1,2,4-Oxadiazole derivatives of phenylalanine: potential inhibitors of substance P endopeptidase

Borg, Susanna; Luthman, Kristina; Nyberg, Fred; Terenius, Lars; Hacksell, Uli

doi:10.1016/0223-5234(93)90115-u

Cited by 22 publications

(15 citation statements)

References 40 publications

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“…Each isostere Xxx//Yyy corresponds to the dipeptide Xxx-Yyy in which the amide has been replaced by a trans-alkene moiety (33,34). These six isosteres cover the entire range of potential molecules formed by substitutions at positions R and δ.…”

Section: Resultsmentioning

confidence: 99%

Exploring the Backbone of Enkephalins To Adjust Their Pharmacological Profile for the δ-Opioid Receptor

Proteau-Gagné

Bournival²,

Rochon³

et al. 2010

ACS Chem. Neurosci.

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The role of each of the four amide bonds in Leu 5 -enkephalin was investigated by systematically and sequentially replacing each with its corresponding trans-alkene. Six Leu 5 -enkephalin analogs based on six dipeptide surrogates and two Met 5 -enkephalin analogs were synthesized and thoroughly tested using a δ-opioid receptor internalization assay, an ERK1/2 activation assay, and a competition binding assay to evaluate their biological properties. We observed that an E-alkene can efficiently replace the first amide bond of Leu 5 -and Met 5 -enkephalin without significantly affecting biological activity. By contrast, the second amide bond was found to be highly sensitive to the same modification, suggesting that it is involved in biologically essential intra-or intermolecular interactions. Finally, we observed that the affinity and activity of analogs containing an E-alkene at either the third or fourth position were partially reduced, indicating that these amide bonds are less important for these intra-or intermolecular interactions. Overall, our study demonstrates that the systematic and sequential replacement of amide bonds by E-alkene represents an efficient way to explore peptide backbones.

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Section: Resultsmentioning

confidence: 99%

Exploring the Backbone of Enkephalins To Adjust Their Pharmacological Profile for the δ-Opioid Receptor

Proteau-Gagné

Bournival²,

Rochon³

et al. 2010

ACS Chem. Neurosci.

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“…The 1,2,4-oxadiazole (A) obtained from the nitrone rearrangement was reacted with 2-mercapto benzoic acid (12) to synthesize new 1,2,4-oxadiazol-benzothiazinones (13). This cyclization reaction progressed via nucleophilic attack of the mercapto group on the oxime carbon and of the amine group on the carboxylic acid.…”

Section: Methodsmentioning

confidence: 99%

“…The structural elucidation of compound 13a was performed by IR, 1 H NMR, 13 C NMR and CHN analysis which confirmed preparation of the product 13a.…”

Section: Methodsmentioning

confidence: 99%

“…To perform such reaction, nitrone 9 obtained from the reaction of DAG (1) and aromatic aldehyde 7 in acetic acid at 100 • C (Scheme 4) after separation and purification was added to a vessel containing (2-amino-5-chlorophenyl) (phenyl) methanone (8) in acetic acid, and stirred at 100 • C. The structural elucidation was performed on the product obtained from this reaction by analyzing the IR, 1 H NMR, 13 C NMR and CHN data.…”

Section: Methodsmentioning

confidence: 99%

“…The derivatives of this oxadiazole have different biological activities such as antiinflammatory, antidiabetic [7], immunosuppressive [8], antimicrobial [9,10], Alzheimer's disease [11], genotoxic activity [12], peptide inhibitory [13], antihyperglycemic [14], anticancer [15][16][17], antitumor [18,19], and antitrypanosomal [20] activity. Furthermore, 1,2,4-oxadiazole derivatives are not only helpful for DNA interaction [21] and inhibiting bacterial infections [22], but also have applications in advanced materials discotic liquid crystals (DLCs) or film forming compounds [23,24].…”

mentioning

confidence: 99%

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Diaminoglyoxime as a versatile reagent in the synthesis of bis(1,2,4-oxadiazoles), 1,2,4-oxadiazolyl-quinazolines and 1,2,4-oxadiazolyl-benzothiazinones

Khanmiri

Moghimi

Shaabani³

et al. 2014

Mol Divers

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Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents

Upare

Gadekar

Sivaramakrishnan

et al. 2019

Bioorganic Chemistry

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1,2,4-Oxadiazole derivatives of phenylalanine: potential inhibitors of substance P endopeptidase

Cited by 22 publications

References 40 publications

Exploring the Backbone of Enkephalins To Adjust Their Pharmacological Profile for the δ-Opioid Receptor

Exploring the Backbone of Enkephalins To Adjust Their Pharmacological Profile for the δ-Opioid Receptor

Diaminoglyoxime as a versatile reagent in the synthesis of bis(1,2,4-oxadiazoles), 1,2,4-oxadiazolyl-quinazolines and 1,2,4-oxadiazolyl-benzothiazinones

Design, synthesis and biological evaluation of (E)-5-styryl-1,2,4-oxadiazoles as anti-tubercular agents

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