10133-88-7Relevant articles and documents
A facile and green synthesis of novel imide and amidic acid derivatives of phenacetin as potential analgesic and anti-pyretic agents
Reddy, Yervala D.,Kumar, Padam P.,Devi, Bhoomireddy R.,Dubey, Pramod K.,Kumari, Yalamanchili B.
, p. 70 - 76 (2013/07/26)
Facile and green syntheses of potential analgesic and antipyretic compounds, N-(4-ethoxy-phenyl)-2-(1,3- dioxo-1,3-dihydroisoindol-2-yl)acetamide derivatives 6a-g and N-[(4-ethoxy-phenylcarbamoyl)methyl]phthalamic acid derivatives 10a-g have been developed. Two synthetic routes (A and B) have been established for the preparation of 6a-g. In the route-A, 4-ethoxyaniline 2 was reacted with chloroacetyl chloride 3 in a solution of potassium acetate and acetic acid to yield N-(4-ethoxyphenyl)-2-chloroacetamide 4. The latter was reacted with imide compounds 5a-g either in triethanolamine as a green solvent or in solid phase in the presence of TEBAC and KI to yield 6a-g. Alternatively, in the route-B, reaction of anhydrides 7a-g with glycine 8 yielded the (1, 3-dioxo-1, 3-dihydroisoindol-2-yl)acetic acid derivatives 9a-g which on reaction with 2 either in triethnolamine and DCC as a dehydrating agent or in solid phase in the presence of DCC gave 6a-g. The latter were hydrolyzed in 0.5N ethanolic KOH to afford 10a-g.
Synthesis and screening of cyclooxygenase inhibitory activity of some 1,3-dioxoisoindoline derivatives
Cizmecioglu, Murat,Pabuccuoglu, Varol,Ballar, Petek,Pabuccuoglu, Aysun,Soyer, Zeynep
experimental part, p. 186 - 190 (2011/10/10)
In this study, 15 compounds bearing N,Nphthaloylacetamide structure designed by the molecular simplification approach based on thalidomide structure were synthesized and evaluated for inhibitory potencies against cyclooxgenase (COX) isoenzymes, namely COX-1 and COX-2. The results suggested that the N,Nphthaloylacetamide structure, as a primary amide, has inhibitory activity against cyclooxygenase isoenzymes with a higher COX-1 selectivity. The conversion of the primary amide to secondary or tertiary derivatives lowered the potency but favored the COX-2 selectivity thus yielding the compounds with stronger COX-2 inhibiting activity. ECV · Editio Cantor Verlag.
Synthesis, characterization and antibacterial activity of N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid dihydrate
Li, Jian
scheme or table, p. 428 - 431 (2011/08/04)
The compound N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid (C 14H10N2O7, M r = 318) was synthesized and its structure was characterized by elemental analysis, 1H NMR and IR spectra. The single crystal of the title compound (C14H14N2O9, M r = 354.27) was cultured and its structure was determined by single crystal X-ray diffraction. The crystal belongs to monoclinic system, space group P21/c with a = 14.3859(19), b = 12.5835(18), c = 8.6934(15) A, β = 102.824(2)°, V = 1534.5(4) A3, Z = 4, D c = 1.534 g cm-3, μ(Mo Kα) = 0.131 mm-1, F(000) = 736. The final refinement gave R = 0.0652, wR(F 2) = 0.1239 for 2,703 observed reflections with I > 2σ(I). X-ray diffraction analysis reveals that the asymmetric unit of the title compound contains one N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid molecule and two water molecules. One of the two water molecules is disordered. The phthalimide group is essentially planar. The crystal structure of the title compound is stabilized by N-H...O and O-H...O hydrogen bonds interactions. The compound N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid possesses moderate antibacterial activity.
