当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks.

Preparation of N-tBoc L-glutathione dimethyl and di-tert-butyl esters: versatile synthetic building blocks.

Abstract：

:The title l-glutathione derivatives, containing acid- and base-labile esters, respectively, were obtained in good overall yields. N-(t)Boc l-glutathione dimethyl ester was prepared via Fischer esterification of l-glutathione disulfide (GSSG) using HCl in dry methanol, protection of the amine with (t)Boc(2)O, and tributylphosphine cleavage of the disulfide in wet isopropanol. Alternatively, Fischer esterification and (t)Boc-protection of l-glutathione (GSH) also furnished N-(t)Boc glutathione dimethyl ester accompanied by a small amount of S-(t)Boc that was removed chromatographically. The di-tert-butyl ester was obtained by S-palmitoylation of GSH in TFA as solvent, N-(t)Boc-protection, esterification using (t)BuOH mediated by diisopropylcarbodiimide/copper(I) chloride, and saponification of the thioester. These l-glutathione derivatives are versatile synthetic building blocks for the preparation of S-glutathione adducts.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Falck JR,Sangras B,Capdevila JH

doi

10.1016/j.bmc.2006.10.022

subject

Has Abstract

pub_date

2007-01-15 00:00:00

pages

1062-6

issue

2

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(06)00855-8

journal_volume

15

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • Chlorine atom substitution influences radical scavenging activity of 6-chromanol.

    abstract：:Synthetic 6-chromanol derivatives were prepared with several chlorine substitutions, which conferred both electron-withdrawing inductive effects and electron-donating resonance effects. A trichlorinated compound (2), a dichlorinated compound (3), and three monochlorinated compounds (4, 5, and 6) were synthesized; comp...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2012.05.008

    authors： Inami K,Iizuka Y,Furukawa M,Nakanishi I,Ohkubo K,Fukuhara K,Fukuzumi S,Mochizuki M

    更新日期：2012-07-01 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

  • Developing new chemical tools for DNA methyltransferase 1 (DNMT 1): a small-molecule activity-based probe and novel tetrazole-containing inhibitors.

    abstract：:DNA methylation is an important epigenetic modification catalyzed by DNA methyltransferases (DNMTs). Abnormal expression of endogenous DNMTs in human causes alterations in the genome methylation patterns which subsequently lead to the development of cancers. Thus detection of endogenous DNMT activities and efficient i...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.03.006

    authors： Zhu B,Ge J,Yao SQ

    更新日期：2015-06-15 00:00:00

  • 1-Benzazepin-2-one calcium channel blockers--VI. Receptor-binding model and possible relationship to desmethoxyverapamil.

    abstract：:We have prepared a series of potent antihypertensive 1-benzazepin-2-one calcium channel blockers (CCBs) 1 that are structurally related to diltiazem 2. Structural studies and the preparation of conformationally constrained analogs of 1-benzazepin-2-ones have led us to postulate a receptor-bound conformation for both 1...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(00)82134-3

    authors： Kimball SD,Hunt JT,Barrish JC,Das J,Floyd DM,Lago MW,Lee VG,Spergel SH,Moreland S,Hedberg SA

    更新日期：1993-10-01 00:00:00

  • Benzanilides with spasmolytic activity: chemistry, pharmacology, and SAR.

    abstract：:The following study describes the synthesis of new benzanilide derivatives and their pharmacological investigation on smooth muscle preparations of guinea pigs. All compounds were synthesized in good yields and showed a spasmolytic activity without significant effect on vascular smooth muscles and heart muscle prepara...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.04.057

    authors： Brunhofer G,Handler N,Leisser K,Studenik CR,Erker T

    更新日期：2008-06-01 00:00:00

  • An evaluation of central penetration from a peripherally administered oxytocin receptor selective antagonist in nonhuman primates.

    abstract：:The physiology of the oxytocin receptor has increasingly become a focus of scientific investigation due to its connection with social behavior and psychiatric disorders with impairments in social funciton. Experimental utilization of small molecule and peptide antagonists for the oxytocin receptor has played a role in...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.10.035

    authors： Smith AL,Walum H,Connor-Stroud F,Freeman SM,Inoue K,Parr LA,Goodman MM,Young LJ

    更新日期：2017-01-01 00:00:00

  • Design, synthesis, and biological evaluation of 1,3-diarylprop-2-en-1-ones : a novel class of cyclooxygenase-2 inhibitors.

    abstract：:A group of regioisomeric (E)-1,3-diarylprop-2-en-1-one derivatives possessing a COX-2 SO2Me pharmacophore at the para position of the C-1 or C-3 phenyl ring, in conjunction with a C-3 or C-1 phenyl (4-H) or substituted-phenyl ring (4-F, 4-OMe and 4-Me), were designed for evaluation as selective cyclooxygenase-2 (COX-2...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.11.041

    authors： Zarghi A,Arfaee S,Rao PN,Knaus EE

    更新日期：2006-04-15 00:00:00

  • Design, synthesis, and biological evaluation of conformationally constrained glycerol 3-phosphate acyltransferase inhibitors.

    abstract：:Glycerol 3-phosphate acyltransferase (GPAT) isozymes are central control points for fat synthesis in mammals. Development of inhibitors of these membrane-bound enzymes could lead to an effective treatment for obesity, but is thwarted by an absence of direct structural information. Based on a highly successful study in...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.06.091

    authors： Wydysh EA,Vadlamudi A,Medghalchi SM,Townsend CA

    更新日期：2010-09-01 00:00:00

  • Preparation and biological activity of 13-substituted retinoic acids.

    abstract：:13-Demethyl or 13-substituted all-E- and 9Z-retinoic acids were synthesized using a palladium-catalyzed coupling reaction of enol triflates and tributylstannylolefins. Their biological activities were then measured. The 13-ethyl analogs exhibited approximately one-half of the antiproliferative and differentiation-indu...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.04.047

    authors： Wada A,Fukunaga K,Ito M,Mizuguchi Y,Nakagawa K,Okano T

    更新日期：2004-07-15 00:00:00

  • Effects of charge and hydrophobicity on the oligomerization of peptides derived from IAPP.

    abstract：:Changes in pH resulting in modifications of charge can dramatically alter the folding and interaction of proteins. This article probes the effects of charge and hydrophobicity on the oligomerization of macrocyclic β-sheet peptides derived from residues 11-17 of IAPP (RLANFLV). Previous studies have shown that a macroc...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.10.001

    authors： Wang Y,Truex NL,Vo NDP,Nowick JS

    更新日期：2018-03-15 00:00:00

  • Carbonic anhydrase inhibitors: Design, synthesis, kinetic, docking and molecular dynamics analysis of novel glycine and phenylalanine sulfonamide derivatives.

    abstract：:The inhibition of two human cytosolic carbonic anhydrase isozymes I and II, with some novel glycine and phenylalanine sulfonamide derivatives were investigated. Newly synthesized compounds G1-4 and P1-4 showed effective inhibition profiles with KI values in the range of 14.66-315μM for hCA I and of 18.31-143.8μM again...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.10.009

    authors： Fidan İ,Salmas RE,Arslan M,Şentürk M,Durdagi S,Ekinci D,Şentürk E,Coşgun S,Supuran CT

    更新日期：2015-12-01 00:00:00

  • Synthesis of novel 5-amino-thiazolo[4,5-d]pyrimidines as E. coli and S. aureus SecA inhibitors.

    abstract：:An efficient synthesis of a library of 5-amino-thiazolo[4,5-d]pyrimidines is reported. Regioselective displacements of chlorines, as well as regioselective diazotation reactions are described, which allow the introduction of structural diversity on the scaffold by consecutive reactions. Screening of this focused libra...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.10.027

    authors： Jang MY,De Jonghe S,Segers K,Anné J,Herdewijn P

    更新日期：2011-01-01 00:00:00

  • In vitro and in vivo evaluation of select kahalalide F analogs with antitumor and antifungal activities.

    abstract：:Kahalalide F (KF) and the regioisomer isoKF are novel anticancer drugs of marine origin and currently under clinical investigation. Here we report the synthesis of two new KF analogs with significant in vitro and in vivo antifungal and antitumor activities. The primary amine hydrogen of ornithine in KF has been replac...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.06.050

    authors： Shilabin AG,Hamann MT

    更新日期：2011-11-15 00:00:00

  • Studies on anti-HIV quinolones: new insights on the C-6 position.

    abstract：:The 6-desfluoroquinolones which have been developed by our group represent a promising class of compounds for the treatment of HIV infection since they act on transcriptional regulation, a crucial step in the replication cycle that has not been clinically exploited, yet. Focussing attention on the N-1 and C-6 position...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.11.056

    authors： Massari S,Daelemans D,Manfroni G,Sabatini S,Tabarrini O,Pannecouque C,Cecchetti V

    更新日期：2009-01-15 00:00:00

  • α-Glucosidase inhibition activity and in silico study of 2-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one, a synthetic derivative of flavone.

    abstract：:A synthetic flavone derivative 2-(benzo[d][1,3]dioxol-5-yl)-4H-chromen-4-one (BDC) was synthesized by the one pot reaction method and assessed for α-glucosidase inhibitory activity. The BDC demonstrated dose dependent inhibition of α-glucosidase activity. A maximum inhibition (99.3 ± 0.26%) of α-glucosidase was observ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.12.021

    authors： Meena SN,Kumar U,Naik MM,Ghadi SC,Tilve SG

    更新日期：2019-06-15 00:00:00

  • Design, synthesis and biological activity of 3-pyrazine-2-yl-oxazolidin-2-ones as novel, potent and selective inhibitors of mutant isocitrate dehydrogenase 1.

    abstract：:Isocitrate dehydrogenases (IDHs) catalyze the oxidative decarboxylation of isocitrate to alpha-ketoglutarate (α-KG) generating carbon dioxide and NADPH/NADH. Evidence suggests that the specific mutations in IDH1 are critical to the growth and reproduction of some tumor cells such as gliomas and acute myeloid leukemia,...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2017.10.009

    authors： Ma T,Zou F,Pusch S,Yang L,Zhu Q,Xu Y,Gu Y,von Deimling A,Zha X

    更新日期：2017-12-15 00:00:00

  • 2-Phenylimidazo[2,1-i]purin-5-ones: structure-activity relationships and characterization of potent and selective inverse agonists at Human A3 adenosine receptors.

    abstract：:Structure-activity relationships of 2-phenyl-imidazo[2,1-i]purin-5-ones as ligands for human A(3) adenosine receptors (ARs) were investigated. An ethyl group in the 8-position of the imidazoline ring of 4-methyl-2-phenyl-imidazopurinone leading to chiral compounds was found to increase affinity for human A(3) ARs by s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(02)00456-x

    authors： Ozola V,Thorand M,Diekmann M,Qurishi R,Schumacher B,Jacobson KA,Müller CE

    更新日期：2003-02-06 00:00:00

  • Design, synthesis, and binding of homologated truncated 4'-thioadenosine derivatives at the human A3 adenosine receptors.

    abstract：:We synthesized homologated truncated 4'-thioadenosine analogues 3 in which a methylene (CH(2)) group was inserted in place of the glycosidic bond of a potent and selective A(3) adenosine receptor antagonist 2. The analogues were designed to induce maximum binding interaction in the binding site of the A(3) adenosine r...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.08.018

    authors： Lee HW,Kim HO,Choi WJ,Choi S,Lee JH,Park SG,Yoo L,Jacobson KA,Jeong LS

    更新日期：2010-10-01 00:00:00

  • Design, synthesis, and in vitro evaluation of new naphthylnitrobutadienes with potential antiproliferative activity: toward a structure/activity correlation.

    abstract：:On the grounds of previous encouraging results on the antitumor activity of (1E,3E)-1,4-bis(1-naphthyl)-2,3-dinitro-1,3-butadiene (1), we have designed and synthesized two new molecules [(1E,3E)-1,4-bis(4-carboxy-1-naphthyl)-2,3-dinitro-1,3-butadiene (2) and methyl (2Z,4E)-2-methylsulfanyl-5-(1-naphthyl)-4-nitro-2,4-p...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.09.042

    authors： Petrillo G,Mariggiò MA,Aiello C,Cordazzo C,Fenoglio C,Morganti S,Croce M,Rizzato E,Spinelli D,Maccagno M,Bianchi L,Prevosto C,Tavani C,Viale M

    更新日期：2008-01-01 00:00:00

  • Synthesis, biological evaluation and molecular modelling of diversely functionalized heterocyclic derivatives as inhibitors of acetylcholinesterase/butyrylcholinesterase and modulators of Ca2+ channels and nicotinic receptors.

    abstract：:The synthesis and the biological activity of compounds 5-40 as inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE), as well as modulators of voltage-dependent Ca(2+) channels and nicotinic receptors, are described. These molecules are tacrine analogues, which have been prepared from polyfunctio...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.02.017

    authors： Marco JL,de los Ríos C,García AG,Villarroya M,Carreiras MC,Martins C,Eleutério A,Morreale A,Orozco M,Luque FJ

    更新日期：2004-05-01 00:00:00

  • The phytoalexins brassilexin and camalexin inhibit cyclobrassinin hydrolase, a unique enzyme from the fungal pathogen Alternaria brassicicola.

    abstract：:Alternaria brassicicola is a fungal pathogen of many agriculturally important cruciferous crops. Cyclobrassinin hydrolase (CH) is an enzyme produced by A. brassicicola that catalyzes the transformation of the cruciferous phytoalexin cyclobrassinin into S-methyl[(2-sulfanyl-1H-indolyl-3)methyl]carbamothioate. The purif...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.11.005

    authors： Pedras MS,Minic Z

    更新日期：2014-01-01 00:00:00

  • Synthesis and anticonvulsant activity of a class of 2-amino 3-hydroxypropanamide and 2-aminoacetamide derivatives.

    abstract：:Several studies have demonstrated that N-substituted amino acid derivatives exhibit weak anticonvulsant activities in vivo. In the present study, a series of amides of aminoacids structurally related to aminoacetamide have been synthesised and investigated for anticonvulsant activity. Among the molecules investigated,...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.12.064

    authors： Ghidini E,Delcanale M,De Fanti R,Rizzi A,Mazzuferi M,Rodi D,Simonato M,Lipreri M,Bassani F,Battipaglia L,Bergamaschi M,Villetti G

    更新日期：2006-05-15 00:00:00

  • Synthesis and binding affinities of fluoroalkylated raloxifenes.

    abstract：:Three fluoroalkylated derivatives (1-3) of the selective estrogen receptor modulator (SERM), raloxifene, have been synthesized. The key step in the synthesis is the C-C bond formation of benzo[b]thiophene and a substituted phenyl group (ring C) using a Stille reaction. The in vitro binding affinities of the substitute...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(03)00362-6

    authors： Lee KC,Moon BS,Lee JH,Chung KH,Katzenellenbogen JA,Chi DY

    更新日期：2003-08-15 00:00:00

  • Synthesis and structure-activity relationship of new 1,5-dialkyl-1,5-benzodiazepines as cholecystokinin-2 receptor antagonists.

    abstract：:This article deals with the synthesis and the activities of some 1,5-dialkyl-3-arylureido-1,5-benzodiazepin-2,4-diones which were prepared as potential CCK2 antagonists, with the intention to find a possible follow up of our lead compound GV150013, showing an improved pharmacokinetic profile. The phenyl ring at N-5 wa...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.05.057

    authors： Roberts K,Ursini A,Barnaby R,Cassarà PG,Corsi M,Curotto G,Donati D,Feriani A,Finizia G,Marchioro C,Niccolai D,Oliosi B,Polinelli S,Ratti E,Reggiani A,Tedesco G,Tranquillini ME,Trist DG,van Amsterdam FT

    更新日期：2011-07-15 00:00:00

  • 6-Hydrophobic aromatic substituent pyrimethamine analogues as potential antimalarials for pyrimethamine-resistant Plasmodium falciparum.

    abstract：:The series of des-Cl (unsubstituted) and m-Cl phenyl analogues of PYR with various flexible 6-substituents were synthesized and studied for the binding affinities with highly resistant quadruple mutant (QM) DHFR. The derivatives carrying 4 atoms linker with a terminal carboxyl substituted on the aromatic ring exhibite...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2019.115158

    authors： Saepua S,Sadorn K,Vanichtanankul J,Anukunwithaya T,Rattanajak R,Vitsupakorn D,Kamchonwongpaisan S,Yuthavong Y,Thongpanchang C

    更新日期：2019-12-15 00:00:00

  • Synthesis of novel progestin-rhenium conjugates as potential ligands for the progesterone receptor.

    abstract：:To assist in the development of technetium-based radiopharmaceuticals that are useful for the diagnostic imaging of steroid receptor-positive breast tumors, we have synthesized a series of small-sized metal chelates according to 'n + 1' mixed-ligand, thioether-carbonyl and organometallic designs. In these preliminary ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(99)00119-4

    authors： Wüst F,Skaddan MB,Leibnitz P,Spies H,Katzenellenbogen JA,Johannsen B

    更新日期：1999-09-01 00:00:00

  • The selective quantification of iron by hexadentate fluorescent probes.

    abstract：:The synthesis of four hexadentate fluorescent probes is described, where the fluorescent moiety is based on either coumarin or fluorescein and the chelating moiety is based on either 3-hydroxypyridin-4-one or 3-hydroxypyran-4-one. The fluorescence is quenched when the probe chelating moieties bind iron. The probes wer...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.09.052

    authors： Ma YM,Hider RC

    更新日期：2009-12-01 00:00:00

  • Conversion of iodine to fluorine-18 based on iodinated chalcone and evaluation for β-amyloid PET imaging.

    abstract：:In the amyloid cascade hypothesis, β-amyloid (Aβ) plaques is one of the major pathological biomarkers in the Alzheimer's disease (AD) brain. We report the synthesis and evaluation of novel radiofluorinated chalcones, [18F]4-dimethylamino-4'-fluoro-chalcone ([18F]DMFC) and [18F]4'-fluoro-4-methylamino-chalcone ([18F]FM...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.05.001

    authors： Kaide S,Ono M,Watanabe H,Shimizu Y,Nakamoto Y,Togashi K,Yamaguchi A,Hanaoka H,Saji H

    更新日期：2018-07-23 00:00:00

  • Synthesis and structure activity relationships of glycine amide derivatives as novel Vascular Adhesion Protein-1 inhibitors.

    abstract：:Vascular Adhesion Protein-1 (VAP-1) is a promising therapeutic target for the treatment of several inflammatory-related diseases including diabetic microvascular complication. We identified glycine amide derivative 3 as a novel structure with moderate VAP-1 inhibitory activity. Structure-activity relationship studies ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.10.025

    authors： Yamaki S,Suzuki D,Fujiyasu J,Neya M,Nagashima A,Kondo M,Akabane T,Kadono K,Moritomo A,Yoshihara K

    更新日期：2017-01-01 00:00:00

  • Proteasome inhibition by peptide-semicarbazones.

    abstract：:Peptide-semicarbazones derived from Z-Trp-Trp-Phe-aldehyde inhibit the chymotryptic activity of the human proteasome at nanomolar concentrations, but are less active in a NFkappaB reporter gene assay. Cyclic semicarbazones, in contrast, combine a strong inhibitory effect on the enzyme with an inhibition of NFkappaB si...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.02.042

    authors： Leban J,Blisse M,Krauss B,Rath S,Baumgartner R,Seifert MH

    更新日期：2008-04-15 00:00:00