Design, modification, and bio-evaluation of salazinic acid derivatives

被引:4
作者
Nguyen-Kim-Tuyen Pham [1 ]
Nguyen-Minh-An Tran [2 ]
Huy Truong Nguyen [3 ]
Duc-Dung Pham [4 ]
Thi-Quynh-Trang Nguyen [1 ]
Thi-Hong-Anh Nguyen [5 ]
Huu-Tri Nguyen [8 ]
Thanh-Hung Do [6 ]
Ngoc-Hong Nguyen [7 ]
Thuc-Huy Duong [4 ]
机构
[1] Sai Gon Univ, Fac Environm Sci, Ho Chi Minh City, Vietnam
[2] Ind Univ Ho Chi Minh City, Ho Chi Minh City, Vietnam
[3] Ton Duc Thang Univ, Fac Pharm, Ho Chi Minh City, Vietnam
[4] Ho Chi Minh City Univ Educ, Dept Chem, 280 An Duong Vuong St,Dist 5, Ho Chi Minh City 748342, Vietnam
[5] Ho Chi Minh City Univ Food Ind, 140 Le Trong Tan St, Tan Phu Dist, Hcmc, Vietnam
[6] Nguyen Tat Thanh Univ, NTT Hitech Inst, Ho Chi Minh City 700000, Vietnam
[7] Ho Chi Minh City Univ Technol HUTECH, CirTech Inst, 475 A Dien Bien Phu St, Ho Chi Minh City 700000, Vietnam
[8] Sai Gon Univ, Fac Pedag Nat Sci, Ho Chi Minh City, Vietnam
关键词
Bromination; Nucleophilic addition; a-glucosidase inhibition; Molecular docking; Kinetic; IN-VITRO; ANTIBACTERIAL ACTIVITY; BIOLOGICAL EVALUATION; DEPSIDONES; INHIBITORS; DOCKING; BROMINATION; DISCOVERY; EXTRACTS; POTENT;
D O I
10.1016/j.arabjc.2021.103535
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Data on synthesized derivatives of salazinic acid are scarce, with existing reports addressing only derivative hexaacetyl salazinic acid. This study investigated a set of novel potential antidiabetic agents. Analogs of salazinic acid were designed and synthesized using bromination, nucleophilic addition, Friedel-Crafts alkylation, and esterification. Ten synthetic compounds were prepared and structurally elucidated, including eight new compounds (1a-1c, 2a, 3a, 3b, 4a, 4b) and two known analogs. Under bromination, salazinic acid (1) enabled the following reaction chain: oxidation, decarboxylation, and substitution. This yielded products 1a-1c, which were found to have unprecedented scaffolds. Parmosidone F (5) was prepared from 1 with orsellinic acid via Friedel-Crafts alkylation, confirming a previously reported biosynthesis route. These analogs were evaluated for enzyme inhibition of a-glucosidase, and all showed more potent activity than that of acarbose, a positive control (IC50 332 lM), with IC50 values in the range 9.32-39.96 lM. An in silico molecular docking model confirmed that, in terms of enzyme inhibition, the compounds ranked as follows: 3b > 4b > 4a > 1c > 2a > 1b > 1a > 3a. The kinetics of enzyme inhibition showed 4a and 5 to be a non-competitive-type and mixed-type inhibitors, respectively. (c) 2021 The Author(s). Published by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).
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页数:23
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