当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.

Synthesis and activity evaluation of the cyclic dipeptides arylidene N-alkoxydiketopiperazines.

Abstract：

:A series of arylidene N-alkoxydiketopiperazines was designed and stereoselectively synthesized via oxime-ether formation and intramolecular acylation. Possible cyclization and acid-catalyzed rearrangement-fragmentation mechanisms were discussed. The crystal structure of the novel diketopiperazine further confirmed the rearrangement mechanism. Most compounds exhibited antitumor activity. Several compounds were more potent against caspase-3. Specifically, compounds 6e, 6g, and 6f inhibited caspase-3 at IC50 values lying within the low micromolar range and demonstrated good selectivity. The binding modes of alkoxydiketopiperazines in the active center of caspase-3 were also discussed based on the molecular docking results.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Tian X,Feng J,Fan SM,Zhen XL,Han JR,Liu SX

doi

10.1016/j.bmc.2016.08.038

subject

Has Abstract

pub_date

2016-11-01 00:00:00

pages

5197-5205

issue

21

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(16)30645-9

journal_volume

24

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • Characterization of a transglycosylase domain of Streptococcus pneumoniae PBP1b.

    abstract：:Inhibitors of transglycosylases may serve as potent antibiotics that are less prone to resistance development in bacterial pathogens. To facilitate the search of such compounds, a transglycosylase (TGase) domain of the membrane integral multidomain Streptococcus pneumoniae PBP1b was cloned and expressed. This TGase do...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.06.058

    authors： Liu H,Wong CH

    更新日期：2006-11-01 00:00:00

  • Chalcone inhibitors of the NorA efflux pump in Staphylococcus aureus whole cells and enriched everted membrane vesicles.

    abstract：:A library of 117 chalcones was screened for efflux pump inhibitory (EPI) activity against NorA mediated ethidium bromide efflux. Five of the chalcones (5-7, 9, and 10) were active and two chalcones (9 and 10) were equipotent to reserpine with IC(50)-values of 9.0 and 7.7 μM, respectively. Twenty chalcones were subsequ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.05.025

    authors： Holler JG,Slotved HC,Mølgaard P,Olsen CE,Christensen SB

    更新日期：2012-07-15 00:00:00

  • Triterpenoids from Momordica balsamina: Reversal of ABCB1-mediated multidrug resistance.

    abstract：:The ability as P-glycoprotein (P-gp, ABCB1) modulators of thirty (1-30) triterpenoids of the cucurbitane-type was evaluated on human L5178 mouse T-lymphoma cell line transfected with the human MDR1 gene, through the rhodamine-123 exclusion assay. Compounds (1-26, and 29, 30) were previously obtained from the African m...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.08.022

    authors： Ramalhete C,Mulhovo S,Molnar J,Ferreira MU

    更新日期：2016-11-01 00:00:00

  • Reversed isoniazids: Design, synthesis and evaluation against Mycobacterium tuberculosis.

    abstract：:Novel reversed isoniazid (RINH) agents were synthesized by covalently linking isoniazid with various efflux pump inhibitor (EPI) cores and their structural motifs. These RINH agents were then evaluated for anti-mycobacterial activity against sensitive, isoniazid mono-resistant and MDR clinical isolates of M. tuberculo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.12.047

    authors： Kumar M,Singh K,Ngwane AH,Hamzabegovic F,Abate G,Baker B,Wiid I,Hoft DF,Ruminski P,Chibale K

    更新日期：2018-02-15 00:00:00

  • Identification of potent farnesoid X receptor (FXR) antagonist showing favorable PK profile and distribution toward target tissues: Comprehensive understanding of structure-activity relationship of FXR antagonists.

    abstract：:Antagonizing transcriptional activity of farnesoid X receptor (FXR) in the intestine has been reported as an effective means for the treatment of nonalcoholic fatty liver disease, type 2 diabetes and obesity. We describe herein that the building blocks necessary to maintain the antagonism of our chemotype were investi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.04.029

    authors： Teno N,Yamashita Y,Masuda A,Iguchi Y,Oda K,Fujimori K,Hiramoto T,Nishimaki-Mogami T,Une M,Gohda K

    更新日期：2019-06-01 00:00:00

  • Activation of anti-oxidant Nrf2 signaling by substituted trans stilbenes.

    abstract：:Nrf2, which is a member of the cap'n'collar family of transcription factors, is a major regulator of phase II detoxification and anti-oxidant genes as well as anti-inflammatory and neuroprotective genes. The importance of inflammation and oxidative stress in many chronic diseases supports the concept that activation o...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.01.005

    authors： Deck LM,Whalen LJ,Hunsaker LA,Royer RE,Vander Jagt DL

    更新日期：2017-02-15 00:00:00

  • Synthesis and in vitro anti-hepatitis B virus activities of some ethyl 6-bromo-5-hydroxy-1H-indole-3-carboxylates.

    abstract：:A series of ethyl 6-bromo-5-hydroxy-1H-indole-3-carboxylates, 8a-11v, were synthesized and evaluated for their anti-hepatitis B virus (HBV) activities in 2.2.15 cells. The selective indexes of inhibition on replication of HBV DNA of compounds 11s (>8.7) and 11t (10.8), which were introduced halogen on the phenyl ring ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.08.041

    authors： Chai H,Zhao Y,Zhao C,Gong P

    更新日期：2006-02-15 00:00:00

  • Characterization and anions inhibition studies of an α-carbonic anhydrase from the teleost fish Dicentrarchus labrax.

    abstract：:Carbonic anhydrase (CA; EC 4.2.1.1) was purified from the gill of the teleost fish Dicentrarchus labrax (European seabass). The purification procedure consisted of a single step affinity chromatography on Sepharose 4B-tyrosine-sulfanilamide. The enzyme was purified 84.9-fold with a yield of 58%, and a specific activit...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.12.033

    authors： Ekinci D,Ceyhun SB,Sentürk M,Erdem D,Küfrevioğlu Oİ,Supuran CT

    更新日期：2011-01-15 00:00:00

  • Active core structure of terfestatin A, a new specific inhibitor of auxin signaling.

    abstract：:The auxins, plant hormones, regulate many aspects of the growth and development of plants. Terfestatin A (TrfA), a novel auxin signaling inhibitor, was identified in a screen of Streptomyces sp. F40 extracts for inhibition of the expression of an auxin-inducible gene. However, the mode of action of TrfA has not been e...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.02.085

    authors： Hayashi K,Yamazoe A,Ishibashi Y,Kusaka N,Oono Y,Nozaki H

    更新日期：2008-05-01 00:00:00

  • New insights into the conformational requirements of B2 bradykinin antagonism.

    abstract：:The conformational profiles of a selected group of a new series of small linear and cyclic penta- and hexapeptides, inspired on the C-terminal segment of second-generation bradykinin (BK) antagonists, were independently computed in order to assess the chemical and geometrical requirements necessary for BK antagonism. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00084-4

    authors： Filizola M,Llorens O,Cartení-Farina M,Perez JJ

    更新日期：1998-09-01 00:00:00

  • Replacement of benzylic hydroxy group by vinyl or hydroxymethyl moiety at the 3-benzazepine scaffold retaining GluN2B affinity.

    abstract：:Since overactivation of NMDA receptors is associated with neurodegenerative disorders, the design and development of subunit-selective NMDA receptor antagonists are of great interest. In order to avoid the formation of quinone-like intermediates as starting point for degradation the benzylic OH group of the lead compo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.07.059

    authors： Rath S,Schepmann D,Wünsch B

    更新日期：2017-10-15 00:00:00

  • Carbon-carbon-linked (pyrazolylphenyl)oxazolidinones with antibacterial activity against multiple drug resistant gram-positive and fastidious gram-negative bacteria.

    abstract：:In an effort to expand the spectrum of activity of the oxazolidinone class of antibacterial agents to include Gram-negative bacteria, a series of new carbon-carbon linked pyrazolylphenyl analogues has been prepared. The alpha-N-substituted methyl pyrazole (10alpha) in the C3-linked series exhibited very good Gram-posi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00233-4

    authors： Lee CS,Allwine DA,Barbachyn MR,Grega KC,Dolak LA,Ford CW,Jensen RM,Seest EP,Hamel JC,Schaadt RD,Stapert D,Yagi BH,Zurenko GE,Genin MJ

    更新日期：2001-12-01 00:00:00

  • Enzyme-catalysed enantioselective hydrolysis of racemic naproxen nitrile.

    abstract：:The bacterial strain Rhodococcus butanica (ATCC 21197), which exhibits nitrilase and nitrile hydratase/amidase activities, catalyses the enantioselective hydrolysis of racemic naproxen nitrile (R/S)-1 to furnish a moderate enantiomeric excess of (S)-naproxen (S)-3. Racemic naproxen amide (R/S)-2 is not a good substrat...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/0968-0896(94)85022-4

    authors： Effenberger F,Böhme J

    更新日期：1994-07-01 00:00:00

  • Studies of TAK1-centered polypharmacology with novel covalent TAK1 inhibitors.

    abstract：:Targeted polypharmacology provides an efficient method of treating diseases such as cancer with complex, multigenic causes provided that compounds with advantageous activity profiles can be discovered. Novel covalent TAK1 inhibitors were validated in cellular contexts for their ability to inhibit the TAK1 kinase and f...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.11.034

    authors： Tan L,Gurbani D,Weisberg EL,Jones DS,Rao S,Singer WD,Bernard FM,Mowafy S,Jenney A,Du G,Nonami A,Griffin JD,Lauffenburger DA,Westover KD,Sorger PK,Gray NS

    更新日期：2017-02-15 00:00:00

  • Novel pyridyl nitrofuranyl isoxazolines show antibacterial activity against multiple drug resistant Staphylococcus species.

    abstract：:A novel series of pyridyl nitrofuranyl isoxazolines were synthesized and evaluated for their antibacterial activity against multiple drug resistant (MDR) Staphylococcus strains. Compounds with piperazine linker between the pyridyl group and isoxazoline ring showed better activity when compared to compounds without the...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.05.037

    authors： Picconi P,Prabaharan P,Auer JL,Sandiford S,Cascio F,Chowdhury M,Hind C,Wand ME,Sutton JM,Rahman KM

    更新日期：2017-08-01 00:00:00

  • Effect of the complexation with cyclodextrins on the in vitro antiviral activity of ganciclovir against human cytomegalovirus.

    abstract：:The toxicity of the molecules currently used in the treatment of human cytomegalovirus (HCMV) in immunocompromised hosts often causes interruption of the therapy. Cyclodextrins (Cds), oligosaccharides possessing a hydrophobic cavity, have the property of forming inclusion complexes with a great number of molecules, im...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00247-9

    authors： Nicolazzi C,Abdou S,Collomb J,Marsura A,Finance C

    更新日期：2001-02-01 00:00:00

  • Structure-activity relationship of leucyladenylate sulfamate analogues as leucyl-tRNA synthetase (LRS)-targeting inhibitors of Mammalian target of rapamycin complex 1 (mTORC1).

    abstract：:Leucyl-tRNA synthetase (LRS) plays an important role in amino acid-dependent mTORC1 signaling, which is known to be associated with cellular metabolism and proliferation. Therefore, LRS-targeting small molecules that can suppress mTORC1 activation may provide an alternative strategy to current anticancer therapy. In t...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.01.037

    authors： Yoon S,Kim SE,Kim JH,Yoon I,Tran PT,Ann J,Kim C,Byun WS,Lee S,Kim S,Lee J,Lee J

    更新日期：2019-03-15 00:00:00

  • Structure-activity relationships on adrenoceptors and imidazoline-preferring binding sites (I(1,2)-PBSs). Part 1: Weak intramolecular H-bond and conformational flexibility in a new I1-PBS-selective imidazoline analogue, trans1-(4',5'-dihydro-1'H-imidazol-

    abstract：:The highly selective I1-PBS imidazoline analogue PMS 952 has been selected to study the incidence of intramolecular hydrogen bond and molecular flexibility on its biological activity. On one hand, the weak energy difference between three calculated conformers does not support the stabilization of one conformer by an i...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)00115-2

    authors： Ye HF,Dive G,Dehareng D,Heymans F,Godfroid JJ

    更新日期：2000-08-01 00:00:00

  • Synthesis of substituted diphenyl sulfones and their structure-activity relationship with the antagonism of 5-НТ6 receptors.

    abstract：:Substituted diphenyl sulfones (10a-n) were synthesised, and the structures were confirmed by NMR, LC-MS and X-ray crystallography. Their antagonistic activities towards 5-HT₆ receptor were assessed in a cell-based functional assay. Diphenyl sulfone 10a, in spite of being the smallest and simplest known sulfonyl-contai...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.05.040

    authors： Ivachtchenko A,Golovina E,Kadieva M,Mitkin O,Tkachenko S,Okun I

    更新日期：2013-08-01 00:00:00

  • Identification of minimal sequence for HIV-1 fusion inhibitors.

    abstract：:Emergence of multi-drug resistant HIV-1 is a serious problem for AIDS treatment. Recently, the virus-cell membrane fusion process has been identified as a promising target for the development of novel drugs against these resistant variants. In this study, we identified a 29-residue peptide fusion inhibitor, SC29EK, wh...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.09.018

    authors： Nishikawa H,Oishi S,Fujita M,Watanabe K,Tokiwa R,Ohno H,Kodama E,Izumi K,Kajiwara K,Naitoh T,Matsuoka M,Otaka A,Fujii N

    更新日期：2008-10-15 00:00:00

  • Synthetic strategies toward carbocyclic purine-pyrimidine hybrid nucleosides.

    abstract：:The blending of key structural features from the purine and pyrimidine nucleobase scaffolds gives rise to a new class of hybrid nucleosides. The purine-pyrimidine hybrid nucleosides can be viewed as either N-3 ribosylated purines or 5,6-disubstituted pyrimidines, thus recognition by both purine- and pyrimidine-metabol...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.06.039

    authors： Sadler JM,Mosley SL,Dorgan KM,Zhou ZS,Seley-Radtke KL

    更新日期：2009-08-01 00:00:00

  • Mapping of possible binding sequences of two beta-sheet breaker peptides on beta amyloid peptide of Alzheimer's disease.

    abstract：:Aggregation of amyloid peptide (Abeta) has been identified as a major feature of the pathogenesis of Alzheimer's disease. Increased risk for disease is associated with increased formation of polymerized Abeta. Inhibition of formation of toxic (aggregated) form of Abeta is one of the therapeutic possibilities. Beta she...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(01)00424-2

    authors： Hetényi C,Körtvélyesi T,Penke B

    更新日期：2002-05-01 00:00:00

  • Investigation of novel pyrazole carboxamides as new apoptosis inducers on neuronal cells in Helicoverpa zea.

    abstract：:Novel pyrazole carboxamides with a diarylamine-modified scaffold were modified based on the bixafen (Bayer) fungicide, which has excellent activity against Rhizoctonia solani, Rhizoctonia cerealis and Sclerotinia sclerotiorum. To discover the potential insecticidal activity of these novel pyrazole carboxamides, the pr...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.03.010

    authors： Ren Y,Yang N,Yue Y,Jin H,Tao K,Hou T

    更新日期：2018-05-15 00:00:00

  • An extended study of dimeric phenyl tropanes.

    abstract：:A series of dimeric phenyl tropanes consisting of two molecules of 4-chloro, 4-iodo or 4-(3-thiopheno)-phenyl tropane tethered together at the carboxylic acid moiety by a diamine or diol linker were prepared. The diamines used were a variety of linear, cyclic and aromatic diamines, while the diol tethered compounds we...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.06.007

    authors： Nielsen S,Pedersen CM,Hansen SG,Petersen MD,Sinning S,Wiborg O,Jensen HH,Bols M

    更新日期：2009-07-15 00:00:00

  • Synthesis and evaluation of acridine- and acridone-based anti-herpes agents with topoisomerase activity.

    abstract：:The discovery of new non-nucleoside antiviral compounds is of significant and growing interest for treating herpes virus infections due to the emergence of nucleoside-resistant strains. Using a whole cell virus-induced cytopathogenic assay, we tested a series of substituted triaryl heterocyclic compounds including acr...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.04.044

    authors： Goodell JR,Madhok AA,Hiasa H,Ferguson DM

    更新日期：2006-08-15 00:00:00

  • Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.

    abstract：:Bioactivity-guided fractionation of the extract from a Fijian red alga Peyssonnelia sp. led to the isolation of two novel sterol glycosides 19-O-β-d-glucopyranosyl-19-hydroxy-cholest-4-en-3-one (1) and 19-O-β-d-N-acetyl-2-aminoglucopyranosyl-19-hydroxy-cholest-4-en-3-one (2), and two known alkaloids indole-3-carboxald...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.10.010

    authors： Lin AS,Engel S,Smith BA,Fairchild CR,Aalbersberg W,Hay ME,Kubanek J

    更新日期：2010-12-01 00:00:00

  • Identification of topoisomerases as molecular targets of cytosporolide C and its analog.

    abstract：:Cytosporolide (Cytos) A-C, isolated from the fungus Cytospora sp., have anti-microbial activity, but their molecular targets in mammalian cells are unknown. We have previously reported the total synthesis of Cytos A by biomimetic hetero-Diels-Alder reaction. In this study, to examine the novel bioactivity of Cytos, we...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.06.014

    authors： Otake K,Yamada K,Miura K,Sasazawa Y,Miyazaki S,Niwa Y,Ogura A,Takao KI,Simizu S

    更新日期：2019-08-01 00:00:00

  • Synergistic reduction of HIV-1 infectivity by 5-azacytidine and inhibitors of ribonucleotide reductase.

    abstract：:Although many compounds have been approved for the treatment of human immunodeficiency type-1 (HIV-1) infection, additional anti-HIV-1 drugs (particularly those belonging to new drug classes) are still needed due to issues such as long-term drug-associated toxicities, transmission of drug-resistant variants, and devel...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.03.052

    authors： Rawson JM,Roth ME,Xie J,Daly MB,Clouser CL,Landman SR,Reilly CS,Bonnac L,Kim B,Patterson SE,Mansky LM

    更新日期：2016-06-01 00:00:00

  • Synthesis of beta-substituted naphth-1-yl ethylamido derivatives as new melatoninergic agonists.

    abstract：:Naphthalene melatoninergic ligands with alkyl groups (Me, Et, Pr, Bz) in the beta position of the ethylamido chain were synthesised. The affinity of the compounds for chicken brain melatonin receptors was evaluated using 2-[125I]-iodomelatonin as the radioligand. An increase in the affinity was observed with the beta-...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(99)00236-9

    authors： Mathé-Allainmat M,Le Gall M,Jellimann C,Andrieux J,Langlois M

    更新日期：1999-12-01 00:00:00

  • Synthesis and biological evaluation of largazole zinc-binding group analogs.

    abstract：:Histone acetylation is an extensively investigated post-translational modification that plays an important role as an epigenetic regulator. It is controlled by histone acetyl transferases (HATs) and histone deacetylases (HDACs). The overexpression of HDACs and consequent hypoacetylation of histones have been observed ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.03.071

    authors： Kim B,Ratnayake R,Lee H,Shi G,Zeller SL,Li C,Luesch H,Hong J

    更新日期：2017-06-15 00:00:00