当前位置： SCI文献检索 > BIOORGANIC CHEMISTRY期刊下所有文献 > Design, synthesis, and evaluations of the antiproliferative activity and aqueous solubility of novel carbazole sulfonamide derivatives as antitumor agents.

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 active against HepG2 cells (IC50: 1.00-10.0 μM) than the other three tumor cell lines. Several representative compounds, selected from each series, showed aqueous solubility (13.4-176.5 µg/mL at pH 7.4 and 2.0) better than 1, with the aqueous solubility of corresponding salts > 30 mg/mL. From the results of evaluating the effects of the compounds 7b, 8c, 9c, 10c and 11c on tubulin in vitro, we speculated that their targets were different from those of 1 and CA-4P. We tested the antitumor activity of the representative compound 7b·HCl (10 mg/kg) in an in vivo study and found that its tumor growth inhibition rate was 41.1%. The tumor growth inhibition rate of 7b·HCl (20 mg/kg) was 54.6%, whereas the tumor growth inhibition rate of CA-4P (50 mg/kg) was 48.3%. And in another batch of in vivo antitumor activity testing, 9c·HCl and 11c·HCl at doses of 10 mg/kg resulted in 61.1% and 50.0% inhibition, respectively. These promising results warrant further development of the derivatives, which may use a novel mechanism and show potential potency as antitumor drug candidates.

journal_name

Bioorg Chem

journal_title

Bioorganic chemistry

authors

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

doi

10.1016/j.bioorg.2020.103766

subject

Has Abstract

pub_date

2020-06-01 00:00:00

pages

103766

eissn

0045-2068

issn

1090-2120

pii

S0045-2068(19)32001-2

journal_volume

99

pub_type

杂志文章

相关文献

BIOORGANIC CHEMISTRY文献大全
  • Synthesis of novel 2-aminobenzothiazole derivatives as potential antimicrobial agents with dual DNA gyrase/topoisomerase IV inhibition.

    abstract：:Novel benzothiazole-based compounds were designed and synthesized as potential antimicrobial agents with dual DNA gyrase/topoisomerase IV inhibitory activity. The structures of the newly synthesized compounds were established on the basis of spectral (IR, NMR, MS) and elemental analyses. Most of the studied compounds ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103437

    authors： Ismail MMF,Abdulwahab HG,Nossier ES,El Menofy NG,Abdelkhalek BA

    更新日期：2020-01-01 00:00:00

  • Design, synthesis and biological evaluation of novel indole derivatives as potential HDAC/BRD4 dual inhibitors and anti-leukemia agents.

    abstract：:HDAC inhibitors and BRD4 inhibitors were considered to be potent anti-cancer agents. Recent studies have demonstrated that HDAC and BRD4 participate in the regulation of some signal paths like PI3K-AKT. In this work, a series of indole derivatives that combine the inhibitory activities of BRD4 and HDAC into one molecu...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.12.011

    authors： Cheng G,Wang Z,Yang J,Bao Y,Xu Q,Zhao L,Liu D

    更新日期：2019-03-01 00:00:00

  • A new nonhydrolyzable reactive cAMP analog, (Sp)-adenosine-3',5'-cyclic-S-(4-bromo-2,3-dioxobutyl)monophosphorothioate irreversibly inactivates human platelet cGMP-inhibited cAMP phosphodiesterase.

    abstract：:Levels of cAMP that control critical platelet functions are regulated by cGMP-inhibited cAMP phosphodiesterase (PDE3A). We previously showed that millimolar concentrations of the hydrolyzable 8-[(4-bromo-2,3-dioxobutyl)thioadenosine 3',5'-cyclic monophosphate (8-BDB-TcAMP) inactivate PDE3A. We have now synthesized a n...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1006/bioo.2001.1226

    authors： Hung SH,Madhusoodanan KS,Beres JA,Boyd RL,Baldwin JL,Zhang W,Colman RW,Colman RF

    更新日期：2002-02-01 00:00:00

  • Chemo-enzymatic synthesis and cell-growth inhibition activity of resveratrol analogues.

    abstract：:The stilbenoid resveratrol (1) was subjected to regioselective acetylation catalysed by Candida antarctica lipase (CAL) to obtain 4'-acetylresveratrol (2). CAL biocatalysed regioselective alcoholysis of 3,5,4'-triacetylresveratrol (3), 3,5,4'-tributanoylresveratrol (6), and 3, 4, 5'-trioctanoylresveratrol (9) afforded...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2004.08.003

    authors： Cardile V,Lombardo L,Spatafora C,Tringali C

    更新日期：2005-02-01 00:00:00

  • First evaluation of organotellurium derivatives as carbonic anhydrase I, II, IV, VII and IX inhibitors.

    abstract：:A series of tellurides was evaluated as carbonic anhydrase (CA, EC 4.2.1.1) inhibitors against the human (h) carbonic anhydrase isoforms hCA I, II, IV, VII and IX, involved in a variety of diseases, including glaucoma, retinitis pigmentosa, epilepsy, arthritis and tumors. These compounds, which are the first tellurium...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2017.12.010

    authors： Angeli A,Tanini D,Capperucci A,Supuran CT

    更新日期：2018-02-01 00:00:00

  • Syntheses of diacyltanshinol derivatives and their suppressive effects on macrophage foam cell formation by reducing oxidized LDL uptake.

    abstract：:A series of diacyltanshinol derivatives were synthesized by esterifying the corresponding o-hydroquinones of tanshinones. The suppressive effects of the synthesized compounds on oxidized low-density lipoprotein (oxLDL) uptake and oxLDL-induced macrophage-derived foam cell formation were evaluated. Our results indicate...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2013.11.001

    authors： Cheng X,Zhang DL,Li XB,Ye JT,Shi L,Huang ZS,Gu LQ,An LK

    更新日期：2014-02-01 00:00:00

  • Synthesis, characterization, anti-proliferative properties and DNA binding of benzochromene derivatives: Increased Bax/Bcl-2 ratio and caspase-dependent apoptosis in colorectal cancer cell line.

    abstract：:3-Amino-1-aryl-1H-benzo[f]chromene-2-carbonitrile derivatives were synthesized from three-component reaction of arylaldehyde, malononitrile and 2-naphthol in the presence of 1, 4-bis(4-ferrocenylbutyl)piperazine as a new catalyst. Cytotoxic potencies of the compounds were tested on HT-29 cells. 3-Amino-1-(4-fluorophen...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103329

    authors： Ahagh MH,Dehghan G,Mehdipour M,Teimuri-Mofrad R,Payami E,Sheibani N,Ghaffari M,Asadi M

    更新日期：2019-12-01 00:00:00

  • Novel sulfonamide incorporating piperazine, aminoalcohol and 1,3,5-triazine structural motifs with carbonic anhydrase I, II and IX inhibitory action.

    abstract：:A new series of s-triazine derivatives incorporating sulfanilamide, homosulfanilamide, 4-aminoethyl-benzenesulfonamide and piperazine or aminoalcohol structural motifs is reported. Molecular docking was exploited to select compounds from virtual combinatorial library for synthesis and subsequent biological evaluation....

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2017.12.034

    authors： Havránková E,Csöllei J,Vullo D,Garaj V,Pazdera P,Supuran CT

    更新日期：2018-04-01 00:00:00

  • 8-Chrysoeriol, as a potential BCL-2 inhibitor triggers apoptosis of SW1990 pancreatic cancer cells.

    abstract：:8-Chrysoeriol, a bioactive flavanoid, was firstly identified to bind directly to BCL-2 as BH3 mimetics by structure-based virtual ligand screening. And 3D docking model revealed the molecular basis of 8-Chrysoeriol targeting to BCL-2. The interaction between 8-Chrysoeriol and BCL-2 was further confirmed using Microsca...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.01.042

    authors： Zhang Y,Li Z,Min Q,Palida A,Zhang Y,Tang R,Chen L,Li H

    更新日期：2018-04-01 00:00:00

  • Design, synthesis and biological evaluation of novel 1,2,3-triazole linked coumarinopyrazole conjugates as potent anticholinesterase, anti-5-lipoxygenase, anti-tyrosinase and anti-cancer agents.

    abstract：:A series of new 1,2,3-triazole linked coumarinopyrazole conjugates 4a-e and 5a-e have been synthesized via the Copper(I)-catalysed Alkyne-Azide Cycloaddition (CuAAC). Going through the reaction of compound 2 with the 3-propargyl bromide gave a mixture of propargylated regioisomers 3 + 3' used as a dipolarophile to acc...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.06.005

    authors： Chekir S,Debbabi M,Regazzetti A,Dargère D,Laprévote O,Ben Jannet H,Gharbi R

    更新日期：2018-10-01 00:00:00

  • Steering the antitumor drug discovery campaign towards structurally diverse indolines.

    abstract：:Indoline framework is often perpended as a privileged heterocycle present in medicinally valuable compounds of natural and synthetic origin. This review article presents the rational approaches/strategies employed for the design of anticancer indolines along with the structure activity relationship and mechanistic ins...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.bioorg.2019.103436

    authors： Thakur A,Singh A,Kaur N,Ojha R,Nepali K

    更新日期：2020-01-01 00:00:00

  • Synthesis of ring-C modified oleanolic acid derivatives and their cytotoxic evaluation.

    abstract：:Ring-C of oleanolic acid was chemically modified by treating with NBS under a variety of experimental conditions. The structures of the synthesized compounds were established by spectral analysis ((1)H &(13)C NMR and Mass). All the compounds were evaluated against a panel of five human cancer cell lines by using MTT a...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2016.08.001

    authors： Pattnaik B,Lakshma Nayak V,Ramakrishna S,Venkata Mallavadhani U

    更新日期：2016-10-01 00:00:00

  • Recent advances in synthesis and medicinal chemistry of benzodiazepines.

    abstract：:Benzodiazepines (BZDs) represent a diverse class of bicyclic heterocyclic molecules. In the last few years, benzodiazepines have emerged as potential therapeutic agents. As a result, several mild, efficient and high yielding protocols have been developed that offer access to various functionalized benzodiazepines (BZD...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.bioorg.2020.103668

    authors： Arora N,Dhiman P,Kumar S,Singh G,Monga V

    更新日期：2020-04-01 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

  • Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property.

    abstract：:Diminution of oxidative stress-mediated diseases is an essential pharmaceutical objective in modern biomedical research. The present work stresses upon the efficient and eco-friendly synthesis of an array of novel diversely functionalized pyrrole derivatives which are found to be antioxidants with reactive oxygen spec...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103734

    authors： Kundu T,Pramanik A

    更新日期：2020-05-01 00:00:00

  • Design, synthesis and photoinduced DNA cleavage studies of [1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones.

    abstract：:An expedient and eco-friendly synthesis of 1-aryl/heteroaryl-[1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones (4) has been accomplished via iodobenzene diacetate mediated oxidative intramolecular cyclization of 3-(2-(aryl/heteroarylidene)hydrazinyl)-quinoxalin-2(1H)-ones (3). Ten synthesized compounds 3 and 4 (10-40 μg) o...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.102932

    authors： Sumran G,Aggarwal R,Mittal A,Aggarwal A,Gupta A

    更新日期：2019-07-01 00:00:00

  • Novel cytisine derivatives exert anti-liver fibrosis effect via PI3K/Akt/Smad pathway.

    abstract：:A series of new cytisine derivatives with a unique endocyclic scaffold were synthesized and evaluated for their inhibitory effect on collagen α1 (I) (COL1A1) promotor in human LX2 cells, taking cytisine as the lead. Structure-activity relationship (SAR) revealed that introducing a 12N-benzyl substitution might signifi...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.103032

    authors： Tang S,Li Y,Bao Y,Dai Z,Niu T,Wang K,He H,Song D

    更新日期：2019-09-01 00:00:00

  • Probing the active site of rat porphobilinogen synthase using newly developed inhibitors.

    abstract：:The structurally related tetrapyrrolic pigments are a group of natural products that participate in many of the fundamental biosynthetic and catabolic processes of living organisms. Porphobilinogen synthase catalyzes a rate-limiting step for the biosyntheses of tetrapyrrolic natural products. In the present study, a v...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2008.11.001

    authors： Li N,Chu X,Liu X,Li D

    更新日期：2009-02-01 00:00:00

  • Novel 8-amino-1,2,4-triazolo[4,3-a]pyrazin-3-one derivatives as potent human adenosine A1 and A2A receptor antagonists. Evaluation of their protective effect against β-amyloid-induced neurotoxicity in SH-SY5Y cells.

    abstract：:In this work, an enlarged series of 1,2,4-triazolo[4,3-a]pyrazin-3-ones was designed to target the human (h) A2A adenosine receptor (AR) or both hA1 and hA2A ARs. The novel 8-amino-1,2,4-triazolopyrazin-3-one derivatives 1-25 featured a phenyl or a benzyl pendant at position 2 while different aryl/heteroaryl substitue...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2019.03.046

    authors： Falsini M,Catarzi D,Varano F,Dal Ben D,Marucci G,Buccioni M,Volpini R,Di Cesare Mannelli L,Ghelardini C,Colotta V

    更新日期：2019-06-01 00:00:00

  • Tacrine-hydroxamate derivatives as multitarget-directed ligands for the treatment of Alzheimer's disease: Design, synthesis, and biological evaluation.

    abstract：:In order to develop multitarget-directed ligands as potential treatments for Alzheimer's disease, twenty-eight new tacrine-hydroxamate derivatives were designed, synthesized, and biologically evaluated. As expected, most of the compounds exhibited inhibitory activities against cholinesterases (ChEs) and histone deacet...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.103721

    authors： Xu A,He F,Zhang X,Li X,Ran Y,Wei C,James Chou C,Zhang R,Wu J

    更新日期：2020-05-01 00:00:00

  • TDP-43 specific reduction induced by Di-hydrophobic tags conjugated peptides.

    abstract：:TAR DNA binding protein 43 (TDP-43) is a key target in amyotrophic lateral sclerosis (ALS) treatment. Here, based on hydrophobic tagging strategy, we designed and synthesized a series of single or double hydrophobic tags conjugated peptides D1-D8. Among them, it was found that D4 displayed strongest ability to induce ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.11.042

    authors： Gao N,Huang YP,Chu TT,Li QQ,Zhou B,Chen YX,Zhao YF,Li YM

    更新日期：2019-03-01 00:00:00

  • Discovery of a novel cathepsin inhibitor with dual autophagy-inducing and metastasis-inhibiting effects on breast cancer cells.

    abstract：:Drug resistance and cancer cells metastasis have been the leading causes of chemotherapy failure and cancer-associated death in breast cancer patients. In present, various active molecules either exhibiting novel mechanism of action such as inducing autophagy or inhibiting metastasis have been developed to address the...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2018.11.025

    authors： Yuan L,Liu J,He W,Bao Y,Sheng L,Zou C,Hu B,Ge W,Liu Y,Wang J,Lin B,Li Y,Ma E

    更新日期：2019-03-01 00:00:00

  • Functional studies of rat hydroxymethylbilane synthase.

    abstract：:The structurally related tetrapyrrolic pigments are a group of natural products that participate in many of the fundamental biosynthetic and catabolic processes of living organisms. Hydroxymethylbilane synthase catalyzes a rate-limiting step for the biosyntheses of tetrapyrrolic natural products. We carried out extens...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2008.07.001

    authors： Li N,Chu X,Wu L,Liu X,Li D

    更新日期：2008-10-01 00:00:00

  • Novel coumarin-pyridazine hybrids as selective MAO-B inhibitors for the Parkinson's disease therapy.

    abstract：:The 3-pyridazinylcoumarin scaffold was previously reported as an efficient core for the discovery of reversible and selective inhibitors of MAO-B, a validated drug target for PD therapy which also plays an important role in the AD progress. Looking for its structural optimization, novel compounds of hybrid structure c...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104203

    authors： Rodríguez-Enríquez F,Costas-Lago MC,Besada P,Alonso-Pena M,Torres-Terán I,Viña D,Fontenla JÁ,Sturlese M,Moro S,Quezada E,Terán C

    更新日期：2020-11-01 00:00:00

  • Design, synthesis and evaluation of newer 5,6-dihydropyrimidine-2(1H)-thiones as GABA-AT inhibitors for anticonvulsant potential.

    abstract：:Several new 5,6-dihydropyrimidine-2(1H)-thione derivatives have been prepared and investigated for their potencies for anticonvulsant activity against maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) test in mice. The acute neurotoxicity was measured by rotarod test. Compounds 3c and 3l were foun...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2017.07.017

    authors： Sahu M,Siddiqui N,Iqbal R,Sharma V,Wakode S

    更新日期：2017-10-01 00:00:00

  • Design, synthesis and pharmacological evaluation of 6,7-disubstituted-4-phenoxyquinoline derivatives as potential antitumor agents.

    abstract：:Two series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 2,4-imidazolinedione/pyrazolone scaffold were designed, synthesized and evaluated for their c-Met kinase inhibition and cytotoxicity against HT-29, H460, A549, MKN-45, and U87MG cancer cell lines in vitro. The pharmacological data indicated that mo...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2014.07.011

    authors： Zhou S,Ren J,Liu M,Ren L,Liu Y,Gong P

    更新日期：2014-12-01 00:00:00

  • Role of the PH domain in regulating in vitro autophosphorylation events required for reconstitution of PDK1 catalytic activity.

    abstract：:In addition to its catalytic domain, phosphoinsositide-dependent protein kinase-1 (PDK1) contains a C-terminal pleckstrin homology (PH) domain, which binds the membrane-bound phosphatidylinositol (3,4,5)-triphosphate [PI(3,4,5)P3] second messenger. Here, we report in vitro kinetic, phosphopeptide mapping, and oligomer...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2006.05.002

    authors： Gao X,Harris TK

    更新日期：2006-08-01 00:00:00

  • Triazinoindole analogs as potent inhibitors of α-glucosidase: synthesis, biological evaluation and molecular docking studies.

    abstract：:A new series of triazinoindole analogs 1-11 were synthesized, characterized by EI-MS and (1)H NMR, evaluated for α-glucosidase inhibitory potential. All eleven (11) analogs showed different range of α-glucosidase inhibitory potential with IC50 value ranging between 2.46±0.008 and 312.79±0.06 μM when compared with the ...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2014.12.001

    authors： Rahim F,Ullah K,Ullah H,Wadood A,Taha M,Ur Rehman A,uddin I,Ashraf M,Shaukat A,Rehman W,Hussain S,Khan KM

    更新日期：2015-02-01 00:00:00

  • Design, synthesis, molecular modeling and biological evaluation of novel 1H-pyrazolo[3,4-b]pyridine derivatives as potential anticancer agents.

    abstract：:In trying to develop new anticancer agents, a series of 1H-pyrazolo[3,4-b]pyridine derivatives was designed and synthesized. Fifteen compounds were evaluated in vitro for their anti-proliferative activity against HePG-2, MCF-7, HCT-116, and PC-3 cell lines. Additionally, DNA binding affinity of the synthesized derivat...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2016.05.006

    authors： Eissa IH,El-Naggar AM,El-Hashash MA

    更新日期：2016-08-01 00:00:00

  • Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity.

    abstract：:A library of 33 polymethoxylated flavones (PMF) was evaluated for heme-binding affinity by biomimetic MS assay and in vitro antiplasmodial activity on two strains of P. falciparum. Stability of heme adducts was discussed using the dissociation voltage at 50% (DV50). No correlation was observed between the methoxylatio...

    journal_title：Bioorganic chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bioorg.2020.104243

    authors： Ortiz S,Vásquez-Ocmín PG,Cojean S,Bouzidi C,Michel S,Figadère B,Grougnet R,Boutefnouchet S,Maciuk A

    更新日期：2020-11-01 00:00:00