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

Year 2021, Volume: 8 Issue: 1, 363 - 374, 28.02.2021

Mohammed Mahbubul Matin , Naimul Islam Aysha Siddika Sreebash C. Bhattacharjee

https://doi.org/10.18596/jotcsa.829658

Cited By: 9

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 (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.

Keywords

Dibutyltin oxide (DBTO) method, Methyl α-L-rhamnopyranoside, Regioselectivity, PASS predication, AdmetSAR.

Supporting Institution

Ministry of Education, Bangladesh and BANBEIS

Project Number

PS 201660, 2016-17

Thanks

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.

References

• 1. Matin MM, Bhattacharjee SC, Chakraborty P, Alam MS. Synthesis, PASS predication, in vitro antimicrobial evaluation and pharmacokinetic study of novel n-octyl glucopyranoside esters. Carbohydrate Research. 2019;485:107812. Doi: 10.1016/j.carres.2019.107812
• 2. Pöhnlein M, Slomka C, Kukharenko O, Gärtner T, Wiemann LO, Sieber V, Syldatk C, Hausmann R. Enzymatic synthesis of amino sugar fatty acid esters. European Journal of Lipid Science and Technology. 2014;116:423. Doi: 10.1002/ejlt.201300380
• 3. Matin MM, Hasan MS, Uzzaman M, Bhuiyan MMH, Kibria SM, Hossain ME, Roshid MHO. Synthesis, spectroscopic characterization, molecular docking, and ADMET studies of mannopyranoside esters as antimicrobial agents. Journal of Molecular Structure. 2020;1222:128821. Doi: 10.1016/j.molstruc.2020.128821
• 4. Neta NS, Teixeira JA, Rodrigues LR. Sugar ester surfactants: Enzymatic synthesis and applications in food industry. Critical Reviews in Food Science and Nutrition. 2015;55(5):595-610, Doi: 10.1080/10408398.2012.667461
• 5. Lou X. Antimicrobial structure-efficacy relationship of sugar fatty acid esters. Journal of Chemical and Pharmaceutical Research. 2014;6(5):944-946.
• 6. Akanbi TO, Barrow CJ. Enzymatic production of antioxidants and their applications. In: Encyclopedia of Food Chemistry; Elsevier; 2019, pp 92-96. Doi: 10.1016/B978-0-08-100596-5.21646-6
• 7. Traxler P, Fritz H, Fuhrer H, Richter WJ. Papulacandins, a new family of antibiotics with antifungal activity. Structures of papulacandins A, B, C and D. Journal of Antibiotics. 1980;33(9):967-978. Doi: 10.7164/antibiotics.33.967
• 8. Watanabe T, Katayama S, Matsubara M, Honda Y, Kuwahara M. Antibacterial carbohydrate monoesters suppressing cell growth of Streptococcus mutans in the presence of sucrose. Current Microbiology. 2000;41:210-213. Doi: 10.1007/s002840010121
• 9. Matin MM, Bhuiyan MMH, Kabir E, Sanaullah AFM, Rahman MA, Hossain ME, Uzzaman M. Synthesis, characterization, ADMET, PASS predication, and antimicrobial study of 6-O-lauroyl mannopyranosides. Journal of Molecular Structure. 2019;1195:189-197. Doi: 10.1016/j.molstruc.2019.05.102
• 10. Matin MM. One step intramolecular cyclization of diol via mesylation: Efficient synthesis of sugar derived [1,4]oxazepanes. Journal of Bangladesh Chemical Society. 2008;21(2):179-183.
• 11. Dhavale DD, Matin MM. Piperidine homoazasugars: Natural occurrence, synthetic aspects and biological activity study. ARKIVOC. 2005;2005(3):110-132. Doi: 10.3998/ark.5550190.0006.314
• 12. Yang L-J, Yang X-D, Yang S, Zhao J-F, Zhang H-B, Liang Li. Two new benzoyl esters of glucose from Lagotis yunnanensis. Chemistry of Natural Compounds. 2006;42(6):649-651. Doi: 10.1080/1028602031000093366
• 13. Jung ME, Koch P. An efficient synthesis of the protected carbohydrate moiety of brasilicardin A. Organic Letters. 2011;13(14):3710-3713. Doi: 10.1021/ol2013704
• 14. Komatsu K, Tsuda M, Tanaka Y, Mikami Y, Kobayashi J. SAR studies of brasilicardin A for immunosuppressive and cytotoxic activities. Bioorganic & Medicinal Chemistry. 2005;13(5):1507-1513. Doi: 10.1016/j.bmc.2004.12.029
• 15. Kim SR, Kim YC. Neuroprotective phenylpropanoid esters of rhamnose isolated from roots of Scrophularia buergeriana. Phytochemistry. 2000;54(5):503-509. Doi: 10.1016/s0031-9422(00)00110-2
• 16. Elmaidomy AH, Mohammed R, Owis AI, Hetta MH, AboulMagd AM, Siddique AB, Abdelmohsen UR, Rateb ME, Sayed KAE, Hassan, HM. Triple-negative breast cancer suppressive activities, antioxidants and pharmacophore model of new acylated rhamnopyranoses from Premna odorata. RSC Advances. 2020;10:10584. Doi: 10.1039/d0ra01697g
• 17. Matin MM. Synthesis and antimicrobial study of some methyl 4-O-palmitoyl-α-L-rhamnopyranoside derivatives. Orbital: The Electronic Journal of Chemistry. 2014;6(1):20-28. Doi: 10.17807/orbital.v6i1.553
• 18. Uddin MT, Kabir AKMS, Manchur MA. Synthesis and antimicrobial activities of some derivatives of L-rhamnose. Pakistan Journal of Biological Sciences. 2004;7(12):2192-2197. Doi: 10.3923/pjbs.2004.2192.2197
• 19. Matin MM, Chakraborty P, Alam MS, Islam MM, Hanee U. Novel mannopyranoside esters as sterol 14α-demethylase inhibitors: Synthesis, PASS predication, molecular docking, and pharmacokinetic studies. Carbohydrate Research. 2020;496:108130. Doi: 10.1016/j.carres.2020.108130
• 20. Matin MM, Uzzaman M, Chowdhury SA, Bhuiyan MMH. In vitro antimicrobial, physicochemical, pharmacokinetics, and molecular docking studies of benzoyl uridine esters against SARS-CoV-2 main protease. Journal of Biomolecular Structure and Dynamics. 2020 (in press). Doi: 10.1080/07391102.2020.1850358
• 21. Jäger M, Minnaard AJ. Regioselective modification of unprotected glycosides. Chemical Communications. 2016;52:656-664. Doi: 10.1039/C5CC08199H
• 22. Ren DB, Zhang L, Zhang M. Progress on selective acylation of carbohydrate hydroxyl groups. Asian Journal of Organic Chemistry. 2019;8(10): 1813-1823. Doi: 10.1002/ajoc.201900400
• 23. Matin MM, Chakraborty P. Synthesis, spectral and DFT characterization, PASS predication, antimicrobial, and ADMET studies of some novel mannopyranoside esters. Journal of Applied Science & Process Engineering. 2020;7(2):572-586. Doi: 10.33736/jaspe.2603.2020
• 24. Kiyoshima K, Sakamoto M, Ishikura T, Fukagawa Y, Yoshioka T, Naganawa H, Sawa T, Takeuchi T. Application of dibutyltin oxide method to regioselective acylation and alkylation of tylosin at C-4''. Chemical and Pharmaceutical Bulletin. 1989;37(4):861-865. doi: 10.1248/cpb.37.861
• 25. Kabir AKMS, Alauddin M, Matin MM, Battacharjee SC. Regioselective monobenzoylation of methyl α-L-rhamnopyranoside. Chittagong University Studies, Part II: Science. 1997;21(2):59-63.
• 26. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Petersson PA, Nakatsuji H. Gaussian 09, 2013, Gaussian Inc. (Wallingford CT).
• 27. Filimonov DA, Lagunin AA, Gloriozova TA, Rudik AV, Druzhilovskii DS, Pogodin PV, Poroikov VV. Prediction of the biological activity spectra of organic compounds using the PASS online web resource. Chemistry of Heterocyclic Compounds. 2014;50(3):444-457. Doi: 10.1007/s10593-014-1496-1
• 28. Pires, DEV, Blundell TL, Ascher DB. pkCSM: predicting small-molecule pharmacokinetic properties using graph-based signatures. Journal of Medicinal Chemistry. 2015;58(9):4066–4072.
• 29. Daina A, Michielin O, Zoete V. SwissADME: a free web tool to evaluate pharmacokinetics, drug-likeness and medicinal chemistry friendliness of small molecules, Scientific Report. 2017;7:42717.
• 30. Kilic-Kurt Z. Synthesis of novel oxadiazole derivatives, molecular properties prediction, and molecular docking studies. Journal of Turkish Chemical Society, Section A: Chemistry. 2020;7(3):753-74. Doi: 10.18596/jotcsa.705951
• 31. Tsuda Y, Haque ME, Yoshimoto K. Regioselective monoacylation of some glycopyranosides via cyclic tin intermediates. Chemical and Pharmaceutical Bulletin. 1983;31:1612-1624. Doi: 10.1248/cpb.31.1612
• 32. Matin MM, Ibrahim M. Synthesis of 2,3-di-O-substituted derivatives of methyl 4-O-acetyl-α-L-rhamnopyranoside. The Chittagong University Journal of Science. 2006;30(2):67-76.
• 33. Lagunin A, Stepanchikova A, Filimonov D, Poroikov V. PASS: prediction of activity spectra for biologically active substances. Bioinformatics. 2000;16(8):747-748. Doi: 10.1093/bioinformatics/16.8.747
• 34. Tok F, Kaymakçıoğlu B, İlhan R, Yılmaz S, Kırmızıbayrak P, Tok T. Design, synthesis, biological evaluation and molecular docking of novel molecules to PARP-1 enzyme. Turkish Journal of Chemistry. 2019;43(5):1290-1305.
• 35. Emen FM, Demi̇rdöğen RE, Avşar G, Kılıç D. 2-Chlorobenzoylthiourea-modified MCM-41 for drug delivery. Journal of the Turkish Chemical Society Section A: Chemistry. 2019;6(1):29-34.