Synthesis, biological evaluation of prenylflavonoids as vasorelaxant and neuroprotective agents.

Abstract:

:A series of prenylflavonoids with multiple hydroxyl groups were synthesized and evaluated for their vasorelaxant activities against rat aorta rings pre-contracted by phenylephrine (PE), as well as their neuroprotective effects against OGD induced PC12 cell injury. The results indicated that the prenyl group at A-ring of prenylflavonoids, as well as hydroxyl groups at B-ring was important for their activities. (+/-)Leachianone G 1b, bearing 8-prenyl and 2',4'-dihydoxyl groups, exhibited the most potent vasorelaxant and neuroprotective effects.

journal_name

Bioorg Med Chem Lett

authors

Dong X,Qi L,Jiang C,Chen J,Wei E,Hu Y

doi

10.1016/j.bmcl.2009.04.120

subject

Has Abstract

pub_date

2009-06-15 00:00:00

pages

3196-8

issue

12

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(09)00630-1

journal_volume

19

pub_type

杂志文章
  • Synthesis of bivalent lactosides and their activity as sensors for differences between lectins in inter- and intrafamily comparisons.

    abstract::The synthesis of nine bivalent lactosides (based on ditriazoles, diamides, a glycocyclophane and an acyclic analogue of the glycocyclophane) and one monovalent lactosyl triazole facilitated the assessment of the sensitivity of plant/animal lectins to this type of ligand display. The inhibitory potency of the compounds...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.11.010

    authors: André S,Jarikote DV,Yan D,Vincenz L,Wang GN,Kaltner H,Murphy PV,Gabius HJ

    更新日期:2012-01-01 00:00:00

  • Design, synthesis and in vitro evaluation of benzothiazole-based ureas as potential ABAD/17β-HSD10 modulators for Alzheimer's disease treatment.

    abstract::Amyloid-beta peptide (Aβ) has been recognized to interact with numerous proteins, which may lead to pathological changes in cell metabolism of Alzheimer's disease (AD) patients. One such known metabolic enzyme is mitochondrial amyloid-binding alcohol dehydrogenase (ABAD), also known as 17β-hydroxysteroid dehydrogenase...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.05.087

    authors: Hroch L,Benek O,Guest P,Aitken L,Soukup O,Janockova J,Musil K,Dohnal V,Dolezal R,Kuca K,Smith TK,Gunn-Moore F,Musilek K

    更新日期:2016-08-01 00:00:00

  • Austalides V and W, new meroterpenoids from the fungus Aspergillus ustus and their antitumor activities.

    abstract::Two new austalide meroterpenoids, named austalides V and W (1 and 2), were isolated from the fungus Aspergillus ustus VKM F-4692. Their structures were elucidated by extensive spectroscopic analysis and by comparison with related known compounds. The main structural feature of both compounds is a tetrahydrofuranyl rin...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.126708

    authors: Antipova TV,Zaitsev KV,Oprunenko YF,Ya Zherebker A,Rystsov GK,Zemskova MY,Zhelifonova VP,Ivanushkina NE,Kozlovsky AG

    更新日期:2019-11-15 00:00:00

  • Synthesis and pharmacological evaluation of the stereoisomers of 3-carba cyclic-phosphatidic acid.

    abstract::Cyclic phosphatidic acid (CPA) is a naturally occurring analog of lysophosphatidic acid (LPA) in which the sn-2 hydroxy group forms a five-membered ring with the sn-3 phosphate. Here, we describe the synthesis of R-3-CCPA and S-3-CCPA along with their pharmacological properties as inhibitors of lysophospholipase D/aut...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.09.115

    authors: Gupte R,Siddam A,Lu Y,Li W,Fujiwara Y,Panupinthu N,Pham TC,Baker DL,Parrill AL,Gotoh M,Murakami-Murofushi K,Kobayashi S,Mills GB,Tigyi G,Miller DD

    更新日期:2010-12-15 00:00:00

  • Synthesis of 7,8-disubstituted benzolactam-V8 and its binding to protein kinase C.

    abstract::7-Methoxy-8-decynyl-benzolactam-V8 4 is synthesized using a catalytic asymmetric alkylation reaction as a key step. This compound shows potent activity to three PKC isozymes tested (Ki =45.6, 91.1, and 121.3 nM to PKCalpha, delta, and epsilon, respectively), indicating that introduction of a suitable substituent at th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00609-0

    authors: Ma D,Zhang T,Wang G,Kozikowski AP,Lewin NE,Blumberg PM

    更新日期:2001-01-22 00:00:00

  • trans-3,4-Disubstituted pyrrolidines as inhibitors of the human aspartyl protease renin. Part II: prime site exploration using an oxygen linker.

    abstract::Inhibition of the aspartyl protease renin is considered as an efficient approach for treating hypertension. Lately, we described the discovery of a novel class of direct renin inhibitors which comprised a pyrrolidine scaffold (e.g., 2). Based on the X-ray structure of the lead compound 2 bound to renin we predicted th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.02.040

    authors: Sellner H,Cottens S,Cumin F,Ehrhardt C,Kosaka T,Lorthiois E,Ostermann N,Webb RL,Rigel DF,Wagner T,Maibaum J

    更新日期:2015-04-15 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

    doi:10.1016/j.bmcl.2016.01.059

    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

  • Five-coordinated oxovanadium(IV) complexes derived from amino acids and ciprofloxacin: synthesis, spectral, antimicrobial, and DNA interaction approach.

    abstract::Five-coordinated oxovanadium(IV) complexes with ciprofloxacin and various uninegative bidentate amino acids have been prepared. The structure of complexes has been investigated using spectral, physicochemical, mass spectroscopy, and elemental analyses. The antimicrobial activities (MIC) of the complexes, ligands, meta...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.10.068

    authors: Patel MN,Patel SH,Chhasatia MR,Parmar PA

    更新日期:2008-12-15 00:00:00

  • Discovery of TD-4306, a long-acting β2-agonist for the treatment of asthma and COPD.

    abstract::A multivalent approach focused on amine-based secondary binding groups was applied to the discovery of long-acting inhaled β2-agonists. Addition of amine moieties to the neutral secondary binding group of an existing β2-agonist series was found to provide improved in vivo efficacy, but also led to the formation of bio...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.04.095

    authors: McKinnell RM,Klein U,Linsell MS,Moran EJ,Nodwell MB,Pfeiffer JW,Thomas GR,Yu C,Jacobsen JR

    更新日期:2014-07-01 00:00:00

  • Discovery, SAR, and X-ray structure of novel biaryl-based dipeptidyl peptidase IV inhibitors.

    abstract::The discovery, SAR, and X-ray crystal structure of novel biarylaminoacyl-(S)-2-cyano-pyrrolidines and biarylaminoacylthiazolidines as potent inhibitors of dipeptidyl peptidase IV (DPP IV) are reported. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.09.037

    authors: Qiao L,Baumann CA,Crysler CS,Ninan NS,Abad MC,Spurlino JC,Desjarlais RL,Kervinen J,Neeper MP,Bayoumy SS,Williams R,Deckman IC,Dasgupta M,Reed RL,Huebert ND,Tomczuk BE,Moriarty KJ

    更新日期:2006-01-01 00:00:00

  • Proapoptotic modification of substituted isoindolinones as MDM2-p53 inhibitors.

    abstract::A series of novel amino acid ester derivatives of 2,3-substituted isoindolinones was synthesized and evaluated for p53-mediated apoptotic activity. The rationale for augmentation of the target activity of 2,3-substituted isoindolinones was based on the introduction of new fragments in the structure of the inhibitor th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.10.049

    authors: Grigoreva TA,Novikova DS,Petukhov AV,Gureev MA,Garabadzhiu AV,Melino G,Barlev NA,Tribulovich VG

    更新日期:2017-12-01 00:00:00

  • 1,3,4-Trisubstituted pyrrolidine CCR5 receptor antagonists: modifications of the arylpropylpiperidine side chains.

    abstract::The 4-(3-phenylprop-1-yl)piperidine moiety of the 1,3,4-trisubstituted pyrrolidine CCR5 antagonist 1 was modified with electron deficient aromatics as well as replacement of the benzylic methylene with sulfones, gem-difluoromethylenes and alcohols in an effort to balance the antiviral potency with reasonable pharmacok...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00829-6

    authors: Lynch CL,Willoughby CA,Hale JJ,Holson EJ,Budhu RJ,Gentry AL,Rosauer KG,Caldwell CG,Chen P,Mills SG,MacCoss M,Berk S,Chen L,Chapman KT,Malkowitz L,Springer MS,Gould SL,DeMartino JA,Siciliano SJ,Cascieri MA,Carella

    更新日期:2003-01-06 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

  • New cytotoxic and anti-inflammatory steroids from the soft coral Klyxum flaccidum.

    abstract::Four new steroids, namely klyflaccisteroids G-J (1-4) were isolated from the Formosan soft coral Klyxum flaccidum. The structures of compounds 1-4 were established by spectral data analysis (IR, MS, 1D and 2D NMR) and comparison of spectral data with those of the related known compounds. Cytotoxicity assay revealed th...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.05.060

    authors: Tseng WR,Huang CY,Tsai YY,Lin YS,Hwang TL,Su JH,Sung PJ,Dai CF,Sheu JH

    更新日期:2016-07-15 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

    doi:10.1016/j.bmcl.2007.08.019

    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

  • Peptidyl aldehyde inhibitors of calpain incorporating P2-proline mimetics.

    abstract::Four new peptidyl aldehydes bearing proline mimetics at the P(2)-position were synthesized and studied as inhibitors of calpain I, cathepsin B, and selected serine proteases. The ring size of the P(2)-constraining residue influenced the inhibitory potency and selectivity of the compounds for calpain I compared to the ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(03)00021-0

    authors: Donkor IO,Korukonda R,Huang TL,LeCour L Jr

    更新日期:2003-03-10 00:00:00

  • Peptide-based inhibitors of protein-protein interactions.

    abstract::Protein-protein interactions (PPIs) are key elements of several important biological processes and have emerged as valuable targets in medicinal chemistry. Importantly, numerous specific protein-protein interactions (e.g., p53-HDM2 and Bcl-2-BH3 domains) were found to be involved in the development of several diseases...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmcl.2015.12.084

    authors: Wójcik P,Berlicki Ł

    更新日期:2016-02-01 00:00:00

  • Arylmethoxypyridines as novel, potent and orally active mGlu5 receptor antagonists.

    abstract::Optimisation of affinity, chemical stability, metabolic stability and solubility led from a chemically labile HTS hit 1 to mGlu5 receptor antagonists (24-26) with high affinity for the allosteric MPEP binding site, improved microsomal metabolic stability and anxiolytic-like activity in vivo as assessed by the Vogel co...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.12.088

    authors: Büttelmann B,Peters JU,Ceccarelli S,Kolczewski S,Vieira E,Prinssen EP,Spooren W,Schuler F,Huwyler J,Porter RH,Jaeschke G

    更新日期:2006-04-01 00:00:00

  • Synthesis and 5 alpha-reductase inhibitory activities of benzofuran derivatives with a carbamoyl group.

    abstract::A series of 2-phenylbenzofuran derivatives with a diphenylmethylcarbamoyl group at the 5 or 6 position of the benzofuran ring were synthesized and evaluated for rat and human testosterone 5 alpha-reductase inhibitory activities in vitro. They had inhibitory activities against both enzymes and the 6-carbamoyl derivativ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00001-8

    authors: Ishibashi K,Nakajima K,Sugioka Y,Sugiyama M,Hamada T,Horikoshi H,Nishi T

    更新日期:1998-03-17 00:00:00

  • Synthesis of miltirone analogues as inhibitors of Cdc25 phosphatases.

    abstract::Miltirone analogues were synthesized and evaluated for inhibitory activity against Cdc25 and PTP1B. Most of the compounds demonstrated potent Cdc25 inhibitory activity, and several exhibited higher selectivity for Cdc25 than for PTP1B. In a cytotoxic assay, most of the compounds displayed cytotoxicity against the tumo...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.12.080

    authors: Huang W,Li J,Zhang W,Zhou Y,Xie C,Luo Y,Li Y,Wang J,Li J,Lu W

    更新日期:2006-04-01 00:00:00

  • Complanadine A, a selective agonist for the Mas-related G protein-coupled receptor X2.

    abstract::The first biological target for the natural product complanadine A has been determined. The pseudosymmetric alkaloid functions as a selective agonist for the Mas-related G protein-coupled receptor X2 (MrgprX2), a G protein-coupled receptor that is highly expressed in neurons. Given the potential of MrgprX2 to function...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.05.060

    authors: Johnson T,Siegel D

    更新日期:2014-08-01 00:00:00

  • Novel antifungals based on 4-substituted imidazole: solid-phase synthesis of substituted aryl sulfonamides towards optimization of in vitro activity.

    abstract::The in vitro activity of novel 4-substituted imidazole antifungals was optimized by solid-phase chemistry and parallel synthesis. Potent yeast-selective as well as broad-spectrum antifungal compounds (32 and 20) were discovered. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00551-5

    authors: Saha AK,Liu L,Marichal P,Odds F

    更新日期:2000-12-18 00:00:00

  • Isoindol-1,3-dione and isoindol-1-one derivatives with high binding affinity to beta-amyloid fibrils.

    abstract::Based on the structural features of Indoprofen and PIB, a series of isoindol-1,3-diones 1a-k and isoindol-1-ones 2a-l were designed and synthesized. These 23 compounds were evaluated by competitive binding assay against aggregated Abeta42 fibrils using [(125)I]TZDM. All the isoindolone derivatives showed very good bin...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.01.066

    authors: Lee HJ,Lim SJ,Oh SJ,Moon DH,Kim DJ,Tae J,Yoo KH

    更新日期:2008-03-01 00:00:00

  • Discovery and optimization of (R)-prolinol-derived agonists of the Growth Hormone Secretagogue receptor (GHSR).

    abstract::The discovery and optimization of a novel series of prolinol-derived GHSR agonists is described. This series emerged from a 11,520-member solid-phase library targeting the GPCR protein superfamily, and the rapid optimization of low micromolar hits into single-digit nanomolar leads can be attributed to the solid-phase ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.07.120

    authors: Zhai W,Flynn N,Longhi DA,Tino JA,Murphy BJ,Slusarchyk D,Gordon DA,Pendri A,Shi S,Stoffel R,Ma B,Sofia MJ,Gerritz SW

    更新日期:2008-09-15 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

    doi:10.1016/s0960-894x(98)00589-7

    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

  • Identification of synthetic compounds active against VRE: the role of the lipidated aminoglucose and the structure of glycopeptide binding pocket.

    abstract::A modified vancomycin binding pocket (D-O-E ring) incorporating an alpha-hydroxy-beta-amino acid at the AA4 position is designed and synthesized. Some of these compounds display potent bioactivities against both sensitive- and resistant-strains (8 microg/ml against VREF). Both the lipidated aminoglucose and the struct...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.06.098

    authors: Jia Y,Gonzalez-Zamora E,Ma N,Liu Z,Bois-Choussy M,Malabarba A,Brunati C,Zhu J

    更新日期:2005-10-15 00:00:00

  • Synthesis and structure-activity relationship of 3,4'-bispyridinylethylenes: discovery of a potent 3-isoquinolinylpyridine inhibitor of protein kinase B (PKB/Akt) for the treatment of cancer.

    abstract::Structure-based design and synthesis of the 3,4'-bispyridinylethylene series led to the discovery of 3-isoquinolinylpyridine 13a as a potent PKB/Akt inhibitor with an IC(50) of 1.3nM against Akt1. Compound 13a shows excellent selectivity against distinct families of kinases such as tyrosine kinases and CAMK, and displ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.12.065

    authors: Li Q,Woods KW,Thomas S,Zhu GD,Packard G,Fisher J,Li T,Gong J,Dinges J,Song X,Abrams J,Luo Y,Johnson EF,Shi Y,Liu X,Klinghofer V,Des Jong R,Oltersdorf T,Stoll VS,Jakob CG,Rosenberg SH,Giranda VL

    更新日期:2006-04-01 00:00:00

  • The synthesis and selective IL-2 inhibitory activity of bis piperazine-phenol Mannich adducts.

    abstract::Novel phenol bis-Mannich adducts were identified as IL-2 expression inhibitors in a T cell proliferation screening assay. Analogues of the lead compound were prepared through parallel synthesis and a highly selective IL-2 inhibitor was discovered that provided a suitable compound for further optimization. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00011-2

    authors: Geng B,Fleming PR,Umlauf S,Lin A,Pallai PV

    更新日期:2002-03-11 00:00:00

  • Targeting EGFR/HER2 tyrosine kinases with a new potent series of 6-substituted 4-anilinoquinazoline hybrids: Design, synthesis, kinase assay, cell-based assay, and molecular docking.

    abstract::Coexpression of EGFR and HER2 has been found in many tumors such as breast, ovarian, colon and prostate cancers, with poor prognosis of the patients. Herein, our team has designed and synthesized new eighteen compounds with 6-substituted 4-anilinoquinazoline core to selectively inhibit EGFR/HER2 tyrosine kinases. Twel...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.10.003

    authors: Elkamhawy A,Farag AK,Viswanath AN,Bedair TM,Leem DG,Lee KT,Pae AN,Roh EJ

    更新日期:2015-11-15 00:00:00

  • 1-(2-Naphthyl)-1H-pyrazole-5-carboxylamides as potent factor Xa inhibitors. Part 2: A survey of P4 motifs.

    abstract::A variety of P4 motifs have been examined to increase the binding affinity and in vitro anticoagulant potency of our biphenyl 1-(2-naphthyl)-1H-pyrazole-5-carboxylamide-based fXa inhibitors. Highly potent 2-naphthyl-P1 fXa inhibitors (K(i)< or =2 nM) with improved in vitro anticoagulant activity (2xTG< or =1 microM) a...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.12.053

    authors: Jia ZJ,Wu Y,Huang W,Zhang P,Clizbe LA,Goldman EA,Sinha U,Arfsten AE,Edwards ST,Alphonso M,Hutchaleelaha A,Scarborough RM,Zhu BY

    更新日期:2004-03-08 00:00:00