1,2,4-Oxadiazoles

Piccionello, Antonio Palumbo; Pibiri, Ivana; Pace, Andrea; Buscemi, Silvestre; Vivona, Nicolò

doi:10.1016/b978-0-12-409547-2.14791-2

Cited by 5 publications

(5 citation statements)

References 215 publications

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“…Because of these syntheses generally require high heat, Tiemann conversion can also be observed as a side reaction. [11,12] 1,2,4-oxadiazoles were synthesized from amidoxime and acyl chloride by Tiemann and Krüger in 1884. It has been stated that two different isomeric structures can be formed according to the structure of amidoxime and acyl chloride used in this synthesis method (Figure 1).…”

Section: General Synthetic Methods Of 124-oxadiazolesmentioning

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: General Synthetic Methods Of 124-oxadiazolesmentioning

confidence: 99%

Bioisosterism: 1,2,4‐Oxadiazole Rings

Camci

Karalı

2023

ChemMedChem

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“…On the basis of the performed calculations, it was found that the aromaticity index for 1,2,4-oxadiazole was lower than for the furan molecule [25]. In recent years, many 1,2,4-oxadiazole derivate structures have been detected using X-ray structure spectroscopy (1-4) [26,27]. The structures that can be used in energetic materials [28] and complex compounds based on 1,2,4-oxadiazole derivatives that can bind copper or cobalt cations, and have biological activity, have been determined [29][30][31] (Figure 4).…”

Section: Chemistry Of Oxadiazolesmentioning

confidence: 99%

“…Due to the realtively low aromaticity and high susceptibility of the O-N bond to reduction, 1,2,4-oxadiazoles are investigated for the possibility of rearrangement into other heterocyclic compounds. Moreover, the nitrogen and carbon atoms present in the molecule are characterized by nucleophilic and electrophilic characteristics, while the entire ring has the properties of an electron withdrawing group, which leads to increased reactivity of the attached substituents [27,32,33].…”

Section: Chemistry Of Oxadiazolesmentioning

confidence: 99%

“…Narella et al proposed the preparation of 1,3,4-oxadiazole derivatives connected to a coumarin core via a methylenoxy linker (Scheme 6). The starting coumarin fragment was prepared from resorcinol (26) and ethyl acetoacetate (27). Then, it was treated with ethyl bromoacetate, yielding an extended coumarin-bearing ester, which was converted to the appropriate hydrazide (30) under the influence of hydrazine hydrate.…”

Section: Investigation Of the Synthesis Of New Biologically Active 13...mentioning

confidence: 99%

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Synthesis and Biological Activity of 1,3,4-Oxadiazoles Used in Medicine and Agriculture

Łuczyński

Kudelko

2022

Applied Sciences

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Biologically active compounds play a key role in the fight against diseases affecting both human and animal living organisms, as well as plants. Finding out about new molecules with a potential biological effect, not yet described in the literature, is one of the most important aspects in the development of medicine and agriculture. Compounds showing desirable biological activity include heterocyclic moieties such as 1,3,4-oxadiazoles. The oxadiazole molecule is composed of two nitrogen atoms and one oxygen atom, forming a five-membered heterocyclic ring. Structures of this type have been successfully used in the treatment of various diseases in humans and animals, and play an important role in modern agriculture. It has been proven that many oxadiazole derivatives exhibit antibacterial, antiviral, blood pressure lowering, antifungal, antineoplastic, anticancer, antioxidant, anti-inflammatory and analgesic properties. In addition, compounds based on 1,3,4-oxadiazole can act as plant protection agents due to their herbicidal, insecticidal and fungicidal activity. Due to the constantly growing interest in heterocyclic systems of this nature, new methods of obtaining complex structures containing oxadiazole rings are sought. This article discusses various methods of synthesis of 1,3,4-oxadiazole derivatives exhibiting biological activity. Based on these techniques, these compounds could be used in the future in medicine and agriculture.

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“…Moreover, progress in the synthesis and medicinal application of the 1,2,4-oxadiazole core is being regularly reported (for recent reviews see Refs. [ 7 , 8 , 9 , 10 , 11 , 12 ]). The interesting feature of the 1,2,4-oxadiazole moiety from a medicinal chemistry viewpoint is its potential coverage of a broad spectrum of therapeutic areas, including oncology [ 13 , 14 , 15 ], immunology [ 16 ], neurology [ 17 , 18 , 19 , 20 ], infectious diseases [ 21 , 22 , 23 , 24 ], metabolism and endocrinology [ 25 , 26 , 27 , 28 ], urology [ 29 , 30 ], gastroenterology [ 31 ], cardiology [ 32 ], rheumatology [ 33 ], and respirology [ 34 ].…”

Section: Introductionmentioning

confidence: 99%

Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

Baykov

Shetnev

Semenov

et al. 2023

IJMS

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1,2,4-Oxadiazole is an essential motif in drug discovery represented in many experimental, investigational, and marketed drugs. This review covers synthetic methods that allow the conversion of different types of organic compounds into 1,2,4-oxadiazole at ambient temperature and the practical application of the latter approaches for the preparation of pharmaceutically important molecules. The discussed methods are divided into three groups. The first combines two-stage protocols requiring the preliminary preparation of O-acylamidoximes followed by cyclization under the action of organic bases. The advantages of this route are its swiftness, high efficiency of the cyclization process, and uncomplicated work--up. However, it requires the preparation and isolation of O-acylamidoximes as a separate preliminary step. The second route is a one-pot synthesis of 1,2,4-oxadiazoles directly from amidoximes and various carboxyl derivatives or aldehydes in aprotic bipolar solvents (primarily DMSO) in the presence of inorganic bases. This recently proposed pathway proved to be highly efficient in the field of medicinal chemistry. The third group of methods consists of diverse oxidative cyclizations, and these reactions have found modest application in drug design thus far. It is noteworthy that the reviewed methods allow for obtaining 1,2,4-oxadiazoles with thermosensitive functions and expand the prospects of using the oxadiazole core as an amide- or ester-like linker in the design of bioactive compounds.

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1,2,4-Oxadiazoles

Cited by 5 publications

References 215 publications

Bioisosterism: 1,2,4‐Oxadiazole Rings

Bioisosterism: 1,2,4‐Oxadiazole Rings

Synthesis and Biological Activity of 1,3,4-Oxadiazoles Used in Medicine and Agriculture

Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

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