Synthesis, characterization and in vitro antimicrobial activity of cyclic imide: Isoindoline-1, 3-dione derivatives

Shipra Baluja; Sumitra Chanda; Kalpen Chavda

doi:10.30574/gscbps.2020.10.1.0243

Authors

Shipra Baluja Department of Chemistry, Saurashtra University, Rajkot-360005 (Gujarat), India.
Sumitra Chanda Department of Biosciences Saurashtra University, Rajkot-360005 (Gujarat), India.
Kalpen Chavda Department of Chemistry, Saurashtra University, Rajkot-360005 (Gujarat), India.

DOI:

https://doi.org/10.30574/gscbps.2020.10.1.0243

Keywords:

Cyclic imide, Isoindoline-1, 3-dione derivatives, N, N-dimethyl formamide, Dimethyl sulfoxide, Gram positive bacteria, Gram negative bacteria, Fungal strains

Abstract

A series of new cyclic imide: isoindoline-1, 3-dione derivatives were synthesized by condensation of 2-hydrazinyl-2-oxo-N-phenylacetamide and phthalic anhydride. The characterization of synthesized compounds was done by IR, ¹H NMR, ¹³C NMR and mass spectroscopy. All these synthesized compounds were tested for in vitro antimicrobial against various bacterial and fungal strains in N, N-dimethyl formamide and Dimethyl sulfoxide. It is observed that almost all the compounds showed moderate antimicrobial activity and N, N-dimethyl formamide is better solvent than dimethyl sulfoxide.

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References

Sultana K, Khan N and Shahid K. (2014). Synthesis characterization and in vitro antibacterial evaluation of Sn, Sb, and Zn coordination complexes of 2-(2-methoxyphenyl)-1H-isoindole-1, 3 (2h)-dione. Int. J. Pharm. Sci. Rev. Res., 28, 1-5.

Alaa A,Angeli A, El-Azab A, El-Enin M and Supuran C. (2017). Synthesis and biological evaluation of cyclic imides incorporating benzenesulfonamide moieties as carbonic anhydrase I, II, IV and IX inhibitors, Bioorg. Med. Chem. 25, 1666-1671.

El‐Kabbani O, Darmanin C, Schneider T, Hazemann I, Ruiz F, Oka M, Joachimiak A, Schulze‐Briese C, Tomizaki T,Mitschler A and Podjarny A. (2004). Ultrahigh resolution drug design. II. Atomic resolution structures of human aldose reductase holoenzyme complexed with Fidarestat and Minalrestat: implications for the binding of cyclic imide inhibitors, Proteins: Struc. Func. Bioinform., 55, 805-813.

Kushwaha N and Kaushik D. (2016). Recent advances and future prospects of phthalimide derivatives, J. App. Pharma. Sci.,6, 159-71.

Asif M. (2019). A Review on Biological and Chemical Potential of Phthalimide and Maleimide Derivatives,Acta Sci. Pharm. Sci., 3, 51-67.

Patil M and Rajput S. (2016). Synthesis and Antimicrobial evaluation of some novel Diazo derivative of Cyclic Imides using Diazotization coupling reaction, Chem. Sci. Rev. Lett., 517, 46-52.

Ahmed W, Mahmood A and Al-Bayati R. (2018). Synthesis and Evaluation of Antimicrobial Activity of New Imides and Schiff Bases Derived from Ethyl-4-Amino Benzoate, Orient. J. Chem., 34, 2477-2486.

Kumari S, Gupta V, Singh S and Gupta Y. (2019).Synthesis, Characterization and Antimicrobial Activities of five and six member Cyclic Imides Derivatives, Res. J. Sci. Tech., 11, 82-86.

Stiz D, Corrêa R, Dauria F,Simonetti G and Cechinel-Filho V. (2016). Synthesis of cyclic imides (Methylphtalimides, carboxylic acid phtalimides and itaconimides) and evaluation of their antifungal potential, Med. Chem., 12, 647-654.

Chaudhari P and Rajput S. (2016). One pot synthesis and antimicrobial evaluation of some novel bis-chalcones and pyrazoles from cyclic imides under microwave irradiation, World J. Pharm. Res., 5, 1301-1313.

Torres E, Duque M, Camps P, Naesens L, Calvet T, Font‐Bardia M and Vázquez S. (2010). Polycyclic N‐Benzamido Imides with Potent Activity against Vaccinia Virus, Chem. Med. Chem., 5, 2072-2078.

Dhivare S and Rajput S. (2015).Synthesis and antimicrobial activity of five membered cyclic imide derivatives of mono, di and tri substituted aromatic amines and napthyl amine, World J. Pharm. Sci., 4,1650-1658.

Andricopulo A, Muller L, CechinelFilho V, Cani G,Roos J, Correa R, Santos A, Nunes R and Yunes R. (2000) Analgesic activity of cyclic imides: 1, 8-naphthalimide and 1, 4, 5, 8-naphthalenediimide derivatives, Farmaco, 55, 319-321.

Alanazi A, El-Azab A, Al-Suwaidan I, ElTahir K, Asiri Y, Abdel-Aziz N and Alaa A. (2015). Structure-based design of phthalimide derivatives as potential cyclooxygenase-2 (COX-2) inhibitors: anti-inflammatory and analgesic activities. European journal of medicinal chemistry, 92, 115-123.

Muller G, Konnecke W, Smith A and Khetani V. (1999).A concise two-step synthesis of thalidomide, Org. Process Res. Dev., 3, 139-140.

W Figg, Eger K, Teubert U, Weiss M, Guetschow M, Hecker T and Hauschildt S. (2008). Analogs of thalidomide as potential angiogenesis inhibitors, National Institutes of Health (NIH), U.S. Patent, 7, 320,991.

Makonkawkeyoon S, Limson-Pobre R, A Moreira, V Schauf and G Kaplan. (1993). Thalidomide inhibits the replication of human immunodeficiency virus type 1. Proc. Natl. Acad. Sci., 90, 5974-5978.

Figg W, Raje S, Bauer K, Tompkins A, Venzon D, Bergan R, Chen A, Hamilton M, Pluda J and Reed E. (1999). Pharmacokinetics of thalidomide in an elderly prostate cancer population, J. Pharm. Sci., 88, 121-125.

Sperka T, Pitlik J, Bagossi P and Tozser J. (2005) Beta-lactam compounds as apparently uncompetitive inhibitors of HIV-1 protease. Bioorg. Med. Chem. Lett., 15, 3086-3090.

Ebrahimi E, Jarrahpour A, Heidari N, Sinou V, Latour C, Brunel J, Zolghadr A and Turos E. (2016)Synthesis and antimalarial activity of new nanocopolymer β-lactams and molecular docking study of their monomers, Med. Chem. Res., 25(2), 247-262.

Sondhi S, Rani R, Roy P, Agrawal S and Saxena A. (2009). Microwave-assisted synthesis of N-substituted cyclic imides and their evaluation for anticancer and anti-inflammatory activities, Bioorg. Med. Chem. Lett.,19, 1534-1538.

Alaa A, El-Azab A, Ghiaty A, Gratteri P, Supuran C and Nocentini A. (2019).4-Substituted benzenesulfonamides featuring cyclic imides moieties exhibit potent and isoform-selective carbonic anhydrase II/IX inhibition, Bioorg.Chem.,83, 198-204.

Patil M and Rajput S. (2014). Succinimides: Synthesis, reaction and biological activity. Int. J. Pharm. Pharm. Sci,6, 8-14.

Campos F, Correa R, de Souza M, Yunes R, Nunes R and Cechinel-Filho V. (2002).Studies on new cyclic imides obtained from aminophenazone with analgesic properties, Arzneimittelforsch., 52, 455-461.

Machado M,Lima L, Araujo-Jr J, Fraga C, Koatz V and Barreiro E. (2005). Design, synthesis and anti-inflammatory activity of novel phthalimide derivatives, structurally related to thalidomide, Bioorg. Med. Chem.Lett.,15, 1169-1172.

Zimmermann-Franco D, Esteves B, Lacerda L, I de Oliveira Souza, J dos Santos, N Pinto, E Scio, A da Silva and G Macedo. (2018). In vitro and in vivo anti-inflammatory properties of imine resveratrol analogues,Bioorg. Med. Chem.,26, 4898-4906.

Hassanzadeh F, Rabbani M, Fasihi A, Hakimelahi G and Mohajeri M. (2008).Synthesis of phthalimide derivatives and evaluation of their anxiolytic activity, Res. Pharm. Sci., 2, 35-41.

Gajare S and Mahajan S. (2012).QSAR studies of phthalimide derivatives for their potent anxiolytic activity. Int. J. Cur. Res. Rev., 4, 151-156.

De Munck L, Vila C and Pedro J. (2018).Catalytic Asymmetric Reactions Involving the Seven‐Membered Cyclic Imine Moieties Present in Dibenzo [b, f] [1, 4] oxazepines, Eur. J. Org. Chem., 2, 140-146.

Stratford E and Curley Jr R. (1983). Synthesis of aminomethyl-substituted cyclic imide derivatives for evaluation as anticonvulsants, J. Med.Chem., 26, 1463-1469.

Kathuria V and Pathak D. (2012).Synthesis and anticonvulsant activity of some N-substituted-phthalimide analogs. The Pharma.Innov., 1, 55-59.

Sena V, Srivastava R, Silva R and Lima V. (2003).Synthesis and hypolipidemic activity of N-substituted phthalimides. Part V, Farmaco., 58, 1283-1288.

Musso D, Cochran F, Kelley J, McLean E, Selph J, Rigdon G, Orr G, Davis R, Cooper B, Styles V, Thompson J and Indanylidenes. (2003). Design and synthesis of (E)-2-(4, 6-difluoro-1-indanylidene) acetamide, a potent, centrally acting muscle relaxant with anti-inflammatory and analgesic activity. J. Med. Chem., 46, 399-408.

Anderson A, Kiernan M and Ho P. (2019). Lenalidomide-related Progressive Multifocal Leukoencephalopathy: A Case Report and Review of Drug-related Cases in Multiple Myeloma,Clin. Lymphoma Myeloma Leuk., 19, 169-171.

E Eleutherakis-Papaiakovou, M Gavriatopoulou, I Ntanasis-Stathopoulos, E Kastritis, ETerpos and M Dimopoulos. (2019). Elotuzumab in combination with pomalidomide and dexamethasone for the treatment of multiple myeloma,Expert Rev. Anticancer Ther., 19, 1-8.

Metyas S, Tomassian C, Messiah R, Gettas T, Chen C and Quismorio A. (2019). Combination therapy of apremilast and biologic agent as a safe option of psoriatic arthritis and psoriasis, Curr. Rheumatol. Rev., 15, 234-237.

Nagasawa H, Elberling J and Shirota F. (1980). Latentiated forms of the transport‐inhibitory α‐amino acid adamantanine. J.Pharm. Sci., 69, 1022-1025.

Hall I, Wong O and Scovill J. (1995).The cytotoxicity of N-pyridinyl and N-quinolinyl substituted derivatives of phthalimide and succinimide, Biomed. Pharm., 49, 251-258.

Riddick J, Bunger W and Sakano T. (1986). Organic solvents: Physical properties and methods of purification, Fourth Edition., Techniques of Chemistry, II, A Wiley-Inter science Publication, John Wiley, New York.

Parekh J, Inamdhar P,Nair R,Baluja R and Chanda S. (2005). Synthesis and antibacterial activity of some Schiff bases derived from 4-aminobenzoic acid, J. Serb. Chem. Soc., 70, 1155-1158.