当前位置： SCI文献检索 > BIOORGANIC CHEMISTRY期刊下所有文献 > Aryl methylene ketones and fluorinated methylene ketones as reversible inhibitors for severe acute respiratory syndrome (SARS) 3C-like proteinase.

Aryl methylene ketones and fluorinated methylene ketones as reversible inhibitors for severe acute respiratory syndrome (SARS) 3C-like proteinase.

Abstract：

:The severe acute respiratory syndrome (SARS) virus depends on a chymotrypsin-like cysteine proteinase (3CL(pro)) to process the translated polyproteins to functional viral proteins. This enzyme is a target for the design of potential anti-SARS drugs. A series of ketones and corresponding mono- and di-fluoro ketones having two or three aromatic rings were synthesized as possible reversible inhibitors of SARS 3CL(pro). The design was based on previously established potent inhibition of the enzyme by oxa analogues (esters), which also act as substrates. Structure-activity relationships and modeling studies indicate that three aromatic rings, including a 5-bromopyridin-3-yl moiety, are key features for good inhibition of SARS 3CL(pro). Compound 11d, 2-(5-bromopyridin-3-yl)-1-(5-(4-chlorophenyl)furan-2-yl)ethanone and its alpha-monofluorinated analogue 12d, gave the best reversible inhibition with IC(50) values of 13 mircoM and 28 microM, respectively. In contrast to inhibitors having two aromatic rings, alpha-fluorination of compounds with three rings unexpectedly decreased the inhibitory activity.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Zhang J,Huitema C,Niu C,Yin J,James MN,Eltis LD,Vederas JC

doi

10.1016/j.bioorg.2008.01.001

subject

Has Abstract

pub_date

2008-10-01 00:00:00

pages

229-40

issue

5

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(08)00003-5

journal_volume

36

pub_type

杂志文章

相关文献

BIOORGANIC CHEMISTRY文献大全
  • Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents.

    abstract：:Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that mo...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2014.07.011

    authors： Zhou S,Ren J,Liu M,Ren L,Liu Y,Gong P

    更新日期：2014-12-01 00:00:00

  • Synthesis and tyrosinase inhibitory activity of novel N-hydroxybenzyl-N-nitrosohydroxylamines.

    abstract：:Several novel N-substituted N-nitrosohydroxylamines were synthesized. They all inhibited mushroom tyrosinase, but the type of inhibition was different depending on the substituent. Some N-(mono- or dihydroxybenzyl)-N-nitrosohydroxylamines exhibited uncompetitive inhibition with respect to L-dopa. Among them, compound ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/S0045-2068(03)00026-9

    authors： Shiino M,Watanabe Y,Umezawa K

    更新日期：2003-04-01 00:00:00

  • TDP-43 specific reduction induced by Di-hydrophobic tags conjugated peptides.

    abstract：:TAR DNA binding protein 43 (TDP-43) is a key target in amyotrophic lateral sclerosis (ALS) treatment. Here, based on hydrophobic tagging strategy, we designed and synthesized a series of single or double hydrophobic tags conjugated peptides D1-D8. Among them, it was found that D4 displayed strongest ability to induce ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.11.042

    authors： Gao N,Huang YP,Chu TT,Li QQ,Zhou B,Chen YX,Zhao YF,Li YM

    更新日期：2019-03-01 00:00:00

  • Multi-target 1,4-dihydropyridines showing calcium channel blockade and antioxidant capacity for Alzheimer's disease therapy.

    abstract：:In this work we describe the synthesis, Ca+2 channel blockade capacity and antioxidant power of N3,N5-bis(2-(5-methoxy-1H-indol-3-yl)ethyl)-2,6-dimethyl-4-aryl-1,4-dihydropyridine-3,5-dicarboxamides 1-9, a number of multi-target small 1,4-dihydropyridines (DHP), designed by juxtaposition of melatonin and nimodipine. A...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103205

    authors： Malek R,Maj M,Wnorowski A,Jóźwiak K,Martin H,Iriepa I,Moraleda I,Chabchoub F,Marco-Contelles J,Ismaili L

    更新日期：2019-10-01 00:00:00

  • Synthesis and biological evaluation of benzofuran-based 3,4,5-trimethoxybenzamide derivatives as novel tubulin polymerization inhibitors.

    abstract：:A new series of derivatives characterized by the presence of the 3,4,5-trimethoxylbenzamide substituted benzofurans were synthesized and evaluated for antiproliferative activity against four cancer cell lines and one normal human cell line. Among them, derivative 6g with greatest cytotoxicity significantly inhibited t...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104076

    authors： Li Q,Jian XE,Chen ZR,Chen L,Huo XS,Li ZH,You WW,Rao JJ,Zhao PL

    更新日期：2020-09-01 00:00:00

  • Heterocyclic periphery in the design of carbonic anhydrase inhibitors: 1,2,4-Oxadiazol-5-yl benzenesulfonamides as potent and selective inhibitors of cytosolic hCA II and membrane-bound hCA IX isoforms.

    abstract：:A series of novel aromatic primary sulfonamides decorated with diversely substituted 1,2,4-oxadiazole periphery groups has been prepared using a parallel chemistry approach. The compounds displayed a potent inhibition of cytosolic hCA II and membrane-bound hCA IX isoforms. Due to a different cellular localization of t...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2017.10.005

    authors： Krasavin M,Shetnev A,Sharonova T,Baykov S,Tuccinardi T,Kalinin S,Angeli A,Supuran CT

    更新日期：2018-02-01 00:00:00

  • Evaluation of angularly condensed diquinothiazines as potential anticancer agents.

    abstract：:We present efficient synthesis of isomeric types of angularly fused diquinothiazines in the reactions of 2,2'-dichloro-3,3'-diquinolinyl disulfide and diquinodithiin with 3-, 5-, 6- and 8-aminoquinolines. The pentacyclic diquinothiazine ring systems were identified as diquino[3,2-b;3',4'-e][1,4]thiazine, diquino[3,2-b...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.04.005

    authors： Jeleń M,Pluta K,Latocha M,Morak-Młodawska B,Suwińska K,Kuśmierz D

    更新日期：2019-06-01 00:00:00

  • Aryl- or heteroaryl-based hydrazinylphthalazine derivatives as new potential antitrypanosomal agents.

    abstract：:A series of twenty phthalazinyl-hydrazones were synthesized and tested as potential anti-Trypanosoma cruzi agents. The phthalazines containing 5-nitroheteroaryl moiety 3l and 3m displayed an excellent in vitro antitrypanosomal profile, exhibiting low micromolar EC50 values against proliferative epimastigote of T. cruz...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2017.03.008

    authors： Romero AH,Rodríguez J,García-Marchan Y,Leañez J,Serrano-Martín X,López SE

    更新日期：2017-06-01 00:00:00

  • Interaction of C20-substituted derivative of pregnenolone acetate with copper (II) leads to ROS generation, DNA cleavage and apoptosis in cervical cancer cells: Therapeutic potential of copper chelation for cancer treatment.

    abstract：:Cervical cancer is a leading cause of cancer-related deaths among women in developing countries. Therefore, development of new chemotherapeutic agents is required. Unlike normal cells, cancer cells contain elevated copper levels which play an integral role in angiogenesis. Thus, targeting copper via copper-specific ch...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.03.031

    authors： Zafar A,Singh S,Ahmad S,Khan S,Imran Siddiqi M,Naseem I

    更新日期：2019-06-01 00:00:00

  • DNA binding studies of novel diazatruxenones analogs as potential anticancer agents: Synthesis, antitumor investigation, DNA binding, SAR and molecular modeling calculation.

    abstract：:A series of polycyclic skeleton of truxene and triazatruxene analogs has been synthesized and evaluated for antitumor and DNA binding activities. The synthesized structures were confirmed by different spectroscopic techniques such as IR, 1HNMR, 13CNMR, and mass spectroscopy. The antitumor screening was performed adopt...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104323

    authors： El Sayed MT,Shabaan SN,Sarhan AE,El-Messery SM,El-Sayed SM,Hassan GS

    更新日期：2020-11-01 00:00:00

  • New fused pyrimidine derivatives with anticancer activity: Synthesis, topoisomerase II inhibition, apoptotic inducing activity and molecular modeling study.

    abstract：:A new series of triazolopyrimidines and thiazolopyrimidine hydrobromides was designed and prepared as topoisomerase II inhibitors. Screening of all synthesized compounds was carried out by the National Cancer Institute (NCI) of USA. Activity against 60 human cancer cell lines representing different cancer types was de...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104134

    authors： Nemr MTM,AboulMagd AM

    更新日期：2020-10-01 00:00:00

  • Combinatorial synthesis and biological evaluation of peptide-binding GPCR-targeted library.

    abstract：:As an effective strategy of the drug discovery for peptide-binding GPCRs based on the natural ligands, beta-turn peptidomimetic compound library with benzodiazepine skeleton was constructed using solid and solution phase parallel synthesis with four different scaffolds containing Phe, Lys, Ser and Glu, respectively. T...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2009.04.001

    authors： Lee JY,Im I,Webb TR,McGrath D,Song MR,Kim YC

    更新日期：2009-06-01 00:00:00

  • Current development of 5-nitrofuran-2-yl derivatives as antitubercular agents.

    abstract：:Pulmonary tuberculosis (TB) is an infectious disease caused by Mycobacterium tuberculosis (MTB) and still remains one of the foremost fatal infectious diseases, infecting nearly a third of the worldwide population. The emergencies of multidrug-resistant and extensively drug-resistant tuberculosis (MDR and XDR-TB) prom...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.bioorg.2019.102969

    authors： Elsaman T,Mohamed MS,Mohamed MA

    更新日期：2019-07-01 00:00:00

  • Synthesis and biological evaluation of bergenin-1,2,3-triazole hybrids as novel class of anti-mitotic agents.

    abstract：:In continuation of our investigation of pharmacologically-motivated natural products, we have isolated bergenin (1) as a major compound from Mallotus philippensis, which is deployed in different Indian traditional systems of medicine. Here, a series of bergenin-1,2,3-triazole hybrids were synthesized and evaluated for...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103161

    authors： Pavan Kumar P,Siva B,Venkateswara Rao B,Dileep Kumar G,Lakshma Nayak V,Nishant Jain S,Tiwari AK,Purushotham U,Venkata Rao C,Suresh Babu K

    更新日期：2019-10-01 00:00:00

  • Exploration of aroyl/heteroaroyl iminothiazolines featuring 2,4,5-trichlorophenyl moiety as a new class of potent, selective, and in vitro efficacious glucosidase inhibitors.

    abstract：:A series of iminothiazolines (4a-j) featuring 2,4,5-trichlorophenyl moiety and aroyl/heteroaroyl substituents has been prepared from readily accessible thioureas. In-vitro screening against glucosidase enzymes showed highly specific inhibition of α-glucosidase with a marked dependence of the potency upon the nature of...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2017.07.012

    authors： Kazmi M,Zaib S,Amjad ST,Khan I,Ibrar A,Saeed A,Iqbal J

    更新日期：2017-10-01 00:00:00

  • Synthesis and molecular docking study of some 3,4-dihydrothieno[2,3-d]pyrimidine derivatives as potential antimicrobial agents.

    abstract：:In continuation of our research program aiming at developing new potent antimicrobial agents, new series of substituted 3,4-dihydrothieno[2,3-d]pyrimidines was synthesized. The newly synthesized compounds were preliminary tested for their in vitro activity against six bacterial and three fungal strains using the agar ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.102934

    authors： Shaaban OG,Issa DAE,El-Tombary AA,Abd El Wahab SM,Abdel Wahab AE,Abdelwahab IA

    更新日期：2019-07-01 00:00:00

  • Synthesis and in vitro antileishmanial activity of 5-substituted-2'-deoxyuridine derivatives.

    abstract：:We report herein the synthesis and the in vitro antileishmanial evaluation of 5-substituted-2'-deoxyuridine nucleosides. The most active compound against Leishmania donovani promastigotes was Thia-dU (3a) with an IC50 =3 microM. This compound exhibited the same activity as zidovudine (3'-azido-2'-deoxythymidine) used ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2005.07.001

    authors： Peyron C,Benhida R,Bories C,Loiseau PM

    更新日期：2005-12-01 00:00:00

  • Eight new glycosides with hepatoprotective activity isolated from the aerial parts of Morinda parvifolia.

    abstract：:Eight new glycosides, morindaparvins P-W, were isolated from the butanol extract of the aerial parts of Morinda parvifolia. These new structures were elucidated by comprehensive spectroscopic analysis and by comparing the experimental and calculated electronic circular dichroism spectra. The butanol extract was observ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.11.055

    authors： Su X,Li L,Sun H,Zhang F,Li C,Li F,Wang H,Li B,Chen R,Kang J

    更新日期：2019-06-01 00:00:00

  • 3, 9-di-O-substituted coumestrols incorporating basic amine side chains act as novel apoptosis inducers with improved pharmacological selectivity.

    abstract：:There is much interest in the use of phytoestrogens such as coumestrol in breast cancer intervention due to their antiestrogenic activity and multiple modes of tumor cell death. However, the clear beneficial effects of naturally occurring estrogen mimetic coumestrol remain controversial due to experimental evidence th...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.12.024

    authors： Luo G,Tang Z,Li X,Hou Q,Chen Y,Lao K,Xiang H

    更新日期：2019-04-01 00:00:00

  • Rational design of pyrrolo.

    abstract：:Models have been developed for the interaction of the pyrrolo[1,2-a]benzimidazole (PBI) antitumor agents with the two-electron activating enzyme DT-diaphorase and the DNA major groove. The DT-diaphorase model and experimental results indicate that the S-enantiomer of 3-carbamido PBI can enantioselect ovarian cancers. ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1006/bioo.2000.1183

    authors： Huang X,Suleman A,Skibo EB

    更新日期：2000-12-01 00:00:00

  • Monoterpene indole alkaloids with acetylcholinesterase inhibitory activity from the leaves of Rauvolfia vomitoria.

    abstract：:Seventeen monoterpene indole alkaloids, including seven new alkaloids (1-7) and ten known analogues (8-17), were isolated and identified from the leaves of R. vomitoria. The structures of new alkaloids were elucidated by extensive spectroscopic analysis and single-crystal X-ray diffraction analysis. Rauvomitorine I (1...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104136

    authors： Zhan G,Miao R,Zhang F,Chang G,Zhang L,Zhang X,Zhang H,Guo Z

    更新日期：2020-09-01 00:00:00

  • Chemoenzymatic synthesis of enantiomerically enriched diprophylline and xanthinol nicotinate.

    abstract：:A concise chemoenzymatic route toward enantiomerically enriched active pharmaceutical ingredients (API) - diprophylline and xanthinol nicotinate - is reported for the first time. The decisive step is an enantioselective lipase-mediated methanolysis of racemic chlorohydrin-synthon acetate, namely 1-chloro-3-(1,3-dimeth...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104448

    authors： Borowiecki P,Młynek M,Dranka M

    更新日期：2021-01-01 00:00:00

  • Design, synthesis, biological evaluation and molecular modeling of novel 1H-pyrrolo[2,3-b]pyridine derivatives as potential anti-tumor agents.

    abstract：:A class of 3-substituted 1H-pyrrolo[2,3-b]pyridine derivatives were designed, synthesized and evaluated for their in vitro biological activities against maternal embryonic leucine zipper kinase (MELK). Among these derivatives, the optimized compound 16h exhibited potent enzyme inhibition (IC50 = 32 nM) and excellent a...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103474

    authors： Wang R,Chen Y,Yang B,Yu S,Zhao X,Zhang C,Hao C,Zhao D,Cheng M

    更新日期：2020-01-01 00:00:00

  • Novel artemisinin derivatives with potent anticancer activities and the anti-colorectal cancer effect by the mitochondria-mediated pathway.

    abstract：:Many artemisinin derivatives have good inhibitory effects on malignant tumors. In this work, a novel series of artemisinin derivatives containing piperazine and fluorine groups were designed and synthesized and their structures were confirmed by 1H NMR, 13C NMR and HRMS technologies. The in vitro cytotoxicity against ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104496

    authors： Lin L,Lu W,Dai T,Chen H,Wang T,Yang L,Yang X,Liu Y,Sun D

    更新日期：2021-01-01 00:00:00

  • Hydrogen transfer pathways of the asymmetric reduction of alpha,beta-unsaturated ketone mediated by baker's yeast.

    abstract：:The hydrogen transfer mechanism of cofactor reduction and recycling processes in the yeast reduction of alpha,beta-unsaturated ketone was studied by using quantitative isotope tracing close to natural abundance measured by (2)H NMR. In the reaction, the active cofactor is NADPH. The cofactor-transferred hydride attack...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2006.04.002

    authors： Chu Y,Zhang BL,Silvestre V,Cheng JP

    更新日期：2006-06-01 00:00:00

  • Synthesis, inhibition properties against xanthine oxidase and molecular docking studies of dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives.

    abstract：:This study focused on synthesis various dimethyl N-benzyl-1H-1,2,3-triazole-4,5-dicarboxylate and (N-benzyl-1H-1,2,3-triazole-4,5-diyl)dimethanol derivatives under the conditions of green chemistry without the use of solvent and catalysts. Their inhibition properties were also investigated on xanthine oxidase (XO) act...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2021.104654

    authors： Yagiz G,Noma SAA,Altundas A,Al-Khafaji K,Taskin-Tok T,Ates B

    更新日期：2021-01-12 00:00:00

  • Synthesis of 4,6-dideoxy-3-fluoro-2-keto-beta-D-glucopyranosyl analogues of 5-fluorouracil, N6-benzoyl adenine, uracil, thymine, N4-benzoyl cytosine and evaluation of their antitumor activities.

    abstract：:The synthesis of the unsaturated 4,6-dideoxy-3-fluoro-2-keto-beta-d-glucopyranosyl nucleosides of 5-fluorouracil (6a), N(6)-benzoyl adenine (6b), uracil (6c), thymine (6d) and N(4)-benzoyl cytosine (6e), is described. Monoiodination of compounds 1a,b, followed by acetylation, catalytic hydrogenation and finally regios...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2009.11.001

    authors： Manta S,Tsoukala E,Tzioumaki N,Kiritsis C,Balzarini J,Komiotis D

    更新日期：2010-04-01 00:00:00

  • Evaluation of guanylhydrazone derivatives as inhibitors of Candida rugosa digestive lipase: Biological, biophysical, theoretical studies and biotechnological application.

    abstract：:This work aimed to evaluate the inhibition of Candida rugosa lipase by five guanylhydrazone derivatives through biological, biophysical and theoretical studies simulating physiologic conditions. The compound LQM11 (IC50 = 14.70 μM) presented the highest inhibition against the enzyme. Therefore, for a better understand...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.03.030

    authors： Santana CC,Silva-Júnior EF,Santos JCN,Rodrigues ÉEDS,da Silva IM,Araújo-Júnior JX,do Nascimento TG,Oliveira Barbosa LA,Dornelas CB,Figueiredo IM,Santos JCC,Grillo LAM

    更新日期：2019-06-01 00:00:00

  • Synthesis of pyrimidine-2,4,6-trione derivatives: Anti-oxidant, anti-cancer, α-glucosidase, β-glucuronidase inhibition and their molecular docking studies.

    abstract：:This paper describes a facile protocol, efficient, and environmentally benign for the synthesis a series of barbiturate acid substituted at C5 position 3a-o. The desired compounds subjected in vitro for different set of bioassays including against anti-oxidant (DPPH and super oxide scavenger assays), anti-cancer, α-gl...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2016.07.009

    authors： Barakat A,Islam MS,Al-Majid AM,Ghabbour HA,Yousuf S,Ashraf M,Shaikh NN,Iqbal Choudhary M,Khalil R,Ul-Haq Z

    更新日期：2016-10-01 00:00:00

  • Enantiomeric 8-O-4'-type neolignans from Crataegus pinnatifida exhibit cytotoxic effect via apoptosis and autophagy in Hep3B cells.

    abstract：:Crataegus pinnatifida has been famous for its nutritional purpose. However, systematic investigation on the bioactive constituents is still lacking, although this fruit has been reported for its cytotoxic effect before. In this study, two pairs of new lignan enantiomers (1a/1b, 2a/2b), which isolated using chiral chro...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104267

    authors： Shang XY,Guo R,Yu XQ,Lin B,Huang XX,Yao GD,Song SJ

    更新日期：2020-11-01 00:00:00