Xanthene

About: Xanthene is a research topic. Over the lifetime, 2132 publications have been published within this topic receiving 34803 citations. The topic is also known as: Xanthene & dibenzo[a,e]pyran.

1,3,5-Trichloro-2,4,6-Triazinetrion: A Versatile Heterocycle for the One-Pot Synthesis of 14-Aryl- or Alkyl -14H-Dibenzo[a,j]xanthene, 1,8-Dioxooctahydroxanthene and 12-Aryl-8,9,10,12-Tetrahydrobenzo[a]xanthene-11-one Derivatives under Solvent-Free Conditions

Abstract: A facile, green, efficient and environment-friendly protocol for the synthesis of 14-aryl- or alkyl-14Hdibenzo[a,j]xanthene, 1,8-dioxooctahydroxanthene and 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthene-11-one have been developed by one-pot condensation of various aldehydes with (i) -naphthol (ii) cyclic 1,3-dicarbonyl compounds and (iii) -naphthol and cyclic 1,3-dicarbonyl compounds, in the presence of 1,3,5-trichloro-2,4,6-triazinetrion (trichloroisocyanuric acid, TCCA) as catalyst under solvent-free conditions. The present approach offers the advantages of clean reaction, simple methodology, short reaction time, easy purification, and economic availability of the catalyst.

Field Effects Induce Bathochromic Shifts in Xanthene Dyes

Abstract: There is ongoing interest in near-infrared (NIR) absorbing and emitting dyes for a variety of biomedical and materials applications. Simple and efficient synthetic procedures enable the judicious tuning of through-space polar (field) effects as well as low barrier hydrogen bonding to modulate the HOMO-LUMO gap in xanthene dyes. This affords unique NIR-absorbing xanthene chromophores.

Inhibitors of β-Site Amyloid Precursor Protein Cleaving Enzyme (BACE1): Identification of (S)-7-(2-Fluoropyridin-3-yl)-3-((3-methyloxetan-3-yl)ethynyl)-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (AMG-8718)

Abstract: We have previously shown that the aminooxazoline xanthene scaffold can generate potent and orally efficacious BACE1 inhibitors although certain of these compounds exhibited potential hERG liabilities. In this article, we describe 4-aza substitution on the xanthene core as a means to increase BACE1 potency while reducing hERG binding affinity. Further optimization of the P3 and P2′ side chains resulted in the identification of 42 (AMG-8718), a compound with a balanced profile of BACE1 potency, hERG binding affinity, and Pgp recognition. This compound produced robust and sustained reductions of CSF and brain Aβ levels in a rat pharmacodynamic model and exhibited significantly reduced potential for QTc elongation in a cardiovascular safety model.