Synthesis of lignan conjugates via cyclopropanation: Antimicrobial and antioxidant studies

Kanchipura Ramachandrappa Raghavendra; Nagamallu Renuka; Vivek H Kameshwar; Bharath Srinivasan; Kariyappa Ajay Kumar; Sheena Shashikanth

doi:10.1016/j.bmcl.2016.06.005

Synthesis of lignan conjugates via cyclopropanation: Antimicrobial and antioxidant studies

Bioorg Med Chem Lett. 2016 Aug 1;26(15):3621-5. doi: 10.1016/j.bmcl.2016.06.005. Epub 2016 Jun 4.

Authors

Kanchipura Ramachandrappa Raghavendra¹, Nagamallu Renuka², Vivek H Kameshwar³, Bharath Srinivasan⁴, Kariyappa Ajay Kumar⁵, Sheena Shashikanth⁶

Affiliations

¹ Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysore, India.
² Department of Chemistry, Yuvaraja College, University of Mysore, India.
³ Central Research Laboratory, Adichunchanagiri Institute of Medical Sciences, B.G. Nagara, India.
⁴ Center for the Study of Systems Biology, School of Biology, Georgia Institute of Technology, Atlanta, GA 30332, USA.
⁵ Department of Chemistry, Yuvaraja College, University of Mysore, India. Electronic address: [email protected].
⁶ Department of Studies in Chemistry, University of Mysore, Manasagangothri, Mysore, India. Electronic address: [email protected].

PMID: 27318538
DOI: 10.1016/j.bmcl.2016.06.005

Abstract

Ethyl 2-(4-methoxyphenyl)-3-(thiophene-2-carbonyl)cyclopropanecarboxylates 2(a-f) and ethyl 4-aryl-7-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-carboxylates 4(a-f) were synthesized by simple procedure. The synthesized new compounds were screened in vitro for their antimicrobial and antioxidant activities. The compounds 2b and 4f showed excellent antibacterial activity; while 2b and 4f showed remarkable antifungal properties. The results of antioxidant activity studies revealed that compounds 4b and 4f manifested profound antioxidant potential. The docking studies were done for the final compounds. The ADME result indicates that all these molecules possess pharmaceutical properties in the range of 95% of drugs.

Keywords: Antimicrobial; Antioxidant; Lignans; MIC; Molecular docking.

MeSH terms

Anti-Bacterial Agents / chemical synthesis
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / pharmacology*
Antifungal Agents / chemical synthesis
Antifungal Agents / chemistry
Antifungal Agents / pharmacology*
Antioxidants / chemical synthesis
Antioxidants / chemistry
Antioxidants / pharmacology*
Bacteria / drug effects
Cyclopropanes / chemistry
Cyclopropanes / pharmacology*
Dose-Response Relationship, Drug
Fungi / drug effects
Lignans / chemistry
Lignans / pharmacology*
Microbial Sensitivity Tests
Molecular Docking Simulation
Molecular Structure
Structure-Activity Relationship

Substances

Anti-Bacterial Agents
Antifungal Agents
Antioxidants
Cyclopropanes
Lignans