Design, synthesis and antiinflammatory activity of novel phthalimide derivatives, structurally related to thalidomide

Machado, Alexandre Légora; Lima, Lı́dia Moreira; Araújo-Jr, João Xavier; Fraga, Carlos A.M.; Koatz, Vera Lúcia Gonçalves; Barreiro, Eliezer J.

doi:10.1016/j.bmcl.2004.12.012

Cited by 67 publications

(31 citation statements)

References 14 publications

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“…Cyclic imides A (Scheme 1) represent an important class of bioactive molecules that shows a wide range of pharmacological activities such as androgen receptor antagonistic, anti-inflammatory, anxiolytic, antiviral, antibacterial, antitumor, antispasmodic, antinociceptive and antineoplastic properties [1][2][3][4][5][6][7][8][9][10][11][12][13].…”

Section: Abstract: Sulfonamide; Cyclic Imide; Nimesulidementioning

confidence: 99%

N-(4-Methylsulfonamido-3-phenoxyphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide

Kavitha¹,

Prakash

Mukkanti

et al. 2011

Molbank

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The title compound,12-dicarboximide was synthesized in high yield by reaction of N-(4-amino-2-phenoxyphenyl)methanesulfonamide and 9,10-dihydroanthracene-9,10-endo-α,β-succinic anhydride in glacial acetic acid. The structure of the compound was fully characterized by IR, 1 H and 13 C NMR, mass spectral analysis and elemental analysis. Keywords: sulfonamide; cyclic imide; nimesulideCyclic imides A (Scheme 1) represent an important class of bioactive molecules that shows a wide range of pharmacological activities such as androgen receptor antagonistic, anti-inflammatory, anxiolytic, antiviral, antibacterial, antitumor, antispasmodic, antinociceptive and antineoplastic properties [1][2][3][4][5][6][7][8][9][10][11][12][13].On the other hand N-(4-nitro-2-phenoxy phenyl)methane sulfonamide or nimesulide (B, Scheme 1), a preferential cyclooxygenase-2 (COX-2) inhibitor is one of the well known non-steroidal antiinflammatory drugs (NSAIDs) that has been utilized to treat pain and other inflammatory diseases. Because of their common anti-inflammatory properties and our interest in nimesulide (N-(4-nitro-2-phenoxy phenyl)methane sulfonamide) derivatives [14][15][16][17][18] as potential anti-inflammatory agents we decided to prepare compound C having structural features of both A and B (Scheme 1). OPEN ACCESS

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Section: Abstract: Sulfonamide; Cyclic Imide; Nimesulidementioning

confidence: 99%

N-(4-Methylsulfonamido-3-phenoxyphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide

Kavitha¹,

Prakash

Mukkanti

et al. 2011

Molbank

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“…Alterman et al have applied the carbonylation-cyclization method for phthalimide synthesis using 2-bromobenzamide as starting product and Mo(CO) 6 as CO source (Scheme 9). C higher than that of the desired reaction temperature is selected.…”

Section: Methodsmentioning

confidence: 99%

“…The exploration of the anti-inflammatory, antiangiogenic, anticancer and immunomodulatory activities of thalidomide has prompted the synthesis and study of thalidomide analogs such as lenalidomide and pomalidomide. 6,[42][43][44][45] It has also been used in AIDS therapy.…”

Section: Figurementioning

confidence: 99%

Microwave-promoted synthesis of cyclic imides

Perillo¹,

Shmidt²,

Prieto³

et al. 2018

Arkivoc

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Cyclic imides have been extensively investigated because of the wide range of biological activities they exert, as well as due to their importance as synthetic intermediates. Nowadays, focus has been placed on this important class of compounds for their potential new applications, especially in the area of pharmaceutical chemistry. Consequently, the strategies applied for the synthesis of these compounds have attracted considerable attention. Several innovative methodologies have been developed to obtain and functionalize this class of compounds. The use of microwave heating, which is an environmentally harmless strategy, has been making successful inroads in many chemistry areas, such as organic synthesis. Herein we present an update of the microwave-promoted methods for the synthesis of cyclic imides.

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“…They exhibit widespread pharmacological effects, including antitumor [1][2][3][4] , anti-inflammatory 5 , immunomodulatory, antiangiogenic and anxiolytic [6][7][8] . Isolation and examination of pharmacologically active natural glutarimides started in 1960s.…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative and antibacterial activity of some glutarimide derivatives

Popović‐Djordjević¹,

Klaus

Žižak

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Antiproliferative and antibacterial activities of nine glutarimide derivatives (1-9) were reported. Cytotoxicity of compounds was tested toward three human cancer cell lines, HeLa, K562 and MDA-MB-453 by MTT assay. Compound 7 (2-benzyl-2-azaspiro[5.11]heptadecane-1,3,7-trione), containing 12-membered ketone ring, was found to be the most potent toward all tested cell lines (IC 50 ¼ 9-27 mM). Preliminary screening of antibacterial activity by a disk diffusion method showed that Gram-positive bacteria were more susceptible to the tested compounds than Gram-negative bacteria. Minimum inhibitory concentration (MIC) determined by a broth microdilution method confirmed that compounds 1, 2, 4, 6-8 and 9 inhibited the growth of all tested Gram-positive and some of the Gram-negative bacteria. The best antibacterial potential was achieved with compound 9 (ethyl 4-(1-benzyl-2,6-dioxopiperidin-3-yl)butanoate) against Bacillus cereus (MIC 0.625 mg/mL; 1.97 Â 10 À3 mol/L). Distinction between more and less active/ inactive compounds was assessed from the pharmacophoric patterns obtained by molecular interaction fields.

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Design, synthesis and antiinflammatory activity of novel phthalimide derivatives, structurally related to thalidomide

Cited by 67 publications

References 14 publications

N-(4-Methylsulfonamido-3-phenoxyphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide

N-(4-Methylsulfonamido-3-phenoxyphenyl)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximide

Microwave-promoted synthesis of cyclic imides

Antiproliferative and antibacterial activity of some glutarimide derivatives

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