Triazole derivatives as inhibitors of Alzheimer's disease: Current developments and structure-activity relationships

Xu, Man; Peng, Yongzhi; Zhu, Li; Wang, Shulin; Ji, Jiayou; Rakesh, K.P.

doi:10.1016/j.ejmech.2019.07.059

Cited by 94 publications

(32 citation statements)

References 70 publications

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“…The bond length C5-S5 of 1.669(5), 1.663 3, and 1.665(3) Å for C1, C12, and C13, respectively, typical for the thione group (1.671(24) Å [45]) and the position of the H atom in the immediate vicinity of N1 atom of 1,2,4-triazole ring in the difference electron-density map indicate unequivocally that the molecule C1, C12, and C13, similar to C2 and C3 [26], exist in N1-amino/S5-thione tautomeric form in the crystalline state. The 1,2,4-triazole, pyridine, and benzene rings in all investigated molecules are planar to within 0.007(3), 0.012(4) and 0.009(3) Å in C1, 0.0011 (19), 0.008(2), and 0.008(2) Å in C12 and 0.010(2), 0.004(3) and 0.006(3) Å in C13, respectively. Approximately perpendicular position of the phenyl substituent in relation to the 1,2,4-triazole ring described by the torsion angle C3-N4-C41-C42 of 88.8 3• in C1, −107.2 3• in C12 and −107.4 2• in C13 is forced by the steric effect of 2-F, 4-methoxy and 2,4-Cl substituents in the benzene ring in C1, C12, and C13, respectively.…”

Section: X-ray Analysismentioning

confidence: 93%

New Application of 1,2,4-Triazole Derivatives as Antitubercular Agents. Structure, In Vitro Screening and Docking Studies

et al. 2020

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A series of 1,2,4-triazole derivatives were synthesized and assigned as potential anti-tuberculosis substances. The molecular and crystal structures for the model compounds C1, C12, and C13 were determined using X-ray analysis. The X-ray investigation confirmed the synthesis pathway and the assumed molecular structures for analyzed 1,2,4-triazol-5-thione derivatives. The conformational preferences resulting from rotational degrees of freedom of the 1,2,4-triazole ring substituents were characterized. The lipophilicity (logP) and electronic parameters as the energy of frontier orbitals, dipole moments, NBO net charge distribution on the atoms, and electrostatic potential distribution for all structures were calculated at AM1 and DFT/B3LYP/6-311++G(d,p) level. The in vitro test was done against M. tuberculosis H37Ra, M. phlei, M. smegmatis, and M. timereck. The obtained results clearly confirmed the antituberculosis potential of compound C4, which turned out to be the most active against Mycobacterium H37Ra (MIC = 0.976 μg/mL), Mycobaterium pheli (MIC = 7.81 μg/mL) and Mycobacerium timereck (62.6 μg/mL). Satisfactory results were obtained with compounds C8, C11, C14 versus Myc. H37Ra, Myc. pheli, Myc. timereck (MIC = 31.25−62.5 μg/mL). The molecular docking studies were carried out for all investigated compounds using the Mycobacterium tuberculosis cytochrome P450 CYP121 enzyme as molecular a target connected with antimycobacterial activity.

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Section: X-ray Analysismentioning

confidence: 93%

New Application of 1,2,4-Triazole Derivatives as Antitubercular Agents. Structure, In Vitro Screening and Docking Studies

et al. 2020

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“…Diversos protótipos bioativos contendo o núcleo triazólico são descritos por suas atividades anticâncer, antibacterianas, antiparasitárias, antimaláricos, antivirais, neuroprotetores, inibidores de colinesterases, etc. 107,108 Devido à ampla utilização de derivados triazólicos em compostos biologicamente ativos, Nisa e colaboradores descreveram uma nova série de derivados 1,2,4-triazóis do escitalopram. 109 Os derivados triazólicos foram submetidos aos ensaios de inibição da atividade de ambas enzimas colinesterásicas.…”

Section: Derivados Triazólicosunclassified

Butyrylcholinesterase - BuChE: A Potential Target for Development of Drugs for Alzheimer's Disease Treatment

Goulart¹,

Caruso²,

Nadur³

et al. 2021

Rev. Virtual Quim.

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“…Recently, 1,2,3‐triazole hybrid derivatives have been synthesized and demonstrated impressive biological activities . However, the introduction of 1,2,3‐triazole moiety into genipin scaffold to give the promising potent biological analogues has not been reported in the literature so far.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Evaluations of New 10‐Triazolyl‐1‐methoxygenipin Analogues for Their Cytotoxicity to Cancer Cells

et al. 2020

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Genipin 1, derived from geniposide present in the fruit of Gardenia jasminoides Ellis has been reported to show diverse pharmacological activity. In this work, a new series of genipintriazole analogues was designed and synthesized yielding high yields from naturally genipin and their cytotoxicity evaluated against six cancer cell lines. Twenty-seven analogues were obtained using a convenient four-step reaction methods. Six analogues showed higher cytotoxic activity than the original genipin and benzylether-triazolegenipin 5 j exhibited the strongest activity against P-388 and A-549 cancer cell lines with IC 50 values of 2.54 and 4.53 μM. The structure-activity relationships (SARs) study indicated that the introduction of dibenzyl ether, substituted silyl and long chain aliphatic-triazoles at C-10 position of genipin were most effective in improving cytotoxicity. Molecular docking results provided the information for further modification of genipin scaffold for development as cytotoxic agent.

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Triazole derivatives as inhibitors of Alzheimer's disease: Current developments and structure-activity relationships

Cited by 94 publications

References 70 publications

New Application of 1,2,4-Triazole Derivatives as Antitubercular Agents. Structure, In Vitro Screening and Docking Studies

New Application of 1,2,4-Triazole Derivatives as Antitubercular Agents. Structure, In Vitro Screening and Docking Studies

Butyrylcholinesterase - BuChE: A Potential Target for Development of Drugs for Alzheimer's Disease Treatment

Design, Synthesis and Evaluations of New 10‐Triazolyl‐1‐methoxygenipin Analogues for Their Cytotoxicity to Cancer Cells

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