Synthesis and anticancer activity of nordihydroguaiaretic acid (NDGA) and analogues was written by McDonald, Russell W.;Bunjobpon, Wilawan;Liu, Tong;Fessler, Sue;Pardo, Olivier E.;Freer, Isabel K. A.;Glaser, Mark;Seckl, Michael J.;Robins, David J.. And the article was included in Anti-Cancer Drug Design in 2001.Category: ethers-buliding-blocks This article mentions the following:
Nordihydroguaiaretic acid (NDGA) is a constituent of the creosote bush Larrea divaricata and is well known to be a selective inhibitor of lipoxygenases. NDGA can also inhibit the platelet derived growth factor receptor and the protein kinase C intracellular signalling family, which both play an important role in proliferation and survival of cancers. Moreover, NDGA induces apoptosis in tumor xenografts. Although it is likely to have several targets of action, NDGA is well tolerated in animals. These encouraging results have prompted interest in the compound for clin. study. However, high concentrations of NDGA are required for efficacy and more potent analogs are required. We have synthesized five analogs of NDGA with different lengths of carbon bridge between the two catechol moieties in order to establish the spacing required for optimum anticancer effect and to compare their activities with NDGA. In order to ascertain if the catechol moieties are essential for anticancer activity, we prepared five analogs of NDGA containing only one hydroxyl group on each aromatic ring. NDGA, its racemic form, and catechol derivatives with five or six carbon atom bridges and the phenol analogs with bridges of three to six carbon atoms all showed similar activity, with IC50 values of â?-5 μM against the H-69 small cell lung cancer cell line. Analogs with shorter or longer bridges were much less active. The most potent analog was the biscatechol with a four-carbon bridge I which was >10 times more active than NDGA and therefore represents a new lead compound in this area. Surprisingly, the tetra-Me ether of this compound was slightly more active than NDGA, but the trihydroxy analog was less active than NDGA. In summary, simplification of the structure of NDGA by removal of the Me groups has produced a new lead compound I, which is >10 times more potent than NDGA as a proliferative inhibitor of H-69 small cell lung cancer cells. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Category: ethers-buliding-blocks).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) belongs to ethers. 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. Ethers can form hydrogen bonds with other molecules (alcohols, amines, etc.) that have O―H or N―H bonds. The ability to form hydrogen bonds with other compounds makes ethers particularly good solvents for a wide variety of organic compounds and a surprisingly large number of inorganic compounds.Category: ethers-buliding-blocks
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem