Yıl 2021, Cilt 8 , Sayı 1, Sayfalar 363 - 374 2021-02-28

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

Mohammed Mahbubul MATİN [1] , Naimul ISLAM [2] , Aysha SİDDİKA [3] , Sreebash C. BHATTACHARJEE [4]

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 (3) with dibutyltin oxide gave the corresponding 2,3-O-(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 (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.
Dibutyltin oxide (DBTO) method, Methyl α-L-rhamnopyranoside, Regioselectivity, PASS predication, AdmetSAR.
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Birincil Dil en
Konular Kimya, Ortak Disiplinler
Yayınlanma Tarihi Winter
Bölüm Makaleler

Orcid: 0000-0003-4965-2280
Yazar: Mohammed Mahbubul MATİN (Sorumlu Yazar)
Kurum: University of Chittagong
Ülke: Bangladesh

Orcid: 0000-0003-4335-9323
Yazar: Naimul ISLAM
Kurum: University of Chittagong
Ülke: Bangladesh

Orcid: 0000-0001-8596-0630
Yazar: Aysha SİDDİKA
Kurum: University of Chittagong
Ülke: Bangladesh

Orcid: 0000-0002-2617-5816
Yazar: Sreebash C. BHATTACHARJEE
Kurum: Bangladesh Council of Scientific & Industrial Research (BCSIR)
Ülke: Bangladesh

Destekleyen Kurum Ministry of Education, Bangladesh and BANBEIS
Proje Numarası PS 201660, 2016-17
Teşekkür We are grateful to the Ministry of Education, Bangladesh and BANBEIS for financial support (grant no. PS 201660, 2016-17) to conduct this research work.

Başvuru Tarihi : 23 Kasım 2020
Kabul Tarihi : 18 Ocak 2021
Yayımlanma Tarihi : 28 Şubat 2021

Vancouver Matin M , Islam N , Siddika A , Bhattacharjee S . Regioselective Synthesis of Some Rhamnopyranoside Esters for PASS Predication, and ADMET Studies. Journal of the Turkish Chemical Society Section A: Chemistry. 2021; 8(1): 363-374.