- A facile and green synthesis of novel imide and amidic acid derivatives of phenacetin as potential analgesic and anti-pyretic agents
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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.
- Reddy, Yervala D.,Kumar, Padam P.,Devi, Bhoomireddy R.,Dubey, Pramod K.,Kumari, Yalamanchili B.
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- Synthesis of phthalyl substituted imidazolones and schiff bases as antimicrobial agents
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A new series of phthalyl substituted imidazolones (4a-g) and Schiff bases (5a-d) were synthesized from 2-methyl-(m-nitro-1,3- dioxo-1,3-dihydro- (2H)-isoindole-2-yl)-5-amino-1,3,4-thiadiazole (3 a-b). Compounds (3a-b) were prepared by cyclisation of 2-(m-nitro-1,3-dioxo-1,3-dihydro-(2H)-isoindole-2- yl)methyl ethanoate (2) with thiosemicarbazide. 2-(m-nitro-1,3-dioxo-1,3- dihydro-(2H)-isoindole-2-yl) ethanoic acid (1) in presence of thionyl chloride and methanol gave the ester (2) while compound (1) was synthesized by aminolysis of phthalic anhydride with glycine. The compounds were characterized by spectral techniques of IR, 1H NMR, Mass and elemental analysis. All the synthesized compounds (4a-g) and (5a-d) were screened for their antibacterial activity against the pathogenic strains E. coli, P. aureus, C. freundii while antifungal activity was evaluated against A. niger, A. flavus, Penicillium sp. and C. albicans.
- Sah, Pramilla,Saraswat, Neha,Seth, Manu
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experimental part
p. 427 - 434
(2012/02/02)
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- Synthesis and screening of cyclooxygenase inhibitory activity of some 1,3-dioxoisoindoline derivatives
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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.
- Cizmecioglu, Murat,Pabuccuoglu, Varol,Ballar, Petek,Pabuccuoglu, Aysun,Soyer, Zeynep
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experimental part
p. 186 - 190
(2011/10/10)
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- Synthesis, characterization and antibacterial activity of N-(N-acetic acid-yl-phthalimide-5-yl) maleamic acid dihydrate
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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.
- Li, Jian
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scheme or table
p. 428 - 431
(2011/08/04)
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- Preparation and physicochemical characterization of a novel water-soluble prodrug of carbamazepine
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N-Acyl-urea derivatives of carbamazepine (CBZ) were synthesized through the reactions of iminostilbene with acyl-isocyanates to form N-glycyl-carbamazepine (N-Gly-CBZ, after a deprotection step) or N-acetyl-carbamazepine (N-acetyl-CBZ). N-Gly-CBZ was isolated as its water-soluble HCl salt and was designed to act as a prodrug and convert to CBZ and glycine in vivo by enzymatic cleavage of the acyl-urea bond. The stability pH-rate profiles for N-Gly-CBZ and N-acetyl-CBZ were determined. The stability of N-Gly-CBZ was found to range over four orders of magnitude with its greatest stability at pH 3-4 and a t 90 value of 5.9 day at pH 4 at 25°C. From the fit of the pH rate profile two pKa values were estimated to be 7.2 (terminal amine) and 10.0 (imide), which were independently verified using UV-visible spectroscopic analysis. The solubility of N-Gly-CBZ in aqueous solution was determined in the range of pH 5.5-7.5. The intrinsic solubility of the neutral form of the prodrug was found to be 4.4 mg/mL, and the solubility of the prodrug increased exponentially (log linear) as pH was decreased below its pKa1 value. N-Gly-CBZ was found to have an aqueous solubility in excess of 50 mg/mL at pH 4. The presence of N-Gly-CBZ was found to increase the aqueous solubility of CBZ, a degradation product. CBZ showed an 8.6-fold greater solubility in an aqueous solution containing 23 mg/mL of N-Gly-CBZ than in water alone. The solubilization of CBZ by N-Gly-CBZ was investigated by examining the diffusion coefficients of the predominant species in D2O and was found to be more consistent with stacking complex formation than micelle formation. The stability ofN-Gly-CBZ makes a ready-to-use parenteral formulation impractical, but a freeze-dried preparation for reconstitution appears to be feasible.
- Hemenway, Jeffrey N.,Jarho, Pekka,Henri, John T.,Nair, Sajiv K.,Vandervelde, David,Georg, Gunda I.,Stella, Valentino J.
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experimental part
p. 1810 - 1825
(2011/03/21)
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- N-(4-(PIPERAZIN-1-YL)-PHENYL-2-OXAZOLIDINONE-5-CARBOXAMIDE DERIVATES AND RELATED COMPOUNDS AS ANTIBACTERIAL AGENTS
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The present invention provides antibacterial agents having the formula I described herein. or-pharmaceutically acceptable salts thereof wherein: A is a structure i, ii, iii, or iv,W is N(H)C(X)-R,. Het, or -Y HET, in which the Hot or Y HET is option
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Page/Page column 128-129
(2010/02/07)
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- Method of inhibiting binding of nerve growth factor to p75 NTR receptor
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The present invention relates to compositions which inhibit the binding of nerve growth factor to the p75NTRcommon neurotrophin receptor and methods of use thereof. In one embodiment, the compound which inhibits binding of nerve growth factor to p75NTRcomprises, particularly when bound to nerve growth factor, at least two of the following: (1) a first electronegative atom or functional group positioned to interact with Lys34of nerve growth factor; (2) a second electronegative atom or functional group positioned to interact with Lys95of nerve growth factor; (3) a third electronegative atom or functional group positioned to interact with Lys88of nerve growth factor; (4) a fourth electronegative atom or functional group positioned to interact with Lys32of nerve growth factor; and (5) a hydrophobic moiety which interacts with the hydrophobic region formed by Ile31, Phe101and Phe86of nerve growth factor.
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- Condensed heterocyclic compounds, their production and use
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Compounds represented by the formula: STR1 wherein ring A is benzene; Ar is aromatic group; R1, R2 and R3 each stands for H, acyl, hydrocarbon or heterocyclic, or R2 and R3, taken together, may form non-aromatic cyclic hydrocarbon; X is methylene or carbonyl; ......... is single bond or double bond; when ......... is single bond, Y is --NR4 -- (R4 is H, acyl, hydrocarbon or heterocyclic), when ......... is double bond, Y is N; n is 1-3, provided that, X is carbonyl and, at the same time, R2 and R3, taken together, form non-aromatic cyclic hydrocarbon, ......... is double bond or R4 is a heterocyclic or --Z(CH2)m --W (Z is methylene or carbonyl, W is optionally substituted amino, and m denotes 0-5), or salts thereof have an excellent GnRH receptor antagonistic action and/or an action of improving sleep disturbances.
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- A convenient one pot asymmetric synthesis of cis-β-lactams: Key precursors for optically active 2-oxaisocephems
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Asymmetric annelation of the disilylated imine 3 generated in situ from D-threonine 2 with acid chlorides 4 and triethylamine followed by esterification provided cis-β-lactams 5 and 6 in excellent yields with high diastereoselectivity under mild condition
- Tsubouchi,Tsuji,Yasumura,Tada,Nishitani,Minamikawa,Ishikawa
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p. 441 - 452
(2007/10/02)
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- 2-Oxa-isocephem compounds and compositions containing same
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A 2-oxa-isocephem compound of the formula (1): STR1 wherein R1, R2, R3 and R4 are as defined, pharmaceutically acceptable salts thereof, composition containing the same and processes for preparing the same are d
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