Synthesis and investigation of inhibition effects of new carbonic anhydrase inhibitors.

Abstract:

:Three new derivatives of 2-substituted 1,3,4-thiadiazole-5-sulfonamide have been synthesized. These compounds are 2-(3-chloropropionylamino)-1,3,4-thiadiazole-5-sulfonamide (1); 2-(2,2-dichloroacetylamino)-1,3,4-thiadiazole-5-sulfonamide (2); and 2-(3-phenylpropionylamino)-1,3,4-thiadiazole-5-sulfonamide (3). Inhibition effects of these compounds on carbonic anhydrase I and II have been investigated. By comparing I50 and Ki values of the compounds, it has been found that compound 1 is a more potent inhibitor than acetazolamide (b) on carbonic anhydrase II.

journal_name

Bioorg Med Chem

authors

Arslan O,Küfrevioĝlu OI,Nalbantoĝlu B

doi

10.1016/s0968-0896(96)00272-6

subject

Has Abstract

pub_date

1997-03-01 00:00:00

pages

515-8

issue

3

eissn

0968-0896

issn

1464-3391

pii

S0968089696002726

journal_volume

5

pub_type

杂志文章
  • The unique chemistry of benzoxaboroles: current and emerging applications in biotechnology and therapeutic treatments.

    abstract::Benzoxaboroles have garnered much attention in recent years due to their diverse applications in bio-sensing technology, material science, and therapeutic intervention. Part of the reason arises from the benzoxaboroles' unique chemical properties, especially in comparison to their acyclic boronic acid counterparts. Fu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.bmc.2014.04.065

    authors: Liu CT,Tomsho JW,Benkovic SJ

    更新日期:2014-08-15 00:00:00

  • Chemical and biological effects of substitution of the 2-position of ring-expanded ('fat') nucleosides containing the imidazo[4,5-e][1,3]diazepine-4,8-dione ring system: the role of electronic and steric factors on glycosidic bond stability and anti-HCV a

    abstract::The attempted removal of the aralkyl group of 2-bromo-1-p-methoxybenzyl-6-octylimidazo[4,5-e][1,3]diazepine (ZP-33) with trifluoroacetic acid resulted in replacement of the bromo group with a carbonyl at position-2 in addition to the desired deprotection at the 1-position. 2'-Deoxynucleosides of 2-bromo-substituted-im...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2007.04.043

    authors: Zhang P,Zhang N,Buckwold VE,Hosmane RS

    更新日期:2007-07-15 00:00:00

  • Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties.

    abstract::Lactenediynes are compounds characterized by the fusion of a beta-lactam with a cyclodeca-3-ene-1,5-diyne. In this work the most promising members of this family have been activated by attaching a carbalkoxy or a carbamoyl group to the azetidinone nitrogen, and conjugated to various DNA-complexing moieties, either act...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.02.022

    authors: Banfi L,Basso A,Bevilacqua E,Gandolfo V,Giannini G,Guanti G,Musso L,Paravidino M,Riva R

    更新日期:2008-04-01 00:00:00

  • Cembrane diterpenoids from the soft coral Sarcophyton trocheliophorum Marenzeller as a new class of PTP1B inhibitors.

    abstract::A detailed investigation of the South China Sea soft coral Sarcophyton trocheliophorum Marenzeller yielded, along with six known terpenes (6-11), the new sarcophytonolides N-R (1-5), whose structures have been elucidated by detailed spectroscopic analysis. Sarcophytonolides N-R are mono- or bicyclic cembranoids charac...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.06.043

    authors: Liang LF,Gao LX,Li J,Taglialatela-Scafati O,Guo YW

    更新日期:2013-09-01 00:00:00

  • A laccase-catalysed one-pot synthesis of aminonaphthoquinones and their anticancer activity.

    abstract::Nuclear monoamination of a 1,4-naphthohydroquinone with primary aromatic amines was catalysed by the commercial laccase, Novozym 51003, from Novozymes to afford aminonaphthoquinones. The synthesis was accomplished by reacting a mixture of the primary amine and 1,4-naphthohydroquinone in succinate-lactate buffer and a ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2012.05.028

    authors: Wellington KW,Kolesnikova NI

    更新日期:2012-07-15 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 and cytotoxic effects of 2-thio-3,4-dihydroquinazoline derivatives as novel T-type calcium channel blockers.

    abstract::In our previous work, a series of 2-amino-3,4-dihydroquinazoline derivativesusing an electron acceptor group was reported to be potent T-type calcium channel blockers and exhibit strong cytotoxic effects against various cancerous cell lines. To investigate the role of the guanidine moiety in the 2-amino-3,4-dihydroqui...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115491

    authors: Nam Y,Ryu KD,Jang C,Moon YH,Kim M,Ko D,Chung KS,Gandini MA,Lee KT,Zamponi GW,Lee JY

    更新日期:2020-06-01 00:00:00

  • The use of a conformational cathepsin D-derived epitope for vaccine development against Schistosoma mansoni.

    abstract::Schistosomiasis is caused by the infection from Schistosoma species. Among these, Schistosoma mansoni is one of the major species that infects millions of people worldwide. The use of praziquantel is effective in clearing the infestation but treatment of a large and widespread population in endemic areas is unsustaina...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.01.033

    authors: Ahmad Fuaad AA,Roubille R,Pearson MS,Pickering DA,Loukas AC,Skwarczynski M,Toth I

    更新日期:2015-03-15 00:00:00

  • Synthesis, binding, nuclease resistance and cellular uptake properties of 2'-O-acetalester-modified oligonucleotides containing cationic groups.

    abstract::We report on the synthesis and properties of oligonucleotides (ONs) with 2'-O-acetalester modifications containing cationic side chains in a prodrug-like approach. In the aim to improve cell penetration and nuclease resistance, various different amino- or guanidino-acetalester were grafted to 2'-OH of uridine and the ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.07.054

    authors: Biscans A,Rouanet S,Bertrand JR,Vasseur JJ,Dupouy C,Debart F

    更新日期:2015-09-01 00:00:00

  • Synthesis of natural product-like polyprenylated phenols and quinones: Evaluation of their neuroprotective activities.

    abstract::Twenty-seven natural product-like polyprenylated phenols and quinones were synthesized and their neuroprotective activity was tested using human monoamine oxidase B (MAO-B) and SH-SY5Y cells. Eight compounds inhibited MAO-B (IC50 values < 25 μM) and the inhibition mode and molecular docking of two (8c and 16c) were in...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.115156

    authors: Kamauchi H,Oda T,Horiuchi K,Takao K,Sugita Y

    更新日期:2020-01-01 00:00:00

  • Synthesis and monoamine transporter binding properties of 2beta-[3'-(substituted benzyl)isoxazol-5-yl]- and 2beta-[3'-methyl-4'-(substituted phenyl)isoxazol-5-yl]-3beta-(substituted phenyl)tropanes.

    abstract::A series of 2beta-[3'-(substituted benzyl)isoxazol-5-yl]- and 2beta-[3'-methyl-4'-(substituted phenyl)isoxazol-5-yl]-3beta-(substituted phenyl)tropanes were prepared and evaluated for affinities at dopamine, serotonin, and norepinephrine transporters using competitive radioligand binding assays. The 2beta-[3'-(substit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.05.073

    authors: Jin C,Navarro HA,Page K,Carroll FI

    更新日期:2008-07-15 00:00:00

  • Development of a cyclosporin A derivative with excellent anti-hepatitis C virus potency.

    abstract::Synthetic modification of cyclosporin A at P3-P4 positions led to the discovery of NIM258, a next generation cyclophilin inhibitor with excellent anti-hepatitis C virus potency, with decreased transporter inhibition, and pharmacokinetics suitable for coadministration with other drugs. Herein is disclosed the evolution...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.09.008

    authors: Fu J,Becker C,Cao L,Capparelli M,Denay R,Fujimoto R,Gai Y,Gao Z,Guenat C,Karur S,Kim H,Li W,Li X,Li W,Lochmann T,Lu A,Lu P,Luneau A,Meier N,Mergo W,Ng S,Parker D,Peng Y,Riss B,Rivkin A,Roggo S,Schroede

    更新日期:2018-02-15 00:00:00

  • Search for alpha-helical propensity in the receptor-bound conformation of glucagon-like peptide-1.

    abstract::To elucidate the receptor-bound conformation of glucagon-like peptide-1 (GLP-1), a series of conformationally constrained GLP-1 analogues were synthesized by introducing lactam bridges between Lys(i) and Glu(i)(+4) to form alpha-helices at various positions. The activity and affinity of these analogues to GLP-1 recept...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.10.006

    authors: Murage EN,Schroeder JC,Beinborn M,Ahn JM

    更新日期:2008-12-01 00:00:00

  • Cytotoxic T lymphocyte epitope analogues containing cis- or trans-4-aminocyclohexanecarboxylic acid residues.

    abstract::In order to improve the immunotherapeutical potential of H-Cys-Leu-Gly-Gly-Leu-Leu-Thr-Met-Val-OH (CLG) peptide, an Epstein-Barr virus (EBV) subdominant epitope derived from the membrane protein LMP2, we have synthesized and tested CLG analogues containing cis- and/or trans-4-aminocyclohexanecarboxylic acid (ACCA) rep...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00033-0

    authors: Marastoni M,Bazzaro M,Micheletti F,Gavioli R,Tomatis R

    更新日期:2002-09-01 00:00:00

  • Chiral resolution of serial potent and selective σ1 ligands and biological evaluation of (-)-[18F]TZ3108 in rodent and the nonhuman primate brain.

    abstract::Twelve optically pure enantiomers were obtained using either crystallization or chiral high performance liquid chromatography (HPLC) separation methodologies to resolve six racemic sigma-1 (σ1) receptor ligands. The in vitro binding affinities of each enantiomer for σ1, σ2 receptors and vesicular acetylcholine transpo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.01.017

    authors: Yue X,Jin H,Luo Z,Liu H,Zhang X,McSpadden ED,Tian L,Flores HP,Perlmutter JS,Parsons SM,Tu Z

    更新日期:2017-02-15 00:00:00

  • Identification of new GATA4-small molecule inhibitors by structure-based virtual screening.

    abstract::Members of the GATA family of transcription factors are zinc finger proteins that were shown to play evolutionary conserved roles in cell differentiation and proliferation in different organisms. We hypothesized that by finding new molecules that inhibit their function to be crucial in future therapeutical interventio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.01.022

    authors: El-Hachem N,Nemer G

    更新日期:2011-03-01 00:00:00

  • Synthesis and cancer cell cytotoxicity of substituted xanthenes.

    abstract::A series of substituted xanthenes was synthesized and screened for activity using DU-145, MCF-7, and HeLa cancer cell growth inhibition assays. The most potent compound, 9 g ([N,N-diethyl]-9-hydroxy-9-(3-methoxyphenyl)-9H-xanthene-3-carboxamide), was found to inhibit cancer cell growth with IC(50) values ranging from ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.01.018

    authors: Giri R,Goodell JR,Xing C,Benoit A,Kaur H,Hiasa H,Ferguson DM

    更新日期:2010-02-15 00:00:00

  • Design and synthesis of 3-fluoro-2-oxo-3-phenylpropionic acid derivatives as potent inhibitors of 4-hydroxyphenylpyruvate dioxygenase from pig liver.

    abstract::Several rationally designed analogs of 3-fluoro-2-oxo-3-phenylpropionic acid were chemically synthesized, and the reactions of the hydrate form of these compounds with 4-hydroxyphenylpyruvate dioxygenase from pig liver as inhibitors were examined. Compounds 14a and 14b were found to be potent competitive inhibitors of...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00062-0

    authors: Ling TS,Shiu S,Yang DY

    更新日期:1999-07-01 00:00:00

  • 2,3-Dihydro-6,7-dichloro-pyrido[2,3-b]pyrazine-8-oxide as selective glycine antagonist with in vivo activity.

    abstract::2,3-Dihydro-6,7-dichloro-pyrido[2,3-b]pyrazine-8-oxide was synthesized and evaluated for in vitro/in vivo antagonistic activity at the strychnine insensitive glycine binding site on the NMDA receptor revealing it to be a useful tool to evaluate the effectiveness of glycine antagonists in vivo. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(97)00156-9

    authors: Micheli F,Cugola A,Donati D,Missio A,Pecunioso A,Reggiani A,Tarzia G

    更新日期:1997-12-01 00:00:00

  • Novel steroidal vinyl fluorides as inhibitors of steroid C17(20) lyase.

    abstract::20-fluoro-17(20)-pregnenolone derivatives were designed as enol mimics of pregnenolone. All of the targeted, novel fluoroolefins were potent inhibitors of C17(20) lyase. ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(01)00354-6

    authors: Burkhart JP,Weintraub PM,Gates CA,Resvick RJ,Vaz RJ,Friedrich D,Angelastro MR,Bey P,Peet NP

    更新日期:2002-04-01 00:00:00

  • Metabolic and electrochemical mechanisms of dimeric naphthoquinones cytotoxicity in breast cancer cells.

    abstract::Cancer cells reprogram their metabolism due to genetic alteration to compensate for increased energy demand and enhanced anabolism, cell proliferation, and protection from oxidative damage. Here, we assessed the cytotoxicity of three dimeric naphthoquinones against the glycolytic MCF-7 versus the oxidative MDA-453 bre...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2011.10.005

    authors: Emadi A,Le A,Harwood CJ,Stagliano KW,Kamangar F,Ross AE,Cooper CR,Dang CV,Karp JE,Vuica-Ross M

    更新日期:2011-12-01 00:00:00

  • Fancy bioisosteres: synthesis, SAR, and pharmacological investigations of novel nonaromatic dopamine D3 receptor ligands.

    abstract::Structural variations of the lead compound FAUC 88 led to dopaminergic enynes with an extended pi-system when Pd-catalyzed cross coupling reactions were employed for the key reaction steps. The dienyne 9b displayed substantial affinity for the dopamine receptor subtype D3 and remarkable selectivity over D4. Compared t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.04.047

    authors: Lenz C,Boeckler F,Hübner H,Gmeiner P

    更新日期:2005-07-15 00:00:00

  • High-throughput evaluation of relative cell permeability between peptoids and peptides.

    abstract::Peptides are limited in their use as drugs due to low cell permeability and vulnerability to proteases. In contrast, peptoids are immune to enzymatic degradation and some peptoids have been shown to be relatively cell permeable. In order to facilitate future design of peptoid libraries for screening experiments, it wo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.04.074

    authors: Tan NC,Yu P,Kwon YU,Kodadek T

    更新日期:2008-06-01 00:00:00

  • Hantzsch 1,4-dihydropyridines containing a diazen-1-ium-1,2-diolate nitric oxide donor moiety to study calcium channel antagonist structure-activity relationships and nitric oxide release.

    abstract::A group of racemic 3-isopropyl 5-[(2-piperazin-1-yl)ethyl] 1,4-dihydro-2,6-dimethyl-4-(pyridyl)-3,5-pyridinedicarboxylates (12a-c), 3-isopropyl 5-{2-[4-nitrosopiperazinyl]ethyl} 1,4-dihydro-2,6-dimethyl-4-(pyridyl)-3,5-pyridinedicarboxylates (14a-c) and 3-isopropyl 5-{2-[(O(2)-acetoxymethyldiazen-1-ium-1,2-diolate)(N,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.12.002

    authors: Nguyen JT,Velázquez CA,Knaus EE

    更新日期:2005-03-01 00:00:00

  • Novel 5-HT7R antagonists, arylsulfonamide derivatives of (aryloxy)propyl piperidines: Add-on effect to the antidepressant activity of SSRI and DRI, and pro-cognitive profile.

    abstract::A novel series of arylsulfonamide derivatives of (aryloxy)propyl piperidines was designed to obtain potent 5-HT7R antagonists. Among the compounds evaluated herein, 3-chloro-N-{1-[3-(1,1-biphenyl-2-yloxy)2-hydroxypropyl]piperidin-4-yl}benzenesulfonamide (25) exhibited antagonistic properties at 5-HT7R and showed selec...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2017.03.057

    authors: Canale V,Partyka A,Kurczab R,Krawczyk M,Kos T,Satała G,Kubica B,Jastrzębska-Więsek M,Wesołowska A,Bojarski AJ,Popik P,Zajdel P

    更新日期:2017-05-15 00:00:00

  • Synthesis, biological activities and pharmacokinetic properties of new fluorinated derivatives of selective PDE4D inhibitors.

    abstract::A new series of selective PDE4D inhibitors has been designed and synthesized by replacing 3-methoxy group with 3-difluoromethoxy isoster moiety in our previously reported cathecolic structures. All compounds showed a good PDE4D3 inhibitory activity, most of them being inactive toward other PDE4 isoforms (PDE4A4, PDE4B...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.04.027

    authors: Brullo C,Massa M,Villa C,Ricciarelli R,Rivera D,Pronzato MA,Fedele E,Barocelli E,Bertoni S,Flammini L,Bruno O

    更新日期:2015-07-01 00:00:00

  • Reaction of thymidine and ascorbic acid induced by UV in the presence of salicylic acid.

    abstract::When a neutral solution of thymidine and ascorbic acid was irradiated with UV light of wavelength longer than 300 nm in the presence of salicylic acid as a photosensitizer, six product peaks appeared in an HPLC chromatogram in addition to small amounts of thymidine dimers. The six products were identified as three pai...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2019.115046

    authors: Suzuki T,Kishida Y

    更新日期:2019-10-01 00:00:00

  • QSAR by LFER model of HIV protease inhibitor mannitol derivatives using FA-MLR, PCRA, and PLS techniques.

    abstract::The present quantitative structure-activity relationship (QSAR) study attempts to explore the structural and physicochemical requirements of mannitol derivatives for HIV protease inhibitory activity using linear free energy related model of Hansch. QSAR models have been developed using electronic (Hammett sigma), hydr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.09.022

    authors: Leonard JT,Roy K

    更新日期:2006-02-15 00:00:00

  • BRACO19 analog dimers with improved inhibition of telomerase and hPot 1.

    abstract::Human chromosomes terminate with telomeres, which contain double-stranded G-rich, repetitive DNA followed by a single-stranded overhang of the G-rich sequence. Single-stranded oligonucleotides containing G-rich telomeric repeats have been observed in vitro to fold into a variety of G-quadruplex topologies depending on...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2009.01.015

    authors: Fu YT,Keppler BR,Soares J,Jarstfer MB

    更新日期:2009-03-01 00:00:00

  • Synthesis, cellular internalization and photodynamic activity of glucoconjugated derivatives of tri and tetra(meta-hydroxyphenyl)chlorins.

    abstract::Glucoconjugated tri and tetra(meta-hydroxyphenyl)chlorins have been synthesized in order to explore how glucoconjugation of the macrocycle affects the photoactivity of the molecule. Internalization processes, photosensitizing efficacy of TPC(m-O-GluOH)(3) and TPC(m-O-GluOH)(4), in HT29 human adenocarcinoma cells have ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(03)00050-6

    authors: Laville I,Figueiredo T,Loock B,Pigaglio S,Maillard P,Grierson DS,Carrez D,Croisy A,Blais J

    更新日期:2003-04-17 00:00:00