Novel fluoro substituted benzo[b]pyran with anti-lung cancer activity

1887-18936-Fluorobenzo[b]pyran-4-one 1 on condensation with aromatic aldehydes yields 3-arylmethylene-6-fluoro-2,3-dihydrobenzo[b]pyran-4-ones 2 which on treatment with phenylhydrazine and thiourea gives the pyrazole and pyrimidine thione derivatives 3 and 4, respectively. Compound 4 reacts with chloroacetic acid in acetic acid-acetic anhydride mixture to afford the thiazolopyrimidines 5 which on condensation with aromatic aldehyde furnish the corresponding arylmethylene­thiazolopyrimidine derivatives 6. The product 6 could be prepared directly by the action of chloroacetic acid and the proper aldehyde on 4 in the presence of acetic acid-acetic anhydride mixture. Product 2 reacts with malononitrile in the presence of ammonium acetate or piperidine to afford the pyridine- and pyran- 7 and 8 derivatives, respectively. Also, compound 1 on treatment with arylmethylenecyanoacetamide yields the pyridone derivatives 9. Condensation of 1 with malononitrile affords the yliedinemalononitrile 10, which on reaction with p-chlorobenzaldehyde-ammonium acetate or arylmethylene-cyano­acetamide yields the pyridine derivative 11 (isomer of 8) and the dicarbonitrile derivative 12, respectively. The synthesized compounds have been tested against three cell lines of human cancer (lung, breast and CNS cancer), and these compounds show anticancer activity at low concentration as compared to reference drug 5-fluorodeoxyuridine

Synthesis and anti-cancer activity of pyridine and thiazolopyrimidine derivatives using 1-ethylpiperidone as a synthon

213-2213,5-Bisarylmethylene-1-ethylpiperidone 2 on reaction with thiourea yield the thioxopyri midine derivatives 3, which on condensation with bromoacetic acid, 2-bromopropanoic acid or 3-bromopropanoic acid afford thiazolopyrimidine 4, 2-methyl-thiazolopyrimidines 5 and thiazinopyrimidine derivatives 6, respectively. Compounds 7 and 8 are also obtained via condensation of compounds 3 with 3-chloropentan-2, 4-dione, bromoacetic acid and aromatic aldehydes, respectively. However, compounds 8 are prepared directly by condensation of compounds 4 with aromatic aldehydes. Compounds 2 on condensation with malononitrile in ethanol/piperidine or acetic acid/ammonium acetate mixture give pyridopyran 9 and pyridopyridine 10, respectively. Also compound 10 could be prepared directly from compound 9. Compounds 2 when condensed with phenylhydrazine, ethyl cyanoacetate or guanidine hydrochloride yields pyridopyrazole 11, pyridopyridone 12 and pyridoaminopyrimidine derivatives 13, respectively

Synthesis of novel tricyclic heterocyclic compounds as potential anticancer agents using chromanone and thiochromanone as synthons

1985-1993The arylmethylene of benzopyrane or benzothiopyrane 3,4 have been synthesized and condensed with hydrazine, guanidine and thiourea to yield pyrazole 5-8, aminopyrimidine 9,10 and thioxopyrimidine derivatives 11,12, respectively. Compounds 3 or 4 on treatment with malononitrile in the presence of ammonium acetate/acetic acid or in the presence of piperidine/ methanol to yield benzopyrano-and benzothiopyranopyridine 13,14 and benzopyrano- and benzothiopyrane 15,16, respectively. The oxirane of compound 3 is prepared and condensed with CS2 to yield the tricyclic system, thioxothienobenzopyrane 21. Ylidenemalononitrile for the ketone 1 and 2 are synthesized and condensed with aromatic aldehyde in presence of ammonium acetate/acetic acid to yield benzopyranopyridine and benzothiopyranopyridine derivatives 24,25, respectively, which are the isomer of compounds 13,14. Ylidenemalononitrilc on condensation with phenylisothiocyanate yields benzo-pyrano- and benzothiopyranothioxopyridine 28,29, respectively