Understanding the chemistry behind the antioxidant activities of butylated hydroxytoluene (BHT): a review.

Abstract:

:Hindered phenols find a wide variety of applications across many different industry sectors. Butylated hydroxytoluene (BHT) is a most commonly used antioxidant recognized as safe for use in foods containing fats, pharmaceuticals, petroleum products, rubber and oil industries. In the past two decades, there has been growing interest in finding novel antioxidants to meet the requirements of these industries. To accelerate the antioxidant discovery process, researchers have designed and synthesized a series of BHT derivatives targeting to improve its antioxidant properties to be having a wide range of antioxidant activities markedly enhanced radical scavenging ability and other physical properties. Accordingly, some structure-activity relationships and rational design strategies for antioxidants based on BHT structure have been suggested and applied in practice. We have identified 14 very sensitive parameters, which may play a major role on the antioxidant performance of BHT. In this review, we attempt to summarize the current knowledge on this topic, which is of significance in selecting and designing novel antioxidants using a well-known antioxidant BHT as a building-block molecule. Our strategy involved investigation on understanding the chemistry behind the antioxidant activities of BHT, whether through hydrogen or electron transfer mechanism to enable promising anti-oxidant candidates to be synthesized.

journal_name

Eur J Med Chem

authors

Yehye WA,Rahman NA,Ariffin A,Abd Hamid SB,Alhadi AA,Kadir FA,Yaeghoobi M

doi

10.1016/j.ejmech.2015.06.026

subject

Has Abstract

pub_date

2015-08-28 00:00:00

pages

295-312

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(15)30101-X

journal_volume

101

pub_type

杂志文章,评审
  • A series of 1, 2-coupled indane dimers with mast cell stabilisation and smooth muscle relaxation properties.

    abstract::Asthma is characterised by bronchoconstriction and inflammation, with infiltration and activation of inflammatory cells such as eosinophils and mast cells, and subsequent release of inflammatory mediators. Much of the therapy directed at the treatment of asthma is either to provide symptomatic relief through bronchodi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.09.005

    authors: Sheridan H,Walsh JJ,Jordan M,Cogan C,Frankish N

    更新日期:2009-12-01 00:00:00

  • A new convenient synthetic method and preliminary pharmacological characterization of triazinediones as prokineticin receptor antagonists.

    abstract::A new efficient synthetic method to obtain prokineticin receptor antagonists based on the triazinedione scaffold is described. In this procedure the overall yield improves from 13% to about 54%, essentially for two factors: 1) N-(chlorocarbonyl) isocyanate is no more used, it represents the yield limiting step with an...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.05.030

    authors: Congiu C,Onnis V,Deplano A,Salvadori S,Marconi V,Maftei D,Negri L,Lattanzi R,Balboni G

    更新日期:2014-06-23 00:00:00

  • Structural features and functional activities of benzimidazoles as NOD2 antagonists.

    abstract::NOD1 and NOD2 are pattern recognition receptors that have important roles in innate immune responses. Although their overactivation has been linked to a number of diseases, NOD2 in particular remains a virtually unexploited target in this respect, with only one structural class of antagonist reported. To gain insight ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112089

    authors: Guzelj S,Gobec M,Urbančič D,Mlinarič-Raščan I,Corsini E,Jakopin Ž

    更新日期:2020-03-15 00:00:00

  • Multifunctional 6-fluoro-3-[3-(pyrrolidin-1-yl)propyl]-1,2-benzoxazoles targeting behavioral and psychological symptoms of dementia (BPSD).

    abstract::Patients suffering from dementia experience cognitive deficits and 90% of them show non-cognitive behavioral and psychological symptoms of dementia (BPSD). The spectrum of BPSD includes agitation, depression, anxiety and psychosis. Antipsychotics, e.g. quetiapine, have been commonly used off-label to control the burde...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112149

    authors: Bucki A,Marcinkowska M,Śniecikowska J,Zagórska A,Jamrozik M,Pawłowski M,Głuch-Lutwin M,Siwek A,Jakubczyk M,Pytka K,Jastrzębska-Więsek M,Partyka A,Wesołowska A,Mierzejewski P,Kołaczkowski M

    更新日期:2020-04-01 00:00:00

  • Substituted arylsulphonamides as inhibitors of perforin-mediated lysis.

    abstract::The structure-activity relationships for a series of arylsulphonamide-based inhibitors of the pore-forming protein perforin have been explored. Perforin is a key component of the human immune response, however inappropriate activity has also been implicated in certain auto-immune and therapy-induced conditions such as...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.05.048

    authors: Spicer JA,Miller CK,O'Connor PD,Jose J,Huttunen KM,Jaiswal JK,Denny WA,Akhlaghi H,Browne KA,Trapani JA

    更新日期:2017-09-08 00:00:00

  • Discovery of diethyl 2,5-diaminothiophene-3,4-dicarboxylate derivatives as potent anticancer and antimicrobial agents and screening of anti-diabetic activity: synthesis and in vitro biological evaluation. Part 1.

    abstract::Series of diethyl 2,5-diaminothiophene-3,4-dicarboxylate (DDTD) derivatives: azomethines of DDTD (2a-l) have been synthesized and screened for their anticancer, antimicrobial and anti-diabetic activities. The novel synthesized compounds were characterized by (1)H, (13)C NMR, MS and FT-IR analyses. All compounds were e...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.07.065

    authors: Bozorov K,Ma HR,Zhao JY,Zhao HQ,Chen H,Bobakulov K,Xin XL,Elmuradov B,Shakhidoyatov K,Aisa HA

    更新日期:2014-09-12 00:00:00

  • Exploration of (S)-3-aminopyrrolidine as a potentially interesting scaffold for discovery of novel Abl and PI3K dual inhibitors.

    abstract::Based on the literature-reported compensatory effect of PI3K on Abl inhibition and the improved preclinical effect of drug combination of Abl and PI3K inhibitors, a series of compounds bearing novel scaffold of (S)-3-aminopyrrolidine was identified as Abl and PI3K dual inhibitors through support vector machine screeni...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.01.020

    authors: Zhang C,Tan C,Zu X,Zhai X,Liu F,Chu B,Ma X,Chen Y,Gong P,Jiang Y

    更新日期:2011-04-01 00:00:00

  • Synthesis of quinoidal molecules: strategies towards bioactive compounds with an emphasis on lapachones.

    abstract::Naphthoquinoidal compounds are of great interest in medicinal chemistry. In recent years, several synthetic routes have been developed to obtain bioactive molecules derived from lapachones. In this mini-review, we focus on the synthetic aspects and strategies used to design these compounds and on the biological activi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2013.07.057

    authors: de Castro SL,Emery FS,da Silva Júnior EN

    更新日期:2013-11-01 00:00:00

  • The novel phosphoramidate derivatives of NSAID 3-hydroxypropylamides: synthesis, cytostatic and antiviral activity evaluations.

    abstract::The target phosphoramidates 5a-e were prepared in one step from 3-hydroxypropyl derivatives 3a-e of nonsteroidal anti-inflammatory drugs (fenoprofen, ketoprofen, ibuprofen, indomethacin, diclofenac). The products 3a-e and 5a-e were evaluated for their cytostatic and antiviral activity against malignant tumour cell lin...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.03.037

    authors: Wittine K,Benci K,Rajić Z,Zorc B,Kralj M,Marjanović M,Pavelić K,De Clercq E,Andrei G,Snoeck R,Balzarini J,Mintas M

    更新日期:2009-01-01 00:00:00

  • Synthesis and anticancer activity of γ-(triazolyl ethylidene)butenolides and polyfunctional pyrrolinones.

    abstract::A series of novel γ-(triazolyl ethylidene)butenolides (4-23) were prepared from commercially available l-ascorbic acid in good yields. These butenolides on reaction with ethanolic ammonia/amines led to formation of respective 5-hydroxy pyrrolinones (24-33). The two of these pyrrolinones on dehydration with p-toluenesu...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.05.042

    authors: Devender N,Ramakrishna KK,Hamidullah,Shukla SK,Konwar R,Tripathi RP

    更新日期:2014-07-23 00:00:00

  • Synthesis and biological evaluation of a novel series of 1,5-benzothiazepine derivatives as potential antimicrobial agents.

    abstract::Two series of novel 1,5-benzothiazepine derivatives (23 compounds) were efficiently synthesized and evaluated for antibacterial and antifungal activities. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed higher activity against fungi than bact...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.12.021

    authors: Wang L,Zhang P,Zhang X,Zhang Y,Li Y,Wang Y

    更新日期:2009-07-01 00:00:00

  • Synthesis and evaluation of novel hybrids β-carboline-4-thiazolidinones as potential antitumor and antiviral agents.

    abstract::A series of novel hybrids β-carboline-4-thiazolidinones were synthesized and evaluated for their in vitro antitumor activity against human cancer cell lines and for antiviral activity towards Herpes simplex virus type-1 (HSV-1). From the N'-(2-ylidene-4-thiazolidinone)-β-carboline-3-carbohydrazide series (9-11), compo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.10.018

    authors: Barbosa VA,Baréa P,Mazia RS,Ueda-Nakamura T,Costa WFD,Foglio MA,Goes Ruiz ALT,Carvalho JE,Vendramini-Costa DB,Nakamura CV,Sarragiotto MH

    更新日期:2016-11-29 00:00:00

  • Discovery and optimization of phthalazinone derivatives as a new class of potent dengue virus inhibitors.

    abstract::Using a dengue replicon cell line-based screening, we identified 3-(dimethylamino)propyl(3-((4-(4-fluorophenyl)-1-oxophthalazin-2(1H)-yl)methyl)phenyl)carbamate (10a) as a potent DENV-2 inhibitor, with an IC50 value of 0.64 μM. A series of novel phthalazinone derivatives based on hit 10a were synthesized and evaluated...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.01.008

    authors: Lu D,Liu J,Zhang Y,Liu F,Zeng L,Peng R,Yang L,Ying H,Tang W,Chen W,Zuo J,Tong X,Liu T,Hu Y

    更新日期:2018-02-10 00:00:00

  • Synthesis, antiproliferative activity and inhibition of tubulin polymerization by anthracenone-based oxime derivatives.

    abstract::A series of anthracenone-based oxime ethers and -esters were synthesized in order to evaluate their antiproliferative activity. Several investigated compounds displayed strong antiproliferative activity against K562 leukemia cells and proved to be strong inhibitors of tubulin polymerization. In this context, anthracen...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.04.019

    authors: Surkau G,Böhm KJ,Müller K,Prinz H

    更新日期:2010-08-01 00:00:00

  • Efficient synthesis and activity of beneficial intestinal flora of two lactulose-derived oligosaccharides.

    abstract::Lactulose is considered as a prebiotic because it promotes the intestinal proliferation of Lactobacillus acidophilus which is added to various milk products. Moreover, lactulose is used in pharmaceuticals as a gentle laxative and to treat hyperammonemia. This study was aimed at the total synthesis of two Lactulose-der...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.03.007

    authors: Zhu ZY,Cui D,Gao H,Dong FY,Liu XC,Liu F,Chen L,Zhang YM

    更新日期:2016-05-23 00:00:00

  • Design and synthesis of novel 4-benzothiazole amino quinazolines Dasatinib derivatives as potential anti-tumor agents.

    abstract::Three series of novel 4-benzothiazole amino quinazolines Dasatinib derivatives have been designed and synthesized. The entire target compounds were investigated for their in vitro cytotoxic activity by the MTT-based assay against 6 human cancer cell lines. Compared with the parental Dasatinib, most of the new compound...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.03.013

    authors: Cai J,Sun M,Wu X,Chen J,Wang P,Zong X,Ji M

    更新日期:2013-05-01 00:00:00

  • Synthesis and evaluation of xanthine oxidase inhibitory and antioxidant activities of 2-arylbenzo[b]furan derivatives based on salvianolic acid C.

    abstract::Xanthine oxidase (XO) is the key enzyme in humans which is related to a variety of diseases such as gout, hyperuricemia and cardiovascular diseases. In this work, a series of 2-arylbenzo[b]furan derivatives were synthesized based on salvianolic acid C, and they were evaluated for xanthine oxidase inhibitory and antiox...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.08.019

    authors: Tang HJ,Zhang XW,Yang L,Li W,Li JH,Wang JX,Chen J

    更新日期:2016-11-29 00:00:00

  • Bioactive thiazole and benzothiazole derivatives.

    abstract::The heterocycles are the versatile compounds existing in almost all natural products and synthetic organic compounds, usually associated with one or the other biological activity. Among the heterocycles the thiazoles and benzothiazoles occupy a prominent position. They possess a broad range of biological activities an...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2014.10.058

    authors: Rouf A,Tanyeli C

    更新日期:2015-06-05 00:00:00

  • 1,8-Naphthyridines IV. 9-substituted N,N-dialkyl-5-(alkylamino or cycloalkylamino) [1,2,4]triazolo[4,3-a][1, 8]naphthyridine-6-carboxamides, new compounds with anti-aggressive and potent anti-inflammatory activities.

    abstract::The title compounds (8) were synthesized through the cyclocondensation of the corresponding N-substituted 4-amino-2-chloro-1,8-naphthyridine-3-carboxamides (4) with the proper hydrazides, in order to evaluate their anti-inflammatory and anti-aggressive properties. Several compounds 8 exhibited high anti-inflammatory a...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)01175-2

    authors: Roma G,Di Braccio M,Grossi G,Mattioli F,Ghia M

    更新日期:2000-11-01 00:00:00

  • Molecular insight into the inhibition mechanism of cyrtominetin to α-hemolysin by molecular dynamics simulation.

    abstract::The protein α-hemolysin (α-HL) is a self-assembling exotoxin that binds to the membrane of a susceptible host cell. In this paper, experimental studies show that cyrtominetin (CTM) can inhibit the hemolytic activity of α-HL. To understand how CTM can affect hemolytic activity, molecular dynamics simulations were carri...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.01.008

    authors: Niu X,Qiu J,Wang X,Gao X,Dong J,Wang J,Li H,Zhang Y,Dai X,Lu C,Deng X

    更新日期:2013-04-01 00:00:00

  • Evaluation of rat intestinal absorption data and correlation with human intestinal absorption.

    abstract::The absorption of 111 drug and drug-like compounds was evaluated from 111 references based on the ratio of urinary excretion of drugs following oral and intravenous administration to intact rats and biliary excretion of bile duct-cannulated rats. Ninety-eight drug compounds for which both human and rat absorption data...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(03)00015-1

    authors: Zhao YH,Abraham MH,Le J,Hersey A,Luscombe CN,Beck G,Sherborne B,Cooper I

    更新日期:2003-03-01 00:00:00

  • Simultaneous tritium labelling of two potent 5-HT4 ligands.

    abstract::Two potent and selective 5-HT(4) ligands, [(3)H]-5-[(N-propylpiperidin-4-yl)methoxy]-1,2,3,4-tetrahydrobenzo[h][1,6] naphthyridine (1a) and [(3)H]-1-methyl-5-[(N-propylpiperidin-4-yl)methoxy]pyrrolo[1,2-a]thieno[2,3-e]pyrazine (2a) were radiolabelled with tritium. Radioactive labelling was achieved by simultaneous tri...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.12.012

    authors: Sobrio F,Lemaitre S,Hinsberger A,Barré L,Rousseau B,Rault S

    更新日期:2010-03-01 00:00:00

  • Platinated benzonaphthyridone is a stronger inhibitor of poly(ADP-ribose) polymerase-1 and a more potent anticancer agent than is the parent inhibitor.

    abstract::Inhibitors of poly(ADP-ribose) polymerase-1 (PARP-1) have shown to be promising in clinical trials against cancer and other diseases, and lots of efforts have been put into the development of organic compounds as more potent PARP-1 inhibitors. Here we describe a strategy to conveniently obtain metal-based PARP-1 inhib...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.10.062

    authors: Wang B,Qian H,Yiu SM,Sun J,Zhu G

    更新日期:2014-01-01 00:00:00

  • Exploring nature profits: development of novel and potent lipophilic antioxidants based on galloyl-cinnamic hybrids.

    abstract::Phenolic acids are ubiquitous antioxidants accounting for approximately one third of the phenolic compounds in our diet. Their importance was supported by epidemiological studies that suggest an inverse relationship between dietary intake of phenolic antioxidants and the occurrence of diseases, such as cancer and neur...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.12.049

    authors: Teixeira J,Silva T,Benfeito S,Gaspar A,Garrido EM,Garrido J,Borges F

    更新日期:2013-04-01 00:00:00

  • Discovery of pyrazole as C-terminus of selective BACE1 inhibitors.

    abstract::We recently discovered and reported dual inhibitor 5 of AChE and BACE1 with N-benzylpiperidine ethyl as C-terminus. Compound 5 showed potent inhibitory activities for BACE1, and could reduce endogenous Aβ1-40 production in APP transgenic mice. In present work, we rapidly identified substituted triazole as the C-termin...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.06.027

    authors: Zou Y,Xu L,Chen W,Zhu Y,Chen T,Fu Y,Li L,Ma L,Xiong B,Wang X,Li J,He J,Zhang H,Xu Y,Li J,Shen J

    更新日期:2013-10-01 00:00:00

  • Discovery of novel VX-809 hybrid derivatives as F508del-CFTR correctors by molecular modeling, chemical synthesis and biological assays.

    abstract::Cystic fibrosis (CF) is the autosomal recessive disorder most recurrent in Caucasian populations. It is caused by different mutations in the cystic fibrosis transmembrane regulator protein (CFTR) gene, with F508del being the most common. During the last years, small-molecule therapy chosen to contrast CF relied on com...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112833

    authors: Parodi A,Righetti G,Pesce E,Salis A,Tasso B,Urbinati C,Tomati V,Damonte G,Rusnati M,Pedemonte N,Cichero E,Millo E

    更新日期:2020-12-15 00:00:00

  • 5-Ene-4-thiazolidinones induce apoptosis in mammalian leukemia cells.

    abstract::The article presents the synthesis of 5-ene-4-thiazolidinone derivatives with pyrazole core linked by enamine group. The structure and purity of compounds were confirmed by analytical and spectral data including X-ray analysis. Target compounds were screened for their anticancer activity and selective antileukemic act...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.03.089

    authors: Senkiv J,Finiuk N,Kaminskyy D,Havrylyuk D,Wojtyra M,Kril I,Gzella A,Stoika R,Lesyk R

    更新日期:2016-07-19 00:00:00

  • Synthesis and neuromuscular blocking activity of 16beta-piperidinosteroidal derivatives.

    abstract::The synthesis and pharmacological profiles of some new steroidal mono- and bisquaternary ammonium derivatives have been described. The compounds featured have been conceptually derived structurally from two lead structures: pancuronium bromide 1 and chandonium iodide 2. In vitro and in vivo neuromuscular blocking stud...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)01205-8

    authors: Jindal DP,Piplani P,Fajrak H,Prior C,Marshall IG

    更新日期:2001-02-01 00:00:00

  • New Atglistatin closely related analogues: Synthesis and structure-activity relationship towards adipose triglyceride lipase inhibition.

    abstract::Adipose Triglyceride Lipase (ATGL) performs the first and rate-limiting step in lipolysis by hydrolyzing triacylglycerols stored in lipid droplets to diacylglycerols. By mediating lipolysis in adipose and non-adipose tissues, ATGL is a major regulator of overall energy metabolism and plasma lipid levels. Since chronic...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.04.021

    authors: Roy PP,D'Souza K,Cuperlovic-Culf M,Kienesberger PC,Touaibia M

    更新日期:2016-08-08 00:00:00

  • Arylnitroalkenes as scavengers of macrophage-generated oxidants.

    abstract::Oxygen and nitrogen derived molecules mediated oxidation and nitration have been involved in several pathological conditions. Conversely, nitric oxide and hydrogen peroxide are important signalization intermediates, whose concentrations are tightly regulated by specialized enzyme repertoires and should remain undistur...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.12.029

    authors: Celano L,Carabio C,Frache R,Cataldo N,Cerecetto H,González M,Thomson L

    更新日期:2014-03-03 00:00:00