36695-16-6Relevant articles and documents
Copper-catalyzed chemoselective oxidative o-aroylation of 2-acetylphenols, alkyl salicylates and 1,3-dicarbonyl compounds using styrene derivatives
Kumar, Upendra,Sharma, Ajay,Kumar, Naveen,Pandey, Satyendra Kumar
, (2021/03/03)
A novel copper-catalyzed chemoselective oxidative O-aroylation of 2-acetylphenols, alkyl salicylates and 1,3-dicarbonyl compounds with a wide range of styrene derivatives are described. This approach provides an efficient chemoselective preparation of phenol, alkyl salicylate and enol esters in good to excellent yields. This method represents an alternative protocol for the classical esterification reactions.
Discovery of 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol- 9(2H)-one as a phosphodiesterase-5 inhibitor and its complex crystal structure
Shang, Na-Na,Shao, Yong-Xian,Cai, Ying-Hong,Guan, Matthew,Huang, Manna,Cui, Wenjun,He, Lin,Yu, Yan-Jun,Huang, Lei,Li, Zhe,Bu, Xian-Zhang,Ke, Hengming,Luo, Hai-Bin
, p. 86 - 98 (2014/05/06)
Phosphodiesterase-5 (PDE5) inhibitors have been approved for the treatment of erectile dysfunction and pulmonary hypertension, but enthusiasm on discovery of PDE5 inhibitors continues for their potential new applications. Reported here is discovery of a series of new PDE5 inhibitors by structure-based design, molecular docking, chemical synthesis, and enzymatic characterization. The best compound, 3-(4-hydroxybenzyl)-1-(thiophen-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one (57), has an IC50 of 17 nM against the PDE5 catalytic domain and good selectivity over other PDE families. The crystal structure of the PDE5 catalytic domain in complex with 57 was determined at 2 A resolution and showed that 57 occupies the same pocket as other PDE5 inhibitors, but has a different binding pattern in detail. On the basis of the binding pattern of 57, a novel scaffold can be proposed as a candidate of PDE inhibitors.
Facile synthesis of new substituted aryl and heteroarylflavones by thermal and microwave assisted Suzuki-Miyaura coupling reaction
Joshi, Vidya,Govind Hatim, Jaywant
experimental part, p. 1002 - 1010 (2012/10/18)
Microwave assisted Suzuki-Miyaura coupling of 4′-bromoflavone 5 with substituted aryl and heteroarylboronic acids 6a-m gives high yields of aryl and heteroarylflavones 7a-m. Couplings have been carried out by three methods i) conventional heating with Pd(OCOCH3)2 catalyst, in solvent DMF(N,N-dimethylformamide) and base, aqueous Na2CO3 (2N) for 6-12 hr, at 110°C, yield 30-70%, ii) conventional heating with Pd[(C6H5)3P]4 catalyst, in DMF and base, aq. Na2CO3 (2N) for 6-12 hr, at 110°C, yield 40-72% and iii) Microwave heating with Pd[(C6H5)3P] 4 catalyst, in solvent (DMF+H2O, 5:2) and base, aq. Na2CO3 (2N) for 2-9 min, yield 50-87%. The substrate 4′-bromoflavone 5 has been synthesized from o-hydroxyacetophenone 1 in 3 steps. Esterification of 1 with 4-bromobenzoyl chloride 2 with montmorillonite-KSF catalyst, DCE (1,2-dichloroethane) and Et3N (triethylamine) which gives 2-(4- bromobenzoyloxy)acetophenone 3. Baker-Venkataraman rearrangement of 3 with pyridine and KOH further gives 1-(4-bromophenyl)-3-(2- hydroxyphenyl)propane-1,3-dione 4, followed by cyclization of 4 with methanolic sulfuric acid (2.5%) which yields 4'-bromoflavone 5, yield 82%.
