Design, Synthesis and Trypanocidal Evaluation of Novel  1,2,4-Triazoles-3-thiones Derived from Natural Piperine

Franklim, Tatiany Nunes; Freire-de-Lima, Leonardo; Diniz, Julliana De Nazareth Sá; Previato, José O.; Castro, Rosane Nora; Mendonça-Previato, Lúcia; Lima, Marco Edílson Freire de

doi:10.3390/molecules18066366

Cited by 50 publications

(36 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The derivatives of 1,2,4-triazole-3-thiol and theophylline are a very promising class of chemical compounds for the synthesis of biologically active compounds based on them, due to the wide spectrum of biological activity of these heterocycles' derivatives [2][3][4][5][6][7]10]. Objective reasons for the search for a number of 1,2,4-triazol-3-thiol and theophylline derivatives are the high synthetic and pharmacological potential of these synthones [2,5,7,10]. Our attention was drawn to previously unexplored amides and 2-[4-R-5-(theophylline-7'-yl)-1,2,4-triazole-3-ylthio]acetic acid.…”

Section: синтез будова та властивості N-r-амідів і гідразидів 2-[4-rmentioning

confidence: 99%

Synthesis, structure and properties of N-R-amides and hydrazides of 2-[4-R-5-(theophylline-7ʹ-yl)-1,2,4-triazole-3-ylthio]acetic acid

Gotsulya¹

2017

Current Issues in Pharmacy and Medicine: Science and Practice

View full text Add to dashboard Cite

Section: синтез будова та властивості N-r-амідів і гідразидів 2-[4-rmentioning

confidence: 99%

Synthesis, structure and properties of N-R-amides and hydrazides of 2-[4-R-5-(theophylline-7ʹ-yl)-1,2,4-triazole-3-ylthio]acetic acid

Gotsulya¹

2017

Current Issues in Pharmacy and Medicine: Science and Practice

View full text Add to dashboard Cite

“…Studies from our group aimed at tracing a structure-activity relationship (SAR) profile have demonstrated the toxic effects of piperine derivatives and analogues against different evolutive forms of L. amazonensis and T. cruzi. [20][21][22][23][24] Azole derivatives were evaluated for CD experimental treatment and exhibited highly promising results. These azoles are commercially available drugs or molecules that were tested against other type of infections.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Trypanocidal Activity, and Studies on Human Albumin Interaction of Novel S-Alkyl-1,2,4-triazoles

Franklim¹,

Freire-de-Lima²,

Chaves³

et al. 2019

J. Braz. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

Chagas disease is a neglected tropical disease caused by the hemoflagellated parasite Trypanosoma cruzi (Kinetoplastida). The only available drug to treat chagasic patients in Brazil, the nitroheterocycle benznidazole, is effective solely during the acute phase of the infection. There is accordingly a need to develop new therapeutic tools for the treatment of Chagas disease. This work reports the synthesis, trypanocidal evaluation and human serum albumin (HSA) interactions of a novel series of 1,2,4-triazoles. The new derivatives were synthesized via microwave irradiation in good yields. Most compounds showed toxic effects against T. cruzi with low toxicity to host cells. Three S-alkylated-triazoles showed the best activity profile against amastigotes, with half maximal inhibitory concentration (IC 50) values of 3.95 ± 1.41, 4.15 ± 0.92 and 3.61 ± 0.65 μmol L-1 , respectively. The interaction between HSA and 3-[(1E,3E)-4-(1,3-benzodioxol-5-yl)buta-1,3-dien-1-yl]-5-(butylthio)-4-cyclohexyl-4,5-dihydro-1H-1,2,4-triazole was investigated using multiple spectroscopic techniques and molecular docking, revealing that serum albumin is a potential endogenous carrier to this compound in the human bloodstream.

show abstract

“…In our time there is a considerable interest in the derivatives of various heterocyclic systems [3]. There are no exceptions to 1,2,4-triazole and 3-methylxanthine, which are important synthones for the synthesis of various biologically active compounds on their basis [4,5,10]. Objective reasons for the search for a number of these derivatives are the high synthetic and pharmacological potential of these synthones.…”

Section: Introductionmentioning

confidence: 99%

“…Objective reasons for the search for a number of these derivatives are the high synthetic and pharmacological potential of these synthones. Our attention was drawn to previously unexplored amides and hydrazides of 2-[4-R-5-((3'-methylxanthin-7'-yl)-1,2,4-triazole-3-ylthiо] acetic acid [2,[4][5][6]9].…”

Section: Introductionmentioning

confidence: 99%

Features of the vegetative state and arterial pressure level in children with chronic gastroduodenal pathology

Gotsulya

2018

Current Issues in Pharmacy and Medicine: Science and Practice

View full text Add to dashboard Cite

Introduction. Heterocyclic compounds are the foundation on which the creation of medicines is successfully carried out. One such system is 1,2,4-triazole and 3-methylxanthine. These heterocycles are characterized by wide range of biological properties, along with low toxicity.The purpose of this work was to synthesize and investigate the properties of N-R-amides and hydrazides 2-[4-R-5-(3'-methylxanthine-7'-yl)-1,2,4-triazole-3-ylthio]acetic acid (R = CH 3 , C 2 H 5 , C 6 H 5 ) when changing the conditions of the chemical process. Methods and results.As initial key reagents we used 7'-((3-thio-4-R-4H-1,2,4-triazole-5-yl)methyl)-3'-methylxanthine and ethers of 2-[4-R-5-((3'-methylxanthine-7'-yl)methyl)-1,2,4-triazole-3-ylthio]acetic acid, which were prepared according to known procedures from available raw materials. In the course of studies, it was found that when heated in ethanol the corresponding primary or secondary alkylamines (methylamine, ethylamine, monoethanolamine, diethylamine) or ammonia solution from prop-1-yl 2-[4-R-5-((3'-methylxanthine-7'-yl)methyl)-1,2,4-triazole-3-ylthio]ethanoate, then the corresponding amidated derivatives of 2-[4-R-5-((3'-methylxanthine-7'-yl)methyl)-1,2,4-triazole-3-ylthio]acetic acid are created. The corresponding amides were obtained by reacting 7'-((3-thio-4-R-4H-1,2,4-triazol-5-yl) methyl)-3'-methylxanthine with 2-chloroacetamide in a high yield sodium hydroxide medium. Hydrazides of 2-[4-R-5-((3'-methylxanthine-7'yl)methyl)-1,2,4-triazole-3-ylthio]-ethane acid are synthesized by the interaction of the corresponding esters of 2-[4-R-5-((3'-methylxanthine-7'-yl)methyl)-1,2,4-triazole-3-ylthio]acetic acid with an aqueous hydrazine hydrate solution in ethanol. The structure of the obtained compounds is confirmed by the data of elemental analysis, 1 H NMR spectroscopy, IR-spectrophotometry. Individuality was established using thin-layer chromatography and chromatography-mass spectrometry. For synthesized compounds, preliminary screening was performed using the PASS On-line ® software and molecular docking. The optimal methods for the preparation hydrazides and amides of 2-[4-R-5-((3'-methylxanthine-7'-yl)methyl)-1,2,4-triazole-3-ylthio]ethane acid were developed. The production of amides in two alternative pathways using the starting thiol and the ester, derived from it, was studied: it was established that the interaction of the starting thiol with 2-chloroacetamide runs with a larger yield of the reaction product in comparison with the reaction of the corresponding ester with ammonia. The results of physical-chemical analysis of synthesized compounds was interpreted. This preliminary assessment of the possible manifestation of anti-inflammatory activity was given. The probability of manifestation of this type of activity was not high. Conclusions. 19 amides and 3 hydrazide of 2-[4-R-5-((3'-methylxanthine-7'-yl)methyl)-1,2,4-triazole-3-ylthio]ethane acid were obtained with high yields and purity, their structure was proven and properties were investigated. N-R-амідів 2-[4-R...

show abstract

Design, Synthesis and Trypanocidal Evaluation of Novel 1,2,4-Triazoles-3-thiones Derived from Natural Piperine

Cited by 50 publications

References 34 publications

Synthesis, structure and properties of N-R-amides and hydrazides of 2-[4-R-5-(theophylline-7ʹ-yl)-1,2,4-triazole-3-ylthio]acetic acid

Synthesis, structure and properties of N-R-amides and hydrazides of 2-[4-R-5-(theophylline-7ʹ-yl)-1,2,4-triazole-3-ylthio]acetic acid

Design, Synthesis, Trypanocidal Activity, and Studies on Human Albumin Interaction of Novel S-Alkyl-1,2,4-triazoles

Features of the vegetative state and arterial pressure level in children with chronic gastroduodenal pathology

Contact Info

Product

Resources

About