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.
Highlights
The more rampant type 2 diabetes (T2D) is a category of metabolic diseases distinguished by hyperglycemia resulting from a flaw in insulin secretion, insulin action, or both
The chronic hyperglycemia of diabetes is affiliated with long-term impairment, dysfunction, and collapse of many organs, the kidneys, heart, eyes, nerves, and blood vessels [1,2]
Compound I reported by Prosidion/OSI is an activator of GK and boosts glycogen synthesis, and escalates insulin secretion from
Summary
The progress of GK sensitizer to reduce blood glufrom pancreatic b-cells. The progress of GK sensitizer to reduce blood glucose cose and normalize insulin secretion is an encouraging area of ongoing research for treatcosenormalize and normalize insulin secretion an encouraging of ongoing research treatand insulin secretion is anisencouraging areaarea of ongoing research for for treating ing II by aa Peroxisome proliferator-activator ing T2D.Compound. In this regard, the assemblage of ligand-based drugswith witha aamore more prevalent medicinal effect. The assemblage of ligand-based drugswith witha aamore more prevalent medicinal effect In this this regard, the assemblage assemblage of ligandligandbased pharmacophores (colored blue) was accomplished. Quantum chemical descriptors were computed by the B3LYP analysis.
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