当前位置： SCI文献检索 > BIOORGANIC & MEDICINAL CHEMISTRY期刊下所有文献 > 5-Nitro-2-furfuriliden derivatives as potential anti-Trypanosoma cruzi agents: design, synthesis, bioactivity evaluation, cytotoxicity and exploratory data analysis.

5-Nitro-2-furfuriliden derivatives as potential anti-Trypanosoma cruzi agents: design, synthesis, bioactivity evaluation, cytotoxicity and exploratory data analysis.

Abstract：

:The anti-Trypanosoma cruzi activity of 5-nitro-2-furfuriliden derivatives as well as the cytotoxicity of these compounds on J774 macrophages cell line and FN1 human fibroblast cells were investigated in this study. The most active compounds of series I and II were 4-butyl-[N'-(5-nitrofuran-2-yl) methylene] benzidrazide (3g; IC50=1.05μM±0.07) and 3-acetyl-5-(4-butylphenyl)-2-(5-nitrofuran-2-yl)-2,3-dihydro,1,3,4-oxadiazole (4g; IC50=8.27μM±0.42), respectively. Also, compound 3g was more active than the standard drugs, benznidazole (IC50=22.69μM±1.96) and nifurtimox (IC50=3.78μM±0.10). Regarding the cytotoxicity assay, the 3g compound presented IC50 value of 28.05μM (SI=26.71) against J774 cells. For the FN1 fibroblast assay, 3g showed IC50 value of 98μM (SI=93.33). On the other hand, compound 4g presented a cytotoxicity value on J774 cells higher than 400μM (SI >48), and for the FN1 cells its IC50 value was 186μM (SI=22.49). Moreover, an exploratory data analysis, which comprises hierarchical cluster (HCA) and principal component analysis (PCA), was carried out and the findings were complementary. The molecular properties that most influenced the compounds' grouping were ClogP and total dipole moment, pointing out the need of a lipophilic/hydrophilic balance in the designing of novel potential anti-T. cruzi molecules.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Palace-Berl F,Jorge SD,Pasqualoto KF,Ferreira AK,Maria DA,Zorzi RR,de Sá Bortolozzo L,Lindoso JÂ,Tavares LC

doi

10.1016/j.bmc.2013.06.017

subject

Has Abstract

pub_date

2013-09-01 00:00:00

pages

5395-406

issue

17

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00548-8

journal_volume

21

pub_type

杂志文章

相关文献

BIOORGANIC & MEDICINAL CHEMISTRY文献大全
  • SAR study of bisamides as cyclophilin a inhibitors for the development of host-targeting therapy for hepatitis C virus infection.

    abstract：:The therapy of chronic hepatitis C virus infections has significantly improved with the development of direct-acting antivirals (DAAs), which contain NS3/4A protease, NS5A, and NS5B polymerase inhibitors. However, mutations in specific residues in these viral target genes are associated with resistance to the DAAs. Es...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2020.115679

    authors： Li X,Han J,Lee HW,Yoon YS,Jin Y,Khadka DB,Yang S,Kim M,Cho WJ

    更新日期：2020-10-01 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

  • Study on dual-site inhibitors of acetylcholinesterase: Highly potent derivatives of bis- and bifunctional huperzine B.

    abstract：:Natural (-)-huperzine B (HupB), isolated from Chinese medicinal herb, displayed moderate inhibitory activity of acetylcholinesterase (AChE). Based on the active dual-site of AChE, a series of novel derivatives of bis- and bifunctional HupB were designed and synthesized. The AChE inhibition potency of most derivatives ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.11.009

    authors： He XC,Feng S,Wang ZF,Shi Y,Zheng S,Xia Y,Jiang H,Tang XC,Bai D

    更新日期：2007-02-01 00:00:00

  • Synthesis, structure, molecular docking, and structure-activity relationship analysis of enamines: 3-aryl-4-alkylaminofuran-2(5H)-ones as potential antibacterials.

    abstract：:Thirty-one 3-aryl-4-alkylaminofuran-2(5H)-ones were designed, prepared and tested for their antibacterial activity. Some of them showed significant antibacterial activity against Gram-positive organisms, especially against Staphylococcus aureus ATCC 25923, but all were inactive against Gram-negative organisms. Out of ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.01.051

    authors： Xiao ZP,He XB,Peng ZY,Xiong TJ,Peng J,Chen LH,Zhu HL

    更新日期：2011-03-01 00:00:00

  • Chemo-enzymatic synthesis of adenine substituted nicotinic acid adenine dinucleotide phosphate (NAADP) analogs.

    abstract：:Nicotinamide adenine dinucleotide phosphate (NADP) is an indispensable metabolic co-substrate and nicotinic acid adenine dinucleotide phosphate (NAADP) is an important Ca2+ releasing intracellular second messenger. Exploration of the NADP and NAADP interactome often requires the synthesis of NADP derivatives substitut...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2020.115901

    authors： Su P,Bretz JD,Gunaratne GS,Marchant JS,Walseth TF,Slama JT

    更新日期：2021-01-15 00:00:00

  • Benzene-1,3-dicarboxylic acid 2,5-dimethylpyrrole derivatives as multiple inhibitors of bacterial Mur ligases (MurC-MurF).

    abstract：:Enzymes catalyzing the biosynthesis of bacterial peptidoglycan represent traditionally a collection of highly selective targets for novel antibacterial drug design. Four members of the bacterial Mur ligase family-MurC, MurD, MurE and MurF-are involved in the intracellular steps of peptidoglycan biosynthesis, catalyzin...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.05.058

    authors： Perdih A,Hrast M,Barreteau H,Gobec S,Wolber G,Solmajer T

    更新日期：2014-08-01 00:00:00

  • Electrophilicity index as a possible descriptor of biological activity.

    abstract：:The purpose of this study is to probe the suitability of DFT based chemical reactivity parameter, electrophilicity index as a possible biological activity descriptor in the development of QSAR. Testosterone derivatives with activity described in terms of various biological activity parameters and the estrogen derivati...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.08.013

    authors： Parthasarathi R,Subramanian V,Roy DR,Chattaraj PK

    更新日期：2004-11-01 00:00:00

  • Irreversibly inhibitory kinetics of 3,5-dihydroxyphenyl decanoate on mushroom (Agaricus bisporus) tyrosinase.

    abstract：:3,5-Dihydroxyphenyl decanoate (DPD) is found to inhibit the diphenolase activity of tyrosinase from mushroom (Agaricus bisporus). The effects of DPD on the diphenolase activity of mushroom tyrosinase have been studied. The results show that the enzyme activity decreases very slowly with an increase in DPD concentratio...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2005.06.034

    authors： Qiu L,Chen QX,Wang Q,Huang H,Song KK

    更新日期：2005-11-15 00:00:00

  • Three-dimensional molecular-field analyses of octopaminergic agonists for the cockroach neuronal octopamine receptor.

    abstract：:The quantitative structure-activity relationship of a set of 40 octopaminergic agonists against receptor 2 in cockroach nervous tissue, was analyzed using molecular-field analysis (MFA). MFA on the study set of those compounds evaluated effectively the energy between a probe and a molecular model at a series of points...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(03)00313-4

    authors： Hirashima A,Morimoto M,Kuwano E,Eto M

    更新日期：2003-08-15 00:00:00

  • Discovery and structure-activity relationship analysis of Staphylococcus aureus sortase A inhibitors.

    abstract：:Methicillin resistant Staphylococcus aureus (MRSA) is a major health problem that has created a pressing need for new antibiotics. Compounds that inhibit the S. aureus SrtA sortase may function as potent anti-infective agents as this enzyme attaches virulence factors to the cell wall. Using high-throughput screening, ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.08.067

    authors： Suree N,Yi SW,Thieu W,Marohn M,Damoiseaux R,Chan A,Jung ME,Clubb RT

    更新日期：2009-10-15 00:00:00

  • Toward discovery of mutant EGFR inhibitors; Design, synthesis and in vitro biological evaluation of potent 4-arylamino-6-ureido and thioureido-quinazoline derivatives.

    abstract：:A new series of 4-anilinoquinazolines with C-6 ureido and thioureido side chains and various substituents at the C-4 anilino moiety was designed, synthesized and evaluated as wild type (WT) and mutant EGFR inhibitors. Most of the compounds inhibited EGFR kinase wild type (EGFR WT) with IC50 values in the low nanomolar...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.05.063

    authors： Mowafy S,Galanis A,Doctor ZM,Paranal RM,Lasheen DS,Farag NA,Jänne PA,Abouzid KA

    更新日期：2016-08-15 00:00:00

  • Identification of 5-nitrofuran-2-amide derivatives that induce apoptosis in triple negative breast cancer cells by activating C/EBP-homologous protein expression.

    abstract：:The transcription factor C/EBP-homologous protein (CHOP) is a key component of the terminal unfolded protein response (UPR) that mediates unresolvable endoplasmic reticulum stress-induced apoptosis. CHOP induction is known to cause cancer cell death. Chemicals that induce CHOP expression would thus be valuable as pote...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2015.06.011

    authors： Duan H,Li Y,Lim HY,Wang W

    更新日期：2015-08-01 00:00:00

  • Secondary assembly of bile salts mediated by beta-cyclodextrin-terbium(III) complex.

    abstract：:A fluorescent cyclodextrin-Tb(III) complex is successfully synthesized and can include bile salts in its hydrophobic cavities. Therefore, it can efficiently induce the secondary assembly of small bile salt primary micelles to large micelle aggregates, and the aggregation process can be easily observed by transmission ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2006.06.002

    authors： Liu Y,Zhang N,Chen Y,Chen GS

    更新日期：2006-10-01 00:00:00

  • Triterpenoids from Momordica balsamina: Reversal of ABCB1-mediated multidrug resistance.

    abstract：:The ability as P-glycoprotein (P-gp, ABCB1) modulators of thirty (1-30) triterpenoids of the cucurbitane-type was evaluated on human L5178 mouse T-lymphoma cell line transfected with the human MDR1 gene, through the rhodamine-123 exclusion assay. Compounds (1-26, and 29, 30) were previously obtained from the African m...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.08.022

    authors： Ramalhete C,Mulhovo S,Molnar J,Ferreira MU

    更新日期：2016-11-01 00:00:00

  • Citral derived amides as potent bacterial NorA efflux pump inhibitors.

    abstract：:Monoterpene citral and citronellal have been used as starting material for the preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid amides and 9-formyl-5-methyl-deca-2,4,8-trienoic acid amides. The amides on bioevaluation as efflux pump inhibitors (EPIs) against Staphylococcus aureus 1199 and NorA overexpressing S. au...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2008.05.030

    authors： Thota N,Koul S,Reddy MV,Sangwan PL,Khan IA,Kumar A,Raja AF,Andotra SS,Qazi GN

    更新日期：2008-07-01 00:00:00

  • Dual inhibitors of inosine monophosphate dehydrogenase and histone deacetylase based on a cinnamic hydroxamic acid core structure.

    abstract：:Small molecules that act on multiple biological targets have been proposed to combat the drug resistance commonly observed for cancer chemotherapy. By combining the structural features of known inhibitors of inosine monophosphate dehydrogense (IMPDH) and histone deacetylase (HDAC), dual inhibitors of IMPDH and HDAC ba...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2010.06.081

    authors： Chen L,Petrelli R,Gao G,Wilson DJ,McLean GT,Jayaram HN,Sham YY,Pankiewicz KW

    更新日期：2010-08-15 00:00:00

  • Cell surface biotinylation by azaelectrocyclization: easy-handling and versatile approach for living cell labeling.

    abstract：:Versatile method for living cell labeling has been established. Cell surfaces are initially biotinylated by azaelectrocyclization, and then treated with the fluorescence-labeled avidin or the anti-biotin antibody. ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2011.12.043

    authors： Tanaka K,Yokoi S,Morimoto K,Iwata T,Nakamoto Y,Nakayama K,Koyama K,Fujiwara T,Fukase K

    更新日期：2012-03-15 00:00:00

  • Antimalarial acridines: synthesis, in vitro activity against P. falciparum and interaction with hematin.

    abstract：:A series of acridine derivatives were synthesised and their in vitro antimalarial activity was evaluated against one chloroquine-susceptible strain (3D7) and three chloroquine-resistant strains (W2, Bre1 and FCR3) of Plasmodium falciparum. Structure-activity relationship showed that two positives charges as well as 6-...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.10.005

    authors： Guetzoyan L,Yu XM,Ramiandrasoa F,Pethe S,Rogier C,Pradines B,Cresteil T,Perrée-Fauvet M,Mahy JP

    更新日期：2009-12-01 00:00:00

  • Carbohydrate transition state mimics: synthesis of imidazolo-pyrrolidinoses as potential nectrisine surrogates.

    abstract：:The syntheses of four glyco-imidazoles, which are pentose-derivatives belonging to the D-series, as well as the syntheses of their L-enantiomers, are reported. Starting from the known linear xylo, lyxo, arabino, and ribo imidazolo-pentoses in both the L- and the D-series, intramolecular Walden inversion led to the cor...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(03)00402-4

    authors： Tschamber T,Gessier F,Dubost E,Newsome J,Tarnus C,Kohler J,Neuburger M,Streith J

    更新日期：2003-08-15 00:00:00

  • An azido-oxazolidinone antibiotic for live bacterial cell imaging and generation of antibiotic variants.

    abstract：:An azide-functionalised analogue of the oxazolidinone antibiotic linezolid was synthesised and shown to retain antimicrobial activity. Using facile 'click' chemistry, this versatile intermediate can be further functionalised to explore antimicrobial structure-activity relationships or conjugated to fluorophores to gen...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2014.05.054

    authors： Phetsang W,Blaskovich MA,Butler MS,Huang JX,Zuegg J,Mamidyala SK,Ramu S,Kavanagh AM,Cooper MA

    更新日期：2014-08-15 00:00:00

  • Inhibitory effects of flavonoids isolated from Fragaria ananassa Duch on IgE-mediated degranulation in rat basophilic leukemia RBL-2H3.

    abstract：:We isolated the 4 kinds of flavonoids from strawberry 'Nohime' and examined the effect of these flavonoids on the degranulation in RBL-2H3 cells. The flavonoids were found to suppress the degranulation from Ag-stimulated RBL-2H3 cells to different extents. To disclose the inhibitory mechanism of degranulation by flavo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.06.050

    authors： Itoh T,Ninomiya M,Yasuda M,Koshikawa K,Deyashiki Y,Nozawa Y,Akao Y,Koketsu M

    更新日期：2009-08-01 00:00:00

  • Downsizing of an HIV-cell fusion inhibitor, T22 ([Tyr5,12, Lys7]-polyphemusin II), with the maintenance of anti-HIV activity and solution structure.

    abstract：:T22 ([Tyr5,12,Lys7]-polyphemusin II) has been shown to have strong anti-human immunodeficiency virus (HIV) activity comparable to that of 3'-azido-2',3'-dideoxythymidine (AZT). T22, an 18-residue peptide amide, takes an antiparallel beta-sheet structure that is maintained by two disulfide bridges. Herein we synthesize...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(97)10055-4

    authors： Tamamura H,Waki M,Imai M,Otaka A,Ibuka T,Waki K,Miyamoto K,Matsumoto A,Murakami T,Nakashima H,Yamamoto N,Fujii N

    更新日期：1998-04-01 00:00:00

  • (1S,2E,4S,7E,11E)-2,7,11-Cembratriene-4,6-diol semisynthetic analogs as novel c-Met inhibitors for the control of c-Met-dependent breast malignancies.

    abstract：:(1S,2E,4S,6R,7E,11E)-2,7,11-Cembratriene-4,6-diol (1) and its 4-epi-analog (2) are the cembranoid precursors to several key flavor ingredients in most Nicotiana (tobacco) species. Nearly 40-60% of 1 and 2 are purposely degraded during the commercial tobacco fermentation. However, 1 and 2 display promising bioactivitie...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2016.09.032

    authors： Ebrahim HY,Mohyeldin MM,Hailat MM,El Sayed KA

    更新日期：2016-11-15 00:00:00

  • Benzochalcones bearing pyrazoline moieties show anti-colorectal cancer activities and selective inhibitory effects on aurora kinases.

    abstract：:Colorectal cancer is the third and fourth leading cause of cancer in males and females, respectively. Flavonoids, including chalcones, are secondary metabolites in plants that exhibit diverse biological activities, including antibacterial, antimalarial, and antitumor activities. In order to find potent and novel chemo...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2013.09.014

    authors： Shin SY,Yoon H,Hwang D,Ahn S,Kim DW,Koh D,Lee YH,Lim Y

    更新日期：2013-11-15 00:00:00

  • Synthesis and structure-activity relationship study of cytotoxic germanicane- and lupane-type 3beta-O-monodesmosidic saponins starting from betulin.

    abstract：:Germanicane-type triterpenes allobetulin (3) and 28-oxoallobetulin (4) can be obtained by the Wagner-Meerwein rearrangement of the more available lupane-type triterpenes betulin (1) and betulinic acid (2), respectively. The medical uses of betulinic acid (2) and its derivatives are limited because of their poor hydros...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2007.06.033

    authors： Thibeault D,Gauthier C,Legault J,Bouchard J,Dufour P,Pichette A

    更新日期：2007-09-15 00:00:00

  • Structural-activity relationship study of highly-functionalized imidazolines as potent inhibitors of nuclear transcription factor-kappaB mediated IL-6 production.

    abstract：:We herein describe the synthesis and anti-inflammatory properties of a small library of imidazoline-based NF-kappaB inhibitors. The structure-activity relationship of various substituents on an imidazoline core structure was evaluated for the ability to inhibit NF-kappaB mediated IL-6 production. Optimization of the s...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2009.03.002

    authors： Kahlon DK,Lansdell TA,Fisk JS,Tepe JJ

    更新日期：2009-04-15 00:00:00

  • Synthesis and binding mode of heterocyclic analogues of suramin inhibiting the human basic fibroblast growth factor.

    abstract：:The design, synthesis, and biological evaluation of a series of pyrrole and pyrazole congeners 2 of suramin, directed toward the development and identification of new ligands that complex the human fibroblast growth factor (bFGF), thereby inhibiting tumor-promoted angiogenesis, is reported. Compounds 2 were evaluated ...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(98)00052-2

    authors： Manetti F,Cappello V,Botta M,Corelli F,Mongelli N,Biasoli G,Borgia AL,Ciomei M

    更新日期：1998-07-01 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.

    abstract：:Quadratic indices of the 'molecular pseudograph's atom adjacency matrix' have been generalized to codify chemical structure information for chiral drugs. These 3D-chiral quadratic indices make use of a trigonometric 3D-chirality correction factor. These indices are nonsymmetric and reduced to classical (2D) descriptor...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2004.07.051

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

    更新日期：2004-10-15 00:00:00

  • 000Synthesis of new α-aminophosphonates: Evaluation as anti-inflammatory agents and QSAR studies.

    abstract：:In this paper, we report the synthesis of a new series of α-aminophosphonates derivatives based in an efficient three-component reaction. All compounds prepared showed significant anti-inflammatory activity, being the compounds 1a, 1c, 1d, 1f, 2b and 2c the most promising ones, in terms of maximal efficacy (over 95%),...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.bmc.2018.12.041

    authors： Romero-Estudillo I,Viveros-Ceballos JL,Cazares-Carreño O,González-Morales A,de Jesús BF,López-Castillo M,Razo-Hernández RS,Castañeda-Corral G,Ordóñez M

    更新日期：2019-06-15 00:00:00

  • Computer-aided design of non sulphonyl COX-2 inhibitors: an improved comparative molecular field analysis incorporating additional descriptors and comparative molecular similarity indices analysis of 1,3-diarylisoindole derivatives.

    abstract：:A set of thirty five molecules of 1,3-diaryl-4,5,6,7-tetrahydro-2H-isoindoles endowed with selective COX-2 inhibitory activity was analyzed using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA). Besides conventional steric and electrostatic fields, seven addi...

    journal_title：Bioorganic & medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0968-0896(03)00404-8

    authors： Chakraborti AK,Thilagavathi R

    更新日期：2003-09-01 00:00:00