ChemInform Abstract: Synthesis and in vitro Activity of New Cephalosporin Derivatives (IV) Containing a Benzoxazolone Ring.

Abstract

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of Benz[d]oxazolones Involving Concomitant Acetyl Migration from Oxygen to Nitrogen

“…General Procedure for the Synthesis of 3-Acetylbenz[d]oxazol-2(3H)-ones (11)(12)(13)(14)(15) A solution of crude o-acetoxybenzoyl azides 6-10 (0.05 mol) in dry toluene (50 mL) was directly placed in a water bath whose temperature was increased slowly. At $ 50 C, the effervescence in dry toluene solution started.…”

“…Benzoxazoles, especially the benz[d]oxazolone compounds, are of interest as established or potential anticonvulsants, [1,2] cardiotonics, [3] central nervous system agents [4] , b-3-adrenergic receptor antagonists, [5] antivirals, [6,7] analgesic and antiinflamatory agents, [8,9] antimicrobials, [9][10][11][12][13] fungicides, [13] and herbicides and plantgrowth regulators. [14] The literature is ambiguous in reporting the syntheses of benz[d]oxazol-2(3H)-ones and benz [d]isoxazol-3(2H)-ones.…”

“…Acetylbenz[d]oxazol-2(3H)-ones(11). Fluffy white crystals (yield 91%); mp 85-86 C; IR: n (cm À1 ) 3100, 3020, 1840 and 1800, 1725,1600, 1480, 1380, 1320; UV: k max (logE) 274.5 (3.25) nm; 1 H NMR:d 2.75 (s, 3H, CH 3 ), 7.20-7.27(m, 3H, H-5, H-6 and H-7), 8.06 (m, 1H, H-4); 13 C NMR: d c 24.80(q, CH 3 ), 109.72 (d, C-7), 115.82 (d, C-4), 126.54 and 125.20 (each d, C-5 and C-6), 127.50 (s, C-3a), 142.00 (s, C-7a), 151.38 (s, C-2), 169.36 (s, CH 3 C¼O); HRMS: 177.04265 (177.042575 for C 9 H 7 NO 3 ); EI-MS (70 eV), m=z: 177 (M þ. , 10.4%), 135 (100%), 91 (7.8%), 79 (14.9%).…”

Interplay of thermochemistry and Structural Chemistry, the journal (volume 19, 2008) and the discipline

“…The 1,2,4-thiadiazole ring system has a wide range of biological activity [256] and 2-benzoxazolinone derivatives possess pharmacological activity [257]. The potential medicinal value of these two groups led Kaynak et al [258] to synthesize and characterize 2-methylamino-5-[(5-methyl-2-benzoxazolinone-3-yl)methyl]-1,3,4-thiadiazole dihydrophosphate, with the results discussed in the subsequent article.…”

Molecular structure of 2-methylamino-5-[(5-methyl-2-benzoxazolinone-3-yl)methyl]-1,3,4-thiadiazole dihydrophosphate: a combined X-ray crystallographic and ab initio study

“…2-Benzoxazolinone derivatives also possess a broad pharmacological activity spectrum such as antibacterial-antifungal [10,11], dopaminergic [12], and analgesic-antiinflammatory [13][14][15][16][17][18][19]. The medicinal value of these two derivatives prompted us to synthesize 2-methylamino-5-[(5-methyl-2-benzoxazolinone-3-yl)methyl]-1,3,4-thiadiazole derivative and clarify its structure.…”