Synthesis and biological evaluation of new symmetric curcumin derivatives.

Abstract:

:A series of novel curcumin bisacetamides aiming of enriching their biological activities have been synthesized. The synthesized compounds were screened for their in vitro antioxidant, anti-inflammatory and cytotoxic activities. All the compounds exhibited potent to good anti-inflammatory, antioxidant and noteworthy cytotoxic activities.

journal_name

Bioorg Med Chem Lett

authors

Sribalan R,Kirubavathi M,Banuppriya G,Padmini V

doi

10.1016/j.bmcl.2015.07.088

subject

Has Abstract

pub_date

2015-10-01 00:00:00

pages

4282-6

issue

19

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(15)00807-0

journal_volume

25

pub_type

杂志文章
  • 2-(Aminomethyl)-benzamide-based glycine transporter type-2 inhibitors.

    abstract::Structure-activity studies on benzamide 1 obtained from library screening led to the discovery of a novel series of potent and selective glycine transporter type-2 inhibitors. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2003.09.080

    authors: Ho KK,Appell KC,Baldwin JJ,Bohnstedt AC,Dong G,Guo T,Horlick R,Islam KR,Kultgen SG,Masterson CM,McDonald E,McMillan K,Morphy JR,Rankovic Z,Sundaram H,Webb M

    更新日期:2004-01-19 00:00:00

  • Submonomer synthesis of azapeptide ligands of the Insulin Receptor Tyrosine Kinase domain.

    abstract::Azapeptide ligands of the Insulin Receptor Tyrosine Kinase (IRTK) were developed by solid-phase submonomer azapeptide synthesis in sufficient isolated yields (36-55%) and purities >95% for structure-activity relationship studies. The azapeptides adopted folded geometries with some proportion of random coil according t...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2014.07.046

    authors: Kurian LA,Silva TA,Sabatino D

    更新日期:2014-09-01 00:00:00

  • Inhibitors of NF-kappaB derived from thalidomide.

    abstract::A series of compounds originally derived from thalidomide were synthesized and evaluated. The most potent compounds in this series, 5HPP-33 and compound 20, inhibited NF-kappaB activation in HeLa cells. Preliminary study indicated that the mechanism of inhibition of NF-kappaB activation is through inhibition of its tr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.01.088

    authors: de-Blanco EJ,Pandit B,Hu Z,Shi J,Lewis A,Li PK

    更新日期:2007-11-01 00:00:00

  • Synthesis of a cosalane analog with an extended polyanionic pharmacophore conferring enhanced potency as an anti-HIV agent.

    abstract::A novel cosalane analog having an extended polyanionic pharmacophore was synthesized in order to target specific cationic residues on the surface of CD4. The design rationale is based on a hypothetical binding model of cosalane to the surface of the protein. The new analog displayed an EC50 of 0.55 microM as an inhibi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00121-8

    authors: Cushman M,Insaf S,Ruell JA,Schaeffer CA,Rice WG

    更新日期:1998-04-07 00:00:00

  • Enantio-dependent binding and transactivation of optically active phenylpropanoic acid derivatives at human peroxisome proliferator-activated receptor alpha.

    abstract::Optically active phenylpropanoic acid derivatives [(S)-5, and (R)-5] were prepared, and their affinities for peroxisome proliferator-activated receptor (PPAR)alpha and PPAR gamma were evaluated. Binding assay and cell-based reporter assay indicated that the activity of these compounds is enantio-dependent, and resides...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(01)00732-6

    authors: Miyachi H,Nomura M,Tanase T,Suzuki M,Murakami K,Awano K

    更新日期:2002-02-11 00:00:00

  • Virtual screening and biochemical evaluation to identify new inhibitors of mammalian target of rapamycin (mTOR).

    abstract::Mammalian target of rapamycin (mTOR) is a promising target for the development of anticancer medicines. Here, we report the first example for a successful application of the structure-based virtual screening to identify new mTOR inhibitors. Using the scoring function improved by implementing the ligand solvation effec...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.12.081

    authors: Park H,Choe H,Hong S

    更新日期:2014-02-01 00:00:00

  • Discovery and biological evaluation of adamantyl amide 11beta-HSD1 inhibitors.

    abstract::A series of adamantyl amide 11beta-HSD1 inhibitors has been discovered and chemically modified. Selected compounds are selective for 11beta-HSD1 over 11beta-HSD2 and possess excellent cellular potency in human and murine 11beta-HSD1 assays. Good pharmacodynamic characteristics are observed in ex vivo assays. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.02.057

    authors: Webster SP,Ward P,Binnie M,Craigie E,McConnell KM,Sooy K,Vinter A,Seckl JR,Walker BR

    更新日期:2007-05-15 00:00:00

  • CC chemokine receptor-3 (CCR3) antagonists: improving the selectivity of DPC168 by reducing central ring lipophilicity.

    abstract::DPC168, a benzylpiperidine-substituted aryl urea CCR3 antagonist evaluated in clinical trials, was a relatively potent inhibitor of the 2D6 isoform of cytochrome P-450 (CYP2D6). Replacement of the cyclohexyl central ring with saturated heterocycles provided potent CCR3 antagonists with improved selectivity against CYP...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.03.065

    authors: Pruitt JR,Batt DG,Wacker DA,Bostrom LL,Booker SK,McLaughlin E,Houghton GC,Varnes JG,Christ DD,Covington M,Das AM,Davies P,Graden D,Kariv I,Orlovsky Y,Stowell NC,Vaddi KG,Wadman EA,Welch PK,Yeleswaram S,Solomon KA

    更新日期:2007-06-01 00:00:00

  • Synthesis of novel orthoalkylaminophenol derivatives as potent neuroprotective agents in vitro.

    abstract::A series of orthoalkylaminophenol derivatives was synthesized and tested in vitro with respect to their neuroprotective effect. Some of these compounds exhibited a potent antioxidant activity close to that of standard alpha-tocopherol. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00504-1

    authors: Larget R,Lockhart B,Pfeiffer B,Neudorffer A,Fleury MB,Largeron M

    更新日期:1999-10-18 00:00:00

  • Solid-phase parallel synthesis of azarene pyrrolidinones as factor Xa inhibitors.

    abstract::A focused library (4 x 14) prepared from 4-aminopyridine and 4-, 5-, and 6-azoindole templates was synthesized using 14 polymer supported 4-amido-2,3,5,6-tetrafluorophenyl (TFP) sulfonate esters inputs. Several compounds were identified as factor Xa inhibitors (IC50< or =0.1 microM) helping to establish the SAR among ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00151-7

    authors: Gong Y,Becker M,Choi-Sledeski YM,Davis RS,Salvino JM,Chu V,Brown KD,Pauls HW

    更新日期:2000-05-15 00:00:00

  • Design, synthesis and biological activity evaluation of novel 4-((1-cyclopropyl-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-yl) oxy) pyridine-2-yl) amino derivatives as potent transforming growth factor-β (TGF-β) type I receptor inhibitors.

    abstract::TGF-β type I receptor (also known as activin-like kinase 5 or ALK5) plays a critical role in the progression of fibrotic diseases and tumor invasiveness and metastasis, as well. The development of small inhibitors targeting ALK5 has been validated as a potential therapeutic strategy for fibrotic diseases and cancer. H...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127339

    authors: Tan B,Zhang X,Quan X,Zheng G,Li X,Zhao L,Li W,Li B

    更新日期:2020-08-15 00:00:00

  • Discovery of 3-aminopicolinamides as metabotropic glutamate receptor subtype 4 (mGlu4) positive allosteric modulator warheads engendering CNS exposure and in vivo efficacy.

    abstract::This letter describes the further chemical optimization of the picolinamide-derived family of mGlu4 PAMs wherein we identified a 3-amino substituent to the picolinamide warhead that engendered potency, CNS penetration and in vivo efficacy. From this optimization campaign, VU0477886 emerged as a potent (EC50=95nM, 89% ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.04.041

    authors: Gogliotti RD,Engers DW,Garcia-Barrantes PM,Panarese JD,Gentry PR,Blobaum AL,Morrison RD,Daniels JS,Thompson AD,Jones CK,Conn PJ,Niswender CM,Lindsley CW,Hopkins CR

    更新日期:2016-06-15 00:00:00

  • Development of an affinity-driven cross-linker: isolation of a vitamin D receptor associated factor.

    abstract::A vitamin D analogue containing an affinity and a photoaffinity probe (affinity-driven cross-linker, Double Label) was synthesized. An unknown factor, associated with vitamin D receptor (VDR), was isolated from rat liver nuclear extract using a GST-VDR-ligand-binding domain fusion protein (GST-VDR-LBD), affinity label...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00009-3

    authors: Swamy N,Addo JK,Ray R

    更新日期:2000-02-21 00:00:00

  • Synthesis and evaluation of 4-deacetoxyagosterol A as an MDR-modulator.

    abstract::4-Deacetoxyagosterol A was synthesized from ergosterol by utilizing reductive regioselective epoxy cleavage as a key reaction. This synthesized congener of agosterol A, a spongean MDR-modulator. showed similar MDR-modulating activity against KB CV-60 cells overexpressing MRP. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00502-3

    authors: Murakami N,Sugimoto M,Morita M,Akiyama S,Kobayashi M

    更新日期:2000-11-20 00:00:00

  • Synthesis and antitumor activity of leinamycin derivatives: modifications of C-8 hydroxy and C-9 keto groups.

    abstract::A series of leinamycin derivatives were synthesized and evaluated for antitumor activity. Modifications at C-8 and C-9 positions revealed a broad structure-activity relationship in vitro and some derivatives showed potent antiproliferative activity against HeLa S3 cells. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(98)00133-4

    authors: Kanda Y,Ashizawa T,Saitoh Y,Saito H,Gomi K,Okabe M

    更新日期:1998-04-21 00:00:00

  • cis-6-oxo-hexahydro-2-oxa-1,4-diazapentalene and cis-6-oxo-hexahydropyrrolo[3,2-c]pyrazole based scaffolds: design rationale, synthesis and cysteinyl proteinase inhibition.

    abstract::The 5,5-bicycles cis-6-oxo-hexahydro-2-oxa-1,4-diazapentalene 3 and cis-6-oxo-hexahydropyrrolo[3,2-c]pyrazole 4 were designed as rotationally restricted templates towards the preparation of inhibitors of CAC1 cysteinyl proteinases. The design strategy was exemplified through the solution and solid phase preparation of...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.01.022

    authors: Wang Y,Benn A,Flinn N,Monk T,Ramjee M,Watts J,Quibell M

    更新日期:2005-03-01 00:00:00

  • Pyrrolidine-carboxamides and oxadiazoles as potent hNK1 antagonists.

    abstract::The preparation and structure-activity-relationships of novel pyrrolidine-carboxamides and oxadiazoles are described. Compounds in this series were found to be potent hNK(1) antagonists in vitro and efficacious in vivo with minimal interactions with P(450) liver enzymes. Oxadiazole analog 22 was determined to have exc...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.08.028

    authors: Young JR,Eid R,Turner C,DeVita RJ,Kurtz MM,Tsao KL,Chicchi GG,Wheeldon A,Carlson E,Mills SG

    更新日期:2007-10-01 00:00:00

  • Discovery of potent selective bioavailable phosphodiesterase 2 (PDE2) inhibitors active in an osteoarthritis pain model. Part II: optimization studies and demonstration of in vivo efficacy.

    abstract::Selective phosphodiesterase 2 (PDE2) inhibitors are shown to have efficacy in a rat model of osteoarthritis (OA) pain. We identified potent, selective PDE2 inhibitors by optimizing residual PDE2 activity in a series of phosphodiesterase 4 (PDE4) inhibitors, while minimizing PDE4 inhibitory activity. These newly design...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.03.082

    authors: Plummer MS,Cornicelli J,Roark H,Skalitzky DJ,Stankovic CJ,Bove S,Pandit J,Goodman A,Hicks J,Shahripour A,Beidler D,Lu XK,Sanchez B,Whitehead C,Sarver R,Braden T,Gowan R,Shen XQ,Welch K,Ogden A,Sadagopan N,Baum H

    更新日期:2013-06-01 00:00:00

  • Analogues and derivatives of ciproxifan, a novel prototype for generating potent histamine H3-receptor antagonists.

    abstract::Novel derivatives of the highly potent and selective histamine H3-receptor antagonist ciproxifan (3) with different chain lengths as well as with structural variants of the cyclopropyl ketone moiety have been prepared and screened for their antagonist H3-receptor potencies in vitro and in vivo. Some derivatives (2, 6-...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00473-x

    authors: Stark H,Ligneau X,Sadek B,Ganellin CR,Arrang JM,Schwartz JC,Schunack W

    更新日期:2000-10-16 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

    doi:10.1016/j.bmcl.2004.09.031

    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

  • Identification of arylsulfonamides as Aquaporin 4 inhibitors.

    abstract::Carbonic anhydrase inhibitors AZA, EZA, and 4-acetamidobenzsulfonamide were found to inhibit human AQP4-M23 mediated water transport by 80%, 68%, and 23%, respectively, at 20 microM in an in vitro functional assay. AZA was found to have an IC50 against AQP4 of 0.9 microM. Phloretin was inactive under the same conditio...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.12.010

    authors: Huber VJ,Tsujita M,Yamazaki M,Sakimura K,Nakada T

    更新日期:2007-03-01 00:00:00

  • Synthesis, antiviral activity and pharmacokinetics of P1/P1' substituted 3-aminoindazole cyclic urea HIV protease inhibitors.

    abstract::A series of P1/P1' substituted cyclic urea analogues were prepared in an attempt to increase the intra-cellular antiviral potency of the nonsymmetrical 3-aminoindazoles DMP 850 and DMP 851. The effect of alkyl substitution of the P1/P1' residues on cellular antiviral potency, protein binding, resistance profile and ph...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)01064-8

    authors: Kaltenbach RF 3rd,Patel M,Waltermire RE,Harris GD,Stone BR,Klabe RM,Garber S,Bacheler LT,Cordova BC,Logue K,Wright MR,Erickson-Viitanen S,Trainor GL

    更新日期:2003-02-24 00:00:00

  • Inhibition of carbonic anhydrase isozymes I, II and IX with benzenesulfonamides containing an organometallic moiety.

    abstract::A novel series of benzenesulfonamides that contain ferrocenyl or ruthenocenyl moieties were synthesized and investigated for their ability to inhibit the enzymatic activity of physiologically relevant carbonic anhydrase (CA) isozymes: hCA I, II and tumour-associated IX (h=human). This manuscript describes the regiosel...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.07.024

    authors: Salmon AJ,Williams ML,Innocenti A,Vullo D,Supuran CT,Poulsen SA

    更新日期:2007-09-15 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

    doi:10.1016/j.bmcl.2007.11.048

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

    更新日期:2008-01-15 00:00:00

  • Nonbenzamidine acylsulfonamide tissue factor-factor VIIa inhibitors.

    abstract::Aminoisoquinoline and isoquinoline groups have successfully replaced the more basic P1 benzamidine group of an acylsulfonamide factor VIIa inhibitor. Inhibitory activity was optimized by the identification of additional hydrophobic and hydrophilic P' binding interactions. The molecular details of these interactions we...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.06.027

    authors: Glunz PW,Zhang X,Zou Y,Delucca I,Nirschl AH,Cheng X,Weigelt CA,Cheney DL,Wei A,Anumula R,Luettgen JM,Rendina AR,Harpel M,Luo G,Knabb R,Wong PC,Wexler RR,Priestley ES

    更新日期:2013-09-15 00:00:00

  • Generation of novel radiolabeled opiates through site-selective iodination.

    abstract::Tritiated opioid radioligands have proven valuable in exploring opioid binding sites. However, tritium has many limitations. Its low specific activity and limited counting efficiency makes it difficult to examine low abundant, high affinity sites and its disposal is problematic due to the need to use organic scintilla...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.05.008

    authors: Majumdar S,Burgman M,Haselton N,Grinnell S,Ocampo J,Pasternak AR,Pasternak GW

    更新日期:2011-07-01 00:00:00

  • Synthesis of PET probe O6-[(3-[11C]methyl)benzyl]guanine by Pd0-mediated rapid C-[11C]methylation toward imaging DNA repair protein O6-methylguanine-DNA methyltransferase in glioblastoma.

    abstract::O6-Benzylguanine (O6-BG) is a substrate of O6-methylguanine-DNA methyltransferase (MGMT), which is involved in drug resistance of chemotherapy in the majority of glioblastoma multiform. For clinical diagnosis, it is hoped that the MGMT expression level could be determined by a noninvasive method to understand the deta...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2017.03.045

    authors: Koyama H,Ikenuma H,Toda H,Kondo G,Hirano M,Kato M,Abe J,Yamada T,Wakabayashi T,Ito K,Natsume A,Suzuki M

    更新日期:2017-05-01 00:00:00

  • Discovery of substituted (4-phenyl-1H-imidazol-2-yl)methanamine as potent somatostatin receptor 3 agonists.

    abstract::We report SAR studies on a novel non-peptidic somatostatin receptor 3 (SSTR3) agonist lead series derived from (4-phenyl-1H-imidazol-2-yl)methanamine. This effort led to the discovery of a highly potent low molecular weight SSTR3 agonist 5c (EC50=5.2 nM, MW=359). The results from molecular overlays of 5c onto the L-12...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2015.06.087

    authors: Lai Z,He S,Sherer EC,Wu Z,Yu Y,Ball R,Hong Q,Yang DX,Guo L,Li D,Tuang Q,Chicchi GG,Trusca D,Tsao KL,Zhou YP,Howard AD,Nargund RP,Hagmann WK

    更新日期:2015-09-01 00:00:00

  • A bivalent ligand (KMN-21) antagonist for mu/kappa heterodimeric opioid receptors.

    abstract::In an effort to develop antagonists for kappa-mu opioid receptor heterodimers, a series of bivalent ligands 3-6 containing kappa- and mu-antagonist pharmacophores were designed and synthesized. Evaluation of the series in HEK-293 cells revealed 4 (KMN-21) to selectively antagonize the activation of kappa-mu heterodime...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.10.045

    authors: Zhang S,Yekkirala A,Tang Y,Portoghese PS

    更新日期:2009-12-15 00:00:00

  • 2,4,5-Tris(alkoxyaryl)imidazoline derivatives as potent scaffold for novel p53-MDM2 interaction inhibitors: Design, synthesis, and biological evaluation.

    abstract::Imidazoline-based small molecule inhibitors of p53-MDM2 interaction intended for the treatment of p53 wild-type tumors are the promising structures for design of anticancer drugs. Based on fragment approach we have investigated a key role of substituents in cis-imidazoline core for biological activity of nutlin family...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2019.06.007

    authors: Bazanov DR,Pervushin NV,Savitskaya VY,Anikina LV,Proskurnina MV,Lozinskaya NA,Kopeina GS

    更新日期:2019-08-15 00:00:00