Carbon‐13 nuclear magnetic resonance spectra of N‐substituted 2‐amino‐4H‐3,1‐benzoxazin‐4‐ones and 3‐substituted 2,4‐(1H,3H)quinazolinediones

Petridou‐Fischer, Joanna; Papadopoulos, E. P.

doi:10.1002/jhet.5570190122

Cited by 20 publications

(1 citation statement)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The corresponding chemical shifts of the benzoxazinones were observed at 154/160 ppm ( 8h ) and 164/159 ppm ( 9i ). These values were in accordance with literature data for 4 H -3,1-benzoxazin-4-ones [ 14 , 32 , 37 , 38 , 39 ]. A similar influence of the sulphur-oxygen exchange on the chemical shift of the C-4 carbon was observed for pairs of 2-thien-2-yl and 2-cyano substituted 4 H -3,1-benzothiazin(oxazin)-4-ones [ 32 , 40 ].…”

Section: Resultssupporting

confidence: 92%

2-Amino- and 2-Alkylthio-4H-3,1-benzothiazin-4-ones: Synthesis, Interconversion and Enzyme Inhibitory Activities

et al. 2009

View full text Add to dashboard Cite

The synthetic access to 2-sec-amino-4H-3,1-benzothiazin-4-ones 2 was explored. Compounds 2 were available from methyl 2-thioureidobenzoates 1, 2-thioureidobenzoic acids 3, and novel 2-thioureidobenzamides 6, respectively, under different conditions. 2-Alkylthio-4H-3,1-benzothiazin-4-ones 5 have been prepared from anthranilic acid following a two step route. Both, benzothiazinones 2 and 5 underwent ring cleavage reactions to produce thioureas 1 and 6, respectively. Twelve benzothiazinones were evaluated as inhibitors against a panel of eight proteases and esterases to identify one selective inhibitor of human cathepsin L, 2b, and one selective inhibitor of human leukocyte elastase, 5i.

show abstract