In 2019,European Journal of Medicinal Chemistry included an article by Hussein, Buthaina; Ikhmais, Balqis; Kadirvel, Manikandan; Magwaza, Rachael N.; Halbert, Gavin; Bryce, Richard A.; Stratford, Ian J.; Freeman, Sally. Quality Control of 3,5-Dihydroxybenzaldehyde. The article was titled 《Discovery of potent 4-aminoquinoline hydrazone inhibitors of NRH:quinone oxidoreductase-2 (NQO2)》. The information in the text is summarized as follows:
N1-ribosyl-, N1-methyl-, N1-benzyl-dihydronicotinamide:quinone oxidoreductase 2 (NQO2) is associated with various processes involved in cancer initiation and progression probably via the production of ROS during quinone metabolism Thus, there is a need to develop inhibitors of NQO2 that are active in vitro and in vivo. As part of a strategy to achieve this, 4-aminoquinoline backbone is used as a starting point and synthesized I [R = Me], II [R1 = Ph, 4-imidazoyl, 2-nitrofuranyl, etc.], III novel analogs. The syntheses utilized p-anisidine with Meldrum’s acid and tri-Me orthoacetate or tri-Me orthobenzoate to give the 4-hydrazin-quinoline scaffold I [R = Me, Ph], which was derivatized with aldehydes R1CHO or acid chlorides R1C(O)Cl to give hydrazone II or hydrazide analogs III, resp. The hydrazones II were the most potent inhibitors of NQO2 in cell free systems, some with low nano-molar IC50 values. Structure-activity anal. highlighted the importance of a small substituent at the 2-position of the 4-aminoquinoline ring, to reduce steric hindrance and improve engagement of the scaffold within the NQO2 active site. Cytotoxicity and NQO2-inhibitory activity in vitro was evaluated using ovarian cancer SKOV-3 and TOV-112 cells (expressing high and low levels of NQO2, resp.). Generally, the hydrazones were more toxic than hydrazide analogs and further, toxicity is unrelated to cellular NQO2 activity. Pharmacol. inhibition of NQO2 in cells was measured using the toxicity of CB1954 as a surrogate end-point. Both the hydrazone II and hydrazide derivs III. are functionally active as inhibitors of NQO2 in the cells, but at different inhibitory potency levels. In particular, 4-((2-(6-methoxy-2-methylquinolin-4-yl)hydrazono)methyl)phenol has the greatest potency of any compound yet evaluated (53 nM), which is 50-fold lower than its toxicity IC50. This compound and some of its analogs could serve as useful pharmacol. probes to determine the functional role of NQO2 in cancer development and response to therapy. The experimental process involved the reaction of 3,5-Dihydroxybenzaldehyde(cas: 26153-38-8Quality Control of 3,5-Dihydroxybenzaldehyde)
3,5-Dihydroxybenzaldehyde(cas: 26153-38-8) is used as a building block in the synthesis of more complex structures. It is also used in the synthesis of terbutaline, which is an important bronchodilator.Quality Control of 3,5-Dihydroxybenzaldehyde
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts