1,2,4-Oxadiazoles

Hemming, K.

doi:10.1016/b978-008044992-0.00504-6

Cited by 22 publications

(5 citation statements)

References 206 publications

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“…[21] Although monosubstituted and unsubstituted 1,2,4-oxadiazoles may be susceptible to thermal and hydrolytic degradation, disubstituted 1,2,4-oxadiazoles are stable structures that are highly resistant to ambient conditions. [11,24] Due to this stability, 1,2,4-oxadiazole rings are used as bioisosteres of ester and amide structures suitable for hydrolytic degradation. In addition, 1,2,4-oxadiazole rings are both hydrogen bond donors and acceptors according to the substituent in their structure.…”

Section: Bioisosteric Replacement 124-oxadiazole Ringsmentioning

confidence: 99%

Bioisosterism: 1,2,4‐Oxadiazole Rings

Camci

Karalı

2023

ChemMedChem

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Although studies in drug discovery have gained momentum in recent years, the conversion of drugs in use today into less toxic derivatives with pharmacologically superior properties is still of great importance in drug research. Bioisosterism facilitates the conversion of drugs into derivatives that present more positive pharmacological and toxicological profiles by changing existing groups in the drug structure within the framework of certain criteria that have been expanded today. The 1,2,4‐oxadiazole ring is used as a bioisostere for ester and amide groups due to its resistance to hydrolysis. However, this ring is not limited to esters and amides, but can also be used as a bioisostere for other functional groups. In this review, cases in which the 1,2,4‐oxadiazole ring is used as a bioisostere for various functional groups are discussed. Herein we shed light on 1,2,4‐oxadiazole bioisosterism in the development of new drug candidates and in enhancing the pharmacological profiles of currently available drugs.

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Section: Bioisosteric Replacement 124-oxadiazole Ringsmentioning

confidence: 99%

Bioisosterism: 1,2,4‐Oxadiazole Rings

Camci

Karalı

2023

ChemMedChem

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“…1,2,4-Oxadiazoles are important heterocyclic compounds due to their various kinds of biological activity. Several reviews on the syntheisis of 1,2,4-oxadiazole derivatives and study of their properties have been recently published. − In medicinal chemistry oxadiazoles are considered as bioisosteric analogues of ester or amide groups . 1,2,4-Oxadiazole ring is found in many drugs.…”

Section: Introductionmentioning

confidence: 99%

“…Another approach is based on the [3 + 2] cycloaddition of nitriles with nitrile oxides or silyl nitronates (Scheme and data in reviews ,, ). One more method is based on the transformations of aldoximes. ,,, …”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2,4-Oxadiazoles by Tandem Reaction of Nitroalkenes with Arenes and Nitriles in the Superacid TfOH

2019

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The tandem reaction of nitroalkenes with arenes and nitriles in the superacid CF3SO3H (TfOH) results in the formation of 1,2,4-oxadiazole derivatives in yields up to 96%. This reaction proceeds via the consequent interaction of arenes and nitriles, as nucleophiles, with intermediate cationic species derived by the protonation of nitroalkenes in TfOH. This is novel and general synthesis of 1,2,4-oxadiazoles, which are very important compounds for medicinal chemistry.

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“…Additionally, 1,2,4-oxadiazoles are also widely used for the design of dipeptidomimetics as peptide building blocks. 8,9 Various methods for the synthesis of 1,2,4-oxadiazoles are available and these include: (i) condensation of amidoximes with derivatives of carboxylic acids followed by cyclization to 1,2,4-oxadiazoles, (ii) cyclization of N-acylamidoximes, (iii) 1,3-dipolar cycloaddition of nitrile oxides to nitriles, (iv) electrocyclic ring closure of ni- trenoids, and (v) oxidation of 4,5-dihydro-1,2,4-oxadiazoles 10,11 and other derivatives of 1,2,4-oxadiazoles. 12 A few reports are available on the synthesis of 3-aryl-1,2,4-oxadiazol-5-amine 13 and 1,2,4-oxadiazole-3,5-diamine.…”

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confidence: 99%

A Diversified Assembly of 1,2,4-Oxadiazol-3-amines: Metallic Thiophile Catalyzed Chemoselective One-Pot Reaction of Aryl Isothiocyanates, Amidines/Guanidines, and Hydroxylamine

Sudarsanam

Vasu

2012

Synthesis

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An efficient one-pot synthesis of 1,2,4-oxadiazol-3-amines from simple starting materials, isothiocyanates, amidines/guanidines, and hydroxylamine, is described. The reaction is facilitated by metallic-thiophile-assisted desulfurization of in situ formed amidino-or guanidinothiourea to give chemoselectively Nhydroxyguanidine intermediates that give exclusively various 1,2,4-oxadiazol-3-amines in good to excellent yields. The reaction mechanistic pathway may proceed through an intramolecular 5-exotrig cyclization.

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1,2,4-Oxadiazoles

Cited by 22 publications

References 206 publications

Bioisosterism: 1,2,4‐Oxadiazole Rings

Bioisosterism: 1,2,4‐Oxadiazole Rings

Synthesis of 1,2,4-Oxadiazoles by Tandem Reaction of Nitroalkenes with Arenes and Nitriles in the Superacid TfOH

A Diversified Assembly of 1,2,4-Oxadiazol-3-amines: Metallic Thiophile Catalyzed Chemoselective One-Pot Reaction of Aryl Isothiocyanates, Amidines/Guanidines, and Hydroxylamine

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