Synthesis, characterization, alkaline phosphatase inhibition assay and molecular modeling studies of 1-benzylidene-2-(4-tert- butylthiazol-2-yl) hydrazines

Aziz, Hamid; Mahmood, Abid; Zaib, Sumera; Saeed, Aamer; El‐Seedi, Hesham R.; Pelletier, Julie; Sévigny, Jean; Iqbal, Jamshed

doi:10.1080/07391102.2020.1802336

Cited by 12 publications

(5 citation statements)

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“…In recent years, several inhibitors of APs based on biaryl sulfonamide, chromone, triazole and coumarin sulfonate motifs have been reported. [25][26][27][28][29][30][31][32] APs have become important target enzymes owing to their considerable pharmacological importance in medicinal chemistry. 33,34a,b Some compounds were found to be effective inhibitors of AP, but most of them inhibited APs non-selectively.…”

Section: Introductionmentioning

confidence: 99%

2-Benzylidenebenzofuran-3(2H)-ones as a new class of alkaline phosphatase inhibitors: synthesis, SAR analysis, enzyme inhibitory kinetics and computational studies

et al. 2021

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Section: Introductionmentioning

confidence: 99%

2-Benzylidenebenzofuran-3(2H)-ones as a new class of alkaline phosphatase inhibitors: synthesis, SAR analysis, enzyme inhibitory kinetics and computational studies

et al. 2021

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“…The (5‐bromo‐2‐hydroxybenzylidene) hydrazinecarbothioamide (H 2 ‐5‐Br‐thsa) Schiff base ligand was synthesized according to a previously reported method. [ 56‐57 ] All the chemicals were used without further purification.…”

Section: Methodsmentioning

confidence: 99%

Controlling Three‐Step and Five‐Step Spin Transitions by Polymorphism in an Fe^III Spin Crossover Complex

Wu,

Peng,

Zhang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryRegulating spin crossover (SCO) behavior, especially controlling the spin transition steps, is an important scientific issue, mainly because people aim to control spin bistability and multistability. Presently, SCO bistability can be regulated by changing the ligand‐modifying species, non‐coordinated anions, guest molecules, and metal‐ion dopant. However, the control of multistability is extremely challenging, especially in Fe(III) SCO compounds. Here, we report that [FeIII(H‐5‐Br‐thsa)(5‐Br‐thsa)]·H2O (5‐Br‐thsa = (5‐bromo‐2‐hydroxybenzylidene)hydrazinecarbothioamide), a compound we have reported before, exists in two polymorphic forms: polymorph 1 exhibits three‐step SCO, and polymorph 2 shows five‐step SCO, with multi‐step SCO behavior effectively regulated by polymorphism. According to single‐crystal and powder X‐ray diffractometry, polymorphs 1 and 2 crystallize in different space groups during their spin transitions, with two‐step symmetry breaking observed (Pbcn → Pnc2 → Pbcn for polymorph 1; P21/n → Pn → P21/n for polymorph 2). We realized that the behavior of these two polymorphs depends significantly on the structure, including (i) the average Fe–N bond distance, (ii) deformation of octahedral FeIII atoms, and (iii) distinct crystal packing, which account for the large differences observed in magnetic properties.This article is protected by copyright. All rights reserved.

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“…13 (19). 55 Following the general method B, using acetophenone 5, compound 19 was obtained as an off-white solid in 68% yield. R f = 0.45 (PE/EA 2:1) 1 (20).…”

Section: General Methods For the Synthesis Of Thiosemicarbazones 21−26 Cmentioning

confidence: 99%

Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

Tabor,

Katsogiannou,

Karta

et al. 2023

ACS Omega

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A series of 32 thiourea-based urease inhibitors were synthesized and evaluated against native bacterial enzyme and whole cells of Sporosarcina pasteurii and Proteus mirabilis strains. The proposed inhibitors represented structurally diverse thiosemicarbazones and thiocarbohydrazones, benzyl-substituted thiazolyl thioureas, 1H-pyrazole-1-carbothioamides, and dihydropirimidine-2(1H)-thiones. Kinetic characteristics with purified S. pasteurii enzyme determined low micromolar inhibitors within each structural group. (E)-2-(1-Phenylethylidene)hydrazine-1-carbothioamide 19 (K i = 0.39 ± 0.01 μM), (E)-2-(4-methylbenzylidene)hydrazine-1-carbothioamide 16 (K i = 0.99 ± 0.04 μM), and N′-((1E,2E)-1,3-diphenylallylidene)hydrazinecarbothiohydrazide 29 (K i = 2.23 ± 0.19 μM) were used in modeling studies that revealed sulfur ion coordination of the active site nickel ion and hydrogen bonds between the amide group and the side chain of Asp363 and Ala366 carbonyl moiety. Whole-cell studies proved the activity of compounds in Gram-positive and Gram-negative microorganisms. Ureolysis control observed in P. mirabilis PCM 543 (e.g., IC 50 = 304 ± 14 μM for 1-benzyl-3-(4-(4-hydroxyphenyl)thiazol-2-yl)thiourea 52) is a valuable achievement, as urease is recognized as a major virulence factor of this urinary tract pathogen.

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Synthesis, characterization, alkaline phosphatase inhibition assay and molecular modeling studies of 1-benzylidene-2-(4-tert- butylthiazol-2-yl) hydrazines

Cited by 12 publications

References 40 publications

2-Benzylidenebenzofuran-3(2H)-ones as a new class of alkaline phosphatase inhibitors: synthesis, SAR analysis, enzyme inhibitory kinetics and computational studies

2-Benzylidenebenzofuran-3(2H)-ones as a new class of alkaline phosphatase inhibitors: synthesis, SAR analysis, enzyme inhibitory kinetics and computational studies

Controlling Three‐Step and Five‐Step Spin Transitions by Polymorphism in an Fe^III Spin Crossover Complex

Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

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Synthesis, characterization, alkaline phosphatase inhibition assay and molecular modeling studies of 1-benzylidene-2-(4-tert- butylthiazol-2-yl) hydrazines

Cited by 12 publications

References 40 publications

2-Benzylidenebenzofuran-3(2H)-ones as a new class of alkaline phosphatase inhibitors: synthesis, SAR analysis, enzyme inhibitory kinetics and computational studies

2-Benzylidenebenzofuran-3(2H)-ones as a new class of alkaline phosphatase inhibitors: synthesis, SAR analysis, enzyme inhibitory kinetics and computational studies

Controlling Three‐Step and Five‐Step Spin Transitions by Polymorphism in an FeIII Spin Crossover Complex

Exploration of Thiourea-Based Scaffolds for the Construction of Bacterial Ureases Inhibitors

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Controlling Three‐Step and Five‐Step Spin Transitions by Polymorphism in an Fe^III Spin Crossover Complex