrugs, that is, docetaxel is generated upon exposure to human plasma, whereas the C7 and C2'...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Du W,Hong L,Yao T,Yang X,He Q,Yang B,Hu Y

    更新日期:2007-09-15 00:00:00

  • Inhibition of the Ser-Thr phosphatases PP1 and PP2A by naturally occurring toxins.

    abstract::The okadaic acid class of naturally occurring toxins is a structurally diverse group of molecules that inhibit the protein phosphatases PP1 and PP2A. Studies providing information about the mode of binding between the toxins and the phosphatases contribute to an overall understanding of the signal transduction pathway...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Sheppeck JE 2nd,Gauss CM,Chamberlin AR

    更新日期:1997-09-01 00:00:00

  • Synthesis and structure-activity relationship of a novel class of 15-membered macrolide antibiotics known as '11a-azalides'.

    abstract::Macrolide antibiotics are widely prescribed for the treatment of respiratory tract infections; however, the increasing prevalence of macrolide-resistant pathogens is a public health concern. Therefore, the development of new macrolide scaffolds with activities against resistant pathogens is urgently needed. An efficie...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sugimoto T,Tanikawa T,Suzuki K,Yamasaki Y

    更新日期:2012-10-01 00:00:00

  • Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.

    abstract::Members of the GATA family of transcription factors are zinc finger proteins that were shown to play evolutionary conserved roles in cell differentiation and proliferation in different organisms. We hypothesized that by finding new molecules that inhibit their function to be crucial in future therapeutical interventio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: El-Hachem N,Nemer G

    更新日期:2011-03-01 00:00:00

  • Halogenated derivatives QSAR model using spectral moments to predict haloacetic acids (HAA) mutagenicity.

    abstract::The risk of the presence of haloacetic acids in drinking water as chlorination by-products and the shortage of experimental mutagenicity data for most of them requires a research work. This paper describes a QSAR model to predict direct mutagenicity for these chemicals. The model, able to describe more than 90% of the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Pérez-Garrido A,González MP,Escudero AG

    更新日期:2008-05-15 00:00:00

  • 18F-Labeled indole-based analogs as highly selective radioligands for imaging sigma-2 receptors in the brain.

    abstract::We have designed and synthesized a series of indole-based σ2 receptor ligands containing 5,6-dimethoxyisoindoline or 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline as pharmacophore. In vitro competition binding assays showed that all ten ligands possessed low nanomolar affinity (Ki=1.79-5.23nM) for σ2 receptors and high...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wang L,Ye J,He Y,Deuther-Conrad W,Zhang J,Zhang X,Cui M,Steinbach J,Huang Y,Brust P,Jia H

    更新日期:2017-07-15 00:00:00

  • Inhibitory activity of Brazilian green propolis components and their derivatives on the release of cys-leukotrienes.

    abstract::The effects of Brazilian green propolis ethanol extract on Cry j1-induced cys-leukotrienes and histamine release from peripheral leukocytes of patients with allergic rhinitis were investigated. One of the key mechanisms for the anti-allergic properties of the extract was revealed to be the suppression of cys-LTs relea...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Tani H,Hasumi K,Tatefuji T,Hashimoto K,Koshino H,Takahashi S

    更新日期:2010-01-01 00:00:00

  • Investigating the activity of 2-substituted alkyl-6-(2,5-dioxopyrrolidin-1-yl)hexanoates as skin penetration enhancers.

    abstract::Skin penetration enhancers are used in the formulation of transdermal delivery systems for drugs that are otherwise not sufficiently skin-permeable. We generated two series of esters by multi-step synthesis with substituted 6-aminohexanoic acid as potential transdermal penetration enhancers by multi-step synthesis. Th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Brychtova K,Opatrilova R,Raich I,Kalinowski DS,Dvorakova L,Placek L,Csollei J,Richardson DR,Jampilek J

    更新日期:2010-12-15 00:00:00

  • Radiofluorinated histamine H₃ receptor antagonist as a potential probe for in vivo PET imaging: radiosynthesis and pharmacological evaluation.

    abstract::The histamine H(3) receptor (H(3)R) plays a role in cognition and memory processes and is implicated in different neurological disorders, including Alzheimer's disease, schizophrenia, and narcolepsy. In vivo studies of the H(3)R occupancy using a radiolabeled PET tracer would be very useful for CNS drug discovery and ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Selivanova SV,Honer M,Combe F,Isensee K,Stark H,Krämer SD,Schubiger PA,Ametamey SM

    更新日期:2012-05-01 00:00:00

  • Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (-)-epigallocatechin gallate.

    abstract::Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Dodo K,Minato T,Noguchi-Yachide T,Suganuma M,Hashimoto Y

    更新日期:2008-09-01 00:00:00