9-Chloro-2,4-(un)substituted acridines (1) on condensation with sulpha-diazine, sulphathiazole, and sulphaacetamide gave condensation products 3a-h. 3-Aryl-4-phenyl-2-imino-4-thiazolines (4) on condensation with 9-chloro-2,4-(un)substituted acridines (1) gave condensation products 5a-5o. Both 3a-3h and 5a-5o were puri ed by crystallization or by chromatography. Structures assigned to 3a-3h and 5a-5o are supported by correct spectral data. Antiinยฎammatory and analgesic activity screening of 3a, 3e, 3f and 5a-5c, 5e, 5g, 5i, 5m, 5n were carried out using carrageenin induced paw oedema and phenyl quinone writhing assay. Some of the compounds exhibited interesting antiinยฎammatory or analgesic activities.
A series of N-(2-Pyridyl) anthranilic acids (Ia-f) have been synthesized by Ullmann reaction. Cyclization of (Ib,d,f) by phosphorusoxy chloride (POCl 3) gives substituted 5chlorobenzo [b][1,8] naphthyridine compounds. The reaction progress was followed by thin layer chromatography (TLC), rate flow (R f) values was recorded, spectral data (IR) and (U.V) were recorded. Elemental analysis (CHNS) and gas chromatography-mass spectrometery (GC/MS) were carried out for some of the synthesized compounds.
The 2-[(6-chloro-2-pyridyl) amino]benzoic acid (I) was synthesized viaUllmann-Goldberg coupling by reaction of anthranilic acid with2,6-dichloropyridine. The compound (I) was cyclized by using poly phosphoric acid (PPA) to give 9-chloro-11H-pyrido[2,1-b]quinazolin-11-one (II). The compound (II) reacted with hydrazine hydrate to give N-{11H-pyrido[2,1-b]quinazolin-11-one-9-yl} hydrazine (III). The compound (III) reacted with various aromatic aldehydes to yield the hydrazones (IVa-p). The reaction progress was followed by thin layer of chromatography (TLC). The physical constants and R f values were recorded. The synthesized compounds were confirmed via the spectral data (UV,I.R, 1 H-NMR, 13 C-NMR, mass spectra). The possible fragmentation pattrene of GC/MS for the compounds (IVa) were investigated (IVh).
The N-(4-methyl-2-pyridyl)anthranilic acid (I) was synthesized by Ullmann condensation. The compound (I) was cyclized by polyphosphoric acid (PPA) to give 4-methyl-10Hbenzo[b][1,8]naphthyridin-5-one (II). The compound (II) was treated with selenium dioxide (SeO 2) and thionyl chloride (SOCl 2) to give the 4-formyl-10H-benzo[b][1,8]naphthyridin-5-one (III) and 4methyl-5-chloro-benzo[b][1,8]naphthyridine (IV) respectively.The compound (III) was reacted with various substituted anilines and aliphatic amines to give the Schiff bases (Va-j). The compound (IV) was reacted with hydrazine hydrate to yield the 5-hydrazino derivative (VI), which was reacted with various aromatic aldehydes to yield the hydrazones (VIIa-j) and the R f values reported.The reaction progress was followed by thin layer chromatography (TLC). The synthesized compounds were confirmed by spectral data (I.R, 1 H-NMR, 13 C-MNR). The possible fragmentation pattern of GC/MS for the compounds (III), (Vc) and (VIIg) were reported.
One side of (o, m and p) benzene diamine reacted with aromatic aldehyde to give Schiff bases (Ia-d) or (IIa-d) and (IIIa-d) respectively. The second amine group of the synthesized Schiff bases (Ia-d or IIa-d and IIIa-d) was reacted with substituted-9-chloroacridine to give the final compounds namely N-(Substituted benzylidene)-N'-(Substituted acridine-9-yl) (1,2 or 1,3 and 1,4) benzene diamine (V,VI,VII).The reaction progress was followed by thin layer chromatography (TLC), and R f values were recorded. I.R. Spectral data for all the synthesized derivatives were reported. The U.V-Vis., and the 1 HNMR(300and 400MHz) were recorded for some derivatives to support the structure of the synthesized compounds.
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