Theoretical DFT and matrix isolation FTIR studies of 2-(1,2,4-triazolyl)phenol isomers

Pagacz-Kostrzewa, Magdalena; Sałdyka, Magdalena; Wierzejewska, Maria; Khomenko, Dmytro M.; Doroschuk, Roman O.

doi:10.1016/j.cplett.2016.06.005

Cited by 5 publications

(6 citation statements)

References 26 publications

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“…2-(1 H -1,2,4-Triazol-3-yl)phenol ( 5c ) . Synthesized from 2-hydroxybenzamide ( 44c ) and hydrazine hydrate according to the general procedure to afford 5c as a white fluffy powder in 75% yield.…”

Section: Methodsmentioning

confidence: 99%

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

et al. 2021

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The heme enzyme indoleamine 2,3-dioxygenase 1 (IDO1) plays an essential role in immunity, neuronal function, and aging through catalysis of the rate-limiting step in the kynurenine pathway of tryptophan metabolism. Many IDO1 inhibitors with different chemotypes have been developed, mainly targeted for use in anti-cancer immunotherapy. Lead optimization of direct heme iron-binding inhibitors has proven difficult due to the remarkable selectivity and sensitivity of the heme−ligand interactions. Here, we present experimental data for a set of closely related small azole compounds with more than 4 orders of magnitude differences in their inhibitory activities, ranging from millimolar to nanomolar levels. We investigate and rationalize their activities based on structural data, molecular dynamics simulations, and density functional theory calculations. Our results not only expand the presently known four confirmed chemotypes of sub-micromolar heme binding IDO1 inhibitors by two additional scaffolds but also provide a model to predict the activities of novel scaffolds.

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Section: Methodsmentioning

confidence: 99%

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

et al. 2021

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“…As mentioned in the Introduction section, we investigated whether the proposed CAT-1 [28] could actually interact with CO 2 and epoxides. First, peak assignment in the 1 H and 13 C NMR spectra was performed through COSY, HSQC, and HMBC experiments (see Supplementary Materials).…”

Section: Resultsmentioning

confidence: 99%

“…The following supporting information can be downloaded at: https: //www.mdpi.com/article/10.3390/catal14010090/s1, Table S1: List of known compounds [28,[30][31][32][33][34][35][36][37][38][39][40][41]; Table S2: Crystallographic data for CAT-6; 1, entry 1; Figure S26: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 1, entry 2; Figure S27: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 1, entry 3; Figure S28: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 1, entry 4; Figure S29: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 1, entry 5; Figure S30: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 1, entry 6; Figure S31: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 1, entry 7; Figure S32: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 1, entry 8; Figure S33: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 1, entry 9; Figure S34: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 2, entry 2; Figure S35: 1 H NMR spectrum for an aliquot of the reaction mixture after reaction in Table 2, entry 3; Figure S36: 1 H NMR spectrum f...…”

Section: Supplementary Materialsmentioning

confidence: 99%

Organocatalysts for the Synthesis of Cyclic Carbonates under the Conditions of Ambient Temperature and Atmospheric CO2 Pressure

Seong,

Lee,

Cho

et al. 2024

Catalysts

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2–(1H–1,2,4–Triazol–3–yl)phenol (CAT–1) was used as an organocatalyst for the coupling reaction of CO2 and epoxides at an ambient temperature and atmospheric CO2 pressure (1 bar). This compound has a structure in which a hydrogen bond donor, a hydrogen bond acceptor, and another hydrogen bond donor are adjacent in sequence in a molecule. The binary catalytic system of CAT–1/nBu4NI showed TON = 19.2 and TOF = 1.60 h−1 under 1 bar CO2 at room temperature within 12 h using 2–butyloxirane. Surprisingly, the activity of CAT–1, in which phenol and 1H–1,2,4–triazole are chemically linked, showed a much greater synergistic effect than when simply mixing the same amount of phenol and 1H–1,2,4–triazole under the same reaction conditions. In addition, our system showed a broad terminal and internal epoxide substrate scope.

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“…Recently, the FTIR matrix isolation studies of 3-amino-1,2,4-triazole and 2-(1,2,4-triazolyl)phenol were performed to characterize the most stable isomers present in low temperature matrices. For the latter compound it was concluded that out of 45 stable minima predicted theoretically, the three most stable structures stabilized by the intramolecular O–H···N hydrogen bond were present in solid argon and nitrogen.…”

Section: Introductionmentioning

confidence: 99%

“…24−26 The ab initio studies show that in the process of proton transfer, the proton moves from azole molecule to the water cluster and the presence of water environment lowers the activation barriers. 27 Recently, the FTIR matrix isolation studies of 3-amino-1,2,4triazole 23 and 2-(1,2,4-triazolyl)phenol 28 were performed to characterize the most stable isomers present in low temperature matrices. For the latter compound it was concluded that out of 45 stable minima predicted theoretically, the three most stable structures stabilized by the intramolecular O−H•••N hydrogen bond were present in solid argon and nitrogen.…”

Section: Introductionmentioning

confidence: 99%

Phototransformations of 2-(1,2,4-Triazol-3-yl)benzoic Acid in Low Temperature Matrices

et al. 2019

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Phototransformations of 2-(1,2,4-triazol-3-yl)benzoic acid induced by tunable UV laser were studied in low temperature matrices by FTIR spectroscopy. Out of 36 possible isomers of this molecule the most stable one, comprising the intramolecular N−H•••O hydrogen bond, was detected experimentally in argon and xenon matrices after deposition. Upon irradiation with λ = 325 nm, two new conformers of the precursor were formed. The corresponding reverse photorotamerizations were also detected at 250 nm partly reproducing the initial molecules. In addition to the conformational changes, an interesting photoisomerization took place in the studied matrices leading to a proton transfer from N atom of the triazole ring to the carbonyl oxygen of the carboxylic group. As a result of this reaction, a new product with two OH groups was identified for the first time. The experimental studies were supported by DFT calculations in both ground and excited electronic states.

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Theoretical DFT and matrix isolation FTIR studies of 2-(1,2,4-triazolyl)phenol isomers

Cited by 5 publications

References 26 publications

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

Azole-Based Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitors

Organocatalysts for the Synthesis of Cyclic Carbonates under the Conditions of Ambient Temperature and Atmospheric CO2 Pressure

Phototransformations of 2-(1,2,4-Triazol-3-yl)benzoic Acid in Low Temperature Matrices

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