Synthesis and biological evaluation of novel gigantol derivatives as potential agents in prevention of diabetic cataract was written by Wu, Jie;Lu, Chuanjun;Li, Xue;Fang, Hua;Wan, Wencheng;Yang, Qiaohong;Sun, Xiaosheng;Wang, Meiling;Hu, Xiaohong;Chen, C.-Y. Oliver;Wei, Xiaoyong. And the article was included in PLoS One in 2015.Name: 3-Hydroxy-5-methoxybenzaldehyde This article mentions the following:
As a continuation of our efforts directed towards the development of natural anti-diabetic cataract agents, gigantol was isolated from Herba dendrobii and was found to inhibit both aldose reductase (AR) and inducible nitric oxide synthase (iNOS) activity, which play a significant role in the development and progression of diabetic cataracts. To improve its bioefficacy and facilitate use as a therapeutic agent, gigantol (compound 14f) and a series of novel analogs were designed and synthesized. Analogs were formulated to have different substituents on the Ph ring (compounds 4, 5, 8, 14a-e), substitute the Ph ring with a larger steric hindrance ring (compounds 10, 17c) or modify the carbon chain (compounds 17a, 17b, 21, 23, 25). All of the analogs were tested for their effect on AR and iNOS activities and on D-galactose-induced apoptosis in cultured human lens epithelial cells. Compounds 5, 10, 14a, 14b, 14d, 14e, 14f, 17b, 17c, 23, and 25 inhibited AR activity, with IC50 values ranging from 5.02 to 288.8 μM. Compounds 5, 10, 14b, and 14f inhibited iNOS activity with IC50 ranging from 432.6 to 1188.7 μM. Compounds 5, 8, 10, 14b, 14f, and 17c protected the cells from D-galactose induced apoptosis with viability ranging from 55.2 to 76.26%. Of gigantol and its analogs, compound 10 showed the greatest bioefficacy and is warranted to be developed as a therapeutic agent for diabetic cataracts. In the experiment, the researchers used many compounds, for example, 3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8Name: 3-Hydroxy-5-methoxybenzaldehyde).
3-Hydroxy-5-methoxybenzaldehyde (cas: 57179-35-8) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Ethers are good solvents partly because they are not very reactive. Most ethers can be cleaved, however, by hydrobromic acid (HBr) to give alkyl bromides or by hydroiodic acid (HI) to give alkyl iodides.Name: 3-Hydroxy-5-methoxybenzaldehyde
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem