88678-15-3Relevant academic research and scientific papers
Water-induced fluorescence quenching of mono- and dicyanoanilines
Oshima, Juro,Yoshihara, Toshitada,Tobita, Seiji
, p. 306 - 311 (2006)
Photophysical properties of monocyano- (2-, 3-, and 4-cyano) and dicyano- (3,4-, 3,5-, 2,3-, 2,4-, 2,5-, and 2,6-dicyano) anilines are investigated by fluorescence measurements. All the monocyanoanilines are virtually nonfluorescent in water (quantum yield 0.01); however, in nonaqueous solvents (cyclohexane, acetonitrile and ethanol), the fluorescence quantum yield is enhanced substantially. In contrast, dicyanoanilines investigated are highly fluorescent both in aqueous and nonaqueous environments. The photophysical data and MO calculations suggest that conformational changes in the amino group and variation of hydrogen-bonding interactions between the solute and solvent water upon electronic excitation are responsible for the water quenching in the monocyanoanilines.
Benzothiazinones: A novel class of adenosine receptor antagonists structurally unrelated to xanthine and adenine derivatives
Gütschow, Michael,Schlenk, Miriam,G?b, Jürgen,Paskaleva, Minka,Alnouri, Mohamad Wessam,Scolari, Silvia,Iqbal, Jamshed,Müller, Christa E.
, p. 3331 - 3341 (2012/06/04)
2-(Acyl)amino-4H-3,1-benzothiazin-4-ones and related thienothiazinones were identified as structurally novel antagonists at adenosine receptors (ARs). 6-Methyl-2-benzoylamino-4H-3,1-benzothiazin-4-one (10d) was found to be a balanced AR antagonist with affinity for all human (h) subtypes (Ki hA1 65.6 nM; hA2A 120 nM; hA2B 360 nM; hA 3 30.4 nM), while in rat (r), 10d was a highly potent A 1-selective antagonist (rA1 7.7 nM; rA2A 546 nM; rA2B 679 nM, rA3 >10000 nM). 2-(4- Methylbenzoylamino)-4H-3,1-benzothiazin-4-one (10g) was found to be a potent antagonist at human A2A (68.8 nM) and A3 ARs (23.0 nM) with high selectivity versus the other human AR subtypes. In contrast to A 1 and A3 ARs, A2A and A2B ARs tolerated bulky 2-acyl substituents. tert-Butyl (4-oxo-4H-3,1-benzothiazin-2- ylcarbamoyl)benzylcarbamate (15g, Ki hA2B 186 nM; hA 2A 603 nM) and 4-(4-benzylpiperazine-1-carbonyl)-N-(4-oxo-4H-3,1- benzothiazin-2-yl)benzamide (15k, hA2A 69.5 nM; hA2B 178 nM) were highly selective versus the other AR subtypes. 2-Acylamino-3,1- benzothiazin-4-ones represent novel scaffolds suitable for the development of potent and selective AR antagonists for each of the four receptor subtypes.
