Bromobenzoylation of Methyl α-D-Mannopyranoside: Synthesis and Spectral Characterization

Abstract

The widening importance of carbohydrate derivatives as unrivaled potential antimicrobial and therapeutic drugs has attracted attentionto the synthesis of mannopyranoside derivatives. In the present study, regioselective 3-bromobenzoylation of methyl α-D-mannopyranoside (1) was carried out using the direct method and gave the corresponding 6-O-(3-bromobenzoyl) derivative (2) in excellent yield. A number of 2,3,4-tri-O-acyl derivatives (3–10) of this 6-substitution product using a wide variety of acylating agents were also prepared in order to obtain newer derivatives of synthetic and biological importance. The chemical structures of the newly synthesized compounds were ascertained by analyzing their physicochemical, elemental, and spectroscopic data. Additionally, the X-ray powder diffraction (XRD) of these acylated products was studiedfor quantitatively identifying crystalline compounds.Therefore, due to the importance of carbohydrates, it might be useful to develop a good method for the synthesis of carbohydrate-based drugs of the current global situation for health and disease

Potential SARS-CoV-2 RdRp inhibitors of cytidine derivatives: Molecular docking, molecular dynamic simulations, ADMET, and POM analyses for the identification of pharmacophore sites

“…Modifications in sugar moieties, such as ribofuranose or deoxyribofuranose of nucleosides, include changes in sugar substituents, the substitute of oxygen with another atom, and the inclusion of a heteroatom in the sugar ring, ring size variations, and replacement with an acyclic moieties [10][11][12][13][14][15]. These alterations may lead to excellent variations in the biological activity and degree of selective toxicity according to the respective chemical and physical properties of the moieties [16][17][18][19][20][21]. The modified compounds exhibit a broad-spectrum biological activity.…”

“…Nucleoside analogs and nucleobases constitute a pharmacologically diverse family, which includes cytotoxic compounds, antiviral agents, and immune suppressive molecules [15,21,[25][26][27]. Cytidine analog 5-AZA-2 ´-deoxycytidine is utilized to control the growth of neuroblastoma malignant tumor [28].…”

Design, Synthesis, In Silico and POM Studies for the Identification of the Pharmacophore Sites of Benzylidene Derivatives

“…Moreover, many scientific reports claim that the major chemical bioactive molecules are either aromatic, heteroaromatic, or acyl substituent groups [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 ]. In addition, benzene and its derivatives, which contain atoms such as nitrogen, sulphur and halogen are known to improve the biological activity of the parent compound [ 20 , 21 , 22 , 23 ]. It has also been reported that the linking of two biologically active nuclei leads to a new molecule—one that might possibly better display biological activity [ 24 , 25 , 26 ].…”

Macromolecules: Synthesis, antimicrobial, POM analysis and computational approaches of some glucoside derivatives bearing acyl moieties

“…This connection is considered a crucial factor in the process ( Hasan et al, 2022 , Kawsar et al, 2011 , Mahmud et al, 2021a , Mahmud et al, 2021b , Maowa et al, 2021a , Maowa et al, 2021b ). According to a study on the regioselective acylation of carbohydrate derivatives and their antimicrobial activities ( Farhana et al, 2021a , Farhana et al, 2021b ), attaching two or more highly electron-rich heteroaromatic nuclei and aliphatic chains significantly improves the derivatives' antimicrobial activity compared to the parent nucleus ( Banerjee et al, 2018 , Bechlem et al, 2010 , Daina et al, 2017 , Mahmud et al, 2021a , Mahmud et al, 2021b ; Kawsar and Kumer 2021 ).…”