Synthesis, biological in vitro evaluation and stereoselectivity of ondansetron analogues: novel 5-HT2A receptor antagonists

Targeting Serotonin 2A and Adrenergic α1Receptors for Ocular Antihypertensive Agents: Discovery of 3,4‐Dihydropyrazino[1,2‐b]indazol‐1(2H)‐one Derivatives

“…For the adrenergic receptor, compounds tested at a concentration of 1 μ m showed generally low to moderate percent inhibition of binding, with the highest values observed for compounds 26 and 27 (83 and 95 %, respectively). The increase in α 1 receptor potency can probably be ascribed, respectively, to the 3‐(4‐phenylpiperidin‐1‐yl)propanamine and [1‐(2‐aminoethyl)piperidin‐4‐yl](phenyl)methanone skeletons, which are structural features already proven for ondansetron and ketanserin analogues with optimal affinity results …”

“…The increase in a 1 receptor potency can probably be ascribed, respectively,t o the 3-(4-phenylpiperidin-1-yl)propanamine and [1-(2-aminoethyl)piperidin-4-yl](phenyl)methanones keletons, which are structuralf eatures already proven for ondansetron and ketanserin analogues with optimal affinity results. [21,22] In an attemptt ob uild on the promising results obtained with compound 12,b oth in the serotoninergic selectivity and in the adrenergic a 1 bindingp otency, we decided to link the indazole-2-nitrogen atom with the nearby 3-carboxamide group,f orming 3,4-dihydropyrazino [1,2-b]indazol-1(2H)-one and 2,3,4,5-tetrahydro-1H- [1,4]diazepino [1,2-b]indazol-1-one tricyclic derivatives. This modificationw as aimed at mimicking the sterich indrance of the indazole N2-ethyl group of 12 by constraining the conformationalf reedom of the amide bond by freezing it in the anti orientation.…”

Microwave-Assisted Synthesis of Tetrahydrocarbazole Linked 1,2-Diazoles in Aqueous-Brønsted Acid Catalytic System

“…KBr discs were used to record FTIR spectra on Midac Corporation FTIR spectrophotometer and values were reported in cm −1 . 1 H NMR spectra were measured on Bruker AXS 400 MHz spectrometer using TMS as an internal standard and DMSO- 6 2 Journal of Chemistry as solvent (chemical shift in , ppm). Mass spectra were recorded by GCMS-QP2010S Shimadzu Scientific Instruments, Inc. CHEM Discover 908010 focused microwave synthesis system was used to carry out all mentioned organic transformations.…”

“…They possess distinct whole transport tendency in solar cells and electroluminescent devices [3]. Due to its synthetic versatility, it is one of the most important and stimulating units of high profiled molecules particularly with medicinal impact [4][5][6][7]. Moreover, 1,2-diazole having carbazole hybrids exhibit prominently enhanced material properties [8].…”

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

“…Elz and Heil [ 57 ] prepared the 1,2,3,9-tetrahydro-4 H -carbazol-4-one ( 140 ) by the reaction of phenylhydrazine ( 138 ) with cyclohexan-1,3-dione ( Scheme 38 ). Classical N -methylation with dimethyl sulfate followed by introduction of an exocyclic double bond using paraformaldehyde in DMF under acidic conditions furnishes the Michael acceptor 189 , which then undergoes conjugate addition with various amines ( Scheme 38 ).…”