Discovery of N-amido-phenylsulfonamide derivatives as novel microsomal prostaglandin E2 synthase-1 (mPGES-1) inhibitors was written by Kim, Misong;Kim, Geuntae;Kang, Minji;Ko, Dohyeong;Nam, Yunchan;Moon, Chang Sang;Kang, Heung Mo;Shin, Ji-Sun;Werz, Oliver;Lee, Kyung-Tae;Lee, Jae Yeol. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2021.Application In Synthesis of 4-Benzyloxyphenol The following contents are mentioned in the article:
Our previous research showed that N-carboxy-phenylsulfonyl hydrazide (scaffold A) could reduce LPS-stimulated PGE2 levels in RAW 264.7 macrophage cells by an inhibition of mPGES-1 enzyme. However, a number of scaffold A derivatives showed the drawbacks such as the formation of regioisomers and poor liver metabolic stability. In order to overcome these synthetic and metabolic problems, therefore, we decided to replace N-carboxy-phenylsulfonyl hydrazide (scaffold A) with N-carboxy-phenylsulfonamide (scaffold B) or N-amido-phenylsulfonamide frameworks (scaffold C) as a bioisosteric replacement. Among them, MPO-0186 (scaffold C) inhibited the production of PGE2 (IC50: 0.24μM) in A549 cells via inhibition of mPGES-1 (IC50: 0.49μM in a cell-free assay) and was found to be approx. 9- and 8-fold more potent than MK-886 as a reference inhibitor, resp. A mol. docking study theor. suggests that MPO-0186 could inhibit PGE2 production by blocking the PGH2 binding site of mPGES-1 enzyme. Furthermore, MPO-0186 demonstrated good liver metabolic stability and no significant inhibition observed in clin. relevant CYP isoforms except CYP2C19. This result provides a potential starting point for the development of selective and potent mPGES-1 inhibitor with a novel scaffold. This study involved multiple reactions and reactants, such as 4-Benzyloxyphenol (cas: 103-16-2Application In Synthesis of 4-Benzyloxyphenol).
4-Benzyloxyphenol (cas: 103-16-2) belongs to ethers. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Application In Synthesis of 4-Benzyloxyphenol
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem