Synthesis and biological activities of some fluorine- and piperazine-containing 1,2,4-triazole thione derivatives

Zhang, Liyuan; Wang, Baolei; Zhan, Yizhou; Zhang, Yan; Zhang, Xiǎo; Li, Zhengming

doi:10.1016/j.cclet.2015.09.015

Cited by 31 publications

(11 citation statements)

References 18 publications

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“…The mono-and bi-dimensional 1 H and 13 C NMR experiments performed here for doxazosin produced a considerable amount of new data. These data may be used as a tool to verify and prove structural modifications in doxazosin for future works.…”

Section: Discussionmentioning

confidence: 95%

“…An enantiomeric (R)/(S) doxazosin mesylate mixture, purchased from Nifty Labs PVT LTD, was solubilized in DMSO-d 6 (20 mg in 0.5 mL) and the nuclear magnetic resonance spectra ( 1 H NMR and 13 C NMR) was recorded in a Bruker Ascend spectrometer with standard pulse sequences operating at 400 MHz for 1 H NMR and 100 MHz for 13 C NMR. Chemical shifts were reported as relative values (ppm) to TMS.…”

Section: Methodsmentioning

confidence: 99%

“…The 1 H NMR AB systems were presented in the following order: hydrogen a (Ha) the most deshielded and hydrogen b (Hb) the most shielded. For validation of these assignments, theoretical calculations of 13 C NMR chemical shifts were performed in a software MestReNova 6.0.2-5475 (MestreLab Research S.L., 2009). FT-IR spectra was recorded in a Perkin Elmer Spectrometer BXII using an ATR probe.…”

Section: Methodsmentioning

confidence: 99%

“…In addition, it may be verified that methoxy groups C 28 and C 29 produced only one signal at 56.18 ppm. The piperazine ring presented signals characteristics of the presence of piperazine rings (13,14) with two multiplets corresponding the two groups of equivalents methylene hydrogens H 12 and H 15 centered at 3.99 ppm, and H 16 and H 13 at 3.54 ppm, which is superposed to singlets from hydrogens of methoxyl 28 and 29. In relation to the NMR 13 C, the four carbons of piperazine linker appeared at 40 to 45 ppm, and due to the similarity of the chemical environment, the assignment of these carbons is very challeging.…”

Section: Nmr Experimentsmentioning

confidence: 99%

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A Complete NMR Study of Doxazosin Characterization

Gonçalves

Gaelzer²,

Azambuja

et al. 2017

Drug Anal. Res.

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Doxazosin is an important drug used for treating hypertension and prostatic hyperplasia. An enantiomeric mixture (R)/(S) doxazosin mesylate was complete characterized by NMR and additionally FT-IR spectroscopy techniques. Were performed different NMR experiments, such as APT, HSQC, and HMBC in order to confirm the NMR signals assignments. All the hydrogens and the most of carbons atoms were assigned.

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Section: Discussionmentioning

confidence: 95%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Nmr Experimentsmentioning

confidence: 99%

See 2 more Smart Citations

A Complete NMR Study of Doxazosin Characterization

Gonçalves

Gaelzer²,

Azambuja

et al. 2017

Drug Anal. Res.

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“…The chemistry of 1,2,4‐triazole derivatives has gained broad attention due to their diverse biological activities such as anticancer, antimycotic, antimalarial, and antitubercular as well as antiparasitic, herbicidal, analgesic, CNS stimulant, antianxiety, and antimigraine activities (rizatriptan; Figure ) . The aldimine‐type Schiff bases of 1,2,4‐triazole which successfully synthesized by Li et al .…”

Section: Introductionmentioning

confidence: 99%

Hybrid Pharmacophore Design, Molecular Docking, Synthesis, and Biological Evaluation of Novel Aldimine‐Type Schiff Base Derivatives as Tubulin Polymerization Inhibitor

Ameri

Khodarahmi

Forootanfar

et al. 2018

Chemistry & Biodiversity

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A series of hybrid aldimine-type Schiff base derivatives including trimethoxyphenyl ring and 1,2,4-triazole-3-thiol/thione were designed as tubulin inhibitors. The molecular docking simulations on tubulin complex (PDB: 1SA0) revealed that derivatives with nitro and/or chloro or dimethylamino substitutes (4-nitro, 2-nitro, 3-nitro, 4-Cl-3-nitro, and 4-Me N) on the aldehyde ring were the best compounds with remarkable binding energies (-9.09, -9.07, -8.63, -8.11, and -8.07 kcal mol , respectively) compared to colchicine (-8.12 kcal mol ). These compounds were also showed remarkable binding energies from -10.66 to -9.79 and -10.12 to -8.95 kcal mol on human (PDB: 1PD8) and Candida albicans (PDB: 3QLS) DHFR, respectively. The obtained results of cytotoxic activities against HT1080, HepG2, HT29, MCF-7, and A549 cancer cell lines indicated that 4-nitro and 2-nitro substituted compounds were the most effective agents by mean IC values of 11.84 ± 1.01 and 19.92 ± 1.36 μm, respectively. 4-Nitro substituted compound (5 μm) and 2-nitro substituted compound (30 μm) were able to strongly inhibit the tubulin polymerization compared to colchicine (5 μm) and 4-nitro substituted compound displayed IC values of 0.16 ± 0.01 μm compared to that of colchicine (0.19 ± 0.01 μm). This compound also showed the lowest MIC values on all tested microbial strains including three Gram-positive, four Gram-negative, and three yeast pathogens.

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Synthesis, Structure and Biological Activities of Novel 2‐(Trifluoromethyl)‐ 6‐arylimidazo[2,1‐b][1,3,4]‐thiadiazole (bis‐)Mannich Base Derivatives Containing Substitutedpiperazine Moiety

Zhang

Song

et al. 2018

Chin. J. Chem.

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A convenient and practicable method for the synthesis of the novel 2‐(trifluoromethyl)‐6‐arylimidazo[2,1‐b][1,3,4]‐thiadiazole (bis‐)Mannich base derivatives containing various substitutedpiperazine motif has been developed based on the fused‐heterocycle intermediate. The new structures were identified through melting points, 1H NMR, 13C NMR, 19F NMR, elemental analysis (or HRMS) and X‐ray single‐crystal diffraction. The pesticidal bioassays showed that some of compounds exhibited good fungicidal activities against Cercospora arachidicola, Physalospora piricola and Rhizoctonia cereali at 50 mg/L; some of them displayed favourable insecticidal activities against oriental armyworm (Mythimna separata Walker) at 200 mg/L, particularly, Vk and Vm with mortality rate of 75% and 80% respectively, could be considered as new insecticidal lead compounds for further structural optimization.

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Synthesis and biological activities of some fluorine- and piperazine-containing 1,2,4-triazole thione derivatives

Cited by 31 publications

References 18 publications

A Complete NMR Study of Doxazosin Characterization

A Complete NMR Study of Doxazosin Characterization

Hybrid Pharmacophore Design, Molecular Docking, Synthesis, and Biological Evaluation of Novel Aldimine‐Type Schiff Base Derivatives as Tubulin Polymerization Inhibitor

Synthesis, Structure and Biological Activities of Novel 2‐(Trifluoromethyl)‐ 6‐arylimidazo[2,1‐b][1,3,4]‐thiadiazole (bis‐)Mannich Base Derivatives Containing Substitutedpiperazine Moiety

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