INDANYL ANALOGS AS POTENTIAL ANTIMICROBIAL AGENTS
DOI:
https://doi.org/10.22159/ajpcr.2018.v11i5.24635Keywords:
Indanyl analogs, Minimum inhibitory concentration, Antibacterial, AntifungalAbstract
 Objective: The wide variety of biological activities of different indane derivatives makes them an interesting moiety in the field of medicinal chemistry. The objective of the study was to identify and develop novel antimicrobial agents from indanyl analogs.
Methods: Recently synthesized indanyl analogs (4a-c and 5a-o) were examined against various pathogenic microorganisms (Gram-positive and Gram-negative bacteria and fungi) using serial dilution method. These analogs were found to possess antibacterial and antifungal activities with minimum inhibitory concentration values ranging between 1.56 and 100 μg/mL.
Results: The results revealed that the entire compounds showed mild-to-moderate antibacterial activities and moderate-to-excellent antifungal activities against the pathogenic microorganisms as compared to the standard drugs ciprofloxacin and fluconazole, respectively. Compounds 4a, 5a, 5b, 5d, 5e, 5i, and 5j exhibited antifungal activities superior to the reference drug.
Conclusion: Based on the structure-activity relationship, it can conclude that the indan-3-oxo-1-acetic acid moiety is essential for the activities and lipophilic alkoxy substituents on indane ring have enhanced the biological activity. Further, structure-activity relationship studies of the compounds 4a, 5a, and 5b are needful to find the new lead as antimicrobial agent.
Downloads
References
Patel A, Giles D, Basavarajaswamy G, Sreedhar C, Patel A. Synthesis, pharmacological evaluation and molecular docking studies of indanone derivatives. Med Chem Res 2012;21:4403-41.
Jubie S, Meena S, Ramaseshu KV, Jawahar N, Vijayakumar S. Synthesis and biological evaluation of some hydrazones and carbazones of indane-1,3-dione. Ind J Chem 2010;49:1261-3.
Patel VM, Bhatt ND, Bhatt PV, Joshi HD. Novel derivatives of 5, 6-dimethoxy-1-indanone coupled with substituted pyridine as potential antimicrobial agents. Arabian J Chem 2014. Available from: http://www.sciencedirect.com/science/article/pii/S1878535214001610.
El-Sheshtawy HS, Abou Baker AM. Synthesis, structural, theoretical studies and biological activities of 3-(Arylamino)-2-phenyl-1H-inden-1-one Derivative. J Mol Struct 2014;1067:225-32.
Fadare OA, Akinpelu DA, Ejemubu H, Obafemi CA. 1-Indanone chalcones and their 2,4-dinitrophenylhydrazone derivatives: Synthesis, physicochemical properties and in vitro antibacterial activity. Afr J Pure Appl Chem 2014;8:68-77.
Jeyachandran M, Ramesh P. Synthesis, antimicrobial, anticoagulant activities of 2-(arylsulfonyl) indane-1, 3-diones. Org Chem Int 2011;47:1-6.
Albrecht R, Kessler HJ, Schroder E. Antimicrobial Indanones. US Patent 3671520, 1972;Filed March 27.
Tithi NS, Hossan MM, Bachar SC. Synthesis and biological activity evaluation of indan-1-carboxylic acid-3-semicarbazone and indan-1-acetic acid-3-semicarbazone. Latin Am J Pharm 2015;34:116-23.
Karthik R, Jasmin SR, Sasikumar S, Kalyan SB, Christina AJ, Athimoolam J, et al. Evaluation of anti-tubercular activity of some synthesised benz spiro-oxirane derivatives of indane-1,3-dione. Pharmacol Online 2008;2:176-91.
Saha DK, Das BK, Chandra S, Datta BK. Synthesis and antitubercular activity of some indanyl thiosemicarbazone derivatives. J Pharm Res Opin 2012;2:125-8.
Charris JE, Lobo GM, Camacho J, Ferrer R, Barazarte A, Dominguez JN, et al. Synthesis and antimalarial activity of (e) 2-(2-chloro-3-quinolinylmethyl idene)-5,7-dimethoxyindanones. Lett Drug Des Discov 2007;4:49-54.
Boettcher I, Elger W, Kirsch G, Siegmund F, Wachtel H. Nonsteroidal antiinflammatory agents 14. Synthesis and pharmacological profile of 6-chloro-5-(cyclopentylmethyl)indan-1-carboxylic acid. J Med Chem 1984;27:413-4.
Sheridan H, Walsh JJ, Cogan C, Jordan M, McCabe T, Passante E, et al. Diastereoisomers of 2-benzyl-2, 3-dihydro-2-(1H-inden-2-yl)-1H-inden-1-ol: Potential anti-inflammatory agents. Bioorg Med Chem Lett 2009;19:5927-30.
Sharma M, Ray SM. Aromatic amide derivatives of 5,6-dimethoxy-2,3-dihydro-1H-inden(-1-yl)acetic acid as anti-inflammatory agents free of ulcerogenic liability. Bioorg Med Chem Lett 2007;17:6790-6.
Mandal SK, Ray SM. Synthesis and biological evaluation of (5,6-dialkoxy-3-oxo-2,3-dihydro-1H-inden-1-yl)acetic acid esters as anti- inflammatory agents with much reduced gastrointestinal ulcerogenic potential. Indo Am J Pharm Res 2014;4:3796-807.
Mandal SK, Ray SM. Synthesis and biological evaluation of (6-chloro-3-oxo-2,3- dihydro-1H-inden-1-yl)acetic acid esters as anti-inflammatory agents devoid of ulcerogenic potential at the tested dose level. Indo Am J Pharm Res 2014;4:343-50.
Saxena HO, Faridi U, Srivastava S, Kumar JK, Darokar MP, Luqman S, et al. Gallic acid-based indanone derivatives as anticancer agents. Bioorg Med Chem Lett 2008;18:3914-8.
Deady LW, Desneves J, Kaye AJ, Finlay GJ, Baguley BC and Denny WA. Positioning of the carboxamide side chain in 11-oxo-11-hindeno[1,2-b]quinoline carboxamide anticancer agents: Effects on cytotoxicity. Bioorg Med Chem 2001;9:445-52.
Finkielsztein LM, Castro EF, Fabián LE, Moltrasio GY, Campos RH, Cavallaro LV, et al. New 1-indanone thiosemicarbazone derivatives active against BVDV. Eur J Med Chem 2008;43:1767-73.
Mostert S, Petzer A, Petzer JP. Indanones as high-potency reversible inhibitors of monoamine oxidase. Chem Med Chem 2015;10:862-73.
Huang L, Miao H, Sun Y, Meng F, Li X. Discovery of indanone derivatives as multi-target-directed ligands against Alzheimer’s disease. Eur J Med Chem 2014;87:429-39.
Rai NP, Narayanaswamy VK, Shashikanth S, Arunachalam PN. Synthesis, characterization and antibacterial activity of 2-[1-(5-chloro-2-methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-5-(substituted-phenyl)-[1,3,4]oxadiazoles. Eur J Med Chem 2009;44:4522-7.
Budhwani S, SharmaS, Kalyane N. Synthesis of aryl (5-substituted benzofuran-2-yl) carbamate derivatives as antimicrobial agents. Asian J Pharm Clin Res 2017;10:377-81.
Xu H, Fan LL. Antifungal agents. Part 4: Synthesis and antifungal activities of novel indole[1,2-c]-1,2,4-benzotriazine derivatives against phytopathogenic fungi in vitro. Eur J Med Chem 2011;46:364-9.
Hassan B, Soumya E, Sanae G, Saad IK. Evaluation of the antifungal activities of three essential oil components against Penicillium expansum spores. Int J Pharm Pharm Sci 2017;9:56-9.
Debnath B, Ganguly S. Synthesis of some novel (2-oxo-3-(arylimino)indolin-1-yl)-n-aryl acetamides and evaluation as antimicrobial agents. Toxicol Environ Chem 2015;97:741-53.
Techaoei S, Eakwaropas P, Jarmkom K, Khobjai W. Structure characterization and evaluation potential of antimicrobial extracts from Phellinus linteus against skin infectious pathogens, Staphylococcus epidermidis atcc12228 and propionibacterium acnes dmst14916. Int J Pharm Pharm Sci 2017;9:78-81.
Published
How to Cite
Issue
Section
The publication is licensed under CC By and is open access. Copyright is with author and allowed to retain publishing rights without restrictions.