Regioselective Synthesis of Some Rhamnopyranoside Esters for PASS Predication, and ADMET Studies

Authors : Mohammed Mahbubul MATİN, Naimul ISLAM, Aysha SİDDİKA, Sreebash C. BHATTACHARJEE

Pages : 363-374

Doi:10.18596/jotcsa.829658

View : 9 | Download : 8

Publication Date : 2021-02-28

Article Type : Research Paper

Abstract :Notable biological activities including brains protective activities have made carbohydrate esters as a topic of great interest over the past several decades. In this context, unimolecular treatment of methyl α-L-rhamnopyranoside insert ignore into journalissuearticles values(3); with dibutyltin oxide gave the corresponding 2,3-O-insert ignore into journalissuearticles values(dibutylstannylene); derivative which was then allowed to react with 3-chlorobenzoyl chloride. The reaction regioselectively furnished the 3-O-substitution product 4 in excellent yield. To get newer rhamnopyranoside esters chlorobenzoate 4 was further converted into four 2,4-di-O-substituted products 5-8 with other acylating agents using direct acylation technique. Moreover, thermodynamic properties indicated that these SEs possess better stability, suitable polar nature and higher binding affinity than the non-ester rhamnopyranoside 3. PASS insert ignore into journalissuearticles values(Prediction of Activity Spectra for Substances); predication showed that these SEs should be more potent against fungal pathogens than the bacterial organisms. With these encouraging results ADMET and drug-likeness properties of the SEs 4-8 are also discussed.
Keywords : Dibutyltin oxide DBTO, method, Methyl α L rhamnopyranoside, Regioselectivity, PASS predication, AdmetSAR