1260016-29-2

Upstream product

• 760190-61-2 methyl 2-{[4-(dimethylamino)phenyl]ethynyl}benzoate 
• 1260016-27-0 2-amino-3-(4-dimethylaminobenzylidene)isoindolin-1-one 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 17573-94-3 4-ethynyl-N,N-dimethylaniline 
• 87-41-2 2-benzofuran-1(3H)-one 
• 100-52-7 benzaldehyde 
• 62970-28-9 4-(4-nitrophenyl)methyl-1-(2H)-phthalazinone 
• 32003-14-8 4-benzyl-2H-phthalazin-1-one 
• 74-88-4 methyl iodide 
• 83-12-5 phenindione 

Relevant academic research and scientific papers

Design and synthesis of 4-benzyl-1-(2H)-phthalazinone derivatives as novel androgen receptor antagonists

The androgen receptor (AR) plays important roles in multiple physiological functions, including differentiation, growth, and maintenance of male reproductive organs, and also has effects on hair and skin. In this paper, we report the synthesis of nonsteroidal AR antagonists having a 4-benzyl-1-(2H)-phthalazinone skeleton. Among the synthesized compounds, 11c with two ortho-substituents on the phenyl group potently inhibited SC-3 cell proliferation (IC50: 0.18 μM) and showed high wt AR-binding affinity (IC50: 10.9 μM), comparable to that of hydroxyflutamide (3). Compound 11c also inhibited proliferation of LNCaP cells containing T877A-mutated AR. Docking study of 11c with the AR ligand-binding domain indicated that the benzyl group is important for the antagonism. These phthalazinone derivatives may be useful for investigating potential clinical applications of AR antagonists.

Base-catalyzed intramolecular heterocyclization of o-alkynylbenzhydrazides

The reaction of methyl o-(2-R-ethynyl)benzoates with hydrazine affords either fused 4-R-methylphthalazin-1-ones or 2-amino-3-R-methylideneisoindolin-1- ones. The latter are on treatment with KOH undergo recyclization into the corresponding 4-R-methylphthalazin- 1-ones.