- Synthesis, characterization, electronic absorption and antimicrobial studies of N-(silatranylpropyl)phthalimide derived from phthalic anhydride
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The transimidization reaction between phthalic anhydride and (3-aminopropyl)triethoxysilane was carried out using 2-(3-methylpyridin-2-yl)isoindoline-1,3-dione 1 to synthesize N-(triethoxysilylpropyl)phthalimide 2 in good yield. New silatranes 3 and 4 containing phthalimide as exocyclic group were prepared by the transesterification reactions of N-(triethoxysilylpropyl)phthalimide 2 with triethanolamine and trisisopropanolamine respectively. All the compounds were characterized by elemental analysis, spectroscopic techniques and thermogravimetric analysis. The compounds 3 and 4 were also characterized by X-ray diffraction analysis. The electronic absorption spectra of compounds 3 and 4 were studied in six solvents with different polarities. N-(silatranylpropyl)phthalimides were evaluated for the preliminary antimicrobial activity using broth microdilution method.
- Singh, Gurjaspreet,Saroa, Amandeep,Girdhar, Shally,Rani, Sunita,Sahoo, Subash,Choquesillo-Lazarte, Duane
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p. 232 - 239
(2015/02/05)
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- PROCESS
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The present application provides a process for the production of 7-azaindole systems by reacting a compound of formula I-1 with base
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- Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αvβ3 and/or αvβ5 integrin.
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- Bicyclic alphavbeta3 antagonists
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αvβ3 and/or αvβ5 integrin.
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- New anti-inflammatory N-pyridinyl(alkyl)phthalimides acting as tumour necrosis factor-α production inhibitors
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This paper describes the synthesis of N-pyridinyl(alkyl)phthalimides related to N-phenyl-4,5,6,7-tetrafluorophthalimides known to be inhibitors of tumour necrosis factor-α (TNFα) production. Pharmacomodulation at the phthalimidic nitrogen led to the selection of two pharmacophoric fragments (2,4-lutidinyl and β-picolyl), allowing significant inhibition of TNFα production (compounds 12 and 17). Variation of the substituents linked to the homocycle of their phthalimide scaffold indicated that high (TNFα production) inhibitory potency could be achieved, notably by 5-fluoro, 4- or 5-nitro, 5-amino and especially tetrafluoro substitution. The most active compound, N-(pyridin-3-ylmethyl)-4,5,6,7-tetrafluorophthalimide (32) (84% inhibition at 10 μM), also produced an anti-oedematous effect in the PMA-induced mouse-ear swelling test. Although less active than dexamethasone, it exerted a marked reduction in ear thickness after oral administration (63% vs. 85% for dexamethasone at 0.2 mM kg-1) and remained efficient after topical application (46% vs. 96% for the dexamethasone). It also induced potent inhibition in the rat carrageenan foot oedema test with an ID50 (0.14 μM kg-1) comparable with that of N-(2,6-diisopropylphenyl)phthalimide (4) (0.15 μM kg-1).
- Collin, Xavier,Robert, Jean-Michel,Wielgosz, Gaetane,Le Baut, Guillaume,Bobin-Dubigeon, Christine,Grimaud, Nicole,Petit, Jean-Yves
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p. 639 - 649
(2007/10/03)
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- Synthesis and anticonvulsant and neurotoxic properties of substituted N- phenyl derivatives of the phthalimide pharmacophore
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A series of compounds including 4-amino (1), 3-amino (2), 4-nitro (3), 2-methyl-3-amino (4), 2-methyl-3-nitro (5), 2-methyl-4-amino (6), 2-methyl-4- nitro (7), 2-methyl-5-amino (8), 2-methyl-5-nitro (9), 2-methyl-6-amino (10), 2-methyl-6-mitro (11), 2,6-dimethyl (12), 2-methyl-3-carboxy (13), 2- methoxycarbonyl (14), 2-methyl-4-methoxy (15), 2,4-dimethoxy (16), 2-chloro- 4-amino (17), and 2-chloro-4-nitro (18) N-phenyl substituents of phthalimide were evaluated along with N-[3-methyl-(2-pyridinyl)]phthalimide (19), N-(3- amino-2-methylphenyl)succinimide (20), and phenytoin for anticonvulsant and neurotoxic properties. Initial screening in the intraperitoneal (ip) maximal electroshock-induced seizure (MES) test and the subcutaneous pentylenetetrazol-induced seizure (scPtz) test in mice led to the selection of 1, 2, 4, 10, 12, 17, and 19 for oral MES evaluation in rats. The resultant ED50 values for 4, 10, 17, and phenytoin were 8.0, 28.3, 5.7 and 29.8 mg/kg, respectively. In the batrachotoxin affinity assay, IC50 values for 17 and phenytoin were 0.15 and 0.93 μM, respectively, and in the recently validated magnesium deficiency-dependent audiogenic seizure test, ED50 values of 5.2 and 23 mg/kg were obtained for 17 and phenytoin, respectively. Electrophysiology studies on compound 17 point out its ability to (i) potentiate GABA-evoked current responses with a failure to directly activate the GABAA receptor and (ii) to affect, at 100 μM excitatory non NMDA, but not NMDA, receptors with a 25% block of kainate-evoked response. Electrophysiology measurements on voltagegated sodium channels in N1E-115 neuroblastoma cells confirm voltage-dependent block of these channels by compound 17. In view of its interaction with multiple ion channels, one would predict that compound 17 might be active in a wide range of seizure models.
- Vamecq, Joseph,Bac, Pierre,Herrenknecht, Christine,Maurois, Pierre,Delcourt, Philippe,Stables, James P.
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p. 1311 - 1319
(2007/10/03)
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- A FACILE SYNTHESIS OF 2-AMINONICOTINALDEHYDE
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A synthesis of 2-aminonicotinaldehyde (1) which does not require chromatography and is easily scaled up has been developed.Bromination of 2-amino-3-picoline, protected as a phthalimide (4), produced the gem-dibromide (5), which was reacted with NH4OH.The imine intermediate (7) was hydrolyzed with acid, producing (1) in a 56percent conversion from 4.
- Moormann, Alan E.,Yen, Chung H.,Yu, Stella
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p. 1695 - 1700
(2007/10/02)
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