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

[ Vol. 16 , Issue. 3 ]

Author(s):

Hummera Rafique*, Aamer Saeed, Ehsan Ullah Mughal, Muhammad Naveed Zafar, Amara Mumtaz, Naghmana Kausar and Kiran Hina   Pages 245 - 248 ( 4 )

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.

Affiliation:

Department of Chemistry, Univeristy of Gujrat, 50700-Gujrat, Department of Chemistry, Quaid-i-Azam Univeristy, Islamabad-45320, Department of Chemistry, Univeristy of Gujrat, 50700-Gujrat, Department of Chemistry, Quaid-i-Azam Univeristy, Islamabad-45320, Department of Chemistry, COMSATS University, Abbottabad Campus, Abbottabad-22060, Department of Chemistry, Univeristy of Gujrat, 50700-Gujrat, Department of Environmental Sciences, Univeristy of Gujrat, Gujrat-50700

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