A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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-tekijät tai -toimittajat
Julkaisun tiedot
Julkaisun kaikki tekijät tai toimittajat: Altowyan, Mezna Saleh; Soliman, Saied M.; Ismail, Magda M. F.; Haukka, Matti; Barakat, Assem; Ayoup, Mohammed Salah
Lehti tai sarja: Crystals
eISSN: 2073-4352
Julkaisuvuosi: 2022
Ilmestymispäivä: 05.02.2022
Volyymi: 12
Lehden numero: 2
Artikkelinumero: 227
Kustantaja: MDPI AG
Julkaisumaa: Sveitsi
Julkaisun kieli: englanti
DOI: https://doi.org/10.3390/cryst12020227
Julkaisun avoin saatavuus: Avoimesti saatavilla
Julkaisukanavan avoin saatavuus: Kokonaan avoin julkaisukanava
Julkaisu on rinnakkaistallennettu (JYX): https://jyx.jyu.fi/handle/123456789/80057
Tiivistelmä
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.
YSO-asiasanat: heterosykliset yhdisteet; bioaktiiviset yhdisteet; glukoosiaineenvaihdunta; kemiallinen synteesi; röntgenkristallografia; tiheysfunktionaaliteoria
Vapaat asiasanat: aminophenoxy; consecutive reaction; hypoglycemic; X-ray; Hirshfeld analysis
Liittyvät organisaatiot
OKM-raportointi: Kyllä
Raportointivuosi: 2022
JUFO-taso: 1