A theoretical study on the structure-activity relationships of metabolites of folates as antioxidants and its implications for rational design of antioxidants.


:To elucidate the structure-activity relationships of metabolites of folates as antioxidants, the O-H bond dissociation enthalpies (BDEs) and ionization potentials (IPs) for these compounds were calculated by density functional theory (DFT) on B3LYP/6-31+G(,3pd) level. Accordingly, the antioxidant activity difference for metabolites of folates can be elucidated by O-H BDE and IP values and can be further explained in terms of electronic effect and intramolecular hydrogen bond effect of substituents. Furthermore, the potential of the active center of metabolites of folates, 4-hydroxypyrimidine (4-HP), as lead antioxidant, was evaluated by comparing the BDEs and IPs of 4-HP with those of 5-hydroxypyrimidine (5-HP). It was revealed that 4-HP and 5-HP held identical IPs, but the O-H BDE of the former was 22.84 kcal/mol higher than that of the latter, which meant 4-HP was inert in H-atom donation. Nevertheless, the O-H BDE of 4-HP was very sensitive to the substituents, which made NH2-derivatives of 4-HP very active as antioxidants. Therefore, 4-HP is also a potential lead antioxidant and deserves attention in rational design of antioxidants.


Bioorg Med Chem


Ji HF,Tang GY,Zhang HY




Has Abstract


2005-02-15 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


    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

  • Elucidation of the topography of the thapsigargin binding site in the sarco-endoplasmic calcium ATPase.

    abstract::Removal of each of the acyl groups of thapsigargin at O-3, O-8 and O-10 significant reduces the affinity of the inhibitors to the SERCA1a pump. Replacement of the acyl groups at O-3 and O-10 with flexible residues could be performed with only a minor decrease of the affinity, whereas introduction of voluminous stiff r...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Skytte DM,Møller JV,Liu H,Nielsen HØ,Svenningsen LE,Jensen CM,Olsen CE,Christensen SB

    更新日期:2010-08-01 00:00:00

  • Synthesis of chlorogenic acid derivatives with promising antifungal activity.

    abstract::Derivatives of chlorogenic acid or its analogues were synthesized by coupling protected chlorogenic acid or its analogues with p-octyloxyaniline and selected amino acids. Most of the compounds exhibited significant potency against Cryptococcus neoformans and Candida species with low toxicity to brine shrimps. The 4,5-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ma CM,Kully M,Khan JK,Hattori M,Daneshtalab M

    更新日期:2007-11-01 00:00:00

  • Antituberculosis drugs: ten years of research.

    abstract::Tuberculosis is today amongst the worldwide health threats. As resistant strains of Mycobacterium tuberculosis have slowly emerged, treatment failure is too often a fact, especially in countries lacking the necessary health care organisation to provide the long and costly treatment adapted to patients. Because of lack...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Janin YL

    更新日期:2007-04-01 00:00:00

  • New, stronger nucleophiles for nucleic acid-templated chemistry: Synthesis and application in fluorescence detection of cellular RNA.

    abstract::Nucleic acid-templated chemistry is a promising strategy for imaging genetic sequences in living cells. Here we describe the synthesis of two new nucleophiles for use in templated nucleophilic displacements with DNA probes. The nucleophilic groups are phosphorodithioate and phosphorotrithioate; we report on synthetic ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Miller GP,Silverman AP,Kool ET

    更新日期:2008-01-01 00:00:00

  • Preparation and antioxidant activity of alpha-pyridoin and its derivatives.

    abstract::Focusing on alpha-pyridoin (1, 1,2-di(2-pyridyl)-1,2-ethenediol) as the lead compound of the novel antioxidative enediol, we synthesized 5,5'- or 6,6'-bis-substituted derivatives of 1 from disubstituted pyridines. The antioxidant activity of 1 and its synthetic derivatives 2-7 was evaluated by DPPH (1,1-diphenyl-2-pic...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Hatanaka M,Takahashi K,Nakamura S,Mashino T

    更新日期:2005-12-15 00:00:00

  • Carbonic anhydrases as targets for medicinal chemistry.

    abstract::Carbonic anhydrases (CAs, EC are zinc enzymes acting as efficient catalysts for the reversible hydration of carbon dioxide to bicarbonate. 16 different alpha-CA isoforms were isolated in mammals, where they play crucial physiological roles. Some of them are cytosolic (CA I, CA II, CA III, CA VII, CA XIII), ot...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Supuran CT,Scozzafava A

    更新日期:2007-07-01 00:00:00

  • Deoxyiminoalditols from aldonolactones--V. Preparation of the four stereoisomers of 1,5-dideoxy-1,5-iminopentitols. Evaluation of these iminopentitols and three 1,5-dideoxy-1,5-iminoheptitols as glycosidase inhibitors.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Godskesen M,Lundt I,Madsen R,Winchester B

    更新日期:1996-11-01 00:00:00

  • Construction of a chemically and conformationally self-replicating system of amyloid-like fibrils.

    abstract::The amyloid-like fibril is considered to be a macromolecular self-assemblage with a highly-ordered quaternary structure, in which numerous beta-stranded polypeptide chains align regularly. Therefore, this kind of fibril has the potential to be engineered into proteinaceous materials, although conformational alteration...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Takahashi Y,Mihara H

    更新日期:2004-02-15 00:00:00

  • Design, synthesis, and evaluation of alpha-ketoheterocycles as class C beta-lactamase inhibitors.

    abstract::A series of specific alpha-ketoheterocycles (benzoxazole, thiazole, imidazole, tetrazole, and thiazole-4-carboxylate) has been synthesized in order to assess their potential as beta-lactamase inhibitors. The syntheses were achieved either by construction of the heterocycle (benzoxazole) from an appropriate alpha-hydro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kumar S,Pearson AL,Pratt RF

    更新日期:2001-08-01 00:00:00

  • Design, synthesis, and subtype selectivity of 3,6-disubstituted β-carbolines at Bz/GABA(A)ergic receptors. SAR and studies directed toward agents for treatment of alcohol abuse.

    abstract::A series of 3,6-disubstituted β-carbolines was synthesized and evaluated for their in vitro affinities at α(x)β(3)γ(2) GABA(A)/benzodiazepine receptor subtypes by radioligand binding assays in search of α(1) subtype selective ligands to treat alcohol abuse. Analogues of β-carboline-3-carboxylate-t-butyl ester (βCCt, 1...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yin W,Majumder S,Clayton T,Petrou S,VanLinn ML,Namjoshi OA,Ma C,Cromer BA,Roth BL,Platt DM,Cook JM

    更新日期:2010-11-01 00:00:00

  • A novel class of Plasmodial ClpP protease inhibitors as potential antimalarial agents.

    abstract::The prokaryotic ATP-dependent ClpP protease, localized in the relict plastid of malaria parasite, represents a potential drug target. In the present study, we utilized in silico structure-based screening and medicinal chemistry approaches to identify a novel pyrimidine series of compounds inhibiting P. falciparum ClpP...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Mundra S,Thakur V,Bello AM,Rathore S,Asad M,Wei L,Yang J,Chakka SK,Mahesh R,Malhotra P,Mohmmed A,Kotra LP

    更新日期:2017-10-15 00:00:00

  • Identification of a new selective dopamine D4 receptor ligand.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sampson D,Zhu XY,Eyunni SV,Etukala JR,Ofori E,Bricker B,Lamango NS,Setola V,Roth BL,Ablordeppey SY

    更新日期:2014-06-15 00:00:00

  • 3D-chiral quadratic indices of the 'molecular pseudograph's atom adjacency matrix' and their application to central chirality codification: classification of ACE inhibitors and prediction of sigma-receptor antagonist activities.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ponce YM,Diaz HG,Zaldivar VR,Torrens F,Castro EA

    更新日期:2004-10-15 00:00:00

  • Design, synthesis, and docking studies of quinazoline analogues bearing aryl semicarbazone scaffolds as potent EGFR inhibitors.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Tu Y,Wang C,Xu S,Lan Z,Li W,Han J,Zhou Y,Zheng P,Zhu W

    更新日期:2017-06-15 00:00:00

  • Synthesis of novel Schiff base analogues of 4-amino-1,5-dimethyl-2-phenylpyrazol-3-one and their evaluation for antioxidant and anti-inflammatory activity.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Alam MS,Choi JH,Lee DU

    更新日期:2012-07-01 00:00:00

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Tan S,He F,Kong T,Wu J,Liu Z

    更新日期:2017-08-01 00:00:00

  • Iromycins from Streptomyces sp. and from synthesis: new inhibitors of the mitochondrial electron transport chain.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Surup F,Shojaei H,von Zezschwitz P,Kunze B,Grond S

    更新日期:2008-02-15 00:00:00

  • ORL1 and opioid receptor preferences of nociceptin and dynorphin A analogues with Dmp substituted for N-terminal aromatic residues.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sasaki Y,Kawano S,Kohara H,Watanabe H,Ambo A

    更新日期:2006-04-01 00:00:00

  • SAR of a series of anti-HSV-1 acridone derivatives, and a rational acridone-based design of a new anti-HSV-1 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridine series.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Bernardino AM,Castro HC,Frugulhetti IC,Loureiro NI,Azevedo AR,Pinheiro LC,Souza TM,Giongo V,Passamani F,Magalhães UO,Albuquerque MG,Cabral LM,Rodrigues CR

    更新日期:2008-01-01 00:00:00

  • Inhibition studies of the β-carbonic anhydrases from the bacterial pathogen Salmonella enterica serovar Typhimurium with sulfonamides and sulfamates.

    abstract::The two β-carbonic anhydrases (CAs, EC from the bacterial pathogen Salmonella enterica serovar Typhimurium, stCA 1 and stCA 2, were investigated for their inhibition with a large panel of sulfonamides and sulfamates. Unlike inorganic anions, which are weak, millimolar inhibitors of the two enzymes [Vullo et a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Nishimori I,Minakuchi T,Vullo D,Scozzafava A,Supuran CT

    更新日期:2011-08-15 00:00:00

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Gautier A,Pitrat D,Hasserodt J

    更新日期:2006-06-01 00:00:00

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Katritzky AR,Pacureanu LM,Slavov S,Dobchev DA,Karelson M

    更新日期:2006-11-15 00:00:00

  • Chemical synthesis and biological activity of novel brominated 7-deazaadenosine-3',5'-cyclic monophosphate derivatives.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Lelle M,Otte M,Thon S,Bertinetti D,Herberg FW,Benndorf K

    更新日期:2019-04-15 00:00:00

  • Characterization, bioinformatic analysis and dithiocarbamate inhibition studies of two new α-carbonic anhydrases, CAH1 and CAH2, from the fruit fly Drosophila melanogaster.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Syrjänen L,Tolvanen ME,Hilvo M,Vullo D,Carta F,Supuran CT,Parkkila S

    更新日期:2013-03-15 00:00:00

  • Amides as bioisosteres of triazole-based geranylgeranyl diphosphate synthase inhibitors.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Goetz DB,Varney ML,Wiemer DF,Holstein SA

    更新日期:2020-08-15 00:00:00

  • Isolation and lipolytic activity of eurycomanone and its epoxy derivative from Eurycoma longifolia.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Lahrita L,Hirosawa R,Kato E,Kawabata J

    更新日期:2017-09-01 00:00:00

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Uwai K,Konno N,Yasuta Y,Takeshita M

    更新日期:2008-02-01 00:00:00

  • Inhibitory effects of flavonol glycosides from Cinnamomum osmophloeum on inflammatory mediators in LPS/IFN-gamma-activated murine macrophages.

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    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Fang SH,Rao YK,Tzeng YM

    更新日期:2005-04-01 00:00:00

  • Synthesis and antitumor activity of 20-O-linked nitrogen-based camptothecin ester derivatives.

    abstract::A series of nitrogen-based 20S-hydroxyl camptothecin ester derivatives were prepared. 3-Aminopropionate of camptothecin was found more cytotoxic in vitro on several human tumor cell lines than 3-amidopropionate of camptothecin. Ester 16 showed best antitumor activity in vivo and in vitro in all esters we prepared. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wang CY,Pan XD,Liu HY,Fu ZD,Wei XY,Yang LX

    更新日期:2004-07-01 00:00:00