Total Synthesis and Antibacterial Screening of (±)-6,8-Dihydroxy-3- undecyl-3,4-dihydroisochromen-1-one: A Structural Analogue of Metabolites from Ononis natrix

Author(s): Hummera Rafique*, Aamer Saeed, Ehsan Ullah Mughal, Muhammad Naveed Zafar, Amara Mumtaz, Naghmana Kausar, Kiran Hina.

Journal Name: Letters in Drug Design & Discovery

Volume 16 , Issue 3 , 2019

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Graphical Abstract:


Background: (±)-6,8-Dihydroxy-3-undecyl-3,4-dihydroisochromen-1-one is one of the structural analog of several substituted undecylisocoumarins isolated from Ononis natrix (Fabaceae), has been successfully synthesized by direct condensation of homopthalic acid (1) with undecanoyl chloride yields isochromen-1-one (2).

Methods: Alkaline hydrolysis of (2) gave the corresponding keto-acid (3), which is then reduced to hydroxy acid (4) then its cyclodehydration was carried out with acetic anhydride to afford 3,4- dihydroisochromen-1-one (5). Followed by demethylation step, the synthesis of target 6,8- dihydroxy-7-methyl-3-undecyl-3,4-dihydroisocoumarin (6) was achieved.

Results: In vitro antibacterial screening of all the synthesized compounds were carried out against ten bacterial strains by agar well diffusion method.

Conclusion: Newly synthesized molecules exhibited moderate antibacterial activity and maximum inhibition was observed against Bacillus subtilus and Salmonella paratyphi.

Keywords: 3, 5-Dimethoxy-4-methylhomophthalic acid, analogues of natural 3, 4-dihydroisochromen-1-one, antibacterial screening, agar well diffusion method, cyclodehydration, bacterial strains.

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Article Details

Year: 2019
Page: [245 - 248]
Pages: 4
DOI: 10.2174/1570180815666180502114402
Price: $58

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