1442115-82-3Relevant articles and documents
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.
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.
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.
