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Palladium(0) catalyzed Suzuki cross-coupling reaction of 2,5-dibromo-3-methylthiophene: selectivity, characterization, DFT studies and their biological evaluations

Rizwan, Komal and Zubair, Muhammad and Rasool, Nasir and Mahmood, Tariq and Ayub, Khurshid and Noorjahan Banu, Alitheen and Muhammad Nazirul Mubin, Aziz and Akhtar, Muhammad Nadeem and Nasim, Faiz-ul-Hassan and Bukhary, Snober Mona and Ahmad, Viqar Uddin and Rani, Mubeen (2018) Palladium(0) catalyzed Suzuki cross-coupling reaction of 2,5-dibromo-3-methylthiophene: selectivity, characterization, DFT studies and their biological evaluations. Chemistry Central Journal, 12 (49). pp. 1-12. ISSN 1752-153X

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Abstract

Thiophene derivatives have shown versatile pharmacological activities. The Suzuki reaction proved a convenient method for C–C bond formations in organic molecules. In the present research work novel derivatives of 2,5-dibromo-3-methylthiophene (3a–k and 3l–p) has been synthesized, via Suzuki coupling reaction in low to moderate yields. A wide range of functional groups were well tolerated in reaction. Density functional theory investigations on all synthesized derivatives (3a–3p) were performed in order to explore the structural properties. The pharmaceutical potential of synthesized compounds was investigated through various bioassays (antioxidant, antibacterial, antiurease activities). The compounds 3l, 3g, 3j, showed excellent antioxidant activity (86.0, 82.0, 81.3%), respectively by scavenging DPPH. Synthesized compounds showed promising antibacterial activity against tested strains. 3b, 3k, 3a, 3d and 3j showed potential antiurease activity with 67.7, 64.2, 58.8, 54.7 and 52.1% inhibition at 50 µg/ml. Results indicated that synthesized molecules could be a potential source of pharmaceutical agents.

Item Type: Article
Additional Information: Indexed by Scopus
Uncontrolled Keywords: Density functional theory; Thiophene; Antioxidant; Antibacterial; Palladium
Subjects: Q Science > QD Chemistry
Faculty/Division: Faculty of Industrial Sciences And Technology
Depositing User: Noorul Farina Arifin
Date Deposited: 11 Oct 2018 06:48
Last Modified: 11 Oct 2018 06:48
URI: http://umpir.ump.edu.my/id/eprint/22383
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