130880-72-7Relevant academic research and scientific papers
Synthesis and adenosine receptors binding studies of new fluorinated analogues of pyrido[2,3-d]pyrimidines and quinazolines
Chandrasekaran, Balakumar,Deb, Pran Kishore,Kachler, Sonja,Akkinepalli, Raghuram Rao,Mailavaram, Raghuprasad,Klotz, Karl-Norbert
, p. 756 - 767 (2017/11/03)
A series of new fluorine containing pyrido[2,3-d]pyrimidines and imidazo[1,2-c]pyrido[3,2-e]pyrimidines along with a series of bioisosteric fluorinated quinazolines were synthesised following appropriate synthetic schemes and characterised by spectral analytical means. X-ray crystal structure of the key precursor 1 (2-amino-3-cyano-4-trifluoro-methyl-6-phenyl-pyridine) was also determined to gain insight into its reactivity. Binding affinity data of all the compounds for adenosine receptors (ARs) showed that pyrido[2,3-d]pyrimidine scaffold with free amino (NH2) group at 2- and 4-position (2a) exhibited the maximum binding affinity for hA3 AR with similar affinity for the hA1 and somewhat lower affinity for hA2A ARs resulting in a compound with no A3 selectivity vs. A1 and moderate selectivity vs. A2A AR (Ki hA1 = 0.62 μM, hA2A = 3.59 μM and hA3 = 0.42 μM). Interestingly, the replacement of both the amino groups with carbonyl (C=O) groups (compound 4) resulted in significantly improved affinity for hA1 AR but with moderate selectivity against hA2A and hA3 ARs (Ki hA1 = 0.17 μM, hA2A = 0.67 μM and hA3 =0.68 μM). In case of fluorinated quinazolines, only compound 18a showed remarkable affinity for hA1 AR with significant selectivity against hA2A and hA3 ARs (Ki hA1 = 0.73 μM, hA2A CloseSPigtSPi 30 μM and hA3 = 9.27 μM). The preliminary results of these compounds demonstrate that the fluorinated pyrido[2,3-d]pyrimidine and imidazo[1,2-c]pyrido[3,2-e]pyrimidine can be considered as promising scaffolds for further optimisation in search of potential antagonists with better affinity and selectivity towards hA1 and hA3 ARs.
A simple one pot synthesis of novel tricyclic quinazolinones
Bingi, Chiranjeevi,Kola, Kaushik Yadav,Kale, Ashok,Nanubolu, Jagadeesh Babu,Atmakur, Krishnaiah
supporting information, p. 1071 - 1074 (2017/03/31)
Synthesis of a series of tricyclic quinazolinones have been accomplished starting from anthranilamide and 1,3-cyclic dione promoted by TsOH·H2O The protocol presented herein based on retro-Dieckmann type reaction, leading to incorporation of dione as an acyclic unit into the product. Simple reaction conditions, broad scope, excellent yields are the advantages of this protocol. Further, this methodology is extended to the synthesis of pyridopyrimidinones and benzimidazopyridines.
A mild and efficient method for the dehydrogenation of dihydropyridopyrimidinones and related compounds by using active MnO2
Bhalerao, U. T.,Krishnaiah, A.
, p. 587 - 590 (2007/10/02)
Various fluorinated dihydropyridopyrimidin-4-ones (3) are conveniently oxidised to respective pyridopyrimidin-4-(3H)-ones (4) in quantitative yields by using active MnO2.This method has been generalised by applying to other related heterocyclic compounds.
