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Synthesis, Characterization and Anti-Bacterial Activity of Isatin Schiff Base Derivatives


Affiliations
1 T. John College of Pharmacy, Basavanapura, Bengaluru, Karnataka - 560083, India
2 Department of Pharmaceutical Chemistry, T. John College of Pharmacy, Basavanapura, Bengaluru, Karnataka - 560083, India
 

Initially, Isatin was treated with 4-amino acetanilide to form Isatin Schiff base, by the reaction of the free amino group on4-amino acetanilide with carbonyl group of Isatin in the presence of ethanol and glacial acetic acid with the elimination of water molecule. The obtained Isatin Schiff base was then treated with substituted aromatic aldehydes in the presence of potassium hydroxide and ethanol to form various Chalcone derivatives (C1-C7). The structures of the synthesized compounds (C1-C7) were examined and confirmed using IR, Mass spectroscopy, 1H-NMR and elemental analysis. By agar disc diffusion method, all given compounds were evaluated for their anti-bacterial activity against four bacteria at concentrations 25, 50 and 100 μg/ml. C4 and C6, were discovered to have possessed the most potent anti-bacterial activity.


Keywords

Aromatic Aldehyde, Antibacterial, Agar Disc Diffusion Method, Chalcone, Isatin, Schiff Base.
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  • Bhrigu B, Pathak D, Siddiqui N. Search for biological activity Isatins: A short review. Int J of Pharm Sci Drug Res. 2010; 2(4):229–35.
  • Erdmann OL, Untersuchungen uber den Indigo. Journal fur Praktische Chemie. 1840; 19(1):321–62. https://doi.org/10.1002/prac.18400190161
  • Singh UK, Pandeya SN, Singh A, Srivastava BK, Pandey M. Synthesis and antimicrobial activity of schiff ’s and N-mannich bases of isatin and its derivatives with 4-aminocarbamimidoyl benzene sulfonamide. Int J Pharm Sci Drug Res. 2010; 2:151–4.
  • Pandeya SN, Sriram D, Nath G, Clercq ED. Synthesis, antibacterial, antifungal and antiHIV activity of Schiff and Mannich bases of isatin with N-6-chlorobenzthiazol-2ylthiosemicarbazide. Indian J Pharm Sci. 1999; 61:358–61.
  • Ozlen G, Nilgun K, Aydın S. Synthesis and antituberculosis activity of 5- methyl/trifluoromethoxy-1H-indole-2,3dione 3-thiosemicarbazone derivatives: Bioorg Med Chem. 2008; 16:8976–8987. https://doi.org/10.1016/j.bmc.2008.08.050 PMid:188043796.
  • Hoyun L, Solomon VR, Changkun H. Hybrid pharmacophore design and synthesis of isatin. Chemistry: Bioorg Med Chem. 2009; 17:7585–92.
  • Gummadi SB, Nanam R, Puttireddy SM, Bethi S, Umasankar K, Jupally VR. Synthesis, characterization and evaluation of novel N-(1Hbenzimidazol-2-yl)-2-Isatinylidene hydrazine carboxamide derivatives as anti-inflammatory agents. Der Pharma Chemica. 2010; 2:196–204.
  • Prakash CR., Raja S, Saravanan G, Dinesh KP, Panneer S. Synthesis and evaluation of antioxidant activities of some novel isatin derivatives and analogs: Asian J Res Pharm Sci. 2011; 1:140–3.
  • Shibinskya MO, Lyakhov SA, Mazepa AV, Andronati SA. Synthesis, cytotoxicity, antiviral activity and interferon inducing ability of 6-(2-aminomethyl)-6H-indolo [2, 3-b] quinoxalines: Euro J Med Chem. 2010; 45:1237–43. https:// doi.org/10.1016/j.ejmech.2009.12.014 PMid:2005651910.
  • Prince PS, Pandeya S, Roy RK, Anurag, Verma K, Gupta S. Synthesis and anticonvulsant activity of some novel isatin schiff ’s bases: Int J Chem Tech Res. 2009; 1:758–63.
  • Zapata-Sudo G, Luana B, Daniele G, Thaiana CFM, Nubia MR, Angelo CP, Margarete M. Trachez., Roberto TS., Sedative–hypnotic profile of novel isatin ketals, Pharmacology. Biochem Behavior. 2007; 86:678–85. https://doi.org/10.1016/j.pbb.2007.02.013 PMid:1738299512.
  • Kang IJ, Wang LW, Hsu TA, Yueh A, Lee CC, Lee YC. Isatin-beta-thiosemicarbazones as potent herpes simplex virus inhibitors. Bioorg Med Chem Lett. 2011; 21: 1948–52. https://doi.org/10.1016/j.bmcl.2011.02.037 PMid:2135658913.
  • Paira P, Hazra A, Kumar S, Paira R, Sahu KB, Naskar S, Saha P, Mondal S, Maity A, Banerjee S, Mondal NB. Efficient synthesis of 3,3-diheteroaromatic oxindole analogues and their in vitro evaluation for spermicidal potential. Bioorg Med Chem Lett. 2009; 19:4786–9. https://doi.org/10.1016/j.bmcl.2009.06.049 PMid:1956410914.
  • Quraishi MA, Ahamad I, Singh AK, Shukla SK. N(Piperidinomethyl)-3-[(pyridylidene)amino]isatin: A new and effective acid corrosion inhibitor for mild steel. Mater Chem Phys. 2008; 3:1035–39. https://doi.org/10.1016/j.matchemphys.2008.07.011
  • Figueiredo GS, Zardo RS, Silva BV, Violante FA, Pinto AC, Fernandes PD. Convolutamydine A and synthetic analogues have antinociceptive properties in mice. Pharmacol Biochem. B. 2013; 3:431–9. https://doi.org/10.1016/j.pbb.2012.09.023 PMid:2304685216.
  • Nagihan B, Kocyigit-Kaymakcioglu B, Salih G, Aricioglu F. Synthesis and anticonvulsant activity of some 2- pyrazolines derived from chalcones. Arab J Chem. 2013; 7:37.
  • Andreani A, Burnelli S, Granaiola M, Leoni A, Locatelli A, Morigi R, Rambaldi M, Varoli L, Cremonini MA, Plaucci G, Cervellati R, Greco E. New isatin derivatives with antioxidant activity. Eur J Med Chem. 2010; 45:1374–8. https://doi.org/10.1016/j.ejmech.2009.12.035 PMid:2006020218.
  • Kumar K, Carrere-Kremer S, Kremer L, Guerardel Y, Biot C, Kumar V. 1H-1,2,3-triazole-tethered isatin-ferrocene and isatin-ferrocenylchalcone conjugates: synthesis and in Vitro antitubercular evaluation. Organometallics. 2013; 32:110–6. https://doi.org/10.1021/om301157z
  • Gonzalez A, Quirante J, Nieto J, Almeida MR, Saraiva MJ, Planas A, Arsequell G, Valencia G. Isatin derivatives, a novel class of transthyretin fibrillogenesis inhibitors. Bioorg Med Chem Lett. 2009; 19: 5270–73. https://doi.org/10.1016/j.bmcl.2009.03.004 PMid:1965150920.
  • Manley-King CI, Bergh JJ, Petzer JP. Inhibition of monoamine oxidase by selected C5- and C6-substituted isatin analogues. Bioorg Med Chem. 2011; 19:261–74. https://doi.org/10.1016/j.bmc.2011.06.070 PMid:2113475621.
  • Prakash CR, Raja S. Design, synthesis and antiepileptic properties of novel 1-(substituted benzylidene)-3-(1(morpholino/piperidino methyl)-2,3-dioxoindolin-5-yl) urea derivatives. Eur J Med Chem. 2011; 46:6057–65. https://doi.org/10.1016/j.ejmech.2011.10.020 PMid:2203725222.
  • Ananthanarayana R, Pariker JCK. Text book of microbiology. 5th ed. Chennai: Orient Longan Ltd; 1987. p. 620–1.

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  • Synthesis, Characterization and Anti-Bacterial Activity of Isatin Schiff Base Derivatives

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Authors

Justin Ebuka Ezekwem
T. John College of Pharmacy, Basavanapura, Bengaluru, Karnataka - 560083, India
D. Visagaperumal
Department of Pharmaceutical Chemistry, T. John College of Pharmacy, Basavanapura, Bengaluru, Karnataka - 560083, India
Vineeth Chandy
T. John College of Pharmacy, Basavanapura, Bengaluru, Karnataka - 560083, India

Abstract


Initially, Isatin was treated with 4-amino acetanilide to form Isatin Schiff base, by the reaction of the free amino group on4-amino acetanilide with carbonyl group of Isatin in the presence of ethanol and glacial acetic acid with the elimination of water molecule. The obtained Isatin Schiff base was then treated with substituted aromatic aldehydes in the presence of potassium hydroxide and ethanol to form various Chalcone derivatives (C1-C7). The structures of the synthesized compounds (C1-C7) were examined and confirmed using IR, Mass spectroscopy, 1H-NMR and elemental analysis. By agar disc diffusion method, all given compounds were evaluated for their anti-bacterial activity against four bacteria at concentrations 25, 50 and 100 μg/ml. C4 and C6, were discovered to have possessed the most potent anti-bacterial activity.


Keywords


Aromatic Aldehyde, Antibacterial, Agar Disc Diffusion Method, Chalcone, Isatin, Schiff Base.

References