Solid-phase synthesis of quinol fatty alcohols, design of N/O-substituted quinol fatty alcohols and comparative activities on axonal growth.


:Following the promising activity of Q2FA15 on axonal growth, two new series of N/O-substituted QFAs were synthesized, based on a SN2-type reaction. O-alkylated QFA bearing 14 carbon atoms on the side chain (n=14) shows a very potent activity on axonal growth though lowered when compared to Q2FA15. While O-alkylation allows good retention of the biological activity, N-alkylation abolishes it nonetheless. A solid-phase-supported synthesis of Q2FA15 allowing the conception of new hybrid compounds is also described.


Bioorg Med Chem Lett


Hanbali M,Bagnard D,Luu B




Has Abstract


2006-08-01 00:00:00














  • Substituted indoles as selective protease activated receptor 4 (PAR-4) antagonists: Discovery and SAR of ML354.

    abstract::Herein we report the discovery and SAR of an indole-based protease activated receptor-4 (PAR-4) antagonist scaffold derived from a similarity search of the Vanderbilt HTS collection, leading to MLPCN probe ML354 (VU0099704). Using a novel PAC-1 fluorescent αIIbβ3 activation assay this probe molecule antagonist was fou...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Wen W,Young SE,Duvernay MT,Schulte ML,Nance KD,Melancon BJ,Engers J,Locuson CW 2nd,Wood MR,Daniels JS,Wu W,Lindsley CW,Hamm HE,Stauffer SR

    更新日期:2014-10-01 00:00:00

  • Benzoindoloquinolines interact with DNA tetraplexes and inhibit telomerase.

    abstract::Telomeric G-rich single-stranded DNA can adopt a G-tetraplex structure which has been shown to inhibit telomerase activity. We have examined benzoindoloquinolines derivatives for their ability to stabilize an intramolecular G-quadruplex. The increase in T(m) value of the G-quadruplex was associated with telomerase inh...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Alberti P,Schmitt P,Nguyen CH,Rivalle C,Hoarau M,Grierson DS,Mergny JL

    更新日期:2002-04-08 00:00:00

  • Synthesis and evaluation of cholecystokinin trimers: a multivalent approach to pancreatic cancer detection and treatment.

    abstract::In the quest for novel tools for early detection and treatment of cancer, we propose the use of multimers targeting overexpressed receptors at the cancer cell surface. Indeed, multimers are prone to create multivalent interactions, more potent and specific than their corresponding monovalent versions, thus enabling th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Brabez N,Nguyen KL,Saunders K,Lacy R,Xu L,Gillies RJ,Lynch RM,Chassaing G,Lavielle S,Hruby VJ

    更新日期:2013-04-15 00:00:00

  • Synthesis of C-5a-chain extended derivatives of 4-epi-isofagomine: Powerful β-galactosidase inhibitors and low concentration activators of GM1-gangliosidosis-related human lysosomal β-galactosidase.

    abstract::From an easily available partially protected formal derivative of 1-deoxymannojirimycin, by hydroxymethyl chain-branching and further elaboration, lipophilic analogs of the powerful β-d-galactosidase inhibitor 4-epi-isofagomine have become available. New compounds exhibit improved inhibitory activities comparable to b...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Thonhofer M,Weber P,Santana AG,Fischer R,Pabst BM,Paschke E,Schalli M,Stütz AE,Tschernutter M,Windischhofer W,Withers SG

    更新日期:2016-03-01 00:00:00

  • Synthesis and biological evaluation of L-cysteine derivatives as mitotic kinesin Eg5 inhibitors.

    abstract::Inhibition of Eg5 represents a novel approach for the treatment of cancer. Here, we report the synthesis and structure-activity relationship of S-trityl-L-cysteine (STLC) derivatives as Eg5 inhibitors. Some of these derivatives such as 4f demonstrated enhanced inhibitory activity against Eg5 and induced mitotic arrest...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Ogo N,Oishi S,Matsuno K,Sawada J,Fujii N,Asai A

    更新日期:2007-07-15 00:00:00

  • Design and synthesis of morpholine derivatives. SAR for dual serotonin & noradrenaline reuptake inhibition.

    abstract::Single enantiomer (SS) and (RR) 2-[(phenoxy)(phenyl)methyl]morpholine derivatives 5, 8-23 are inhibitors of monoamine reuptake. Target compounds were prepared using an enantioselective synthesis employing a highly specific enzyme-catalysed resolution of racemic n-butyl 4-benzylmorpholine-2-carboxylate (26) as the key ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Fish PV,Deur C,Gan X,Greene K,Hoople D,Mackenny M,Para KS,Reeves K,Ryckmans T,Stiff C,Stobie A,Wakenhut F,Whitlock GA

    更新日期:2008-04-15 00:00:00

  • Rethinking the old antiviral drug moroxydine: Discovery of novel analogues as anti-hepatitis C virus (HCV) agents.

    abstract::The discovery of a novel class of HCV inhibitors is described. The new amidinourea compounds were designed as isosteric analogues of the antiviral drug moroxydine. The two derivatives 11g and 11h showed excellent HCV inhibition activity and viability and proved to inhibit a step(s) of the RNA replication. The new comp...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Magri A,Reilly R,Scalacci N,Radi M,Hunter M,Ripoll M,Patel AH,Castagnolo D

    更新日期:2015-11-15 00:00:00

  • Diaminocyclobutenediones as potent and orally bioavailable CXCR2 receptor antagonists: SAR in the phenolic amide region.

    abstract::A series of potent and orally bioavailable 3,4-diaminocyclobutenediones with various amide modifications and substitution on the left side phenyl ring were prepared and found to show significant inhibitory activities towards both CXCR2 and CXCR1 receptors. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Aki C,Chao J,Ferreira JA,Dwyer MP,Yu Y,Chao J,Merritt RJ,Lai G,Wu M,Hipkin RW,Fan X,Gonsiorek W,Fosseta J,Rindgen D,Fine J,Lundell D,Taveras AG,Biju P

    更新日期:2009-08-01 00:00:00

  • Dual-targeting GroEL/ES chaperonin and protein tyrosine phosphatase B (PtpB) inhibitors: A polypharmacology strategy for treating Mycobacterium tuberculosis infections.

    abstract::Current treatments for Mycobacterium tuberculosis infections require long and complicated regimens that can lead to patient non-compliance, increasing incidences of antibiotic-resistant strains, and lack of efficacy against latent stages of disease. Thus, new therapeutics are needed to improve tuberculosis standard of...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Washburn A,Abdeen S,Ovechkina Y,Ray AM,Stevens M,Chitre S,Sivinski J,Park Y,Johnson J,Hoang QQ,Chapman E,Parish T,Johnson SM

    更新日期:2019-07-01 00:00:00

  • A dual fluorinated and iodinated radiotracer for PET and SPECT imaging of β-amyloid plaques in the brain.

    abstract::We report a fluorinated and iodinated radiotracer as a probe for PET/SPECT to detect of β-amyloid (Aβ) plaques in the brain of patients with Alzheimer's disease (AD). We successfully designed and synthesized the fluorinated and iodinated aurone derivative (3) and its radiolabels ([(125)I]3 and [(18)F]3). In binding ex...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Watanabe H,Ono M,Kimura H,Kagawa S,Nishii R,Fuchigami T,Haratake M,Nakayama M,Saji H

    更新日期:2011-11-01 00:00:00

  • Synthesis and structure-activity relationships of 7-(2-aminoalkyl)morpholinoquinolones as anti-Helicobacter pylori agents.

    abstract::A series of the titled compounds was synthesized and tested for anti-Helicobacter pylori activities. We discovered Y-34867 having the most potent activity against Helicobacter pylori among the quinolones tested along with high photostability. Furthermore, Y-34867 showed an excellent therapeutic effect in the experimen...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Sakurai N,Sano M,Hirayama F,Kuroda T,Uemori S,Moriguchi A,Yamamoto K,Ikeda Y,Kawakita T

    更新日期:1998-08-18 00:00:00

  • Analogs of penfluridol as chemotherapeutic agents with reduced central nervous system activity.

    abstract::Several recent reports have highlighted the feasibility of the use of penfluridol, a well-known antipsychotic agent, as a chemotherapeutic agent. In vivo experiments have confirmed the cytotoxic activity of penfluridol in triple-negative breast cancer model, lung cancer model, and further studies have been proposed to...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Ashraf-Uz-Zaman M,Sajib MS,Cucullo L,Mikelis CM,German NA

    更新日期:2018-12-15 00:00:00

  • In vitro selection of a photoresponsive RNA aptamer to hemin.

    abstract::A photoresponsive RNA aptamer to hemin was selected in vitro from a random sequence library of RNAs with azobenzene residues. The aptamer bound to hemin under visible light irradiation and was released by ultraviolet light. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Liu M,Jinmei H,Abe H,Ito Y

    更新日期:2010-05-01 00:00:00

  • The search for novel TRPV1-antagonists: from carboxamides to benzimidazoles and indazolones.

    abstract::Based on a series of diaryl amides the corresponding inverse amides have been found to be potent TRPV1 receptor antagonists. Benzimidazole and indazolone derivatives prepared retained good potency in vitro and indazolone 4a was identified as a novel TRPV1 receptor antagonist suitable for evaluating orally in animal mo...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Fletcher SR,McIver E,Lewis S,Burkamp F,Leech C,Mason G,Boyce S,Morrison D,Richards G,Sutton K,Jones AB

    更新日期:2006-06-01 00:00:00

  • Novel benzothiazinones (BTOs) as allosteric modulator or substrate competitive inhibitor of glycogen synthase kinase 3β (GSK-3β) with cellular activity of promoting glucose uptake.

    abstract::Glycogen synthase kinase 3β (GSK-3β) plays a key role in insulin metabolizing pathway and therefore inhibition of the enzyme might provide an important therapeutic approach for treatment of insulin resistance and type 2 diabetes. Recently, discovery of ATP noncompetitive inhibitors is gaining importance not only due t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zhang P,Li S,Gao Y,Lu W,Huang K,Ye D,Li X,Chu Y

    更新日期:2014-12-15 00:00:00

  • Hybrids of arenobufagin and benzoisoselenazol reducing the cardiotoxicity of arenobufagin.

    abstract::Arenobufagin is a naturally occurring bufadienolide showing promising antitumor activity accompanied however with apparent cardiac toxicity. Following the recent discovery that oxidative damage possibly be an important cause of the cardiac toxicity of cardenolides, a strategy fusing the antitumor agent arenobufagin wi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Hou W,Huang ZX,Xu HG,Lin J,Zhang DM,Peng QL,Lin H,Chang YQ,Wang LH,Yao Z,Sun PH,Chen WM

    更新日期:2018-11-01 00:00:00

  • Recent progress in human telomere RNA structure and function.

    abstract::Human telomeric DNA is transcribed into telomeric RNA in cells. Telomeric RNA performs the fundamental biological functions such as regulation and protection of chromosome ends. This digest highlights the human telomere RNA G-quadruplex structures, telomere RNA functions, G-quadruplex-binding small molecules, and futu...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,评审


    authors: Xu Y

    更新日期:2018-08-15 00:00:00

  • Catalysis of imido group hydrolysis in a maleimide conjugate.

    abstract::Maleimides are often used for biomolecular conjugation with thiols. An underappreciated aspect of the imido group in a maleimide conjugate is its susceptibility to spontaneous hydrolysis, resulting in undesirable heterogeneity. Here, a chromophoric maleimide is used to demonstrate that both molybdate and chromate cata...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kalia J,Raines RT

    更新日期:2007-11-15 00:00:00

  • Identification of free fatty acid receptor 2 agonists using virtual screening.

    abstract::Structure- and ligand-based virtual-screening methods (docking, 2D- and 3D-similarity searching) were analyzed for their effectiveness in virtual screening against FFAR2. To evaluate the performance of these methods, retrospective virtual screening was performed. Statistical quality of the methods was evaluated by BED...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Fells JI,Ai X,Weinglass A,Feng W,Lei Y,Finley M,Hoveyda HR,Fraser GL,Machacek M

    更新日期:2020-11-01 00:00:00

  • Discovery of two aminoglycoside antibiotics as inhibitors targeting the menin-mixed lineage leukaemia interface.

    abstract::Menin functions as an oncogenic cofactor of mixed lineage leukaemia (MLL) fusion proteins in leukaemogenesis. The menin-MLL interface is a potential therapeutic target in acute leukaemia cases. In this study, approximately 900 clinical compounds were evaluated and ranked using pharmacophore-based virtual screening, th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Li L,Zhou R,Geng H,Yue L,Ye F,Xie Y,Liu J,Kong X,Jiang H,Huang J,Luo C

    更新日期:2014-05-01 00:00:00

  • Heterobiaryl purine derivatives as potent antiproliferative agents: inhibitors of cyclin dependent kinases. Part II.

    abstract::C-6 Biarylmethylamino purine derivatives of roscovitine (1) inhibit cyclin dependent kinases and demonstrate potent antiproliferative activity. Replacement of the aryl rings of the C-6 biarylmethylamino group with heterobiaryl rings has provided compounds with significantly improved activity. In particular, derivative...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Trova MP,Barnes KD,Alicea L,Benanti T,Bielaska M,Bilotta J,Bliss B,Duong TN,Haydar S,Herr RJ,Hui Y,Johnson M,Lehman JM,Peace D,Rainka M,Snider P,Salamone S,Tregay S,Zheng X,Friedrich TD

    更新日期:2009-12-01 00:00:00

  • Discovery of a new series of monoamine reuptake inhibitors, the 1-amino-3-(1H-indol-1-yl)-3-phenylpropan-2-ols.

    abstract::A novel series of monoamine reuptake inhibitors, the 1-amino-3-(1H-indol-1-yl)-3-phenylpropan-2-ols, have been discovered by combining virtual and focused screening efforts with design techniques. Synthesis of the two diastereomeric isomers of the molecule followed by chiral resolution of each enantiomer revealed the ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kim CY,Mahaney PE,McConnell O,Zhang Y,Manas E,Ho DM,Deecher DC,Trybulski EJ

    更新日期:2009-09-01 00:00:00

  • 1-[(Benzofuran-2-yl)phenylmethyl]-triazoles and -tetrazoles - potent competitive inhibitors of aromatase.

    abstract::The synthesis of a series of novel 1-[(benzofuran-2-yl)phenylmethyl]-triazoles and -tetrazoles is described. The compounds were tested for human placental aromatase inhibition in vitro, using [1beta-3H]-androstenedione as the substrate for the aromatase enzyme, the percentage inhibition and IC50 data is included. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Vinh TK,Ahmadi M,Delgado PO,Perez SF,Walters HM,Smith HJ,Nicholls PJ,Simons C

    更新日期:1999-07-19 00:00:00

  • Design and synthesis of functionalized piperazin-1yl-(E)-stilbenes as inhibitors of 17α-hydroxylase-C17,20-lyase (Cyp17).

    abstract::The synthesis of steroid hormones is critical to human physiology and improper regulation of either the synthesis of these key molecules or activation of the associated receptors can lead to disease states. This has led to intense interest in developing compounds capable of modulating the synthesis of steroid hormones...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Blass BE,Iyer P,Abou-Gharbia M,Childers WE,Gordon JC,Ramanjulu M,Morton G,Arumugam P,Boruwa J,Ellingboe J,Mitra S,Reddy Nimmareddy R,Paliwal S,Rajasekhar J,Shivakumar S,Srivastava P,Tangirala RS,Venkataramanaiah K,Bob

    更新日期:2018-07-15 00:00:00

  • Optimization of pancreatic lipase inhibition by Cudrania tricuspidata fruits using response surface methodology.

    abstract::The fruits of Cudrania tricuspidata (Carr.) Bur. (Moraceae) significantly inhibited pancreatic lipase, which plays a key role in fat absorption. Optimization of extraction conditions with minimum pancreatic lipase activity and maximum yield was determined using response surface methodology with three-level-three-facto...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Jeong JY,Jo YH,Lee KY,Do SG,Hwang BY,Lee MK

    更新日期:2014-05-15 00:00:00

  • Reduction of hERG inhibitory activity in the 4-piperidinyl urea series of H3 antagonists.

    abstract::Structural features of the substituted 4-piperidinyl urea analogs 1, responsible for the H3 antagonist activity, have been identified. Structure-activity relationship of the H3 receptor affinity, hERG ion channel inhibitory activity and their separation is described. Preliminary pharmacokinetic evaluation of the compo...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Berlin M,Lee YJ,Boyce CW,Wang Y,Aslanian R,McCormick KD,Sorota S,Williams SM,West RE Jr,Korfmacher W

    更新日期:2010-04-01 00:00:00

  • Pleuromutilin derivatives having a purine ring. Part 1: new compounds with promising antibacterial activity against resistant Gram-positive pathogens.

    abstract::In the course of our research aimed at the discovery of metabolic stable pleuromutilin derivatives with more potent antibacterial activity against Gram-positive pathogens than previous analogues, a series of compounds bearing a purine ring were prepared and evaluated. From SAR studies, we identified two promising comp...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Hirokawa Y,Kinoshita H,Tanaka T,Nakamura T,Fujimoto K,Kashimoto S,Kojima T,Kato S

    更新日期:2008-06-15 00:00:00

  • Synthesis and structure activity relationships of a series of 4-amino-1H-pyrazoles as covalent inhibitors of CDK14.

    abstract::The TAIRE family of kinases are an understudied branch of the CDK kinase family, that have been implicated in a number of cancers. This manuscript describes the design, synthesis and SAR of covalent CDK14 inhibitors, culminating in identification of FMF-04-159-2, a potent, covalent CDK14 inhibitor with a TAIRE kinase ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Ferguson FM,Doctor ZM,Ficarro SB,Marto JA,Kim ND,Sim T,Gray NS

    更新日期:2019-08-01 00:00:00

  • Estradiol-mimetic probes. Preparation of 17 alpha-(6-aminohexynyl)estradiol biotin, fluorescein and acridinium conjugates.

    abstract::3-O-tert-Butyldimethylsilyl-17 alpha-(6-mesyloxyhexynyl)estradiol was converted to the azide in 60-70% yield with NaN3/DMPU, then reduced to the corresponding amine (> 95% yield). Acylation with the N-hydroxysuccinimide esters of biotin, 5-carboxyfluorescein and 10-(3-sulfopropyl)-N-tosyl-N-(3- carboxypropyl)acridiniu...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Adamczyk M,Chen YY,Moore JA,Mattingly PG

    更新日期:1998-06-02 00:00:00

  • Discovery and synthesis of novel benzofurazan derivatives as inhibitors of influenza A virus.

    abstract::The identification of a novel hit compound inhibitor of the protein-protein interaction between the influenza RNA-polymerase PA and PB1 subunits has been accomplished by means of high-throughput screening. A small family of structurally related molecules has been synthesized and biologically evaluated with most of the...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kessler U,Castagnolo D,Pagano M,Deodato D,Bernardini M,Pilger B,Ranadheera C,Botta M

    更新日期:2013-10-15 00:00:00