A1 Journal article (refereed)
Efficient Consecutive Synthesis of Ethyl-2-(4-Aminophenoxy) Acetate, a Precursor for Dual GK and PPARγ Activators, X-ray Structure, Hirshfeld Analysis, and DFT Studies (2022)

Altowyan, M. S., Soliman, S. M., Ismail, M. M. F., Haukka, M., Barakat, A., & Ayoup, M. S. (2022). Efficient Consecutive Synthesis of Ethyl-2-(4-Aminophenoxy) Acetate, a Precursor for Dual GK and PPARγ Activators, X-ray Structure, Hirshfeld Analysis, and DFT Studies. Crystals, 12(2), Article 227. https://doi.org/10.3390/cryst12020227

JYU authors or editors

Publication details

All authors or editors: Altowyan, Mezna Saleh; Soliman, Saied M.; Ismail, Magda M. F.; Haukka, Matti; Barakat, Assem; Ayoup, Mohammed Salah

Journal or series: Crystals

eISSN: 2073-4352

Publication year: 2022

Publication date: 05/02/2022

Volume: 12

Issue number: 2

Article number: 227

Publisher: MDPI AG

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/cryst12020227

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/80057

Abstract

Herein, we report a facile synthesis of ethyl-2-(4-aminophenoxy)acetate 4 as a building synthon for novel dual hypoglycemic agents. This building template was synthesized by alkylation of 4-nitrophenol with ethyl bromo-acetate followed by selective reduction of the nitro group. This reduction methoddoes not require nascent hydrogen or any reaction complexity; it goes easily via consecutive reaction in NH4Cl/Fe to yield our target synthon as very pure crystals. This product was characterized by 1HNMR, 13CNMR, COSY, NOESY NMR spectroscopy, and elemental analysis. Additionally, its structure was studied and approved by X-ray single crystal structure determination. The unit cell parameters are a = 8.2104(6)Å, b = 10.3625(9)Å, c = 11.9562(9)Å, α = 101.787(7), β = 91.849(6), and γ = 102.755(7)°, indicating that 4 was crystallized in the triclinic crystal system. The cooperative non-covalent interactions are also discussed with the aid of Hirshfeld surface analysis. The H…H, H…C, and O…H interactions have a major contribution in the molecular packing of 4. Moreover, different quantum chemical parameters were computed and discussed based on DFT calculations. The experimental UV/Vis spectra showed two bands at 299 and 234 nm, which were calculated using the TD-DFT method at 286 (f = 0.068) and 226 nm (f = 0.294), respectively. These bands were assigned to HOMO→LUMO (95%) and HOMO→LUMO+2 (86%) transitions, respectively.

Keywords: heterocyclic compounds; bioactive compounds; glucose metabolism; chemical synthesis; x-ray crystallography; density functional theory

Free keywords: aminophenoxy; consecutive reaction; hypoglycemic; X-ray; Hirshfeld analysis

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2022

JUFO rating: 1