Novel anthraquinone based chalcone analogues containing an imine fragment: synthesis, cytotoxicity and anti-angiogenic activity.

Abstract:

:A new class of imine derivatives of hybrid chalcone analogues containing anthraquinone scaffold was synthesized and evaluated for their in vitro cytotoxic activity against HeLa, LS174, and A549 cancer cells. The compound 5n with furan ring linked to imino group showed potent activity against all target cells with IC50 values ranging from 1.76 to 6.11μM. A mode of action study suggested that compounds induced changes typical for apoptosis in HeLa cells. The most active compounds inhibited tubulogenesis and 5h was found to exhibit a strong anti-angiogenic effect.

journal_name

Bioorg Med Chem Lett

authors

Kolundžija B,Marković V,Stanojković T,Joksović L,Matić I,Todorović N,Nikolić M,Joksović MD

doi

10.1016/j.bmcl.2013.11.075

subject

Has Abstract

pub_date

2014-01-01 00:00:00

pages

65-71

issue

1

eissn

0960-894X

issn

1464-3405

pii

S0960-894X(13)01366-8

journal_volume

24

pub_type

杂志文章
  • Design and synthesis of o-trifluoromethylbiphenyl substituted 2-amino-nicotinonitriles as inhibitors of farnesyltransferase.

    abstract::A non-methionine FT inhibitor lead structure (1) was designed through computer modeling of the peptidomimetic FT inhibitor ABT839. Optimization of this lead resulted in compounds 2e and 2g, with FT IC(50) values of 1.3 and 1.8 nM, GGT IC(50) of 1400 nM, and EC(50) (Ras processing) values of 13 and 11 nM, respectively....

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.10.014

    authors: Wang GT,Wang X,Wang W,Hasvold LA,Sullivan G,Hutchins CW,O'Conner S,Gentiles R,Sowin T,Cohen J,Gu WZ,Zhang H,Rosenberg SH,Sham HL

    更新日期:2005-01-03 00:00:00

  • Design and synthesis of 2-substituted benzoxazoles as novel PTP1B inhibitors.

    abstract::A series of benzoxazole compounds containing oxamic acid were synthesized and screened for the PTP1B inhibition. Compound 31d showed best biochemical potency (Ki) of 6.7 μM. Structure-activity relationship were explained with the help of molecular modeling approach. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.02.109

    authors: Chandrasekharappa AP,Badiger SE,Dubey PK,Panigrahi SK,Manukonda SR

    更新日期:2013-05-01 00:00:00

  • Selective inactivation of triosephosphate isomerase from Trypanosoma cruzi by brevifolin carboxylate derivatives isolated from Geranium bellum Rose.

    abstract::In the search of molecules that can serve as leads in the design of a new drug for the treatment of Chagas' disease, we found that some brevifolin carboxylate derivatives isolated from Geranium bellum Rose, inactivate triosephosphate isomerase from Trypanosoma cruzi (TcTIM) in a species-specific manner. After spectros...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2009.08.055

    authors: Gayosso-De-Lucio J,Torres-Valencia M,Rojo-Domínguez A,Nájera-Peña H,Aguirre-López B,Salas-Pacheco J,Avitia-Domínguez C,Téllez-Valencia A

    更新日期:2009-10-15 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

  • 3,4-Dihydronaphthalen-1(2H)-ones: novel ligands for the benzodiazepine site of alpha5-containing GABAA receptors.

    abstract::A series of substituted 3,4-dihydronaphthalen-1(2H)-ones with high binding affinity for the benzodiazepine site of GABAA receptors containing the alpha5-subunit has been identified. These compounds have consistently higher binding affinity for the GABAA alpha5 receptor subtype over the other benzodiazepine-sensitive G...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2004.03.054

    authors: Szekeres HJ,Atack JR,Chambers MS,Cook SM,Macaulay AJ,Pillai GV,MacLeod AM

    更新日期:2004-06-07 00:00:00

  • 4-Alkyl and 4,4'-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione derivatives as new inhibitors of bacterial cell wall biosynthesis.

    abstract::Over 195 4-alkyl and 4,4-dialkyl 1,2-bis(4-chlorophenyl)pyrazolidine-3,5-dione derivatives were synthesized, utilizing microwave accelerated synthesis, for evaluation as new inhibitors of bacterial cell wall biosynthesis. Many of them demonstrated good activity against MurB in vitro and low MIC values against gram-pos...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.03.058

    authors: Kutterer KM,Davis JM,Singh G,Yang Y,Hu W,Severin A,Rasmussen BA,Krishnamurthy G,Failli A,Katz AH

    更新日期:2005-05-16 00:00:00

  • Thiazolone-acylsulfonamides as novel HCV NS5B polymerase allosteric inhibitors: convergence of structure-based drug design and X-ray crystallographic study.

    abstract::A novel series of thiazolone-acylsulfonamides were designed as HCV NS5B polymerase allosteric inhibitors. The structure based drug designs (SBDD) were guided by docking results that revealed the potential to explore an additional pocket in the allosteric site. In particular, the designed molecules contain moieties of ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.01.024

    authors: Yan S,Appleby T,Larson G,Wu JZ,Hamatake RK,Hong Z,Yao N

    更新日期:2007-04-01 00:00:00

  • Dihydrodibenzothiepine: Promising hydrophobic pharmacophore in the influenza cap-dependent endonuclease inhibitor.

    abstract::This work describes a set of discovery research studies of an influenza cap-dependent endonuclease (CEN) inhibitor with a carbamoyl pyridone bicycle (CAB) scaffold. Using influenza CEN inhibitory activity, antiviral activity and pharmacokinetic (PK) parameters as indices, structure activity relationships (SAR) studies...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2020.127547

    authors: Taoda Y,Miyagawa M,Akiyama T,Tomita K,Hasegawa Y,Yoshida R,Noshi T,Shishido T,Kawai M

    更新日期:2020-11-15 00:00:00

  • Production of aminoglycosides in non-aminoglycoside producing Streptomyces lividans TK24.

    abstract::The pRBM4 cosmid, which harbors a putative cluster of genes spanning a 31.8-kb chromosomal region of the ribostamycin producer Streptomyces ribosidificus ATCC 21294, was heterologously expressed in Streptomyces lividans TK24. ESI-MS/MS, HPLC, and LC-ESI MS analyses showed that the transformation gave rise to ribostamy...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.01.035

    authors: Subba B,Kurumbang NP,Jung YS,Yoon YJ,Lee HC,Liou K,Sohng JK

    更新日期:2007-04-01 00:00:00

  • Convergent solution-phase synthesis of a nucleopeptide using a protected oligonucleotide.

    abstract::A nucleopeptide was prepared in a convergent manner via segmental coupling of the protected biopolymers in solution. The resulting nucleopeptide (4b, 72%) containing the binding site of lambda repressor and a peptide containing the consensus sequence of the DNA binding helix of the helix turn-helix-proteins was obtain...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00051-7

    authors: McMinn DL,Greenberg MM

    更新日期:1999-02-22 00:00:00

  • Inhibition of estrone sulfatase (ES) by derivatives of 4-[(aminosulfonyl)oxy] benzoic acid.

    abstract::In our search for potent inhibitors of the enzyme estrone sulfatase (ES), we have undertaken the synthesis and biochemical evaluation of a range of straight chain alkyl esters of 4-[(aminosulfonyl)oxy] benzoic acid. The results of the study show that the synthesised compounds possess greater inhibitory activity when c...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(02)00383-9

    authors: Ahmed S,James K,Owen CP

    更新日期:2002-09-02 00:00:00

  • Preventive effect of a novel diosgenin derivative on arterial and venous thrombosis in vivo.

    abstract::Current therapy for blood vessel thrombosis has the risk of leading to gastrointestinal bleeding and thrombocytopenia. We previously reported that a new derivative of diosgenin, compound 5, had significant anti-inflammatory activity superior to that of aspirin, prolonged bleeding time, and inhibited platelet aggregati...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.05.032

    authors: Zheng H,Wei Z,Xin G,Ji C,Wen L,Xia Q,Niu H,Huang W

    更新日期:2016-07-15 00:00:00

  • Dicarboxylic acid esters as transdermal permeation enhancers: effects of chain number and geometric isomers.

    abstract::A series of transdermal permeation enhancers based on dicarboxylic acid esters was studied. Single-chain amphiphiles were markedly more effective than the double-chain ones. Monododecyl maleate, that is a cis derivative, was a more potent enhancer than its trans isomer, while the activity of succinates strongly depend...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.11.083

    authors: Novotný M,Hrabálek A,Janůsová B,Novotný J,Vávrová K

    更新日期:2009-01-15 00:00:00

  • Structural requirements of (E)-6-benzylidene-4a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one derivatives as novel melanogenesis inhibitors.

    abstract::Chalcone type compound 1a ((E)-6'-benzylidene-4a'-methyl-4',4a',7',8'-tetrahydro-3'H-spiro[[1,3]dithiolane-2,2'-naphthalen]-5'(6'H)-one) was discovered as an potent inhibitor in melanogenesis. To define its structure-activity relationship, a series of analogs 1b-n, dithiolane truncated 2a-b and ring A removed 3a-e wer...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.02.060

    authors: Thanigaimalai P,Lee KC,Sharma VK,Rao EV,Roh E,Kim Y,Jung SH

    更新日期:2011-04-01 00:00:00

  • Potent and selective CC-chemokine receptor-2 (CCR2) antagonists as a potential treatment for asthma.

    abstract::A number of compounds bearing a quaternary ammonium moiety were found to be antagonists with nanomolar binding affinity for the chemokine receptor-2. The structure-activity relationships in the series are described herein along with some detailed characterization of the interesting compounds. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2007.01.115

    authors: Lagu B,Gerchak C,Pan M,Hou C,Singer M,Malaviya R,Matheis M,Olini G,Cavender D,Wachter M

    更新日期:2007-08-01 00:00:00

  • Anion inhibition studies of a β-carbonic anhydrase from Clostridium perfringens.

    abstract::A β-carbonic anhydrases (CAs, EC 4.2.1.1) was recently cloned, purified and characterized kinetically in the pathogen Clostridium perfringens. We report here the first inhibition study of this enzyme (CpeCA). CpeCA was poorly inhibited by iodide and bromide, and was inhibited with KIs in the range of 1-10mM by a range...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.10.037

    authors: Vullo D,Sai Kumar RS,Scozzafava A,Capasso C,Ferry JG,Supuran CT

    更新日期:2013-12-15 00:00:00

  • N-Heteroaryl glycinamides and glycinamines as potent NPY5 antagonists.

    abstract::Subtype specific ligands are needed to evaluate the therapeutic potential of modulating the brain's neuropeptide Y system. The benzothiazepine glycinamide 1a was identified as an NPY5 antagonist lead. While having acceptable solubility, the compound was found to suffer from high clearance and poor exposure. Optimizati...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2011.06.078

    authors: Wu L,Lu K,Desai M,Packiarajan M,Joshi A,Marzabadi MR,Jubian V,Andersen K,Chandrasena G,Boyle NJ,Walker MW

    更新日期:2011-09-15 00:00:00

  • Discovery and optimization of a series of liver X receptor antagonists.

    abstract::The present report describes our efforts to convert an existing LXR agonist into an LXR antagonist using a structure-based approach. A series of benzenesulfonamides was synthesized based on structural modification of a known LXR agonist and was determined to be potent dual liver X receptor (LXR α/β) ligands. Herein we...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.07.048

    authors: Jiao X,Kopecky DJ,Fisher B,Piper DE,Labelle M,McKendry S,Harrison M,Jones S,Jaen J,Shiau AK,Escaron P,Danao J,Chai A,Coward P,Kayser F

    更新日期:2012-09-15 00:00:00

  • Transformation of 8-prenylnaringenin by Absidia coerulea and Beauveria bassiana.

    abstract::Beauveria bassiana AM278 and Absidia coerulea AM93 converted 8-prenylnaringenin (1) into two glycoside derivatives (7-O-β-D-glucopyranoside) (2) and 7-O-β-D-4'''-O-methylglucopyranoside) (3) in high yields in processes conducted in Saboraud medium. 8-Prenylnaringenin 7-O-β-D-4'''-O-methylglucopyranoside (3) is a new c...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.08.060

    authors: Bartmańska A,Tronina T,Huszcza E

    更新日期:2012-10-15 00:00:00

  • Design and synthesis of tamoxifen derivatives as a selective estrogen receptor down-regulator.

    abstract::We designed and synthesized an estrogen receptor (ER) down-regulator (5), which is a derivative of tamoxifen with a long alkyl side chain. Compound 5 effectively reduced ER protein levels in MCF-7 cells and had an antagonistic effect. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.11.078

    authors: Shoda T,Okuhira K,Kato M,Demizu Y,Inoue H,Naito M,Kurihara M

    更新日期:2014-01-01 00:00:00

  • Structure-based design of ketone-containing, tripeptidyl human rhinovirus 3C protease inhibitors.

    abstract::Tripeptide-derived molecules incorporating C-terminal ketone electrophiles were evaluated as reversible inhibitors of the cysteine-containing human rhinovirus 3C protease (3CP). An optimized example of such compounds displayed potent 3CP inhibition activity (K = 0.0045 microM) and in vitro antiviral properties (EC50=0...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(99)00587-9

    authors: Dragovich PS,Zhou R,Webber SE,Prins TJ,Kwok AK,Okano K,Fuhrman SA,Zalman LS,Maldonado FC,Brown EL,Meador JW 3rd,Patick AK,Ford CE,Brothers MA,Binford SL,Matthews DA,Ferre RA,Worland ST

    更新日期:2000-01-03 00:00:00

  • Enediynes: Exploration of microbial genomics to discover new anticancer drug leads.

    abstract::The enediyne natural products have been explored for their phenomenal cytotoxicity. The development of enediynes into anticancer drugs has been successfully achieved through the utilization of polymer- and antibody-drug conjugates (ADCs) as drug delivery systems. An increasing inventory of enediynes would benefit curr...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmcl.2014.11.019

    authors: Shen B,Hindra,Yan X,Huang T,Ge H,Yang D,Teng Q,Rudolf JD,Lohman JR

    更新日期:2015-01-01 00:00:00

  • Exploring amino acids derivatives as potent, selective, and direct agonists of sphingosine-1-phosphate receptor subtype-1.

    abstract::In the quest to discover a potent and selective class of direct agonists to the sphingosine-1-phosphate receptor, we explored the carboxylate functional group as a replacement to previously reported lead phosphates. This has led to the discovery of potent and selective direct agonists with moderate to substantial in v...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2012.11.053

    authors: Evindar G,Deng H,Bernier SG,Doyle E,Lorusso J,Morgan BA,Westlin WF

    更新日期:2013-01-15 00:00:00

  • Substituted aminobenzimidazole pyrimidines as cyclin-dependent kinase inhibitors.

    abstract::A series of aminobenzimidazole-substituted pyrimidines were synthesized and evaluated for biochemical activity against CDK1. A high-speed parallel synthesis approach enabled the identification of a potent lead series having improved potency in the CDK1 assay (IC(50)<10nM). Cell cycle analysis showed that the compounds...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2005.02.076

    authors: Verma S,Nagarathnam D,Shao J,Zhang L,Zhao J,Wang Y,Li T,Mull E,Enyedy I,Wang C,Zhu Q,Altieri M,Jordan J,Dang TT,Reddy S

    更新日期:2005-04-15 00:00:00

  • N-[1-(2-Phenylethyl)pyrrolidin-3-yl]-1-adamantanecarboxamides as novel 5-HT2 receptor antagonists.

    abstract::A series of 1-adamantanecarboxamides was synthesized and examined for their potency as a selective 5-HT2 receptor antagonist. We found (S)-N-[1-[2-(4-fluorophenyl)ethyl]pyrrolidin-3-yl]-1-adamantane carboxamide hydrochloride hydrate (10-(S), Y-39241) to have a high affinity and selectivity for 5-HT2 receptors, and thi...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/s0960-894x(00)00492-3

    authors: Fujio M,Kuroita T,Sakai Y,Nakagawa H,Matsumoto Y

    更新日期:2000-11-06 00:00:00

  • Inhibition of amyloid fibril formation and cytotoxicity by caffeic acid-conjugated amyloid-β C-terminal peptides.

    abstract::Amyloid-β (Aβ) deposition and oxidative stress observed in the brains of patients with Alzheimer's disease (AD) are important targets for therapeutic intervention. In this study, we conjugated the antioxidants caffeic acid (CA) and dihydrocaffeic acid (DHCA) to Aβ1-42 C-terminal motifs (Aβx-42: x=38, 40) to synthesize...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2016.10.027

    authors: Arai T,Ohno A,Mori K,Kuwata H,Mizuno M,Imai K,Hara S,Shibanuma M,Kurihara M,Miyata N,Nakagawa H,Fukuhara K

    更新日期:2016-11-15 00:00:00

  • 99mTc/Re complexes based on flavone and aurone as SPECT probes for imaging cerebral β-amyloid plaques.

    abstract::Two (99m)Tc/Re complexes based on flavone and aurone were tested as potential probes for imaging β-amyloid plaques using single photon emission computed tomography. Both (99m)Tc-labeled derivatives showed higher affinity for Aβ(1-42) aggregates than did (99m)Tc-BAT. In sections of brain tissue from an animal model of ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2010.08.004

    authors: Ono M,Ikeoka R,Watanabe H,Kimura H,Fuchigami T,Haratake M,Saji H,Nakayama M

    更新日期:2010-10-01 00:00:00

  • Evaluation of steroidal amines as lipid raft modulators and potential anti-influenza agents.

    abstract::The influenza A virus (IFV) possesses a highly ordered cholesterol-rich lipid envelope. A specific composition and structure of this membrane raft envelope are essential for viral entry into cells and virus budding. Several steroidal amines were investigated for antiviral activity against IFV. Both, a positively charg...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2013.07.015

    authors: Agarwal S,Schroeder C,Schlechtingen G,Braxmeier T,Jennings G,Knölker HJ

    更新日期:2013-09-15 00:00:00

  • Synthesis and structure-activity relationship of N-acyl-Gly-, N-acyl-Sar- and N-blocked-boroPro inhibitors of FAP, DPP4, and POP.

    abstract::The structure-activity relationship of various N-acyl-Gly-, N-acyl-Sar-, and N-blocked-boroPro derivatives against three prolyl peptidases was explored. Several N-acyl-Gly- and N-blocked-boroPro compounds showed low nanomolar inhibitory activity against fibroblast activation protein (FAP) and prolyl oligopeptidase (PO...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2006.11.072

    authors: Tran T,Quan C,Edosada CY,Mayeda M,Wiesmann C,Sutherlin D,Wolf BB

    更新日期:2007-03-01 00:00:00

  • Investigation of novel 7,8-disubstituted-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-ones as potent Chk1 inhibitors.

    abstract::The synthesis and structure-activity relationships (SAR) of Chk1 inhibitors based on a 5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one core are described. Specifically, an exploration of the 7 and 8 positions on this previously disclosed core afforded compounds with improved enzymatic and cellular potency. ...

    journal_title:Bioorganic & medicinal chemistry letters

    pub_type: 杂志文章

    doi:10.1016/j.bmcl.2008.02.080

    authors: Hasvold LA,Wang L,Przytulinska M,Xiao Z,Chen Z,Gu WZ,Merta PJ,Xue J,Kovar P,Zhang H,Park C,Sowin TJ,Rosenberg SH,Lin NH

    更新日期:2008-04-01 00:00:00