88301-81-9Relevant academic research and scientific papers
Synthesis and biological evaluation of a new class of benzothiazines as neuroprotective agents
Mancini, Alessandra,Chelini, Alessia,Di Capua, Angela,Castelli, Loretta,Brogi, Simone,Paolino, Marco,Giuliani, Germano,Cappelli, Andrea,Frosini, Maria,Ricci, Lorenzo,Leonelli, Erminia,Giorgi, Gianluca,Giordani, Antonio,Magistretti, Jacopo,Anzini, Maurizio
, p. 614 - 630 (2016/12/09)
Neurodegenerative diseases are disorders related to the degeneration of central neurons that gradually lead to various, severe alterations of cognitive and/or motor functions. Currently, for no such diseases does any pharmacological treatment exist able to arrest its progression. Riluzole (1) is a small molecule able to interfere with multiple cellular and molecular mechanisms of neurodegeneration, and is the only approved treatment of amyotrophic lateral sclerosis (ALS), the progression of which proved to significantly slow, thus increasing somewhat average survival. Here we report the synthesis of differently functionalized 4H-3,1-benzothiazine (5–6) and 2H-1,4-benzothiazine (7) series as superior homologues of 1. Biological evaluation demonstrated that amidine 4H-3,1-benzothiazine derivatives 5b-d can reduce glutamate and LDH release in the oxygen/glucose deprivation and reperfusion model (OGD/R) applied to brain slices with a higher potency than 1. Moreover the mentioned compounds significantly reduce glutamate- and 6-hydroxydopamine (6-OHDA)-induced cytotoxicity in neuroblastoma cells. In addition, the same compounds limit ROS formation in both neuronal preparations. Finally, 5c proved effective in inhibiting neuronal voltage-dependent Na+and Ca2+-channels, showing a profile comparable with that of 1.
Exceptional isolation of both imine and enamine desmotropes of 4,1-benzothiazepines
Csomós, Péter,Fodor, Lajos,Csámpai, Antal,Sohár, Pál
experimental part, p. 3207 - 3213 (2010/05/19)
The desmotropy of differently substituted (R*)-3-ethoxycarbonyl-2-aryl-3,5-dihydro-4,1-benzothiazepines and 3-ethoxycarbonyl-2-aryl-1,5-dihydro-4,1-benzothiazepines was investigated. The target 4,1-benzothiazepines were obtained via the ring transformation of (2R*,2aS*)-2-chloro-2a-aryl-2,2a-dihydro-2H,4H-azeto[1,2-a][ 3,1]benzothiazin-1-ones with sodium ethoxide in ethanol. The β-amino ester intermediate of the ring-enlargement reaction was isolated. Surprisingly, the desmotropes obtained could be separated by column chromatography and proved to be unexpectedly stable in solution. Further comparative studies revealed the existence of only the enamine forms of regioisomeric 2-ethoxycarbonyl-3-aryl-4,5-dihydro-7,8-dimethoxy-1,4-benzothiazepine derivatives; in this case, no desmotropy occurred. The structures were proved by means of NMR and IR spectroscopy.
Novel β-lactam condensed 3-thiaquinolines: an efficient synthesis and structural characterization
Csomós, Péter,Fodor, Lajos,Bernáth, Gábor,Sinkkonen, Jari,Salminen, Jari,Wiinam?ki, Kirsti,Pihlaja, Kalevi
, p. 1002 - 1011 (2008/09/17)
Quinoline analog 2-aryl-4H-3,1-benzothiazine derivatives 8-13, obtained by the condensation of o-aminobenzyl chloride 1 with?substituted thiobenzamides 2-7, were transformed to azeto[2,1-a][3,1]benzothiazin-1-one derivatives 18-23a,b,c and 24d,e by reaction with the corresponding substituted acetyl chlorides 14-17 in the presence of triethylamine. The structures of the new molecules were determined by NMR spectroscopy and electron ionization (EI) mass spectrometry. The typical EI+ mass spectrometric fragmentations of 8-13 and 18-23a,b,c and 24d,e are discussed in detail.
Behavior of Benzyl Sulfoxides toward Acid Chlorides. Useful Departures from the Pummerer Reaction
Chupp, John P.,Balthazor, Terry M.,Miller, Michael J.,Pozzo, Mark J.
, p. 4711 - 4716 (2007/10/02)
The present study extends the reaction of certain electrophilic reagents with electron-rich sulfides and sulfoxides beyond previously known limits.Thus, treatment of methoxy- and, more particularly, aminobenzyl sulfoxides 2 with acyl or hydrogen chlorides gives rise in high yields to the corresponding benzyl chlorides, a departure from the normally expected Pummerer reaction.It is demonstrated that ideal substrates for this reaction are o-anilines 1 derived from the well-known rearrangment of aromatic sulfilimines.Further, certain of the o-ammoniobenzyl chloride salts 4 so produced provide a basis for a novel and superior desulfurization of 1 to the corresponding o-methylaniline without resorting to Raney nickel.
