Synthesis, characterization and DFT calculated properties of electron-rich hydrazinylthiazoles: Experimental and computational synergy

Mehmood, Hasnain; Khalid, Muhammad; Haroon, Muhammad; Akhtar, Tashfeen; Ashfaq, Muhammad; Tahir, Muhammad Nawaz; Khan, Muhammad Usman; Imran, Muhammad; Braga, Ataualpa Albert Carmo; Woodward, Simon

doi:10.1016/j.molstruc.2021.131043

Cited by 24 publications

(7 citation statements)

References 67 publications

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“…The up‐field carbon signals in range δ 55.3–56.2 ppm were assigned to the methoxy carbons. The synthesis of compounds was further confirmed when NMR spectra were compared with literature reported similar skeleton compounds [38–45] …”

Section: Resultsmentioning

confidence: 71%

“…The synthesis of compounds was further confirmed when NMR spectra were compared with literature reported similar skeleton compounds. [38][39][40][41][42][43][44][45] After establishing the synthesis of the expected hydrazinyl-4-methoxyphenylthiazoles their biological significance was investigated by α-amylase inhibitory potential, antiglycation activity, antioxidant potential and cytotoxic behaviour by haemolytic assay.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents

Haroon

Mehmood

Akhtar

et al. 2022

Chemistry & Biodiversity

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Thiazole has been a key scaffold in antidiabetic drugs. In quest of new and more effective drugs a simple, efficient, high yielding (67-79 %) and convenient synthesis of arylidenehydrazinyl-4-methoxyphenyl)thiazoles is accomplished over two steps. The synthesis involved the condensation of aryl substituted thiosemicarbazones and 2-bromo-4-methoxyacetophenone in absolute ethanol. The structures of the resulting thiazoles are in accord with their UV/VIS, FT-IR, 1 H-, 13 C-NMR and HRMS data. All compounds were evaluated for alpha(α)-amylase inhibition potential, antiglycation, antioxidant abilities and biocompatibility. The compounds library identified 2-(2-(3,4-dichlorobenzylidene)hydrazinyl)-4-(4-methoxyphenyl)thiazole as a lead molecule against α-amylase inhibition with an IC 50 of 5.75 � 0.02 μM. α-Amylase inhibition is also supported by molecular docking studies against α-amylase. All the obtained thiazoles also showed promising antiglycation activity with 4-(4methoxyphenyl)-2-{2-[2-(trifluoromethyl)benzylidene]hydrazinyl}thiazole exhibiting the best inhibition (IC 50 = 0.383 � 0.001 mg/mL) compared to control. The tested compounds are also biocompatible at the concentration used i. e., 10 μM.

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Section: Resultsmentioning

confidence: 71%

Section: Resultsmentioning

confidence: 99%

Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents

Haroon

Mehmood

Akhtar

et al. 2022

Chemistry & Biodiversity

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“…12.5 ppm. The studies proved that compounds with similar core exist in trans form, 32,33 hence synthesized compounds should also exist in trans conguration.…”

Section: Synthesis Of 4-substituted 2-hydrazinylthiazole Species (3)mentioning

confidence: 88%

Design, and synthesis of selectively anticancer 4-cyanophenyl substituted thiazol-2-ylhydrazones

et al. 2022

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“…[33][34][35] The Hirshfeld surface plotted over d norm is more important than the other Hirshfeld surfaces as it provides information about the H-bonding interactions. [34,[36][37][38][39] HS d norm utilizes blue, white, and red colors to recognize the interatomic contacts, which are longer, at Van der Waals separations, and short interatomic contacts, respectively. [40][41][42] Figures 4a and 4b are the Hirshfeld surfaces plotted over d norm for 2AP6NO and 2AP4ETH, respectively.…”

Section: Hirshfeld Surface Investigationmentioning

confidence: 99%

Synthesis, Characterization, Crystal Structure and Computational Study of Third‐Order NLO Properties of Schiff bases

et al. 2022

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The current study involves the synthesis of two azomethine compounds, (E)‐2‐((6‐nitrobenzo[d][1,3]dioxol‐5‐yl)methylene)amino)phenol (2AP6NO) and (E)‐2‐((4‐ethylbenzylidene)amino)phenol (2AP4ETH), as well as their theoretical investigations. The synthesized azomethine compounds were then characterized by combustion analysis (CHN), FT‐IR, NMR (1H and 13C), and single crystal X‐ray diffraction (SC‐XRD) analysis. The SC‐XRD study confirmed the enol tautomeric form of 2AP6NO as well as 2AP4ETH. The strong and comparatively weak intermolecular interactions were elaborated by Hirshfeld surface analysis. For both compounds, intermolecular interaction energies between the pair of molecules, energy framework, and void analysis were calculated to visualize the three‐dimensional topology of the crystal packing. Additionally, quantum chemical computations were also utilized to study the optical and nonlinear optical (NLO) response. The molecular geometries were optimized at the M06‐2X/6‐311G* method and equated to their respective experimental counterparts. The third‐order NLO polarizabilities were also calculated at the same level of theory. The calculated average third‐order NLO polarizabilities were 62.55×10−36 esu and 55.08×10−36 esu, respectively, predicting the modest behavior of the above compounds when displaying NLO properties.

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Synthesis, characterization and DFT calculated properties of electron-rich hydrazinylthiazoles: Experimental and computational synergy

Cited by 24 publications

References 67 publications

Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents

Synthesis of Arylidenehydrazinyl‐4‐methoxyphenylthiazole Derivatives: Docking Studies, Probing Type II Diabetes Complication Management Agents

Design, and synthesis of selectively anticancer 4-cyanophenyl substituted thiazol-2-ylhydrazones

Synthesis, Characterization, Crystal Structure and Computational Study of Third‐Order NLO Properties of Schiff bases

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