m-Carborane bisphenol structure as a pharmacophore for selective estrogen receptor modulators.


:A series of m-carborane derivatives was prepared based upon the structures of antiestrogenic drugs and their activities were evaluated by estrogen receptor alpha (ERalpha) binding assay and transactivation assay using human breast cancer cell line, MCF-7 cells. The m-carborane bisphenol 5 exhibited about a thousand times more potent ER agonistic activity than the o-carborane bisphenol 11. The m-carborane bisphenol structure appears to be a favorable hydrophobic pharmacophore for the development of novel selective estrogen receptor modulators (SERMs).


Bioorg Med Chem Lett


Ogawa T,Ohta K,Yoshimi T,Yamazaki H,Suzuki T,Ohta S,Endo Y




Has Abstract


2006-08-01 00:00:00














  • Functionalized 1,3-teraryls as a new class of hepatoprotectants. Part V.

    abstract::Functionalized 1,3-teraryls, synthesized through ring transformation of 6-aryl-3-carbomethoxy-4-methylthio-2H-pyran-2-one from arylketone have been screened for their hepatoprotective activity and of them have demonstrated significant protection in animal model. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Ram VJ,Goel A,Patnaik GK

    更新日期:1998-03-03 00:00:00

  • Design and synthesis of new bis-pyridinium oxime reactivators for acetylcholinesterase inhibited by organophosphorous nerve agents.

    abstract::New bis-pyridinium oxime reactivators connected with a CH(2)CH(2)OCH(2)CH(2) linker between two pyridinium rings were designed and synthesized. In the test of their potency to reactivate AChE inhibited by cyclosarin, the bis-pyridinium oxime 6b achieved reactivation potency higher than 10% at the lower concentration 1...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kim TH,Kuca K,Jun D,Jung YS

    更新日期:2005-06-02 00:00:00

  • Synthesis and preliminary evaluation of mono-[123I]iodohypericin monocarboxylic acid as a necrosis avid imaging agent.

    abstract::Hypericin monocarboxylic acid was synthesized in an overall yield of 25% in four steps and radiolabelled with iodine-123 in good yield (>75%). The resulting mono-[(123)I]iodohypericin monocarboxylic acid was evaluated in normal mice and in rats with ethanol induced liver necrosis. In this model, tracer concentration i...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Fonge H,Jin L,Wang H,Ni Y,Bormans G,Verbruggen A

    更新日期:2007-07-15 00:00:00

  • Enhancing the activity of membrane remodeling epsin-peptide by trimerization.

    abstract::Modulating the structural dynamics of biomembranes by inducing bilayer curvature and lipid packing defects has been highlighted as a practical tool to modify membrane-dependent cellular processes. Previously, we have reported on an amphipathic helical peptide derived from the N-terminal segment (residues 1-18, EpN18) ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Hsu WY,Masuda T,Afonin S,Sakai T,Arafiles JVV,Kawano K,Hirose H,Imanishi M,Ulrich AS,Futaki S

    更新日期:2020-06-15 00:00:00

  • A tetradecapeptide somatostatin dicarba-analog: Synthesis, structural impact and biological activity.

    abstract::We described here the first tetradecapeptide somatostatin-analogue where the disulfide bridge has been replaced by a carbon-carbon double bond. This analogue was prepared using microwave assisted ring closing metathesis (RCM) using the 2nd generation Grubbs as catalyst. Under our optimized conditions the cyclization b...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Martín-Gago P,Ramón R,Aragón E,Fernández-Carneado J,Martin-Malpartida P,Verdaguer X,López-Ruiz P,Colás B,Cortes MA,Ponsati B,Macias MJ,Riera A

    更新日期:2014-01-01 00:00:00

  • Design and synthesis of potent, selective phenylimidazole-based FVIIa inhibitors.

    abstract::Heterocyclic amide isosteres were incorporated into a phenylglycine-based tissue factor/factor VIIa (TF-FVIIa) inhibitor chemotype, providing potent inhibitors. An X-ray co-crystal structure of phenylimidazole 19 suggested that an imidazole nitrogen atom effectively mimics an amide carbonyl, while the phenyl ring form...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Glunz PW,Cheng X,Cheney DL,Weigelt CA,Wei A,Luettgen JM,Wong PC,Wexler RR,Priestley ES

    更新日期:2015-01-01 00:00:00

  • Potent inhibitors of the MAP kinase p38.

    abstract::The MAP kinase p38 plays a key role in the biosynthesis of the inflammatory cytokines TNF-alpha and IL-1. We have developed a novel series of potent p38 inhibitors that could lead to new methods of treatment for inflammatory diseases such as rheumatoid arthritis and inflammatory bowel disease. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Henry JR,Rupert KC,Dodd JH,Turchi IJ,Wadsworth SA,Cavender DE,Schafer PH,Siekierka JJ

    更新日期:1998-12-01 00:00:00

  • Prototyping kinase inhibitor-cytotoxin anticancer mutual prodrugs activated by tumour hypoxia: A chemical proof of concept study.

    abstract::Amide- and ester-linked kinase inhibitor-cytotoxin conjugates were rationally designed and synthesised as prototype hypoxia-activated anticancer mutual prodrugs. Chemical reduction of an aryl nitro trigger moiety was shown to initiate a spontaneous cyclisation/fragmentation reaction that simultaneously released the ki...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Sansom GN,Kirk NS,Guise CP,Anderson RF,Smaill JB,Patterson AV,Kelso MJ

    更新日期:2019-05-15 00:00:00

  • Design and synthesis of potent, isoxazole-containing renin inhibitors.

    abstract::The design and optimization of a novel isoxazole S(1) linker for renin inhibitor is described herein. This effort culminated in the identification of compound 18, an orally bioavailable, sub-nanomolar renin inhibitor even in the presence of human plasma. When compound 18 was found to inhibit CYP3A4 in a time dependent...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Fournier PA,Arbour M,Cauchon E,Chen A,Chefson A,Ducharme Y,Falgueyret JP,Gagné S,Grimm E,Han Y,Houle R,Lacombe P,Lévesque JF,MacDonald D,Mackay B,McKay D,Percival MD,Ramtohul Y,St-Jacques R,Toulmond S

    更新日期:2012-04-15 00:00:00

  • Structure activity relationships of benzylproline-derived inhibitors of the glutamine transporter ASCT2.

    abstract::The glutamine transporter ASCT2 has been identified as a promising target to inhibit rapid growth of cancer cells. However, ASCT2 pharmacology is not well established. In this report, we performed a systematic structure activity analysis of a series of substituted benzylproline derivatives. Substitutions on the phenyl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Singh K,Tanui R,Gameiro A,Eisenberg G,Colas C,Schlessinger A,Grewer C

    更新日期:2017-02-01 00:00:00

  • Synthesis and SAR of 4-carboxy-2-azetidinone mechanism-based tryptase inhibitors.

    abstract::A series of N1-activated C4-carboxy azetidinones was prepared and tested as inhibitors of human tryptase. The key stereochemical and functional features required for potency, serine protease specificity and aqueous stability were determined. From these studies compound 2, BMS-262084, was identified as a potent and sel...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Sutton JC,Bolton SA,Hartl KS,Huang MH,Jacobs G,Meng W,Ogletree ML,Pi Z,Schumacher WA,Seiler SM,Slusarchyk WA,Treuner U,Zahler R,Zhao G,Bisacchi GS

    更新日期:2002-11-04 00:00:00

  • From benzimidazole to indole-5-carboxamide Thumb Pocket I inhibitors of HCV NS5B polymerase. Part 1: indole C-2 SAR and discovery of diamide derivatives with nanomolar potency in cell-based subgenomic replicons.

    abstract::Replacement of the benzimidazole core of allosteric Thumb Pocket 1 HCV NS5B finger loop inhibitors by more lipophilic indole derivatives provided up to 30-fold potency improvements in cell-based subgenomic replicon assays. Optimization of C-2 substitution on the indole core led to the identification of analogs with EC...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Beaulieu PL,Gillard J,Jolicoeur E,Duan J,Garneau M,Kukolj G,Poupart MA

    更新日期:2011-06-15 00:00:00

  • Synthesis and biological evaluation of sulfonamidooxazoles and beta-keto sulfones: selective inhibitors of 11beta-hydroxysteroid dehydrogenase type I.

    abstract::The design, synthesis, and biological evaluation of arylsulfonamidooxazoles as 11beta-HSD1 inhibitors and the serendipitous discovery of beta-keto sulfones as potent 11beta-HSD1 inhibitors are described here. These two classes of compounds are not active against 11beta-HSD2 and therefore may have significant therapeut...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Xiang J,Ipek M,Suri V,Massefski W,Pan N,Ge Y,Tam M,Xing Y,Tobin JF,Xu X,Tam S

    更新日期:2005-06-02 00:00:00

  • Novel endoperoxides: synthesis and activity against Candida species.

    abstract::Fifteen new endoperoxides have been synthesised and tested for activity against pathogenic Candida species. These endoperoxides can be prepared in high yields, in one to three steps, from inexpensive starting materials. Despite chemical and structural similarities, their inhibitory activity against Candida growth vari...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Macreadie P,Avery T,Greatrex B,Taylor D,Macreadie I

    更新日期:2006-02-15 00:00:00

  • Orally active esters of dihydroartemisinin: Synthesis and antimalarial activity against multidrug-resistant Plasmodium yoelii in mice.

    abstract::A series of artemisinin derived esters 7a-j, incorporating pharmacologically privileged substructure, such as biphenyl, adamantane and fluorene, have been prepared and evaluated for antimalarial activity against multidrug-resistant (MDR) Plasmodium yoelii nigeriensis by oral route. Several of these compounds were foun...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Singh C,Chaudhary S,Puri SK

    更新日期:2008-02-15 00:00:00

  • 2-O-carboxymethylpyrogallol derivatives as PTP1B inhibitors with antihyperglycemic activity.

    abstract::2-O-carboxymethylpyrogallol derivatives (4-17) were synthesized, with their in vitro inhibitory activities against PTP1B and in vivo antihyperglycemic effects examined. Compound 14, the most potent among the series, showed a K(i) value of 1.1 microM against PTP1B, 7-fold lower than that against TC-PTP. When compound 1...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Bhattarai BR,Shrestha S,Ham SW,Kim KR,Cheon HG,Lee KH,Cho H

    更新日期:2007-10-01 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

  • Quinazoline Based HSP90 Inhibitors: Synthesis, Modeling Study and ADME Calculations Towards Breast Cancer Targeting.

    abstract::A new 2-thioquinazolinones series was designed and synthesized as HSP90 inhibitors based on the structure of hit compound VII obtained by virtual screening approach. Their in vitro anti-proliferative activity was evaluated against three human cancer cell lines rich in HSP90 namely; colorectal carcinoma (HCT-116), and ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: El-Shafey HW,Gomaa RM,El-Messery SM,Goda FE

    更新日期:2020-08-01 00:00:00

  • Identification of novel estrogen receptor (ER) agonists that have additional and complementary anti-cancer activities via ER-independent mechanism.

    abstract::In this study, a series of bis(4-hydroxy)benzophenone oxime ether derivatives such as 12c, 12e and 12h were identified as novel estrogen receptor (ER) agonists that have additional and complementary anti-proliferative activities via ER-independent mechanism in cancer cells. These compounds are expected to overcome the...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kim T,Kim HI,An JY,Lee J,Lee NR,Heo J,Kim JE,Yu J,Lee YS,Inn KS,Kim NJ

    更新日期:2016-04-01 00:00:00

  • Triptolide derivatives as potential multifunctional anti-Alzheimer agents: Synthesis and structure-activity relationship studies.

    abstract::Owning to the promising neuroprotective profile and the ability to cross the blood-brain barrier, triptolide has attracted extensive attention. Although its limited solubility and toxicity have greatly hindered clinical translation, triptolide has nonetheless emerged as a promising candidate for structure-activity rel...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Ning C,Mo L,Chen X,Tu W,Wu J,Hou S,Xu J

    更新日期:2018-02-15 00:00:00

  • Synthesis of novel oxime-containing pyrazole derivatives and discovery of regulators for apoptosis and autophagy in A549 lung cancer cells.

    abstract::A series of novel oxime-containing pyrazole derivatives were synthesized by the reaction of ethyl 3-phenyl-1H-pyrazole-5-carboxylate derivatives and 2-bromo-1-phenylethanone followed by the reaction with hydroxylamine hydrochloride. The structures were determined by IR, (1)H NMR, HRMS, and X-ray analysis. A dose- and ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Zheng LW,Li Y,Ge D,Zhao BX,Liu YR,Lv HS,Ding J,Miao JY

    更新日期:2010-08-15 00:00:00

  • Identification of Darmstoff analogs as selective agonists and antagonists of lysophosphatidic acid receptors.

    abstract::Darmstoff describes a family of gut smooth muscle-stimulating acetal phosphatidic acids initially isolated and characterized from the bath fluid of stimulated gut over 50 years ago. Despite similar structural and biological profiles, Darmstoff analogs have not previously been examined as potential LPA mimetics. Here, ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Gududuru V,Zeng K,Tsukahara R,Makarova N,Fujiwara Y,Pigg KR,Baker DL,Tigyi G,Miller DD

    更新日期:2006-01-15 00:00:00

  • Exploration of potential prodrug approach of the bis-thiazolium salts T3 and T4 for orally delivered antimalarials.

    abstract::We report here the synthesis and biological evaluation of a series of 37 compounds as precursors of potent antimalarial bis-thiazolium salts (T3 and T4). These prodrugs were either thioester, thiocarbonate or thiocarbamate type and were synthesized in one step by reaction of an alkaline solution of the parent drug wit...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Caldarelli SA,Boisbrun M,Alarcon K,Hamzé A,Ouattara M,Salom-Roig X,Maynadier M,Wein S,Peyrottes S,Pellet A,Calas M,Vial H

    更新日期:2010-07-01 00:00:00

  • Identification of urine metabolites of TFAP, a cyclooxygenase-1 inhibitor.

    abstract::Only a few COX-1-selective inhibitors are currently available, and the research on COX-1 selective inhibitors is not fully developed. The authors have produced several COX-1 selective inhibitors including N-(5-amino-2-pyridinyl)-4-trifluoromethylbenzamide: TFAP (3). Although 3 shows potent analgesic effect without gas...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Kakuta H,Fukai R,Xiaoxia Z,Ohsawa F,Bamba T,Hirata K,Tai A

    更新日期:2010-03-15 00:00:00

  • Conversion of human-selective PPARalpha agonists to human/mouse dual agonists: a molecular modeling analysis.

    abstract::To understand the species selectivity in a series of alpha-methyl-alpha-phenoxy carboxylic acid PPARalpha/gamma dual agonists (1-11), structure-based molecular modeling was carried out in the ligand binding pockets of both human and mouse PPARalpha. This study suggested that interaction of both 4-phenoxy and phenyloxa...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Wang M,Winneroski LL,Ardecky RJ,Babine RE,Brooks DA,Etgen GJ,Hutchison DR,Kauffman RF,Kunkel A,Mais DE,Montrose-Rafizadeh C,Ogilvie KM,Oldham BA,Peters MK,Rito CJ,Rungta DK,Tripp AE,Wilson SB,Xu Y,Zink RW,McCarthy

    更新日期:2004-12-20 00:00:00

  • Antibacterial activity of quinolone-macrocycle conjugates.

    abstract::Novel quinolone-macrocycle conjugates displayed submicromolar antibacterial activity against Escherichia coli and Staphylococcus aureus bacterial strains. An analogous open-chain structure was not active at 100 microM against the same pathogenic strains. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Jefferson EA,Swayze EE,Osgood SA,Miyaji A,Risen LM,Blyn LB

    更新日期:2003-05-19 00:00:00

  • Characterizing hydration sites in protein-ligand complexes towards the design of novel ligands.

    abstract::Water is an essential part of protein binding sites and mediates interactions to ligands. Its displacement by ligand parts affects the free binding energy of resulting protein-ligand complexes. Therefore the characterization of solvation properties is important for design. Of particular interest is the propensity of l...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,评审


    authors: Matter H,Güssregen S

    更新日期:2018-08-01 00:00:00

  • Design and synthesis of hydroxyethylamine (HEA) BACE-1 inhibitors: prime side chromane-containing inhibitors.

    abstract::The structure activity relationship of the prime region of conformationally restricted hydroxyethylamine (HEA) BACE inhibitors is described. Variation of the P1' region provided selectivity over Cat-D with a series of 2,2-dioxo-isothiochromanes and optimization of the P2' substituent of chromane-HEA(s) with polar subs...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Ng RA,Sun M,Bowers S,Hom RK,Probst GD,John V,Fang LY,Maillard M,Gailunas A,Brogley L,Neitz RJ,Tung JS,Pleiss MA,Konradi AW,Sham HL,Dappen MS,Adler M,Yao N,Zmolek W,Nakamura D,Quinn KP,Sauer JM,Bova MP,Ruslim

    更新日期:2013-08-15 00:00:00

  • Macrocyclic hexapeptide analogues of the thrombin receptor (PAR-1) activation motif SFLLRN.

    abstract::The thrombin receptor (PAR-1) is activated by alpha-thrombin to stimulate various cell types, including platelets, through the tethered-ligand sequence SFLLRN. Macrocyclic peptide analogues of SFLLRN were synthesized and evaluated in vitro. In general, the compounds were much less potent in inducing platelet aggregati...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: McComsey DF,Hecker LR,Andrade-Gordon P,Addo MF,Maryanoff BE

    更新日期:1999-01-18 00:00:00

  • Thiol-based angiotensin-converting enzyme 2 inhibitors: P1 modifications for the exploration of the S1 subsite.

    abstract::Screening of a metalloprotease library led to the identification of a thiol-based dual ACE/NEP inhibitor as a potent ACE2 inhibitor. Modifications of the P(1) benzyl moiety led to improvements in ACE2 potency as well as to increased selectivity versus ACE and NEP. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章


    authors: Deaton DN,Gao EN,Graham KP,Gross JW,Miller AB,Strelow JM

    更新日期:2008-01-15 00:00:00