87325-80-2Relevant academic research and scientific papers
Design, synthesis, and activity evaluation of novel N-benzyl deoxynojirimycin derivatives for use as α-glucosidase inhibitors
Zeng, Fanxin,Yin, Zhongping,Chen, Jiguang,Nie, Xuliang,Lin, Ping,Lu, Tao,Wang, Meng,Peng, Dayong
, (2019/09/19)
To obtain α-glucosidase inhibitors with high activity, 19 NB-DNJDs (N-benzyldeoxynojirimycin derivatives) were designed and synthesized. The results indicated that the 19 NBDNJDs displayed different inhibitory activities towards α-glucosidase in vitro. Compound 18a (1- (4-hydroxy-3-methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol) showed the highest activity, with an IC50 value of 0.207 ± 0.11 mM, followed by 18b (1-(3-bromo-4-hydroxy-5- methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol, IC50: 0.276 ± 0.13 mM). Both IC50 values of 18a and 18b were significantly lower than that of acarbose (IC50: 0.353 ± 0.09 mM). According to the structure-activity analysis, substitution of the benzyl and bromine groups on the benzene ring decreased the inhibition activity, while methoxy and hydroxyl group substitution increased the activity, especially with the hydroxyl group substitution. Molecular docking results showed that three hydrogen bonds were formed between compound 18a and amino acids in the active site of α- glucosidase. Additionally, an arene-arene interaction was also modelled between the phenyl ring of compound 18a and Arg 315. The three hydrogen bonds and the arene-arene interaction resulted in a low binding energy (-5.8 kcal/mol) and gave 18a a higher inhibition activity. Consequently, compound 18a is a promising candidate as a new α-glucosidase inhibitor for the treatment of type II diabetes.
Design, synthesis and biological evaluation of novel pyrimidinedione derivatives as DPP-4 inhibitors
Li, Ning,Wang, Li-Jun,Jiang, Bo,Guo, Shu-Ju,Li, Xiang-Qian,Chen, Xue-Chun,Luo, Jiao,Li, Chao,Wang, Yi,Shi, Da-Yong
supporting information, p. 2131 - 2135 (2018/05/25)
A series of novel pyrimidinedione derivatives were designed and evaluated for in vitro dipeptidyl peptidase-4 (DPP-4) inhibitory activity and in vivo anti-hyperglycemic efficacy. Among them, the representative compounds 11, 15 and 16 showed excellent inhibitory activity of DPP-4 with IC50 values of 64.47 nM, 188.7 nM and 65.36 nM, respectively. Further studies revealed that compound 11 was potent in vivo hypoglycemic effect. The structure–activity relationships of these pyrimidinedione derivatives had been discussed, which would be useful for developing novel DPP-4 inhibitors as treating type 2 diabetes.
Discovery of novel bromophenol 3,4-dibromo-5-(2-bromo-3,4-dihydroxy-6- (isobutoxymethyl)benzyl)benzene-1,2-diol as protein tyrosine phosphatase 1B inhibitor and its anti-diabetic properties in C57BL/KsJ-db/db mice
Jiang, Bo,Guo, Shuju,Shi, Dayong,Guo, Chao,Wang, Tao
, p. 129 - 136 (2013/07/27)
In an effort to develop novel small molecule PTP1B inhibitors, a series of bromophenol derivatives were designed, synthesized and evaluated in vitro and in vivo. All of the synthesized compounds displayed weak to potent PTP1B inhibitory activities (5.62-96.25%) at 20 μg/mL. Among these compounds, 3,4-dibromo-5-(2-bromo-3,4-dihydroxy-6-(isobutoxymethyl)benzyl)benzene-1,2-diol (9) exhibited enhanced PTP1B inhibitory activity (IC50 = 1.50 μM) than the lead compound BDDPM (IC50 = 2.42 μM) and high selectivity against other PTPs (TCPTP, LAR, SHP-1 and SHP-2). Results of anti-diabetic assay using C57BL/KsJ-db/db mouse model demonstrated that compound 9 was effective at lowering blood glucose, total cholesterol and HbA1c (P 0.01).
A Simple Synthesis of Methyl Ethers of Tribromophenols from the Red Alga Symphyocladia latiuscla
Mori, Takao,Bando, Hideo,Kanaiwa, Yoshio,Amiya, Takashi,Kurata, Kazuya
, p. 1754 - 1756 (2007/10/02)
Bis(2,3,6-tribromo-4,5-dimethoxybenzyl) ether (IV), 2,3,6-tribromo-4,5-dimethoxybenzyl methyl ether (V), 2,3,6-tribromo-4,5-dimethoxybenzyl ethyl ether (VI) and 2,3,6-tribromo-4,5-dimethoxybenzyl alcohol (VIII) were prepared by simple procedures involving
DISODIUM 2,3,6-TRIBROMO-5-HYDROXYBENZYL 1',4-DISULFATE, A NEW BROMOPHENOL FROM THE RED ALGA, SYMPHYOCLADIA LATIUSCULA
Kurata, Kazuya,Amiya, Takashi
, p. 279 - 280 (2007/10/02)
A new sulfated bromophenol, disodium 2,3,6-tribromo-5-hydroxybenzyl 1',4-disufate has been isolated from the red alga, Symphyocladia latiuscula.Its structure was established from the spectral properties and the chemical transformations.
