473826-38-9Relevant academic research and scientific papers
Microwave assisted synthesis and photophysical properties of blue emissive 2-amino-3-carboxamide-1,1′-biaryls and 4-(arylamino)-[1,1′-biphenyl]-3-carboxamides via Suzuki and Chan-Evans-Lam coupling
Novanna, Motakatla,Kannadasan, Sathananthan,Shanmugam, Ponnusamy
, (2019/11/26)
An efficient microwave assisted synthesis of 2-amino-3-carboxamide-1,1′-biaryls derivatives 4a-p and terphenyl derivative 5a from 2-amino-5-iodobenzamide 2a, 2-amino-3,5-diiodobenzamide 2b and (het)aryl boronic acids via Suzuki coupling has been achieved. Synthetic utility of the product 4-amino-4′-cyano-[1,1′-biphenyl]-3-carboxamide 4j has been demonstrated for the synthesis of 4-(aryl amino)-[1,1′-biphenyl]-3-carboxamide derivatives 10a-c via Chan-Evans-Lam coupling reaction. Furthermore, 4-(4′-oxo-3′, 4′-dihydro-1′H-spiro[fluorene-9,2′-quinazolin]-6′-yl)benzonitrile 12a was obtained from biaryl derivative 4j and fluorenone 11a and 6(4- methoxyphenyl)2-(ferrocenyl) quinazolin-4(3H)-one 12b from biaryl derivative 4k and ferrocenealdehyde 11b using phosphotungstic acid as green catalyst and solvent free microwave irradiation condition. Remarkably, all the synthesized 2-amino-3-carboxamide-1,1′-biaryls and 4-(aryl amino)-[1,1′-biphenyl]-3-carboxamide derivatives 4a-p showed luminescence in the blue region with large Stokes shift. Significantly, 2-amino-3-carboxamide-1,1′-biaryls 4d and 4j showed high fluorescence quantum yields (Φf) 0.54 and 0.84, respectively.
Design, synthesis and biological activities of 2,3-dihydroquinazolin-4(1H)-one derivatives as TRPM2 inhibitors
Zhang, Han,Liu, Huan,Luo, Xiao,Wang, Yuxi,Liu, Yuan,Jin, Hongwei,Liu, Zhenming,Yang, Wei,Yu, Peilin,Zhang, Liangren,Zhang, Lihe
, p. 235 - 252 (2018/05/09)
Transient receptor potential melastatin 2 (TRPM2), a Ca2+-permeable cationic channel, plays critical roles in insulin release, cytokine production, body temperature regulation and cell death as a reactive oxygen species (ROS) and temperature sensor. However, few TRPM2 inhibitors have been reported, especially TRP-subtype selective inhibitors, which hampers the investigation and validation of TRPM2 as a drug target. To discover novel TRPM2 inhibitors, 3D similarity-based virtual screening method was employed, by which 2,3-dihydroquinazolin-4(1H)-one derivative H1 was identified as a TRPM2 inhibitor. A series of novel 2,3-dihydroquinazolin-4(1H)-one derivatives were subsequently synthesized and characterized. Their inhibitory activities against the TRPM2 channel were evaluated by calcium imaging and electrophysiology approaches. Some of the compounds exhibited significant inhibitory activity, especially D9 which showed an IC50 of 3.7 μM against TRPM2 and did not affect the TRPM8 channel. The summarized structure-activity relationship (SAR) provides valuable insights for further development of specific TRPM2 targeted inhibitors.
