Preparation of L-alpha-phosphatidyl-D-myo-inositol 3-phosphate (3-PIP) and 3,5-bisphosphate (3,5-PIP2).

Abstract:

:Practical, asymmetric total syntheses of the title phospholipids from a readily available myo-inositol derivative as well as short chain and cross-linkable aminoether analogues are described.

journal_name

Bioorg Med Chem Lett

authors

Falck JR,Krishna UM,Capdevila JH

doi

10.1016/s0960-894x(00)00315-2

subject

Has Abstract

pub_date

2000-08-07 00:00:00

pages

1711-3

issue

15

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(00)00315-2

journal_volume

10

pub_type

杂志文章
  • 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

    doi:10.1016/s0960-894x(03)00285-3

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

    更新日期:2003-05-19 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

    doi:10.1016/j.bmcl.2004.12.036

    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

  • Cyclopenta[g]quinazoline-based antifolates: the effect of the chirality at the 6-position on the inhibition of thymidylate synthase (TS).

    abstract::Cyclopenta[g]quinazoline-based inhibitors of thymidylate synthase (TS) possess a chiral centre at the 6-position of the molecule. The effect of this chirality on the inhibition of TS was investigated by synthesising compounds 6S-1a-c, 6R-1a-c. It was shown, in particular with the diastereoisomers 6S-1c, 6R-1c, that th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00612-6

    authors: Bavetsias V,Marriott JH,Theti DS,Melin JC,Wilson SC,Jackman AL

    更新日期:2001-12-03 00:00:00

  • Rapid nuclear import of short nucleic acids.

    abstract::Exogenous short-chain nucleic acids undergo rapid import into the nucleus. Fluorescence-labeled dT1-13 DNA microinjected into the cytoplasm domain of a HeLa cell was rapidly imported into the nucleus domain within 1min. This is much more rapid than what has been observed for intracellular diffusion of small molecules....

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.08.085

    authors: Kitagawa M,Okamoto A

    更新日期:2016-10-01 00:00:00

  • The synthesis and biological evaluation of dopamine transporter inhibiting activity of substituted diphenylmethoxypiperidines.

    abstract::The synthesis of potent 4-aryl methoxypiperidinol inhibitors of the dopamine transporter is described. Symmetrical para substituents of the benzene rings are important for high potency in binding to the dopamine transporter. 4-[Bis(4-fluorophenyl) methoxy]-1-methylpiperidine has an IC50 of 22.1+/-5.73 nM and increases...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.08.028

    authors: Lapa GB,Byrd GD,Lapa AA,Budygin EA,Childers SR,Jones SR,Harp JJ

    更新日期:2005-11-15 00:00:00

  • Diastereoselective synthesis of fused cyclopropyl-3-amino-2,4-oxazine β-amyloid cleaving enzyme (BACE) inhibitors and their biological evaluation.

    abstract::The diastereoselective synthesis and structure activity relationship (SAR) of a series of fused cyclopropyl-3-amino-2,4-oxazine (2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine)-containing BACE inhibitors is described. Through these efforts compound 2 was identified as a potent (cell IC50 = 15 nM) BACE inhibitor with accep...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2018.01.056

    authors: Low JD,Bartberger MD,Cheng Y,Whittington D,Xue Q,Wood S,Allen JR,Minatti AE

    更新日期:2018-04-01 00:00:00

  • Substrate and inhibitor specificity of kynurenine monooxygenase from Cytophaga hutchinsonii.

    abstract::Kynurenine monooxygenase (KMO) is a potential drug target for treatment of neurodegenerative disorders such as Huntington's and Alzheimer's diseases. We have evaluated substituted kynurenines as substrates or inhibitors of KMO from Cytophaga hutchinsonii. Kynurenines substituted with a halogen at the 5-position are ex...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.02.080

    authors: Phillips RS,Anderson AD,Gentry HG,Güner OF,Bowen JP

    更新日期:2017-04-15 00:00:00

  • Discovery, synthesis and biochemical profiling of purine-2,6-dione derivatives as inhibitors of the human poly(A)-selective ribonuclease Caf1.

    abstract::Eukaryotic mRNA contains a 3' poly(A) tail, which plays important roles in the regulation of mRNA stability and translation. Well-characterized enzymes involved in the shortening of the poly(A) tail include the multi-subunit Ccr4-Not deadenylase, which contains the Caf1 (Pop2) and Ccr4 catalytic components, and poly(A...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.07.095

    authors: Jadhav GP,Kaur I,Maryati M,Airhihen B,Fischer PM,Winkler GS

    更新日期:2015-10-01 00:00:00

  • Phenylacetic acid regioisomers possessing a N-difluoromethyl-1,2-dihydropyrid-2-one pharmacophore: evaluation as dual inhibitors of cyclooxygenases and 5-lipoxygenase with anti-inflammatory activity.

    abstract::A novel class of phenylacetic acid regioisomers possessing a N-difluoromethyl-1,2-dihydropyrid-2-one pharmacophore attached to its C-2, C-3 or C-4 position was designed for evaluation as anti-inflammatory (AI) agents. A number of compounds exhibited a combination of potent in vitro cyclooxygenase-2 (COX-2) and 5-lipox...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.12.073

    authors: Yu G,Chowdhury MA,Abdellatif KR,Dong Y,Praveen Rao PN,Das D,Velázquez CA,Suresh MR,Knaus EE

    更新日期:2010-02-01 00:00:00

  • Synthesis and inhibitory activity of 4-alkynyl and 4-alkenylquinazolines: identification of new scaffolds for potent EGFR tyrosine kinase inhibitors.

    abstract::The present study identified several 4-alkynyl and 4-alkenylquinazolines that serve as novel and potent EGFR tyrosine kinase inhibitors. The IC(50) values of these compounds are in the nanomolar range. In addition, the 4-(4-phenylbut-1-yn/en-yl)quinazolines provided scaffolds for potent enzyme inhibition. Chiral discr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.08.020

    authors: Kitano Y,Suzuki T,Kawahara E,Yamazaki T

    更新日期:2007-11-01 00:00:00

  • Pyrrolo[2,3-h]quinolinones: synthesis and photochemotherapic activity.

    abstract::A series of derivatives of the new ring system pyrrolo[2,3-h]quinoline-2-one was synthesized and evaluated as photoreagents toward cultured human tumor cells. Remarkable phototoxycity resulted for some derivatives, especially those bearing the phenyl group at the 7-position. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00529-8

    authors: Barraja P,Diana P,Lauria A,Montalbano A,Almerico AM,Dattolo G,Cirrincione G,Viola G,Dall'Acqua F

    更新日期:2003-08-18 00:00:00

  • Tri-substituted acylhydrazines as tertiary amide bioisosteres: HCV NS5B polymerase inhibitors.

    abstract::The use of a tri-substituted acylhydrazine as an isostere of a tertiary amide was explored in a series of HCV NS5B thumb site II inhibitors. Direct replacement generated an analog with similar conformational and physicochemical properties. The series was extended to produce compounds with potent binding affinities and...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.05.025

    authors: Canales E,Carlson JS,Appleby T,Fenaux M,Lee J,Tian Y,Tirunagari N,Wong M,Watkins WJ

    更新日期:2012-07-01 00:00:00

  • Muscarinic acetylcholine receptor binding affinities of pethidine analogs.

    abstract::A series of pethidine analogs were synthesized and their affinities for the [(3)H]N-methyl-scopolamine (NMS) binding site on muscarinic acetylcholine receptors (mAChRs) were determined using M1, M3 or M5 human mAChRs expressed by Chinese hamster ovary (CHO) cell membranes. Compound 6b showed the highest binding affini...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.10.029

    authors: Lee NR,Zhang X,Darna M,Dwoskin LP,Zheng G

    更新日期:2015-11-15 00:00:00

  • Identification of novel 7-amino-5-methyl-1,6-naphthyridin-2(1H)-one derivatives as potent PI3K/mTOR dual inhibitors.

    abstract::Inhibition of the phosphoinositide 3-kinase (PI3K)/AKT/mammalian target of rapamycin (mTOR) signaling pathway is one of the most intensively studied approaches to cancer therapy. Rational design led to the identification of novel 7-amino-5-methyl-1,6-naphthyridin-2(1H)-one derivatives as potent PI3K/mTOR dual inhibito...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.12.112

    authors: Lin S,Han F,Liu P,Tao J,Zhong X,Liu X,Yi C,Xu H

    更新日期:2014-02-01 00:00:00

  • Antioxidative oligostilbenes from Caragana sinica.

    abstract::Two new oligostilbenes, caragasinins A (5) and B (10), and eight known compounds, kobophenol A (1), (+)-α-viniferin (2), (+)-ampelopsin F (3), pallidol (4), (+)-isoampelopsin F (6), miyabenol C (7), carasinaurone (8) and caraphenol B (9) were isolated from the ethylacetate-soluble extract of the roots of Caragana sini...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.12.012

    authors: Jin Q,Han XH,Hong SS,Lee C,Choe S,Lee D,Kim Y,Hong JT,Lee MK,Hwang BY

    更新日期:2012-01-15 00:00:00

  • Discovery of novel antagonists of glycoprotein IIb/IIIa-mediated platelet aggregation through virtual screening.

    abstract::The glycoprotein IIb/IIIa receptor is the final common pathway of platelet aggregation, regardless of the agonist, and thus represents an ideal therapeutic target for blocking thrombus formation. RUC-2 is a novel glycoprotein IIb/IIIa inhibitor of adenosine-5'-diphosphate (ADP)-induced platelet aggregation, importantl...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.01.053

    authors: Wang Y,Zhao Y,Sun R,Kong W,Wang B,Yang G,Li Y

    更新日期:2015-03-15 00:00:00

  • Inhibition of neutral lipid synthesis by avarols from a marine sponge.

    abstract::The effects of 14 sesquiterpene hydroquinones, including 8 marine sponge-derived avarols (1-8) and 6 semisynthetic derivatives (9-14), on lipid droplet accumulation and neutral lipid synthesis in Chinese hamster ovary (CHO) K1 cells were investigated. In intact CHO-K1 cell assays, avarol (1) markedly decreased the num...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.06.026

    authors: Ohshiro T,Kobayashi K,Suzuki A,Yamazaki H,Uchida R,Namikoshi M,Tomoda H

    更新日期:2019-08-15 00:00:00

  • Kinetic investigation of human 5-lipoxygenase with arachidonic acid.

    abstract::Human 5-lipoxygenase (5-LOX) is responsible for the formation of leukotriene (LT)A4, a pivotal intermediate in the biosynthesis of the leukotrienes, a family of proinflammatory lipid mediators. 5-LOX has thus gained attention as a potential drug target. However, details of the kinetic mechanism of 5-LOX are still obsc...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.06.025

    authors: Mittal M,Kumar RB,Balagunaseelan N,Hamberg M,Jegerschöld C,Rådmark O,Haeggström JZ,Rinaldo-Matthis A

    更新日期:2016-08-01 00:00:00

  • Small-molecule microarrays: development of novel linkers and an efficient detection method for bound proteins.

    abstract::Novel isocyanate and diazoketone linkers possessing polyoxypropylenediamine as a spacer for small-molecule microrray are developed. White light interferometry is introduced to detect bound proteins on the glass slides without using chemically modified proteins. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.04.057

    authors: Kurosu M,Mowers WA

    更新日期:2006-07-01 00:00:00

  • Sialidase inhibitory activity of diarylnonanoid and neolignan compounds extracted from the seeds of Myristica fragrans.

    abstract::Sialidases are key virulence factors that remove sialic acid from host cell surface glycans, thus unmasking receptors to facilitate bacterial adherence and colonization. In this study, we report the isolation and characterization of novel inhibitors of the Streptococcus pneumoniae sialidases NanA, NanB, and NanC from ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.05.055

    authors: Park JY,Hwan Lim S,Ram Kim B,Jae Jeong H,Kwon HJ,Song GY,Bae Ryu Y,Song Lee W

    更新日期:2017-07-15 00:00:00

  • Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole and related heterocycles.

    abstract::A series of potent arenavirus inhibitors sharing a benzimidazole core were previously reported by our group. SAR studies were expanded beyond the previous analysis, which involved the attached phenyl rings and methylamino linker portion, to include modifications focused on the benzimidazole core. These changes include...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.11.093

    authors: Burgeson JR,Moore AL,Gharaibeh DN,Larson RA,Cerruti NR,Amberg SM,Hruby DE,Dai D

    更新日期:2013-02-01 00:00:00

  • Design and synthesis of novel PEG-conjugated 20(S)-camptothecin sulfonylamidine derivatives with potent in vitro antitumor activity via Cu-catalyzed three-component reaction.

    abstract::In our continuing search for camptothecin (CPT)-derived antitumor drugs, novel structurally diverse PEG-based 20(S)-CPT sulfonylamidine derivatives were designed, synthesized via a Cu-multicomponent reaction (MCR), and evaluated for cytotoxicity against four human tumor cell lines (A-549, MDA-MB-231, KB, and KBvin). A...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.04.060

    authors: Song ZL,Chen HL,Wang YH,Goto M,Gao WJ,Cheng PL,Morris-Natschke SL,Liu YQ,Zhu GX,Wang MJ,Lee KH

    更新日期:2015-07-01 00:00:00

  • 4-(Alkylthio)- and 4-(arylthio)-benzonitrile derivatives as androgen receptor antagonists for the topical suppression of sebum production.

    abstract::The first examples of thioether-substituted benzonitriles as potential soft-drug androgen receptor antagonists are reported. A number of 4-(alkylthio)- and of 4-(arylthio)-benzonitrile analogs were evaluated in human androgen receptor binding and cellular functional assays. Analogs with potent in vitro binding and cel...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.01.063

    authors: Mitchell L,Wang Z,Hu LY,Kostlan C,Carroll M,Dettling D,Du D,Pocalyko D,Wade K

    更新日期:2009-03-01 00:00:00

  • The sulfamide moiety affords higher inhibitory activity and oral bioavailability to a series of coumarin dual selective RAF/MEK inhibitors.

    abstract::Introducing a sulfamide moiety to our coumarin derivatives afforded enhanced Raf/MEK inhibitory activity concomitantly with an acceptable PK profile. Novel sulfamide 17 showed potent HCT116 cell growth inhibition (IC50=8 nM) and good PK profile (bioavailability of 51% in mouse), resulting in high in vivo antitumor eff...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.10.001

    authors: Aoki T,Hyohdoh I,Furuichi N,Ozawa S,Watanabe F,Matsushita M,Sakaitani M,Ori K,Takanashi K,Harada N,Tomii Y,Tabo M,Yoshinari K,Aoki Y,Shimma N,Iikura H

    更新日期:2013-12-01 00:00:00

  • Novel and highly potent histamine H3 receptor ligands. Part 1: withdrawing of hERG activity.

    abstract::Pre-clinical investigation of some aryl-piperidinyl ether histamine H3 receptor antagonists revealed a strong hERG binding. To overcome this issue, we have developed a QSAR model specially dedicated to H3 receptor ligands. This model was designed to be directly applicable in medicinal chemistry with no need of molecul...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.07.006

    authors: Levoin N,Labeeuw O,Calmels T,Poupardin-Olivier O,Berrebi-Bertrand I,Lecomte JM,Schwartz JC,Capet M

    更新日期:2011-09-15 00:00:00

  • Discovery of furan carboxylate derivatives as novel inhibitors of ATP-citrate lyase via virtual high-throughput screening.

    abstract::The enzyme ATP citrate lyase (ACL) catalyzes the formation of cytosolic acetyl CoA, the starting material for de novo lipid and cholesterol biosynthesis. The dysfunction and upregulation of ACL in numerous cancers makes it an attractive target for developing anticancer therapies. ACL inhibition by shRNA knockdown limi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.01.001

    authors: Jernigan FE,Hanai JI,Sukhatme VP,Sun L

    更新日期:2017-02-15 00:00:00

  • Discovery of novel sphingosine kinase-1 inhibitors. Part 2.

    abstract::Building on our initial work, we have identified additional novel inhibitors of sphingosine kinase-1 (SK1). These new analogs address the shortcomings found in our previously reported compounds. Inhibitors 51 and 54 demonstrated oral bioavailability in a rat PK study. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.06.019

    authors: Xiang Y,Hirth B,Kane JL Jr,Liao J,Noson KD,Yee C,Asmussen G,Fitzgerald M,Klaus C,Booker M

    更新日期:2010-08-01 00:00:00

  • Genotoxic activity of halogenated phenylglycine derivatives.

    abstract::The discovery of genotoxic amino acids derived from phenylglycine, and possessing halogen substituents, is described. The utility of hypervalent iodine reagents in the synthesis of this class of compounds is highlighted. The mechanism of action of the (haloaryl)glycines was studied in Saccharomyces cerevisiae. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.08.111

    authors: Boto A,Gallardo JA,Hernández R,Ledo F,Muñoz A,Murguía JR,Menacho-Márquez M,Orjales A,Saavedra CJ

    更新日期:2006-12-01 00:00:00

  • In vitro inhibition of human erythrocyte glutathione reductase by some new organic nitrates.

    abstract::Glutathione reductase (GR), is responsible for the existence of GSH molecule, a crucial antioxidant against oxidative stress reagents. The antimalarial activities of some redox active compounds are attributed to their inhibition of antioxidant flavoenzyme glutathione reductase, and inhibitors are therefore expected to...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.04.087

    authors: Sentürk M,Talaz O,Ekinci D,Cavdar H,Küfrevioğlu OI

    更新日期:2009-07-01 00:00:00

  • Novel targeting strategy based on multimeric ligands for drug delivery and molecular imaging: homooligomers of alpha-MSH.

    abstract::Homooligomers constructed with 4- and 6-amino acid fragments of melanocortin (alpha-MSH) bind with higher affinity and with apparent cooperativity to melanocortin receptor, compared to their constituent monomers. Individual ligands were tethered with various spacers of different length and rigidity and the influence o...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.09.079

    authors: Vagner J,Handl HL,Gillies RJ,Hruby VJ

    更新日期:2004-01-05 00:00:00