158399-65-6

Upstream product

• 158399-64-5 4-(4-(5-methoxypyridin-2-yl)piperazin-1-yl)aniline 
• 1885-14-9 phenyl chloroformate 
• 6269-89-2 1-(4-Nitrophenyl)piperazine 
• 105170-27-2 2-bromo-5-methoxypyridine 
• 158399-63-4 1-(5-methoxypyridin-2-yl)-4-(4-nitrophenyl)piperazine 

Downstream Products

• 158399-66-7 N-[4-[4-(5-methoxy-2-pyridinyl)-1-piperazinyl]phenyl]hydrazinecarboxamide 

Relevant academic research and scientific papers

Design and Synthesis of Tetrazole- And Pyridine-Containing Itraconazole Analogs as Potent Angiogenesis Inhibitors

Itraconazole, a widely used antifungal drug, was found to possess antiangiogenic activity and is currently undergoing multiple clinical trials for the treatment of different types of cancer. However, it suffers from extremely low solubility and strong interactions with many drugs through inhibition of CYP3A4, limiting its potential as a new antiangiogenic and anticancer drug. To address these issues, a series of analogs in which the phenyl group is replaced with pyridine or fluorine-substituted benzene was synthesized. Among them the pyridine- and tetrazole-containing compound 24 has significantly improved solubility and reduced CYP3A4 inhibition compared to itraconazole. Similar to itraconazole, compound 24 inhibited the AMPK/mTOR signaling axis and the glycosylation of VEGFR2. It also induced cholesterol accumulation in the endolysosome and demonstrated binding to the sterol-sensing domain of NPC1 in a simulation study. These results suggested that compound 24 may serve as an attractive candidate for the development of a new generation of antiangiogenic drug.

Substituted azolone derivatives

The use for the manufacture of a medicament for treating Helicobacter-related diseases of a compound of formula STR1 a pharmaceutically acceptable acid addition salt or a stereochemically isomeric form thereof, wherein X and Y each independently are CH or N; R1, R2 and R3 each independently are hydrogen or C1-4 alkyl; R4 and R5 each independently are hydrogen, halo, C1-4 alkyl, C1-4 alkyloxy, hydroxy, trifluoromethyl, trifluoromethyloxy or difluoromethyloxy; Z is C=O or CHOH; and Ar is phenyl optionally substituted with up to three substituents selected from hydroxy, C1-4 alkyl, C1-4 alkyloxy, halo, trifluoromethyl, triC1-4 alkylsilyloxy, nitro, amino and cyano or pyridinyl substituted with hydroxy or C1-4 alkyloxy; and --A-- is a radical of formula STR2