Synthesis, Characterization and Biological Evaluation of some New Thieno[2,3-d]Pyrimidine Derivatives

Abstract

10-Oxo-4,6,7,8,9,10-hexahydroprazolo[1,5-a][1]benzothieno[2,3-d]pyrimidine-3-carbaldehyde (2) was prepared by Vilsmeier-Haack reaction of 3-amino-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (1). Reaction of carbaldehyde derivative 2 with malononitrile afforded arylidene malononitrile 3. Cyclization of the latter compound with thiourea yielded pyrimidinethione 4. Interaction of carbaldehyde derivative 2 in presence of thiourea with keto- compounds such as ethyl acetoacetate, or acetylacetone, or dimedone or ethyl cyanoacetate gave pyrimidine derivatives 5-8. Hydrazinolysis of carbaldehyde derivative 2 gave the hydrazone 9. Reaction of the latter with phenyl isothiocyanate afforded thiosemicarbazone 10, which underwent cyclization with oxalyl chloride to give thioxoimidazolidinedione 11. Condensation of compound 2 with thiosemicarbazide furnished thiosemicarbazone derivative 12. Reaction of compound 2 with aminopyrazolone in the presence of an acid and/or a base afforded pyrazolones 13 and 14. Treatment of carbaldehyde derivative 2 with cyanoacetohydrazide gave acrylohydrazide 15. Interaction of the latter with carbon disulfide yielded mercaptooxadiazole 16. Condensation of compound 2 with acetylpyridazinone 17 produced chalcone 18. Reaction of compound 18 with malononitrile in pyridine gave cyanopyran 19, while its reaction with malononitrile in presence of ammonium acetate in ethanol yielded cyanopyridine 20. Structures of the newly synthesized products have been deduced on the basis of elemental analysis and spectral data. The synthesized compounds were screened for their antimicrobial activity.

Synthesis and Antimicrobial Evaluation of some Functionalized Heterocycles Derived from Novel Quinolinyl Chalcone

“…The desired hybrid chalcone, 3‐[ E ‐3‐(4‐hydroxy‐1‐methyl‐2‐oxo‐1,2‐dihydroquinolin‐3‐yl)‐3‐oxoprop‐1‐en‐1‐yl]‐6,7,8,9‐tetrahydropyrazolo[1,5‐ a ][1]benzothieno[2,3‐ d ]pyrimidin‐10(4 H )‐one ( 3) , has been designed and synthesized via the best known base‐catalyzed Claisen–Schmidt condensation reaction of equimolar amounts of 3‐acetyl‐4‐hydroxyl‐1‐methylquinolin‐2(1 H )‐one ( 1 ) with 10‐oxo‐4,6,7,8,9,10‐hexahydropyrazolo[1,5‐ a ][1]benzothieno[2,3‐ d ]pyrimidine‐3‐carbaldehyde ( 2 ) , in presence of catalytic amount of piperidine in 80% yield (Scheme ).…”

“…Elemental microanalyses were performed Perkin–Elmer 2400II at the Chemical War department, Ministry of Defense. The purity of the synthesized compounds was checked by thin‐layer chromatography on 0.2‐mm silica gel F‐254 (Merck) plates, using UV light (254 and 366 nm) for detection.10‐Oxo‐4,6,7,8,9,10‐hexahydroprazolo[1,5‐ a ][1]benzothieno[2,3‐ d ]pyrimidine‐3‐carbaldehyde ( 2 ) has been prepared according to the reported method and 3‐acetyl‐4‐hydroxy1‐1‐methyl‐1 H ‐quinolin‐2‐one ( 1 ) has been prepared according to the reported method .…”

Medicinal Attributes of Thienopyrimidine Based Scaffold Targeting Tyrosine Kinases and Their Potential Anticancer Activities

“…Over the last two decades, many thienopyrimidines have been found to exhibit a variety of pronounced activities as kinase inhibitors. Many of their derivatives have been synthesized as potential anticancer , analgesic , antimicrobial , and antiviral agents .…”

of Some New Heterocyclic Schiff Bases Derived from Thiocarbohydrazide

“…Thus, condensation reaction of 10-oxo-4,6,7,8,9,10-hexahydroprazolo [1,5-a] [1]benzothieno [2,3-d]pyrimidine-3-carbaldehyde (1) 13 with thiocarbohydrazide 2 14 in boiling absolute ethanol containing a catalytic amount of acetic acid gave the corresponding N'-[ (10-oxo-4,6,7,8,9,10-…”

“…Infrared spectra were recorded on FT-IR Jasco 4100 spectrophotometer using a KBr wafer technique. The 1 H and 13 C NMR spectra were recorded in DMSO-d 6 or CDCl 3 on Gemini spectrometer (300 MHz for 1 H NMR and 75 MHz for 13 C NMR) and the chemical shift ar given as δ downfield from TMS as an internal standard, measured at the Main Laboratories of the War Chemical. Elemental microanalyses were recorded on a Perkin Elmer series II CHNS analyzer 2400.…”