当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Synthesis of imidazo[1,5,4-de]quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products.

Synthesis of imidazo[1,5,4-de]quinoxalin-9-ones, benzimidazole analogues of pyrroloiminoquinone marine natural products.

Abstract：

:The imidazoquinoxalinones 1 and 2 are benzimidazole analogues of indole-based marine natural products called makaluvamins. The stabilized cation 1 and the zwitterion 2 were prepared in approximately 9 steps from readily available starting materials. Compound 1 is more cytostatic and cytotoxic than 2 and also shows activity in the hollow fiber assay. Unlike the indole-based natural products, 1 and 2 are not potent topoisomerase II inhibitors. Their pattern of cytotoxic and cyostatic activity could be related to inhibition of protein tyrosine kinases.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Labarbera DV,Skibo EB

doi

10.1016/j.bmc.2004.10.016

subject

Has Abstract

pub_date

2005-01-17 00:00:00

pages

387-95

issue

2

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(04)00790-4

journal_volume

13

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • New minor taxanes analogues from the needles of Taxus canadenis.

    abstract：:Seven new taxanes were isolated from the needles of the Canadian yew: unusual functional groups, positions and/or stereochemical features are described. Their chemical structures were rigorously characterized by detailed high resolution NMR analyses and confirmed by high resolution Fast Atom Bombardment Mass Spectrome...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00347-4

    authors： Shi QW,Sauriol F,Mamer O,Zamir LO

    更新日期：2003-01-17 00:00:00

  • Natural daucane sesquiterpenes with antiproliferative and proapoptotic activity against human tumor cells.

    abstract：:Plants of the genera Ferula and Ferulago are known for their complex content in bioactive secondary metabolites such as coumarins, phenylpropanoids, and sesquiterpenes. We used the ground parts of Ferula communis subsp. communis, Ferula glauca subsp. glauca and Ferulago campestris as natural sources for the isolation ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.08.021

    authors： Dall'Acqua S,Linardi MA,Maggi F,Nicoletti M,Petitto V,Innocenti G,Basso G,Viola G

    更新日期：2011-10-01 00:00:00

  • Substituted indolin-2-ones as p90 ribosomal S6 protein kinase 2 (RSK2) inhibitors: Molecular docking simulation and structure-activity relationship analysis.

    abstract：:A series of novel indolin-2-ones inhibitors against p90 ribosomal S6 protein kinase 2 (RSK2) were designed and synthesized and their structure-activity relationship (SAR) was studied. The most potent inhibitor, compound 3s, exhibited potent inhibition against RSK2 with an IC50 value of 0.5 μM and presented a satisfact...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.01.047

    authors： Zhong Y,Xue M,Zhao X,Yuan J,Liu X,Huang J,Zhao Z,Li H,Xu Y

    更新日期：2013-04-01 00:00:00

  • Evaluation of 1,2,5-thiadiazoles as modulators of M₁/M₅ muscarinic receptor subtypes.

    abstract：:Studies have demonstrated the presence of allosteric binding sites on each of the muscarinic acetylcholine receptor (mAChR) subtypes. Since most drugs targeting muscarinic receptors bind to the highly conserved orthosteric binding site, they fail to achieve appreciable subtype selectivity. Targeting non-conserved allo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.01.049

    authors： Maheshwari A,Rao PS,Messer WS Jr

    更新日期：2014-03-15 00:00:00

  • Halogenated derivatives QSAR model using spectral moments to predict haloacetic acids (HAA) mutagenicity.

    abstract：:The risk of the presence of haloacetic acids in drinking water as chlorination by-products and the shortage of experimental mutagenicity data for most of them requires a research work. This paper describes a QSAR model to predict direct mutagenicity for these chemicals. The model, able to describe more than 90% of the...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.03.070

    authors： Pérez-Garrido A,González MP,Escudero AG

    更新日期：2008-05-15 00:00:00

  • Antitumor activity of some natural flavonoids and synthetic derivatives on various human and murine cancer cell lines.

    abstract：:The effect of various natural flavonoids, cinnamic acid derivatives, and a series of synthetic flavones on cell proliferation was evaluated in vitro in a panel of established human and murine tumor cell lines. The most potent antiproliferative agents were caffeic acid n-butyl ester (12) > 2'-nitroflavone (26) > caffei...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.12.021

    authors： Cárdenas M,Marder M,Blank VC,Roguin LP

    更新日期：2006-05-01 00:00:00

  • Effective syntheses of 2',4'-BNANC monomers bearing adenine, guanine, thymine, and 5-methylcytosine, and the properties of oligonucleotides fully modified with 2',4'-BNANC.

    abstract：:We efficiently synthesized 2'-O,4'-C-aminomethylene-bridged nucleic acid (2',4'-BNANC) monomers bearing the four nucleobases, guanine, adenine, thymine, and 5-methylcytosine and incorporated these monomers into oligonucleotides. Initially, we carried out the transglycosylation reaction on several 2'-O-substituted 5-me...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.02.034

    authors： Fujisaka A,Hari Y,Takuma H,Rahman SMA,Yoshikawa H,Pang J,Imanishi T,Obika S

    更新日期：2019-04-15 00:00:00

  • Conformational studies of dithymidine boranomonophosphate diastereoisomers.

    abstract：:The boranophosphate ester nucleotides are a new class of nucleic acid analogues that are isoelectronic and isostructural to normal phosphodiester nucleic acids and that maintain the anionic charge of the nucleic acid backbone. The two P-diastereoisomers of dithymidine boranomonophosphates were separated using reverse ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(96)00259-3

    authors： Li H,Huang F,Shaw BR

    更新日期：1997-05-01 00:00:00

  • Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines.

    abstract：:A series of novel twenty-eight rigid 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines were synthesized and evaluated for their topoisomerase inhibitory activity as well as their cytotoxicity against several human cancer cell lines. Generally, hydroxylated compounds (16-18, 22-25, and 29-31) containi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.04.031

    authors： Kadayat TM,Song C,Shin S,Magar TB,Bist G,Shrestha A,Thapa P,Na Y,Kwon Y,Lee ES

    更新日期：2015-07-01 00:00:00

  • An altered zinc-binding site confers resistance to a covalent inactivator of New Delhi metallo-beta-lactamase-1 (NDM-1) discovered by high-throughput screening.

    abstract：:Due to the global threat of antibiotic resistance mediated by New Delhi metallo-beta-lactamase-1 (NDM-1) and the lack of structurally diverse inhibitors reported for this enzyme, we developed screening and counter-screening assays for manual and automated formats. The manual assay is a trans-well absorbance-based endp...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.03.031

    authors： Thomas PW,Spicer T,Cammarata M,Brodbelt JS,Hodder P,Fast W

    更新日期：2013-06-01 00:00:00

  • The search for potent, small molecule NNRTIs: A review.

    abstract：:AIDS has become the leading pandemic disease, and is the cause of death worldwide. Presently, HAART treatment, a combination of reverse transcriptase (RT) and protease inhibitors is also unsuccessful due to the virus getting resistant to the drugs because of mutational changes. Two types of RT inhibitors exist namely ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.bmc.2009.06.060

    authors： Prajapati DG,Ramajayam R,Yadav MR,Giridhar R

    更新日期：2009-08-15 00:00:00

  • 1-(1-Arylethylidene)thiosemicarbazide derivatives: a new class of tyrosinase inhibitors.

    abstract：:A series of 1-(1-arylethylidene)thiosemicarbazide compounds and their analogues were synthesized and characterized by 1H NMR, MS. Their tyrosinase inhibitory activities were investigated by an assay based on the catalyzing ability of tyrosinase for the oxidation of L-DOPA, comparing with 4-methoxycinnamic acid and arb...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.10.102

    authors： Liu J,Yi W,Wan Y,Ma L,Song H

    更新日期：2008-02-01 00:00:00

  • Design, synthesis, and biological evaluation of 1,3-diarylprop-2-en-1-ones : a novel class of cyclooxygenase-2 inhibitors.

    abstract：:A group of regioisomeric (E)-1,3-diarylprop-2-en-1-one derivatives possessing a COX-2 SO2Me pharmacophore at the para position of the C-1 or C-3 phenyl ring, in conjunction with a C-3 or C-1 phenyl (4-H) or substituted-phenyl ring (4-F, 4-OMe and 4-Me), were designed for evaluation as selective cyclooxygenase-2 (COX-2...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.11.041

    authors： Zarghi A,Arfaee S,Rao PN,Knaus EE

    更新日期：2006-04-15 00:00:00

  • Synthesis, biological evaluation, and modeling studies of inhibitors aimed at the malarial proteases plasmepsins I and II.

    abstract：:The increasing resistance of the malarial parasite to antimalarial drugs is a major contributor to the reemergence of the disease and increases the need for new drug targets. The two aspartic proteases, plasmepsins I and II, from Plasmodium falciparum have recently emerged as potential targets. In an effort to inhibit...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.06.048

    authors： Muthas D,Nöteberg D,Sabnis YA,Hamelink E,Vrang L,Samuelsson B,Karlén A,Hallberg A

    更新日期：2005-09-15 00:00:00

  • Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks.

    abstract：:The title l-glutathione derivatives, containing acid- and base-labile esters, respectively, were obtained in good overall yields. N-(t)Boc l-glutathione dimethyl ester was prepared via Fischer esterification of l-glutathione disulfide (GSSG) using HCl in dry methanol, protection of the amine with (t)Boc(2)O, and tribu...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.10.022

    authors： Falck JR,Sangras B,Capdevila JH

    更新日期：2007-01-15 00:00:00

  • Tyrenes: synthesis of new antiproliferative compounds with an extended conjugation.

    abstract：:A series of substituted styryl-acrylonitriles was designed and synthesized. The new compounds, called tyrenes, were tested for the ability to inhibit acute lymphocytic leukemia (ALL) cancer cell growth, as well as on their toxicity to normal bone marrow (NBM) cells. The results showed that 3,4-dihydroxystyryl-acryloni...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.03.043

    authors： Demin P,Rounova O,Grunberger T,Cimpean L,Sharfe N,Roifman CM

    更新日期：2004-06-01 00:00:00

  • An investigation of the N-demethylation of 3-deoxymorphine and the affinity of the alkylation products to mu, delta, and kappa receptors.

    abstract：:The N-demethylation of 3-deoxymorphine (1) was investigated using methyl chloroformate and hydrazine. 3-Deoxynormorphine (2) was obtained in 70% yield, and 3-deoxydihydronormorphine (3) was also obtained as a side product. The mu, delta, and kappa receptor binding affinity of a series of N-substituted 3-deoxynormorphi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.03.011

    authors： Csutoras C,Zhang A,Bidlack JM,Neumeyer JL

    更新日期：2004-05-15 00:00:00

  • Hippuryl-alpha-methylphenylalanine and hippuryl-alpha-methylphenyllactic acid as substrates for carboxypeptidase A. Syntheses, kinetic evaluation and mechanistic implication.

    abstract：:(R)- and (S)-Hippuryl-alpha-methylphenylalanine [(R)- and (S)-Hipp-alpha-MePhe] and (S)-hippuryl-alpha-methylphenyllactic acid [(S)-Hipp-alpha-MeOPhe] were synthesized and evaluated as substrates for carboxypeptidase A (CPA) in an effort to shed further light on the catalytic mechanism of the enzyme. The rate of CPA-c...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00006-7

    authors： Lee M,Kim DH

    更新日期：2000-04-01 00:00:00

  • Discovery of novel phenoxazinone derivatives as DKK1/LRP6 interaction inhibitors: Synthesis, biological evaluation and structure-activity relationships.

    abstract：:Amino derivatives of NCI8642 were synthesized and evaluated as inhibitors of DKK1/LRP6 interactions. The new inhibitors were able to activate the Wnt signaling pathway as indicated by the increased levels of β-catenin, and decrease the DKK1-induced Tau phosphorylation at serine 396. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.01.025

    authors： Thysiadis S,Mpousis S,Avramidis N,Katsamakas S,Balomenos A,Remelli R,Efthimiopoulos S,Sarli V

    更新日期：2016-03-01 00:00:00

  • Synthesis and biological evaluation of novel flexible nucleoside analogues that inhibit flavivirus replication in vitro.

    abstract：:Flaviviruses, such as Dengue (DENV) and Zika (ZIKV) viruses, represent a severe health burden. There are currently no FDA-approved treatments, and vaccines against most flaviviruses are still lacking. We have developed several flexible analogues ("fleximers") of the FDA-approved nucleoside Acyclovir that exhibit activ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2020.115713

    authors： Thames JE,Waters CD 3rd,Valle C,Bassetto M,Aouadi W,Martin B,Selisko B,Falat A,Coutard B,Brancale A,Canard B,Decroly E,Seley-Radtke KL

    更新日期：2020-08-31 00:00:00

  • New highly active taxoids from 9beta-dihydrobaccatin-9,10-acetals. Part 4.

    abstract：:It was shown that a new taxane analogue 3, which exhibited both in vitro antitumor activity and in vivo efficacy by both i.v. and p.o. administration, was prone to be metabolized by human liver microsomes. We identified a major metabolite, M-1, generated by human liver microsomes as 20a, a hydroxylated compound at the...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(03)00454-1

    authors： Takeda Y,Uoto K,Chiba J,Horiuchi T,Iwahana M,Atsumi R,Ono C,Terasawa H,Soga T

    更新日期：2003-10-01 00:00:00

  • Generation of highly potent DYRK1A-dependent inducers of human β-Cell replication via Multi-Dimensional compound optimization.

    abstract：:Small molecule stimulation of β-cell regeneration has emerged as a promising therapeutic strategy for diabetes. Although chemical inhibition of dual specificity tyrosine-phosphorylation-regulated kinase 1A (DYRK1A) is sufficient to enhance β-cell replication, current lead compounds have inadequate cellular potency for...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.115193

    authors： Allegretti PA,Horton TM,Abdolazimi Y,Moeller HP,Yeh B,Caffet M,Michel G,Smith M,Annes JP

    更新日期：2020-01-01 00:00:00

  • Synthesis and biological evaluation of new camptothecin derivatives obtained by modification of position 20.

    abstract：:The preparation and biological evaluation of a novel series of dimeric camptothecin derivatives are described. All the new compounds showed a significant ability to inhibit human tumor cell growth with IC(50) values ranging from 0.03 to 12.2 μM. The interference with the activity of the nuclear enzymes topoisomerases ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.09.069

    authors： Riva E,Comi D,Borrelli S,Colombo F,Danieli B,Borlak J,Evensen L,Lorens JB,Fontana G,Gia OM,Via LD,Passarella D

    更新日期：2010-12-15 00:00:00

  • Structural design, synthesis and pharmacological evaluation of 4-thiazolidinones against Trypanosoma cruzi.

    abstract：:Chagas disease is an infection caused by protozoan Trypanosoma cruzi, which affects approximately 8-10million people worldwide. Benznidazole is the only drug approved for treatment during the acute and asymptomatic chronic phases of Chagas disease; however, it has poor efficacy during the symptomatic chronic phase. Th...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.10.048

    authors： de Oliveira Filho GB,de Oliveira Cardoso MV,Espíndola JW,Ferreira LF,de Simone CA,Ferreira RS,Coelho PL,Meira CS,Magalhaes Moreira DR,Soares MB,Lima Leite AC

    更新日期：2015-12-01 00:00:00

  • Novel anticancer agents, kayeassamins C-I from the flower of Kayea assamica of Myanmar.

    abstract：:A CHCl3-soluble fraction of 70% EtOH extract of the flower of Kayea assamica from Myanmar exhibited 100% preferential cytotoxicity (PC(100)) against human pancreatic cancer PANC-1 cells under nutrient-deprived conditions at 1 microg/mL. Bioassay-guided fractionation and isolation afforded nine new coumarins, kayeassam...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.07.091

    authors： Win NN,Awale S,Esumi H,Tezuka Y,Kadota S

    更新日期：2008-09-15 00:00:00

  • The influence of substitution at aromatic part of 1,2,3,4-tetrahydroisoquinoline on in vitro and in vivo 5-HT(1A)/5-HT(2A) receptor activities of its 1-adamantoyloaminoalkyl derivatives.

    abstract：:Further structure-activity relationship (SAR) studies with the 1,2,3,4-tetrahydroisoquinoline (THIQ) class of 5-HT(1A) ligands led to the synthesis of new 1-adamantoyloaminoalkyl derivatives. The impact of substituent variations in the aromatic part of THIQ moiety on 5-HT(1A) and 5-HT(2A) receptor affinities, as well ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00236-x

    authors： Bojarski AJ,Mokrosz MJ,Minol SC,Kozioł A,Wesołowska A,Tatarczyńska E,Kłodzińska A,Chojnacka-Wójcik E

    更新日期：2002-01-01 00:00:00

  • Glycoprotein-inspired materials promote the proteolytic release of cell surface L-selectin.

    abstract：:The proteolytic release, or shedding, of a cell surface protein can serve a regulatory role; the process liberates a soluble form of the protein into circulation while downregulating its cell surface concentration. The characteristics that render a protein susceptible to proteolytic cleavage are not known. We hypothes...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00122-9

    authors： Gordon EJ,Strong LE,Kiessling LL

    更新日期：1998-08-01 00:00:00

  • Synthesis and structure-activity relationships of benzyloxyphenyl derivatives as a novel class of NCX inhibitors: effects on heart failure.

    abstract：:In the context of heart failure and myocardial ischemia reperfusion, the activity of the sodium-calcium exchanger can lead to calcium overload, which in turn can lead to contractile dysfunction and arrhythmia. Therefore, NCX is an attractive target for treatment of heart failure and myocardial ischemia reperfusion. We...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.10.048

    authors： Kuramochi T,Kakefuda A,Yamada H,Ogiyama T,Taguchi T,Sakamoto S

    更新日期：2005-02-01 00:00:00

  • In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities.

    abstract：:Kahalalide F (KF) and the regioisomer isoKF are novel anticancer drugs of marine origin and currently under clinical investigation. Here we report the synthesis of two new KF analogs with significant in vitro and in vivo antifungal and antitumor activities. The primary amine hydrogen of ornithine in KF has been replac...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.06.050

    authors： Shilabin AG,Hamann MT

    更新日期：2011-11-15 00:00:00

  • Synthesis and biochemical activity of novel amidine derivatives as m1 muscarinic receptor agonists.

    abstract：:As part of a continuing effort aimed at the development of selective, efficacious, and centrally active m1 muscarinic agonists for the treatment of Alzheimer's disease, a series of amide and hydrazide amidine derivatives (2a-e and 3b-d) was synthesized and examined for muscarinic agonist activity. Preliminary biochemi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/0968-0896(96)00152-6

    authors： Ojo B,Dunbar PG,Durant GJ,Nagy PI,Huzl JJ 3rd,Periyasamy S,Ngur DO,el-Assadi AA,Hoss WP,Messer WS Jr

    更新日期：1996-10-01 00:00:00