Synthesis and Antimicrobial Evaluation of Some Novel Pyrimidine, Pyrazole, Chromene and Tetrahydrobenzo[b]thiophene Derivatives Bearing Pyrimidinthione Moiety

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Author(s): Mohamed Ahmed Mahmoud Abdel Reheim*, Ibrahim Saad Abdel Hafiz, Mohamed Ahmed Elian

Journal Name: Current Organic Synthesis

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Aim and Objective: A novel collection of fused pyrimidine, pyridine, pyrazole, chromene, thiophene derivatives 2-30 had been newly synthesized by using the 1a, b as starting material. Fused pyran show off a range of pharmacological activity such as cancer agents [1], antimicrobial [2-4], antioxidant [5], anti-proliferative [6], cytotoxic activity [7], anticipated antitumor [8], antiparkinsonian [9] and anti-inflammatory [10]. Also, pyran derivatives are well known for bacterial biofilm disruptor [11], anticonvulsant [12] and inhibtors of mycobacterium bovis [13].

Materials and Methods: All melting points were measured using Akofler Block instrument and are uncorrected. IR spectra (KBr) were recorded on a FTIR 5300 spectrometer (υ, cm-1). The 1H-NMR spectra were recorded on a Varian Gemini spectrometer. The 1H-NMR spectra were run at 300, 400 MHz and 13C-NMR spectra were run at 100 MHz in DMSO-d6, CDCl3 as solvents. The chemical shifts are expressed in parts per million (ppm) by using tetramethylsilane (TMS) as internal refernce. 1000 EX mass spectrometer at 70 eV. The purity of synthesized compounds was checked by thin layer chromatography (TLC) (aluminum sheets) using n-hexane, EtOAc (9:1, V/V, 7:3 V/V) eluent. Elemental analysis were carried out by the Microanalytical Research Center, Faculty of Science, and Microanalytical Unit, Faculty of Pharmacy, Cairo University, Egypt.

Results: A novel series of azoles and azines were designed and prepared via the reaction of 7-amino-5-(4-chlorophenyl)- 4-phenyl-2-thioxo-2,5-dihydro-1H-pyrano- [2,3-d]pyrimidine-6-carbonitrile 1a and 7-amino-4,5-diphenyl-2-thioxo-2,5- dihydro-1H-pyrano[2,3-d]-pyrimidine-6-carbonitrile 1b with some electrophilic and nucleophilic reagents. The structures of target compounds were confirmed by elemental analyses and spectral data. The novel synthesized compounds showed a good antimicrobial activity against the previously mentioned microorganisms.

Conclusion: In conclusion, compounds 1a, 1b that underwent ready cyclization to give fused heterocyclic compounds through its reaction with different reagents and under different conditions and subjected to antimicrobial screening.

Keywords: Thiopyrimidine, Pyranopyridine, Pyranopyrimidine, Antimicrobial activity, Chromene, thiophene.

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(E-pub Ahead of Print)
DOI: 10.2174/1570179417666200628021125
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