当前位置： SCI文献检索 > BIOORGANIC CHEMISTRY期刊下所有文献 > Quinazoline-4(3H)-one derivatives as novel and potent inhibitors of soluble epoxide hydrolase: Design, synthesis and biological evaluation.

Quinazoline-4(3H)-one derivatives as novel and potent inhibitors of soluble epoxide hydrolase: Design, synthesis and biological evaluation.

Abstract：

:Inhibition of soluble epoxide hydrolase (sEH) is considered as a promising target to reduce blood pressure, improve insulin sensitivity, and decrease inflammation. In this study, a series of some novel quinazoline-4(3H)-one derivatives (3a-t) with varying steric and electronic properties was designed, synthesized and evaluated as sEH Inhibitors. Most of the synthesized compounds had similar inhibitory activity to the commercial reference inhibitor, 12-(3-adamantan-1-ylureido)dodecanoic acid, and amongst them, 4-chloro-N-(4-(4-oxo-3,4-dihydroquinazoline-2-yl)phenyl)benzamide (3g) was identified as the most active sEH inhibitor (IC50 = 0.5 nM), about 2-fold more potent compared to the reference inhibitor. The results of molecular modeling followed by biological studies indicate that a quinazolinone ring serves as a suitable scaffold to develop novel small molecule candidates to inhibit sEH and the nature of substituent on the amide moiety has a moderate effect on the activity.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

Hejazi L,Rezaee E,Tabatabai SA

doi

10.1016/j.bioorg.2020.103736

subject

Has Abstract

pub_date

2020-06-01 00:00:00

pages

103736

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(19)31676-1

journal_volume

99

pub_type

杂志文章

相关文献

BIOORGANIC CHEMISTRY文献大全
  • Facile synthesis of 1,2,3-triazole-fused indolo- and pyrrolo[1,4]diazepines, DNA-binding and evaluation of their anticancer activity.

    abstract：:A facile synthetic strategy has been developed for the generation of structurally diverse N-fused heterocycles. The formation of fused 1,2,3-triazole indolo and pyrrolodiazepines proceeds through an initial Knoevenagel condensation followed by intramolecular azide-alkyne cycloaddition reaction at room temperature with...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103306

    authors： Gour J,Gatadi S,Pooladanda V,Ghouse SM,Malasala S,Madhavi YV,Godugu C,Nanduri S

    更新日期：2019-12-01 00:00:00

  • Sulfonamides incorporating piperazine bioisosteres as potent human carbonic anhydrase I, II, IV and IX inhibitors.

    abstract：:Starting from the molecular simplification of (R) 4-(3,4-dibenzylpiperazine-1-carbonyl)benzenesulfonamide 9a, a compound endowed with selectivity for human Carbonic Anhydrase (hCA) IV, a series of piperazines and 4-aminopiperidines carrying a 4-sulfamoylbenzamide moiety as Zn-binding group have been designed and teste...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103130

    authors： Chiaramonte N,Bua S,Angeli A,Ferraroni M,Picchioni I,Bartolucci G,Braconi L,Dei S,Teodori E,Supuran CT,Romanelli MN

    更新日期：2019-10-01 00:00:00

  • Molecular-docking-guided design and synthesis of new IAA-tacrine hybrids as multifunctional AChE/BChE inhibitors.

    abstract：:A series of new indole-3-acetic acid (IAA)-tacrine hybrids as dual acetylcholinesterase (AChE)/butyrylcholinesterase (BChE) inhibitors were designed and prepared based on the molecular docking mode of AChE with an IAA derivative (1a), a moderate AChE inhibitor identified by screening our compound library for anti-Alzh...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.10.057

    authors： Cheng ZQ,Zhu KK,Zhang J,Song JL,Muehlmann LA,Jiang CS,Liu CL,Zhang H

    更新日期：2019-03-01 00:00:00

  • Exploring the interaction between citrus flavonoids and phytopathogenic fungi through enzymatic activities.

    abstract：:Flavonoids are involved in citrus defense against phytopathogens. In this study, we applied in vitro biocatalysis assays using the flavanones glycosides hesperidin and naringin to explore the enzymatic activities involved in such interaction. The main enzymatic activity observed was the hydrolysis catalyzed by fungi n...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104126

    authors： Costa JH,Fernandes LS,Akiyama DY,Fill TP

    更新日期：2020-09-01 00:00:00

  • QM/MM study of the reaction mechanism of Cl-cis,cis-muconate with muconate lactonizing enzyme.

    abstract：:The lactonization process of Cl-cis,cis-muconate catalyzed by anti-muconate lactonizing enzyme (anti-MLE) was studied theoretically with the aid of a combined quantum mechanics/molecular mechanics (QM/MM) approach. Two elementary processes steps involved in the lactanization process were investigated. The calculated e...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.05.007

    authors： Zhu L,Tang X,Li Y,Zhang R,Wang J,Zhang Q,Wang W

    更新日期：2018-10-01 00:00:00

  • Development of pyridazine derivatives as potential EGFR inhibitors and apoptosis inducers: Design, synthesis, anticancer evaluation, and molecular modeling studies.

    abstract：:Novel hybrids of pyridazine-pyrazoline were synthesized aiming to develop new antiproliferative candidates. All compounds were submitted to the National Cancer Institute (NCI), USA, and many were proved to have significant antiproliferative activity. In addition, in vitro studies of the epidermal growth factor recepto...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104473

    authors： Ahmed MF,Santali EY,Mohi El-Deen EM,Naguib IA,El-Haggar R

    更新日期：2021-01-01 00:00:00

  • Ethyl benzoate bearing pyrrolizine/indolizine moieties: Design, synthesis and biological evaluation of anti-inflammatory and cytotoxic activities.

    abstract：:Two new series of ethyl benzoate bearing pyrrolizine and indolizine moieties 8-11 were synthesized and evaluated for their anti-inflammatory and anticancer activities. Among these derivatives, compounds 9a, 10b and 11b displayed in vivo anti-inflammatory and analgesic activity comparable to ibuprofen. The acute ulcero...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103371

    authors： Attalah KM,Abdalla AN,Aslam A,Ahmed M,Abourehab MAS,ElSawy NA,Gouda AM

    更新日期：2020-01-01 00:00:00

  • Fusicoccane-derived diterpenoids with bridgehead double-bond-containing tricyclo[9.2.1.03,7]tetradecane ring systems from Alternaria brassicicola.

    abstract：:Fusicoccane-derived diterpenoids bearing a unique bridgehead double-bond-containing tricyclo[9.2.1.03,7]tetradecane (5-9-5 ring system) core skeleton represent a rarely reported class of rearranged terpenoids, which traced back to fusicoccanes with a classical dicyclopenta[a,d]cyclooctane (5-8-5 ring system) core skel...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103887

    authors： Li F,Pan L,Lin S,Zhang S,Li H,Yang B,Liu J,Wang J,Hu Z,Zhang Y

    更新日期：2020-07-01 00:00:00

  • Spectroscopic investigation of the interaction of water-soluble azocalix[4]arenes with bovine serum albumin.

    abstract：:In this work, three hydrosoluble azocalix[4]arene derivatives, 5-(o-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]arene (o-MAC-Calix), 5-(m-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]arene (m-MAC-Calix) and 5-(p-methylphenylazo)-25,26,27-tris(carboxymethoxy)-28-hydroxycalix[4]a...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2014.12.002

    authors： Fan P,Wan L,Shang Y,Wang J,Liu Y,Sun X,Chen C

    更新日期：2015-02-01 00:00:00

  • Exploiting the 4-hydrazinobenzoic acid moiety for the development of anticancer agents: Synthesis and biological profile.

    abstract：:Thirteen 4-hydrazinobenzoic acid derivatives were elaborated and characterized by spectral analyses (NMR and MS). Evaluation of their in vitro cytotoxic activity showed that some of the targets demonstrated potent inhibitory effects against HCT-116 and MCF-7 cancer cells. The IC50 values ranged between 21.3 ± 4.1 and ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104098

    authors： Abuelizz HA,Awad HM,Marzouk M,Nasr FA,Bakheit AH,Naglah AM,Al-Shakliah NS,Al-Salahi R

    更新日期：2020-09-01 00:00:00

  • Design, synthesis and melatoninergic potency of new N-acyl 8,9-dihydro-4-methoxy-7H-2-benzo[de]quinolinalkanamines.

    abstract：:A series of new N-acyl 8,9-dihydro-4-methoxy-7H-2-benzo[de]quinolinalkanamines have been prepared and tested for their ability to activate pigment granule aggregation in Xenopus laevis melanophores and bind to the recombinant human MT(1) and MT(2) melatonin receptor subtypes expressed in NIH 3T3 cells. Compounds with ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2006.11.006

    authors： Tsotinis A,Eleutheriades A,Hough KA,Davidson K,Sugden D

    更新日期：2007-04-01 00:00:00

  • Imidazole-pyrazole hybrids: Synthesis, characterization and in-vitro bioevaluation against α-glucosidase enzyme with molecular docking studies.

    abstract：:Herein, substituted imidazole-pyrazole hybrids (2a-2n) were prepared via a multi component reaction employing pyrazole-4-carbaldehydes (1a-1d), ammonium acetate, benzil and arylamines as reactants. All the new compounds were characterized through their spectral and elemental analyses. Further these compounds were test...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.10.047

    authors： Chaudhry F,Naureen S,Ashraf M,Al-Rashida M,Jahan B,Munawar MA,Khan MA

    更新日期：2019-02-01 00:00:00

  • Sesquiterpenoids from the roots of Inula helenium inhibit acute myelogenous leukemia progenitor cells.

    abstract：:One new eudesmane sesquiterpenoid, 11β-hydroxy-13-chloro-eudesm-5-en-12, 8-olide (1), was isolated from the roots of Inula helenium together with nine eudesmanolides (2-10) and one germacranolide (11). Their structures were elucidated on the basis of detailed spectroscopic analyses. All isolates were evaluated for the...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.01.055

    authors： Ding Y,Pan W,Xu J,Wang T,Chen T,Liu Z,Xie C,Zhang Q

    更新日期：2019-05-01 00:00:00

  • An alkali tolerant α-l-rhamnosidase from Fusarium moniliforme MTCC-2088 used in de-rhamnosylation of natural glycosides.

    abstract：:Analkali tolerant α-l-rhamnosidase has been purified to homogeneity from the culture filtrate of a new fungal strain, Fusarium moniliforme MTCC-2088, using concentration by ultrafiltration and cation exchange chromatography on CM cellulose column. The molecular mass of the purified enzyme has been found to be 36.0 kDa...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.11.027

    authors： Kumar D,Yadav S,Yadava S,Yadav KDS

    更新日期：2019-03-01 00:00:00

  • Design, synthesis and molecular modeling studies of new series of s-triazine derivatives as antimicrobial agents against multi-drug resistant clinical isolates.

    abstract：:Three novel series of s-triazine derivatives, including thirty-five new compounds 2a-d, 3a-3p, 4b-d, 5b-d, 6d-6d, and 7a-7f were synthesized comprising a diversity of substituents based on the structure of Astrazeneca arylaminotriazine DNA gyrase B inhibitor. The antimicrobial activity was determined for all compounds...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103013

    authors： Haiba NS,Khalil HH,Moniem MA,El-Wakil MH,Bekhit AA,Khattab SN

    更新日期：2019-08-01 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, computational molecular docking analysis and effectiveness on tyrosinase inhibition of kojic acid derivatives.

    abstract：:Tyrosinase inhibitors have become increasingly important as whitening agents and for the treatment of pigmentary disorders. In this study, the synthesis of kojic acid derivatives having 2-substituted-3-hydroxy-6-hyroxymethyl/chloromethyl/methyl/morpholinomethylpiperidinyl- methyl/pyrrolidinylmethyl-4H-pyran-4-one stru...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.102950

    authors： Karakaya G,Türe A,Ercan A,Öncül S,Aytemir MD

    更新日期：2019-07-01 00:00:00

  • Synthesis, cytotoxic evaluation, and molecular docking studies of novel quinazoline derivatives with benzenesulfonamide and anilide tails: Dual inhibitors of EGFR/HER2.

    abstract：:We synthesized a new series of 2-[(3-(4-sulfamoylphenethyl)-4(3H)-quinazolinon-2-yl)thio]anilide derivatives (2-16) and evaluated their cytotoxic activity against breast adenocarcinoma (MCF-7), colorectal adenocarcinoma (HT-29), and acute myeloid leukemia (HL-60 and K562) cells. To reveal their selectivity toward canc...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103461

    authors： Alkahtani HM,Abdalla AN,Obaidullah AJ,Alanazi MM,Almehizia AA,Alanazi MG,Ahmed AY,Alwassil OI,Darwish HW,Abdel-Aziz AA,El-Azab AS

    更新日期：2020-01-01 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

  • Building fluorescent sensors for carbohydrates using template-directed polymerizations.

    abstract：:The ability to custom-make fluorescent sensors for different analytes could have a tremendous impact in a variety of areas. Template-directed polymerization or molecular imprinting seems to be a promising approach for the preparation of high-affinity and specific binding sites for different template molecules. However...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1006/bioo.2001.1219

    authors： Gao S,Wang W,Wang B

    更新日期：2001-10-01 00:00:00

  • Synthesis and evaluation of antioxidant and antiproliferative activity of 2-arylbenzimidazoles.

    abstract：:Three series of arylbenzimidazole derivatives 3-40, 45 have been simply synthesized and tested for their antioxidant capacity. The 2-arylbenzimidazoles were tested against various radicals by the DPPH, FRAP and ORAC tests and showed different activity profiles. It has been observed that the number and position of the ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103396

    authors： Baldisserotto A,Demurtas M,Lampronti I,Tacchini M,Moi D,Balboni G,Pacifico S,Vertuani S,Manfredini S,Onnis V

    更新日期：2020-01-01 00:00:00

  • Synthesis of triphenylphosphonium dibenzothiophene S-oxide derivatives and their effect on cell cycle as photodeoxygenation-based cytotoxic agents.

    abstract：:Photodeoxygenation of Dibenzothiophene-S-oxide (DBTO) in UV-A light produces atomic oxygen [O(3P)] and the corresponding sulfide, dibenzothiophene (DBT). Recently, DBTO has been derivatized to study the effect of UV-A light-driven photodeoxygenation in lipids, proteins, and nucleic acids. In this study, two DBTO deriv...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104442

    authors： Isor A,O'Dea AT,Petroff JT 2nd,Skubic KN,Grady SF,Arnatt CK,McCulla RD

    更新日期：2020-12-01 00:00:00

  • Design, synthesis, and evaluations of the antiproliferative activity and aqueous solubility of novel carbazole sulfonamide derivatives as antitumor agents.

    abstract：:Optimization of IG-105 (1) on the carbazole ring provided five series of new carbazole sulfonamides derivatives, 7a-e, 8a-g, 9a-g, 10a-e, and 11a-g. All of the compounds were evaluated against HepG2, MCF-7, MIA PaCa-2, and Bel-7402 cells for antiproliferative activity. Each series of compounds was 2-5 times more activ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103766

    authors： Sun L,Wang C,Hu X,Wu Y,Jiang Z,Li Z,Chen X,Hu L

    更新日期：2020-06-01 00:00:00

  • α-bisabolol β-D-fucopyranoside as a potential modulator of β-amyloid peptide induced neurotoxicity: An in vitro &in silico study.

    abstract：:Alzheimer's disease (AD) is a multifaceted neurodegenerative disorder affecting the elderly people. For the AD treatment, there is inefficiency in the existing medication, as these drugs reduce only the symptoms of the disease. Since multiple pathological proteins are involved in the development of AD, searching for a...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.102935

    authors： Jeyakumar M,Sathya S,Gandhi S,Tharra P,Suryanarayanan V,Singh SK,Baire B,Pandima Devi K

    更新日期：2019-07-01 00:00:00

  • Development of broad-spectrum enterovirus antivirals based on quinoline scaffold.

    abstract：:Non-polio enteroviruses such as enterovirus A71 (EV-A71), EV-D68, and coxsackievirus B3 (CVB3) are significant human pathogens with disease manifestations ranging from mild flu-like symptoms to more severe encephalitis, myocarditis, acute flaccid paralysis/myelitis, and even death. There is currently no effective anti...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103981

    authors： Musharrafieh R,Kitamura N,Hu Y,Wang J

    更新日期：2020-08-01 00:00:00

  • Heterocyclic cellular lipid peroxidation inhibitors inspired by the marine antioxidant barettin.

    abstract：:The marine environment remains a rich source for the discovery and development of novel bioactive compounds. The present paper describes the design, synthesis and biological evaluation of a library of small molecule heterocyclic mimetics of the marine 2,5-diketopiperazine barettin which is a powerful natural antioxida...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.11.024

    authors： Labrière C,Andersen JH,Albrigtsen M,Hansen JH,Svenson J

    更新日期：2019-03-01 00:00:00

  • Differential metabolism of diastereoisomeric diterpenes by Preussia minima, found as endophytic fungus in Cupressus lusitanica.

    abstract：:The plant diastereoisomeric diterpenes ent-pimara-8(14)-15-dien-19-oic acid, obtained from Viguiera arenaria, and isopimara-8(14)-15-dien-18-oic acid, isolated from Cupressus lusitanica, were distinctly functionalized by the enzymes produced in whole cell cultures of the fungus Preussia minima, isolated from surface s...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.04.003

    authors： Ud Din Z,de Medeiros LS,Abreu LM,Pfenning LH,Lopes Jymeni DB,Rodrigues-Filho E

    更新日期：2018-08-01 00:00:00

  • The management of diabetes mellitus-imperative role of natural products against dipeptidyl peptidase-4, α-glucosidase and sodium-dependent glucose co-transporter 2 (SGLT2).

    abstract：:Diabetes mellitus is a chronic metabolic disorder which is rapidly spreading worldwide. It is characterized by persistent elevated blood glucose level above normal values (hyperglycemia) due to defect in either insulin secretion or in insulin action or both of them. Currently approved oral synthetic antidiabetic drugs...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.bioorg.2019.02.009

    authors： Abbas G,Al Harrasi A,Hussain H,Hamaed A,Supuran CT

    更新日期：2019-05-01 00:00:00

  • A novel derivatives of thiazol-4(5H)-one and their activity in the inhibition of 11β-hydroxysteroid dehydrogenase type 1.

    abstract：:11β-Hydroxysteroid dehydrogenase type 1 (11β-HSD1) is an enzyme that catalyzes the conversion of inactive cortisone into physiologically active cortisol. Inhibiting the activity of this enzyme plays a key role in the treatment of Cushing's syndrome, metabolic syndrome and type 2 diabetes. Therefore, new compounds that...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.04.014

    authors： Studzińska R,Kołodziejska R,Kupczyk D,Płaziński W,Kosmalski T

    更新日期：2018-09-01 00:00:00

  • Ellagitannin and flavonoid constituents from Agrimonia pilosa Ledeb. with their protein tyrosine phosphatase and acetylcholinesterase inhibitory activities.

    abstract：:A new ellagitannin, agritannin (1), a new flavone glycoside, agriflavone (2), and another flavone glycoside with spectroscopic data reported for the first time, kaempferol-3-O-[(S)-3-hydroxy-3-methylglutaryl (1→6)]-β-d-glucoside (3), along with 16 known compounds were isolated from the aerial parts of Agrimonia pilosa...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2017.04.017

    authors： Nguyen DH,Seo UM,Zhao BT,Le DD,Seong SH,Choi JS,Min BS,Woo MH

    更新日期：2017-06-01 00:00:00