1442115-82-3Relevant academic research and scientific papers
Synthesis, characterization, and biological evaluation of new heterocyclic systems 1, 2, 3-triazole-isoxazoline from eugenol by the mixed condensation reactions
Taia, Abdelmaoujoud,Essaber, Mohamed,Oubella, Ali,Aatif, Abdeljalil,Bodiguel, Jacques,Jamart-Grégoire, Brigitte,Ait Itto, My Youssef,Morjani, Hamid
, p. 2052 - 2065 (2020)
We report the synthesis of new series of heterocyclic systems eugenol 1 derivatives by the mixed condensation reaction of 1,3-dipolar azide and the oxide of p-chlorophenylnitrile on the 4-allyl-2-methoxy-1-(prop-2-yn-1-yloxy)benzene 2. The mono and bicycloadducts, whose structure is homologous to compounds having a broad spectrum of activity, were obtained in good yields. The monocondensation reaction of azides on 4-allyl-2-methoxy-1-(prop-2-yn-1-yloxy)benzene 2 is completely chemoselective, regioselective and stereospecific. The condensation of nitrile oxide on 1,2,3-triazole monocycloadducts prepared was chemoselective and regioselective. The structure of all cycloadducts were characterized and confirmed by the 1H, 13C, 2D nuclear magnetic resonance and mass spectrometry analysis. All the newly synthesized mono and bis-heterocyclic compounds have been selected for their antiproliferative activity against HT-1080 fibrosarcoma, A549 lung carcinoma, and MCF-7 and MDA-MB-231 breast carcinoma cell lines. Among the derivatives, only the compounds 4a, 4b, 5a, 5b, 5d, 5e and 5g showed significant cytotoxicity with IC50 values ranging from 15.31 to 18.81 μM against HT-1080 cells, and 17.32 to 25.94 μM against the other cell lines.
Discovery of novel West Nile Virus protease inhibitor based on isobenzonafuranone and triazolic derivatives of eugenol and indan-1,3-dione scaffolds
De Oliveira, André S.,Gazolla, Poliana A.R.,Da Oliveira, Ana Flávia C.S.,Pereira, Wagner L.,De Viol, Lívia C.S.,Da Maia, Angélica F.S.,Santos, Edjon G.,Da Silva, ítalo E.P.,De Oliveira Mendes, Tiago A.,Da Silva, Adalberto M.,Dias, Roberto S.,Da Silva, Cynthia C.,Polêto, Marcelo D.,Teixeira, Róbson R.,De Paula, Sergio O.
, (2019)
The West Nile Virus (WNV) NS2B-NS3 protease is an attractive target for the development of therapeutics against this arboviral pathogen. In the present investigation, the screening of a small library of fifty-eight synthetic compounds against the NS2-NB3 protease of WNV is described. The following groups of compounds were evaluated: 3-(2-aryl-2-oxoethyl)isoben-zofuran-1(3H)-ones; eugenol derivatives bearing 1,2,3-triazolic functionalities; and indan-1,3-diones with 1,2,3-triazolic functionalities. The most promising of these was a eugenol derivative, namely 4-(3-(4-allyl-2-methoxyphenoxy)-propyl)-1-(2-bromobenzyl)-1H-1,2,3-triazole (35), which inhibited the protease with IC50of 6.86 μmol L-1. Enzyme kinetic assays showed that this derivative of eugenol presents competitive inhibition behaviour. Molecular docking calculations predicted a recognition pattern involving the residues His51and Ser135, which are members of the catalytic triad of the WNV NS2B-NS3 protease.
Synthesis and leishmanicidal activity of eugenol derivatives bearing 1,2,3-triazole functionalities
Teixeira, Róbson Ricardo,Gazolla, Poliana Aparecida Rodrigues,da Silva, Adalberto Manoel,Borsodi, Maria Paula Gon?alves,Bergmann, Bartira Rossi,Ferreira, Rafaela Salgado,Vaz, Boniek Gontijo,Vasconcelos, Géssica Adriana,Lima, Wallace Pacienza
, p. 274 - 286 (2018/02/10)
In this paper, it is described the synthesis and the evaluation of the leishmanicidal activity of twenty-six eugenol derivatives bearing 1,2,3-triazole functionalities. The evaluation of the compounds on promastigotes of Leishmania amazonensis (WHOM/BR/75/Josefa) showed that eugenol derivatives present leishmanicidal activities with varying degrees of effectiveness. The most active compound, namely 4-(3-(4-allyl-2-methoxyphenoxy)propyl)-1-(4-methylbenzyl)-1H-1,2,3-triazole (7k) (IC50 = 7.4 ± 0.8 μmol L?1), also targeted Leishmania parasites inside peritoneal macrophages (IC50 = 1.6 μmol L?1) without interfering with cell viability. The cytotoxicity of 7k against macrophage cells presented IC50 of 211.9 μmol L?1 and the selective index was equal to 132.5. Under similar conditions, compound 7k was more effective than glucantime and pentamidine, two drugs currently in the clinic. In addition, theoretical calculations showed that this compound also presents most physicochemical and pharmacokinetic properties within the ranges expected for orally available drugs. It is believed that eugenol bearing 1,2,3-triazole functionalities may represent a scaffold to be explored toward the development of new agents to treat leishmaniasis.
Cu2O spheres as an efficient source of catalytic Cu(I) species for performing azide-alkyne click reactions
Rodrigues, Thenner S.,da Silva, Anderson G.M.,de Oliveira, Lucas C.,da Silva, Adalberto M.,Teixeira, Róbson R.,Camargo, Pedro H.C.
, p. 590 - 595 (2017/01/16)
We report herein the high yield synthesis of Cu2O spheres displaying well-defined shapes and monodisperse sizes that could be employed as the source of highly catalytic active Cu(I) species towards click reactions between several of alkynes and azides to produce a variety of 1,2,3-triazoles under ligand-free and ambient conditions (in an open reactor). The utilization of Cu2O spheres enabled superior performance as compared to a conventional protocol in which CuSO4is employed in combination with sodium ascorbate as the catalyst system. In addition, the compounds were obtained in synthetically useful yields, and seven of them have not been previously reported. We believe the results reported herein shed new insights into the optimization of activity and versatility of click reactions towards the synthesis of target molecules in environmentally friendly conditions.
A recyclable and water soluble copper(i)-catalyst: One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their biological evaluation
Nekkanti, Shalini,Veeramani, Karuna,Sujana Kumari,Tokala, Ramya,Shankaraiah, Nagula
, p. 103556 - 103566 (2016/11/13)
A facile protocol for the regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles via a three-component 'click' reaction of alkyl/benzyl bromides, sodium azide, and terminal alkynes catalyzed by an efficient water soluble copper(i) complex has been developed. The halides have been directly converted into 1,2,3-triazoles via in situ generation of azides and hence, handling of hazardous azide intermediates can be avoided. Gratifyingly, the inherent advantages of this one-pot process are the use of water as solvent, catalyst recyclability, reduced reaction times, simple recrystallization and high yields of the products. The broad scope of this protocol was also explored for the synthesis of a variety of diversely substituted biologically relevant DNA-interactive 1,2,3-triazolo-tetrahydro-β-carboline derivatives. These 1,2,3-triazolo-tetrahydro-β-carbolines were further evaluated for their in vitro cytotoxicity on selected human cancer cell lines of A-549, HCT-116, BT-549, MDA-MB-231, PC-3, NCI-H460 and HCT-15. DNA binding affinity through viscometry experiment and molecular modeling studies have indicated efficient minor groove binding of these new scaffolds.
Synthesis, QSAR and anticandidal evaluation of 1,2,3-triazoles derived from naturally bioactive scaffolds
Irfan, Mohammad,Aneja, Babita,Yadava, Umesh,Khan, Shabana I.,Manzoor, Nikhat,Daniliuc, Constantin G.,Abid, Mohammad
, p. 246 - 254 (2015/03/04)
In the present study, we used eight natural precursors (1a-h) with most of them having promising antimicrobial activities and synthesised their novel 1,2,3-triazole derivatives (3a-h). In the reaction sequences, the precursor compounds (1a-h) were convert
