Synthesis and pharmacological activity of benzodipyran derivatives

1,2-dihydropyrano [3,2-g] [1] benzopyran-5-one derivatives IV a,b, VII and 1,2,3,4-tetrahydropyrano [3,2,g] [1] benzopypran-5-one derivatives VIII a-k were synthesized from the o-hydroxyaldehyde II. Compounds IVb, V, VIb, VII, VIIIb,c were tested for analgesic anti-inflammatory and ulcerogenic effects. Compounds VIIIb,c, VIb and VII were found to be potent analgesics with minimal ulcerogenic effect except VIb. None of the tested compounds was found to have anti-inflammatory activity

Synthesis and biological activities of substituted indolypyridines and indolylpyrimidines

A number of indolylpyridines [IVd] and indolylpyridopyrimidines [V, VIa-b] were prepared from 2,3-diphenyl-5-methoxyindole via the 6- formyl derivative [II]. The 6-formyl derivative gave Schiff bases [VIIa-f] which were reduced to the corresponding Mannich bases. The effect of structural variation of these molecules on biological activities was examined. None of the tested compounds was found to be toxic up to 5 g/kg body weight. Compounds II, VIId and VIIIa were found to demonstrate a smooth muscle relaxant effect and a temporary hypotensive effect. Analgesic effect was abolished by substitution of the parent compound

Synthesis and reactions of some arylazo derivatives of B-diketones

Claisen condensation of both visnaginone methyl ether and Khellinone methyl benzoate lead to the formation of w-benzoatovisnaginone methyl ether and w-benzoate-Khellinone methyl ether. The B-diketones couple with aromatic diazonium compounds in the presence of sodium acetate to give the arylazo compounds. The arylazo compounds react with diazomethane, hydrazine hydrate, phenylhydrazine or hydroxylamine hydrochloride to form pyrazole or isoxazole derivatives

Reaction of methylene-bis [5-hydroxyfurocoumarins] with amines and hydrazines

Fusion of 6, 6'-methylene-bis-[5-hydroxybergapten] [IIIa] or [5- hydroxyisopimpinellin] [IIIb] with aromatic amines and hydrazine hydrate led to the formation of 6, 6'-methylene-bis-[5-amino] [IVa-f] or [5-hydrazino] [IVg], h] derivatives. On the other hand, when IIIa or IIIb were refluxed with aliphatic amines, cleavage of the methylene bridge followed by opening of the coumarin ring occurred to give the corresponding alpa-substituted acetamides [Va-d]. Fusion of IIIa or IIIb with phenylhydrazine also led to the methylene bridge followed by opening of the coumarin ring to form VIa, b. The reaction of 5- hydroxybergapten or 5-hydroxyisopimpinellin with propylamine or benzylamine in ethanol led to the respective 5-amino-derivatives [VIIa-c]. The antimicrobial activity of compounds IVa, b, e, f, Va, b, d and VIa, b has been tested. Only compound Vb showed a broad spectrum activity

Synthesis of biologically active hydrazides and their derivatives

4-methoxy-[II a] and 4, 7-dimethoxy-6-hydroxybenzofuran-5-carboxylic acid [II b] give the esters [III a-c] upon treatment with diazomethane. IIIa and IIIb form the hydrazides [IV a-b] which on benzoylation in pyridine give the N-benzoyl derivatives [V a-b]. Cyclization of Va, b with phosphoryl chloride leads to the 2-phenyl- 5-substituted-1, 3, 4-oxadiazole derivatives [VI a, b]. Schotten- Baumann benzoylation of IVa affords the O-N-dibenzoyl derivative [VII]. The hydrazide [IVa] condenses with aromatic aldehydes and ketones to form the corresponding hydrazones [VIII a-i]. Compounds IIIa, IVa, VIII b, c, e and i have been found to possess antiaflatoxigenic activity

Some amino derivatives of 4-substituted -a-phenylpropiophenones and their antimicrobial activity

Aminomethylation of p-CH3OC6H4 COCH2C6H5 [I] using formaldehyde solution and different amines gave the corresponding new 4-methoxy- alpha-phenyl-beta-aminopropio-phenone derivatives III a-c. The Mannich reaction was run for p-HOC6H4 COCH2C6H3 [II] using different amines to yield the new [IV a-d]. Glyoxalic acid may replace formaldehyde in the Mannich reaction of II with morpholine to produce the new morpholinium salt V of the corresponding amino acid. Hydrolysis of the salt gave the unsaturated acid VI which was esterified to the ester VII. Compound IIIc was found to be active against gram positive bacteria [Bacillus subtilus], IVd and VI found to be active against fungi [A. niger], whileas VI and VII found to be active against gram negative bacteria [E. coli]