Home About us Editorial board Ahead of print Current issue Search Archives Submit article Instructions Subscribe Contacts Login 
  • Users Online: 238
  • Home
  • Print this page
  • Email this page

 Table of Contents  
Year : 2017  |  Volume : 12  |  Issue : 6  |  Page : 526-534

Synthesis and evaluation of antimicrobial activity of cyclic imides derived from phthalic and succinic anhydrides

1 Department of Medicinal Chemistry and Isfahan Pharmaceutical Sciences Research Center, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, I.R. Iran
2 Department of Medicinal Chemistry, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, I.R. Iran
3 Department of Pharmaceutical Biotechnology and Isfahan Pharmaceutical Sciences Research Center, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, I.R. Iran

Date of Web Publication3-Nov-2017

Correspondence Address:
Farshid Hassanzadeh
Department of Medicinal Chemistry and Isfahan Pharmaceutical Sciences Research Center, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan
I.R. Iran
Login to access the Email id

Source of Support: None, Conflict of Interest: None

DOI: 10.4103/1735-5362.217433

Rights and Permissions

Cyclic imides are a group of compounds which have valuable biological properties including cytotoxic, anti-inflammatory, antibacterial and antifungal activities. In this study, succinic and phthalic anhydrides were treated with glycinamide in pyridine to yield the corresponding amic acids. These amic acids underwent ring closure with acetic anhydride and anhydrous sodium acetate to form cyclic imides. In another procedure, succinic and phthalic anhydrides upon reaction with 2-amino-benzylamine in pyridine gave the corresponding cyclic imides. The imides were screened for their antimicrobial activities against three types of bacteria and one type of fungi. Phthalimide derived from benzylamine exhibited remarkable antimicrobial activity against E. coli.

Keywords: Cyclic imides; Glycinamide; 2-Amino-benzylamine; Antimicrobial

How to cite this article:
Jafari E, jarah-Najafabadi NT, Jahanian-Najafabadi A, Poorirani S, Hassanzadeh F, Sadeghian-Rizi S. Synthesis and evaluation of antimicrobial activity of cyclic imides derived from phthalic and succinic anhydrides. Res Pharma Sci 2017;12:526-34

How to cite this URL:
Jafari E, jarah-Najafabadi NT, Jahanian-Najafabadi A, Poorirani S, Hassanzadeh F, Sadeghian-Rizi S. Synthesis and evaluation of antimicrobial activity of cyclic imides derived from phthalic and succinic anhydrides. Res Pharma Sci [serial online] 2017 [cited 2022 Oct 3];12:526-34. Available from: https://www.rpsjournal.net/text.asp?2017/12/6/526/217433

  Introduction Top

Cyclic imides and their N-derivatives as an important class of organic compounds, contain bis-amide linkages with a general structure of [-CO-N(R)-CO-]. Their hydrophobicity and neutral structures enable them to easily cross biological membranes [1],[2],[3],[4],[5],[6]. These molecules are reported to exhibit valuable biological effects including antifungal [7],[8],[9], antibacterial [10],[11],[12],[13],[14] anticancer, apoptosis induction [6],[15], anti-inflammatory [16], androgen receptor antagonists [3], anxiolytic, and anticonvulsant [2],[3]. Structure activity relationship studies of these systems in some literatures revealed that incorporation of heterocyclic moiety in the imide portion or linkage with nitrogen improve their anti-inflammatory and antitumor activities. Antitubercular activity was reported for cyclic imides with a para-sulphonamide group [1],[3]. These molecules could be used as building blocks in the synthesis of natural products such as coumarins and atacoumarins and also as core structures in the design and synthesis of peptidomimetics [1],[3]. The alkaloid phyllanthimide isolated from leaves of Phyllanthus sellowianus (euphorbiaceae) has been used as a precursor for the synthesis of some analogs of cyclic imides [1]. Some examples with cyclic imide structure are shown in [Figure 1]. Gayoso, et al. have reported antifungal effectiveness of 3,4-dichloro-N-phenyl-alkyle-maleimide derivatives. Compounds 3, 4-dichloro-N-phenyl-methyl-maleimide and 3,4-dichloro-N-phenyl-propilmaleimide displayed antifungal activities with MIC of 100 μg/mL against fungal strains [7]. Sultana, et al. succeeded to synthesize 2-(2-methoxyphenyl)-1H-isoindole- 1, 3(2H)-dione ligand and some of the metal complexes by using a simple method. Synthesized complexes exhibited improved antibacterial effects in comparison to their parent ligand [14].
Figure 1: Some dugs with cyclic imide structure.

Click here to view

Al-Azzawi, et al. synthesized N-(2-acetyl amino-5-substituted -1, 3, 4-oxadiazole -2-yl)- 1,8-naphthalimide derivatives with remarkable antimicrobial activity against E. coli [17] [Figure 2].
Figure 2: Cyclic imides with antimicrobial activity.

Click here to view

There are some procedures available for cyclic imides synthesis, such as the dehydrative condensation of a cyclic anhydride and amine [2], the use of expensive catalysts [18], and microwave synthesis [9]. In this study, the first method, with some modifications was used to prepare the compounds.

  Materials and Methods Top


Melting points were determined in open capillaries using electrothermal 9200 melting point apparatus (UK) (England) and are uncorrected. IR (KBr discs) was recorded with a WQF-510 FT-IR spectrophotometer (China). 1H-NMR spectra were recorded on Bruker 400 MHz spectrometers (Germany) using TMS as an internal standard and either DMSO-d6 or CDCl3 as solvents. Mass spectra were recorded on Finnigan TSQ-70 Mass spectrometer (United States). All chemicals were purchased from Merck Company (Germany).

Amic acids synthesis procedures from (2-amino acetamide or glycinamide) (A1G, A2G, A3G)

Phthalic, succinic and maleic anhydride (0.01 mol) and glycinamide (0.01 mol) were transferred separately to round bottom flasks and then freshly distilled and dried pyridine was added slowly while shaking. The mixture was heated under refluxed for 5 h. Excess of pyridine was distilled off under reduced pressure, and then methanol was added to residue to obtain crystalline solids [Figure 3].
Figure 3: Synthesis of cyclic imides of (2-amino acetamide or glycinamide).

Click here to view

Preparation of phthalimide

Obtained amic acid of phthalic anhydride (0.01 mol) in 20 mL acetic anhydride and 0.001 mol anhydrous sodium acetate was refluxed with stirring for 4 h [4],[12],[17]. The resulted homogenous solution was cooled to room temperature and then poured into excess cold water with vigorous stirring. The obtained precipitate was filtered, washed with distilled water, dried and finally purified by column chromatography on silica gel using CHCl3- MeOH (49:1) as eluent to give FA1G and FA1GAc [Figure 3].

Preparation of succinimide

Obtained amic acid of succinic anhydride (0.01 mol) was dissolved in acetic anhydride (20 mL) and anhydrous sodium acetate (0.001 mol) and refluxed with stirring for 4 h [4],[12],[17]. The solvent was removed by distillation under reduced pressure.

The obtained residue was dissolved in chloroform, then solvent was removed by distillation under reduced pressure. The obtained product was purified by column chromatography on silica gel using CHCl3- MeOH (49:1) as eluent to afford FA3G [Figure 3].

Preparation of cyclic imides of (2-amino benzylamine)

Preparation of phthalimide

Phthalic anhydride (0.01 mol) and 2-aminobenzylamine (0.01 mol) were placed in a round bottom flask and freshly distilled and dried pyridine was then added slowly while shaking. The mixture was heated under reflux for 5 h. The solvent was distilled off under reduced pressure. Obtained residue was dissolved in ethyl acetate and purified by column chromatography to afford A1B [Figure 4].
Figure 4: Synthesis of cyclic imides of (2-amino benzylamine).

Click here to view

Preparation of succinimide

Succinic anhydride (0.01 mol) and 2-aminobenzylamine (0.01 mol) were put in a round bottom flask and freshly distilled and dried pyridine was then added slowly while shaking. The mixture was heated under reflux for 5 h. Excess of pyridine was distilled off under reduced pressure; then ethanol and water were added to the residue to obtain light brown precipitant A3B [Figure 4].

Antimicrobial activity

Microorganisms were obtained from Persian Type Culture Collection (PTCC). Staphylococcus aureus PTCC1337 as Gram-positive,  Escherichia More Details coli, PTCC 1338 and Pseudomonas aeruginosa, PTCC1074, as Gram-negative bacteria and Candida albicans PTCC, 5027 as fungus. Mueller Hinton Agar, Mueller Hinton Broth and Sabouraud Dextrose Agar were purchased from Merck (Germany) Roswell Park Memorial Institute (RPMI)-1640 culture medium was procured from Gibco, USA.

Microplate alamar blue assay (MABA) for antimicrobial evaluation

The inocula of bacterial and fungal strains (1.5 × 108 CFU/mL) were prepared from Mueller Hinton Agar and Sabouraud Dextrose Agar cultures respectively. Prepared suspensions of bacteria were adjusted to 0.5 Mc Farland standard turbidity and the fungal suspensions turbidity was measured spectrometrically at 580 nm. Finally, prepared inoculum density for bacterial and fungal strains were equal to 1.0 × 105 CFU/mL and 1.0 × 106 CFU/mL respectively. The synthesized compounds were dissolved in DMSO (0.5 mL) and diluted with water up to 1 mL to obtain concentration of 5120 μg/mL as the stock solution. The stock solution was serially diluted to give concentrations of 2560 to 80 μg/mL.

Mueller Hinton Broth was used as medium for bacterial growth and RPMI 1640 was used as medium for fungal growth. 20 μL of bacterial suspension was distributed in all 96 wells of microplate.

Then 20 μL of each concentration of the compounds were added to wells with the exception of those wells acting as positive control (containing standard antibiotic) and growth control (containing culture media without testing materials). After adding alamar blue (20 μL) to all of 96 wells the total volume in each well was adjusted to 200 μL using culture medium.

The final concentrations of the compounds in the wells were 512, 256, 32, 16, and 8 μg/mL. After incubation, the MIC was defined as the lowest concentration, which prevented a color change from blue to pink. The test was carried out in triplicates.

Following the MIC test, the content of each well that showed no growth was removed and spread onto a plate containing appropriate medium for bacteria and fungi to determine MBC (minimum bactericidal concentration) and MFC (minimum fungicidal concentration) results.

Pharmacokinetic parameters estimation using Swiss ADME

Absorption and Lipinski's “rule of five” parameters of the compound A1B which exhibited remarkable antimicrobial activity were calculated using online Swiss ADME. Lipinski's “rule of five” including molecular weight (MW), number of H-bond donors (NHBD), number of H-bond acceptors (NHBA) and log P are widely used as a filter for drug-like properties [19].

  Results Top

4-(2-amino-2-oxoethylamino)-4-oxobut-2- enoic acid (A2G)

Brown powder, yield: 40%, m.p.: 244-246 °C, MS (m/z, %): 172 (100) for C6H8N2O4, M.W.: 172.14, IR (KBr, cm-1), 3420, 3324 (NH2), 3197 (NH), 1702,1 657 (C=O). 1H-NMR δH (400 MHz; DMSO), 8.70 (1H, t, J = 4Hz, NH), 7.4, 7.04 (2H, s, NH2), 6.98 (1H, d, J = 15.2 Hz, OH-CO-CH=CH-CONH-CH2-CO-NH2), 6.50 (1H, d, J = 15.6 Hz, OH- CO- CH=CH-CONH-CH2-CO-NH2), 3.73 (2H, d, J = 4 Hz, OH-CO-CH=CH-CONH-CH2-CO- NH2).

4-(2-amino-2-oxoethylamino)-4-oxobutanoic acid (A3G)

White powder, yield: 50%. m.p.: 155-157 °C, MS (m/z, %): 174 (100) for C6H10N2O4, M.W.: 174.15, IR (KBr, cm-1), 3422, 3332 (NH2), 1718, 1651 (C=O).1H-NMR (400 MHz, DMSO) δ: 12.1 (1H, OH), 8.11 (1H, t, J = 4 Hz, NH), 7.1, 7.03 (2H, s ,NH2), 3.6 (2H, d, J = 4 Hz, OH-CO-CH2-CH2-CONH-CH2-CO- NH2), 2.43 (2H, t, J = 8 Hz, OH-CO-CH2-CH2-CONH-CH2-CO-NH2), 2.37 (2H, t, J = 8 Hz, OH-CO-CH2-CH2-CONH-CH2-CO-NH2).

2-(1, 3-dioxoisoindolin-2-yl) acetamide (FA1G)

White powder, yield: 40% , m.p.: 255-256 °C (lit. 255-257 °C), MS (m/z, %): 204 [6] for C10H8N2O3, M.W.: 204.18, IR (KBr, cm-1), 3413, 3321 (NH2), 3066 (CH, Ar), 1770, 1682 (C=O) 1H-NMR (400 MHz, DMSO) δ: 7.88 (2H, dd, J = 6 Hz, J = 2.8 Hz, CO-C=CH-CH=CH-CH=C-CO), 7.86 (2H, dt, J = 6 Hz, J = 2.8 Hz CO-C=CH-CH=CH-CH=C-CO), 4.13 (2H, s, CH2), 7.68, 7.23 (NH2, s).

N-[2-(1, 3-dioxoisoindolin-2-yl) acetyl]- acetamide (FA1GAc)

White powder, yield: 10%, m.p.: 263-265 °C, C12H10N2O4, M.W.: 246, IR (KBr, cm-1), 3237 (NH), 3097 (CH, Ar), 1783, 1640, 1690 (C=O), 1H-NMR (400 MHz, CDCl3) δ: 8.35, (NH, s) , 7.89 (2H, dd, J = 5.2 Hz, J = 3.2 Hz, CO-C=CH-CH=CH-CH=C-CO), 7.75 (2H, dt, J = 5.2 Hz, J = 3.2 Hz CO-C=CH-CH= CH-CH=C-CO), 4.81 (2H, s, CH2), 2.27 (3H,s, CH3).

2-(2, 5-dioxopyrrolidin-1-yl) actamide (FA3G)

White powder, yield: 23 %, m.p.: 165-167.5 °C, MS (m/z, %), 156 (6) for C6H8N2O3, M.W.: 156, IR (KBr, cm-1), 3413, 3321 (NH2), 1770, 1682 (C=O) 1H-NMR (400 MHz, CDCl3) δ: 5.51 (2H, s, NH2), 4.14 (2H, s, CH2), 2.75 (4H, s, O=C -CH2-CH2-C=O).

Isoindolo [1,2-b]quinazolin-12(10H)-one (A1B)

Yellow powder, yield: 30% , m.p.: 174-176 °C (lit. 175-177 °C), MS (m/z, %): 234 (6) for C15H10N2O, M.W.: 234, IR (KBr, cm-1), 1650 (C=N), 1601 (C=C), 1H-NMR (400 MHz, CDCl3) δ: 8.08 (1H, d, J = 7.2 Hz, N-CO-C=CH-CH=CH-CH=C-C=N), 7.92 (1H, d, J = 8Hz, N-CO-C=CH-CH=CH-CH=C-C=N), 7.67-7.74 (2H, t, J = 8 Hz, N-CO-C=CH-CH=CH-CH=C-C=N), 7.51 (1H, d, J = 8 HZ, N-C=CH-CH=CH-CH =C-CH2), 7.34 (1H, t, J = 8 Hz, N-C=CH-CH=CH-CH =C-CH2), 7.25 (1H, t, J = 8 Hz, N-C=CH-CH=CH-CH=C-CH2), 7.21 (1H, d, J = 8 Hz, N-C=CH- CH=CH-CH =C-CH2), 5.01 (2H, s, CH2).

2, 3-dihydropyrrolo [2, 1-b]quinazoline-1 (9H)-one (A3B)

Light brown powder, yield: 30% , m.p.: 165-166 °C (lit. 185-187 °C), C11H10N2O,

M.W.: 186, IR (KBr, cm-1), 3026, 3066 (CH, Ar), 1685 (C=N), 1662 (C=O), 1H-NMR (400 MHz, CDCl3) δ: 7.23-7.06 (4H, m, Ar-H), 4.85 (2H, s, CH2), 2.94 (2H, t, J = 4 Hz CH2- C=O), 2.68 (2H, t, J = 4 Hz, CH2-C=N).

Results of online Swiss ADME software

Absorption and Lipinski's “rule of five” properties of the compound A1B are shown in [Table 1].
Table 1: Absorption and Lipinski parameters of A1B.

Click here to view

Antimicrobial results

The MICs of all tested compounds were evaluated at concentrations 8 to 512 μg/mL. Compound A1B showed significant inhibition at 16 μg/mL concentration against E. coli as a gram-negative bacteria.

Results of MIC, MBC and MFC are depicted in [Table 2] and [Table 3].
Table 2: Minimum inhibitory concentrations of synthesized compounds against bacteria and fungi.

Click here to view
Table 3: Minimum fungicidal and minimum bactericidal concentrations of synthesized compounds against bacteria and fungi.

Click here to view

  Discussion Top

In the first step to produce cyclic imides, the reaction was proceed via nucleophilic attack of amino group (NH2-CH2) of glycinamide on one carbonyl group in cyclic anhydrides to yield corresponding amic acids. Treatment of amic acids with acetic anhydride gave the cyclic imides through dehydrative cyclization mechanism [Figure 5]. In another procedure, benzylic amine of 2-amino-benzylamine acted as a nucleophile and attacked the carbonyl group of the cyclic anhydride which resulted in the ring opening and subsequently forming the cyclic imides. NH2-ph group of 2-amino-benzylamin attacked the carbonyl group of cyclic imide and the second ring closure was achieved simultaneously to produce cyclic imide [Figure 6]. Reaction between maleic anhydride and the same amines could not produced cyclic imides by these methods.
Figure 5: Proposed mechanism for the synthesis of compound.

Click here to view
Figure 6: Proposed mechanism for the synthesis of compound A1B.

Click here to view

IR spectra of the prepared imides (FA1G and FA3G) showed disappearance of absorption bands which belong to (O-H) carboxylic and (N-H). This can be clear proof for the synthesis of cyclic imides.

According to the antimicrobial evaluations, phthalimide derived from benzylamine (A1B) exhibited remarkable antimicrobial activity against  E.coli Scientific Name Search . Phthalimide, isoindoline-1,3- dione have shown a wide array of pharmacological activities. Schiff base, azetidinone and acetyl oxadiazole derivatives of this cyclic imide with high antibacterial activities were synthesized and reported by Azzawi, et al. [12].

Literature survey revealed that naphthalimides, one type of cyclic imides with strong hydrophobicity, have remarkable antimicrobial activities [4],[20],[21],[22]. Relative similarity of this compound (A1B) with naphthalimides, can be responsible for its antibacterial activity. Sortino, et al. demonstrated that N-phenyl- and N- phenylalkylmaleimides can display antifungal activities with their intact maleimide ring and opening of the maleimide ring would lead to the loss of antifungal activity [7],[8]. In our study, cyclic imides derived from succinic anhydride, A3G (opened derivative) or FA3G (intact ring), did not show significant activity against tested microorganisms.

Lipinski's “rule of five” explains four physicochemical properties for orally active drugs. In this regard , most molecules with acceptable membrane permeability, exhibit hydrogen bond donors (OH, NH) of less than 5, hydrogen bond acceptor of less than 10, molecular weight under 500 g/mol and partition coefficient (log P) less than 5. Any value greater than these ranges is considered as a violation. The number of violations less than 4 is acceptable for drug-like molecule. Compound A1B can, therefore, be considered as a drug-like molecule according to Lipinski's “rule of five”.

  Conclusion Top

Compound A1B with significant efficacy against E. coli at 16 μg/mL concentration and acceptable Lipinski's parameters can be regarded as a drug likeness molecule. The activity of this compound can be associated with its stability as well as relatively lipophilic structure. Other compounds showed weak activities against tested microorganisms.

  Acknowledgements Top

The content of this paper is extracted from the Pharm. D thesis (No. 292243) which was financially supported by the Pharmaceutical Sciences Research Center, Isfahan University of Medical Sciences, Isfahan, I.R. Iran.

  References Top

Marulasiddaiah R, Kalkhambkar RG, Kulkarni MV. Synthesis and Biological Evaluation of Cyclic Imides with Coumarins and Azacoumarins. Open J Med Chem. 2012,2:89-97.  Back to cited text no. 1
PATIL M.M. RAJPUT S.S. Succinimides: synthesis, reaction, and biological activity. Int J Pharm Pharm Sci. 2014,6(11): 8-14.  Back to cited text no. 2
Dhivare RS, Rajput SS. 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. 2015;4(6):1650-1658.  Back to cited text no. 3
Al-Majidi SMH, Ahmad MR, Kareem Khan A. Synthesis and characterization of novel 1,8-Naphthalimide derivatives containing 1,3-oxazoles, 1,3-thiazoles, 1,2,4-triazoles as antimicrobial agents. J Al-Nahrain Uni. 2013;16(4):55-66.  Back to cited text no. 4
Al-Azzawi AA, Hassan AS. Synthesis and preliminary evaluation of antimicrobial activity of new sulfonamido and acetamido cyclic imides linked to benzothiazole moiety K. J Pharm Sci. 2011,2:59-80.  Back to cited text no. 5
Tozato Prado SR, Cechinel-Filho V, Campos-Buzzi F, Correa R, Correia Suter Cadena SM, Martinelli de Oliveira MB. Biological evaluation of some selected cyclic imides: Mitochondrial effects and in vitro cytotoxicity. Z Naturforsch. 2004;59c: 663D672.  Back to cited text no. 6
Gayoso CW, Lima EO, Souza EL, Filho VC, Trajano VN, Pereira FO, Lima IO. Antimicrobial effectiveness of maleimides on fungal strains isolated from onychomycosis. Brazilian Archives of Bio & Tech. 2006, 49(4): 661-664.  Back to cited text no. 7
Sortino M, Filho VC, Corre R, Zacchino S. N-Phenyl and N-phenylalkyl-maleimides acting against Candida spp.: Time-to-kill, stability, interaction with maleamic acids. Bioorg Med Chem. 2008;16: 560-568.  Back to cited text no. 8
Dhivare RS, Rajput SS. Microwave assisted solvent free synthesis and antifungal evaluation of 3, 5-bis-(4- hydroxy-3-methoxybenzylidene)-nphenyl-piperidine-2, 6-dione derived from N-phenyl glutarimides. Int J Chem Tech Res. 2016,9(3):325-331.  Back to cited text no. 9
Guri D, QingPeng W, HuiZhen Z, YiYi Z, Song LVJ, ChengHe Z. A series of naphthalimide azoles: design, synthesis and bioactive evaluation as potential antimicrobial agents. Sci China Chem. 2013;56(7):952-969.  Back to cited text no. 10
Khalil AEG, Berghot MA, Gouda MA. Synthesis and study of some new N-substituted imide derivatives as potential antibacterial agents. Chem paper. 2010;64(5):637-644.  Back to cited text no. 11
AL- Azzawi AM, Al-Obiadi KKH. Synthesis and antimicrobial screening of new BisSchiff bases and their acetyl oxadiazole azetidinone derivatives from pyromellitic diimid. Int J Res Pharm & Chem. 2016,6(1):1-8.  Back to cited text no. 12
Dhivare RS, Rajput SS. Synthesis and antimicrobial evaluation of some novel bis-heterocyclic chalcones from cyclic imides under microwave irradiation. Chem Sci Rev Lett. 2015,4(15):937-944.  Back to cited text no. 13
Sultana K, Khan NH, Shahid K. 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. 2014;28(2):1-5.  Back to cited text no. 14
Yunesa JA, Cardosob AA, Yunesc RA, Corread R, Campos-Buzzid F, Cechinel Filhod V. Antiproliferative effects of a series of cyclic imides on primary endothelial cells and a leukemia cell line. Z Naturforsch. 2008;63c:675-680.  Back to cited text no. 15
Campos-Buzzid F, Corread R, Souzaa MM, Yunes RA, Nunes RJ,Cechinel-Filho V. Studies on new cyclic imides obtained from aminophenazone with analgesic properties. Arzneim.-Forsch./Drug Res. 2002;52,6:455-461.  Back to cited text no. 16
Al-Azzawi AM. Synthesis, characterization and evaluation of antibacterial activity of several new 3,4-dimethyl maleimides and 1,8-naphthalimides containing 1,3,4-xadiazole ring. J Al-Nahrain Uni Sci. 2011;14(1):15-29.  Back to cited text no. 17
Abdel-Aziz AAM. Novel and versatile methodology for synthesis of cyclic imides and evaluation of their cytotoxic, DNA binding, apoptotic inducing activities and molecular modeling study. Eur J Med Chem: 2007;42:614-626.  Back to cited text no. 18
Bakhta MF, Shahar Yar M, Abdel-Hamid SG, Qasoumi SIA, Samad A. Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives. Eur J Med Chem. 2010;45:5862-5869.  Back to cited text no. 19
Al-Azzawi AM, Hamd AS. Synthesis and antimicrobial screening of new naphthalimides linled to oxadiazole, thiadiazole and triazole cycles. Int J Res Pharm & Chem. 2014,4(2):283-290.  Back to cited text no. 20
Shaki H, Khosravi A, Gharanjig K, Mahboubi A. Synthesis and biological properties of novel cationic fluorescent dye. Int J Tec Res & App. 2015;29: 103-106.  Back to cited text no. 21
Kumari G, Singh RK. Green synthesis, antibacterial activity, and SAR of some novel naphthalimides and allylidenes. Med Chem Res. 2015;24:171-181.  Back to cited text no. 22


  [Figure 1], [Figure 2], [Figure 3], [Figure 4], [Figure 5], [Figure 6]

  [Table 1], [Table 2], [Table 3]

This article has been cited by
1 The potential of Eucheuma cottonii extract as a candidate for fish anesthetic agent
Ninik Purbosari,Endang Warsiki,Khaswar Syamsu,Joko Santoso
Aquaculture and Fisheries. 2021;
[Pubmed] | [DOI]
2 Antibacterial and genotoxic activity of Bixa orellana, a folk medicine and food supplement against multidrug resistant clinical isolates
Bipasa Kar,Brinda Chandar,Suman Smruti Rachana,Haimanti Bhattacharya,Debdutta Bhattacharya
Journal of Herbal Medicine. 2021; : 100502
[Pubmed] | [DOI]
3 Synthesis, characterization of amic acids and cyclic imides derived from acriflavine and evaluation of their antibacterial and antioxidant activity
Malath Khalaf Rasheed,Deena Saady Mohammed Subhi,Amenh Mohammed Abdulrahnan
Materials Today: Proceedings. 2021;
[Pubmed] | [DOI]
4 In Vitro Assessment of N-Phenyl Imides in the Management of Meloidogyne Incognita
O.A. Fabiyi,A.O. Claudius-Cole,G.A. Olatunji
Scientia Agriculturae Bohemica. 2021; 52(3): 60
[Pubmed] | [DOI]
5 Comparative chemometric and quantitative structure-retention relationship analysis of anisotropic lipophilicity of 1-arylsuccinimide derivatives determined in high-performance thin-layer chromatography system with aprotic solvents
Strahinja Kovacevic,Milica Karadžic Banjac,Nataša Miloševic,Jelena Curcic,Dunja Marjanovic,Nemanja Todorovic,Jovana Krmar,Sanja Podunavac-Kuzmanovic,Nebojša Banjac,Gordana Ušcumlic
Journal of Chromatography A. 2020; 1628: 461439
[Pubmed] | [DOI]
6 Maleic anhydride-functionalized graphene nanofillers render epoxy coatings highly resistant to corrosion and microbial attack
Govind Chilkoor,Roman Sarde,Jamil Islam,K.E. ArunKumar,Ishara Ratnayake,Shane Star,Bharat K. Jasthi,Grigoriy Sereda,Nikhil Koratkar,M. Meyyappan,Venkataramana Gadhamshetty
Carbon. 2019;
[Pubmed] | [DOI]


Similar in PUBMED
   Search Pubmed for
   Search in Google Scholar for
 Related articles
Access Statistics
Email Alert *
Add to My List *
* Registration required (free)

  In this article
Materials and Me...
   Article Figures
   Article Tables

 Article Access Statistics
    PDF Downloaded606    
    Comments [Add]    
    Cited by others 6    

Recommend this journal