e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Convenient synthesis and biological profile of 5-amino-substituted 1, 2, 4-oxadiazole derivatives

…, AE Koumbis, KE Litinas, D Hadjipavlou-Litina…

Index: Ispikoudi, Maria; Amvrazis, Michalis; Kontogiorgis, Christos; Koumbis, Alexandros E.; Litinas, Konstantinos E.; Hadjipavlou-Litina, Dimitra; Fylaktakidou, Konstantina C. European Journal of Medicinal Chemistry, 2010 , vol. 45, # 12 p. 5635 - 5645

Full Text: HTML

Citation Number: 32

Abstract

We describe herein a convenient straightforward synthesis of 5-amino-substituted 1, 2, 4- oxadiazoles, upon the reactions of amidoximes with carbodiimides, as well as their further derivatization to acetamides, in good yields. Most of the compounds exhibited in general low interaction with the stable radical 1, 1-diphenyl-2-picryl-hydrazyl. Compounds 32 and 39 inhibited significantly soybean lipoxygenase. Selected compounds were screened for ...

N/A Structure

Dicyclohexylcarbodiimide Structure

Dicyclohexylcar...

~0%

N-cyclohexyl-3-(4-nitrophenyl)-1,2,4-oxadiazol-5-amine Structure

N-cyclohexyl-3-...

1,3-Dicyclohexylurea Structure

1,3-Dicyclohexylurea

N-Hydroxy-4-methylbenzenecarboximidamide Structure

N-Hydroxy-4-met...

Dicyclohexylcarbodiimide Structure

Dicyclohexylcar...

~0%

N-cyclohexyl-3-(4-methylphenyl)-1,2,4-oxadiazol-5-amine Structure

N-cyclohexyl-3-...

1,3-Dicyclohexylurea Structure

1,3-Dicyclohexylurea

N-HYDROXY-4-METHOXY-BENZAMIDINE Structure

N-HYDROXY-4-MET...

Dicyclohexylcarbodiimide Structure

Dicyclohexylcar...

~0%

N-cyclohexyl-3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-amine Structure

N-cyclohexyl-3-...

1,3-Dicyclohexylurea Structure

1,3-Dicyclohexylurea

N-HYDROXY-3-NITROBENZENECARBOXIMIDAMIDE Structure

N-HYDROXY-3-NIT...

Dicyclohexylcarbodiimide Structure

Dicyclohexylcar...

~0%

N-cyclohexyl-3-(3-nitrophenyl)-1,2,4-oxadiazol-5-amine Structure

N-cyclohexyl-3-...

1,3-Dicyclohexylurea Structure

1,3-Dicyclohexylurea

N-Hydroxybenzenecarboximidamide Structure

N-Hydroxybenzen...

Dicyclohexylcarbodiimide Structure

Dicyclohexylcar...

~0%

N-cyclohexyl-3-phenyl-1,2,4-oxadiazol-5-amine Structure

N-cyclohexyl-3-...

1,3-Dicyclohexylurea Structure

1,3-Dicyclohexylurea

Benzeneethanimidamide,N-hydroxy-4-nitro- Structure

Benzeneethanimi...

Dicyclohexylcarbodiimide Structure

Dicyclohexylcar...

~0%

N-cyclohexyl-3-(4-nitrobenzyl)-1,2,4-oxadiazol-5-amine Structure

N-cyclohexyl-3-...

1,3-Dicyclohexylurea Structure

1,3-Dicyclohexylurea

N'-hydroxy-2-phenylethanimidamide Structure

N'-hydroxy-2-ph...

Dicyclohexylcarbodiimide Structure

Dicyclohexylcar...

~0%

3-benzyl-N-cyclohexyl-1,2,4-oxadiazol-5-amine Structure

3-benzyl-N-cycl...

1,3-Dicyclohexylurea Structure

1,3-Dicyclohexylurea

Dicyclohexylcarbodiimide Structure

Dicyclohexylcar...

Cyclohexanecarboximidamide, N-hydroxy- (Related Reference) Structure

Cyclohexanecarb...

~0%

N,3-dicyclohexyl-1,2,4-oxadiazol-5-amine Structure

N,3-dicyclohexy...

1,3-Dicyclohexylurea Structure

1,3-Dicyclohexylurea

Dicyclohexylcarbodiimide Structure

Dicyclohexylcar...

Benzeneethanimidamide,4-chloro-N-hydroxy- Structure

Benzeneethanimi...

~0%

3-(4-chlorobenzyl)-N-cyclohexyl-1,2,4-oxadiazol-5-amine Structure

3-(4-chlorobenz...

1,3-Dicyclohexylurea Structure

1,3-Dicyclohexylurea

N/A Structure

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Structure

1-(3-Dimethylam...

~0%

N/A Structure

N/A Structure

Detail

N-Hydroxy-4-methylbenzenecarboximidamide Structure

N-Hydroxy-4-met...

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Structure

1-(3-Dimethylam...

~0%

N-ethyl-3-p-tolyl-1,2,4-oxadiazol-5-amine Structure

N-ethyl-3-p-tol...

N1,N1-dimethyl-N3-(3-p-tolyl-1,2,4-oxadiazol-5-yl)propane-1,3-diamine Structure

N1,N1-dimethyl-...

Detail

N-HYDROXY-4-METHOXY-BENZAMIDINE Structure

N-HYDROXY-4-MET...

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Structure

1-(3-Dimethylam...

~0%

N/A Structure

N/A Structure

Detail

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride Structure

1-(3-Dimethylam...

N-Hydroxybenzenecarboximidamide Structure

N-Hydroxybenzen...

~0%

N1,N1-dimethyl-N3-(3-phenyl-1,2,4-oxadiazol-5-yl)propane-1,3-diamine Structure

N1,N1-dimethyl-...

N-ethyl-3-phenyl-1,2,4-oxadiazol-5-amine Structure

N-ethyl-3-pheny...

Detail

N'-hydroxy-2-phenylethanimidamide Structure

N'-hydroxy-2-ph...

N,N′-diisopropylcarbodiimide Structure

N,N′-diisopropy...

~0%

1,3-Diisopropylurea Structure

1,3-Diisopropylurea

N/A Structure

N/A Structure

N,N′-diisopropylcarbodiimide Structure

N,N′-diisopropy...

~0%

1,3-Diisopropylurea Structure

1,3-Diisopropylurea

N-isopropyl-3-(4-nitrophenyl)-1,2,4-oxadiazol-5-amine Structure

N-isopropyl-3-(...

N-Hydroxy-4-methylbenzenecarboximidamide Structure

N-Hydroxy-4-met...

N,N′-diisopropylcarbodiimide Structure

N,N′-diisopropy...

~0%

1,3-Diisopropylurea Structure

1,3-Diisopropylurea

N-isopropyl-3-p-tolyl-1,2,4-oxadiazol-5-amine Structure

N-isopropyl-3-p...

N-Hydroxybenzenecarboximidamide Structure

N-Hydroxybenzen...

N,N′-diisopropylcarbodiimide Structure

N,N′-diisopropy...

~0%

1,3-Diisopropylurea Structure

1,3-Diisopropylurea

N/A Structure

N-HYDROXY-4-METHOXY-BENZAMIDINE Structure

N-HYDROXY-4-MET...

N,N′-diisopropylcarbodiimide Structure

N,N′-diisopropy...

~0%

1,3-Diisopropylurea Structure

1,3-Diisopropylurea

N/A Structure

N-HYDROXY-2-NITRO-BENZAMIDINE Structure

N-HYDROXY-2-NIT...

N,N′-diisopropylcarbodiimide Structure

N,N′-diisopropy...

~0%

1,3-Diisopropylurea Structure

1,3-Diisopropylurea

N/A Structure

n,n'-bis(4-nitrophenyl)carbodiimide Structure

n,n'-bis(4-nitr...

N-Hydroxybenzenecarboximidamide Structure

N-Hydroxybenzen...

~0%

N-(4-nitrophenyl)-3-phenyl-1,2,4-oxadiazol-5-amine Structure

N-(4-nitropheny...

4,4'-dinitrocarbanilide Structure

4,4'-dinitrocar...

Cyclodimerization and cyclotrimerization of isocyanates prom...

[Wang, He-Ming; Li, Hong-Xi; Yu, Xiang-Yang; Ren, Zhi-Gang; Lang, Jian-Ping Tetrahedron, 2011 , vol. 67, # 8 p. 1530 - 1535]

1 H, 13 C NMR, FT-IR, ESI MS and PM5 studies of a new 3, 6, ...

[Lowicki, Daniel; Huczynski, Adam; Brzezinski, Bogumil; Bartl, Franz Journal of Molecular Structure, 2011 , vol. 990, # 1-3 p. 121 - 131]

Organocatalyzed synthesis of ureas from amines and ethylene ...

[Saliu, Francesco; Rindone, Bruno Tetrahedron Letters, 2010 , vol. 51, # 48 p. 6301 - 6304]