Rearrangements of 1,2,4-Oxadiazole: “One Ring to Rule Them All”

Piccionello, Antonio Palumbo; Pace, Andrea; Buscemi, Silvestre

doi:10.1007/s10593-017-2154-1

Cited by 41 publications

(19 citation statements)

References 44 publications

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“…In recent years, focus has shift to the compounds of isoxazoles and oxadiazoles which have practical uses in many civilian and military applications [22][23][24][25][26][27][28][29]. Various bis-isoxazoles and bis-oxazoles have been synthesized which show potential for melt-castable applications, including the compound of 3,3'-bis-oxadiazole-5,5'-bis-methylene dinitrate (BODN, Figure 1) [30].…”

Section: Introductionmentioning

confidence: 99%

Thermal Kinetic Performance and Thermal Safety of 3,3’‐Bis‐Oxadiazole‐5,5’‐Bis‐Methylene Dinitrate

Li¹,

Luo²,

Wang³

et al. 2020

Propellants Explo Pyrotec

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DSC and TG/DTG were performed to investigate the thermal kinetic performance and thermal safety of 3,3'bis-oxadiazole-5,5'-bis-methylene dinitrate (BODN) under a non-isothermal condition. The results reveal that the thermal behavior of BODN can be divided into three stages including a melting endothermic process and two decomposition exothermic processes. The apparent activation energy (E) and pre-exponent parameters (A) of the first exothermic decomposition reaction are 147.45 kJ mol À 1 and 10 13.77 s À 1 , and its kinetic equation was obtained from the DSC curves. The self-accelerating decomposition temperatures (T SADT), thermal ignition temperatures (T TIT), and critical temperatures of the thermal explosion (T b) to evaluate its thermal stability and safety are 166.41°C, 178.09°C, and 204.47°C, respectively. The positive values of free energy of activation (ΔG ¼ 6 = 135.49 kJ mol À 1) indicate that the decomposition process of BODN must proceed under the heating condition.

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Section: Introductionmentioning

confidence: 99%

Thermal Kinetic Performance and Thermal Safety of 3,3’‐Bis‐Oxadiazole‐5,5’‐Bis‐Methylene Dinitrate

Li¹,

Luo²,

Wang³

et al. 2020

Propellants Explo Pyrotec

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“…For instance, 1,2,4-oxadiazoles have lower water solubility than 1,3,4-oxadiazoles because of the reduced hydrogen bond acceptor character of the nitrogen in 1,2,4-oxadiazole ring [43]. Moreover, they have been extensively studied because of their peculiar reactivity [43,48] and possible applications in material chemistry [49,50,51,52,53,54,55] or as bioactive compounds [44,56,57,58].…”

Section: Classes Of Translational Readthrough-inducing Drugs (Trids)mentioning

confidence: 99%

Strategies against Nonsense: Oxadiazoles as Translational Readthrough-Inducing Drugs (TRIDs)

Campofelice

Lentini

Leonardo

et al. 2019

IJMS

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This review focuses on the use of oxadiazoles as translational readthrough-inducing drugs (TRIDs) to rescue the functional full-length protein expression in mendelian genetic diseases caused by nonsense mutations. These mutations in specific genes generate premature termination codons (PTCs) responsible for the translation of truncated proteins. After a brief introduction on nonsense mutations and their pathological effects, the features of various classes of TRIDs will be described discussing differences or similarities in their mechanisms of action. Strategies to correct the PTCs will be presented, particularly focusing on a new class of Ataluren-like oxadiazole derivatives in comparison to aminoglycosides. Additionally, recent results on the efficiency of new candidate TRIDs in restoring the production of the cystic fibrosis transmembrane regulator (CFTR) protein will be presented. Finally, a prospectus on complementary strategies to enhance the effect of TRIDs will be illustrated together with a conclusive paragraph about perspectives, opportunities, and caveats in developing small molecules as TRIDs.

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“…Various oxadiazole derivatives show different kinds of activity against cancer [6,7], tuberculosis [8], Gram-positive bacteria [9], and they are used in treatment of Scheme 1: Synthesis of 5-arylethynyl-3-aryl-1,2,4-oxadiazoles 3a-e. epilepsy [10] and Alzheimer disease [11][12][13]. The synthesis of compounds of the 1,2,4-oxadiazole series is an actual task in organic and medicinal chemistry (see selected reviews on this topic [14][15][16][17][18][19][20][21][22]). However, among all the varieties of 1,2,4-oxadiazoles, their acetylenic derivatives are quite rare.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions

Puzanov

Ryabukhin

Zalivatskaya

et al. 2021

Beilstein J. Org. Chem.

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Acetylene derivatives of 1,2,4-oxadiazoles, i.e., 5-(2-arylethynyl)-3-aryl-1,2,4-oxadiazoles, have been obtained, for the first time reported, from 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles by their bromination at the carbon–carbon double bond followed by di-dehydrobromination with NaNH2 in liquid NH3. The reaction of the acetylenyl-1,2,4-oxadiazoles with arenes in neat triflic acid TfOH (CF3SO3H) at room temperature for 1 h resulted in the formation of E/Z-5-(2,2-diarylethenyl)-3-aryl-1,2,4-oxadiazoles as products of regioselective hydroarylation of the acetylene bond. The addition of TfOH to the acetylene bond of these oxadiazoles quantitatively resulted in E/Z-vinyl triflates. The reactions of the cationic intermediates have been studied by DFT calculations and the reaction mechanisms are discussed.

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Rearrangements of 1,2,4-Oxadiazole: “One Ring to Rule Them All”

Cited by 41 publications

References 44 publications

Thermal Kinetic Performance and Thermal Safety of 3,3’‐Bis‐Oxadiazole‐5,5’‐Bis‐Methylene Dinitrate

Thermal Kinetic Performance and Thermal Safety of 3,3’‐Bis‐Oxadiazole‐5,5’‐Bis‐Methylene Dinitrate

Strategies against Nonsense: Oxadiazoles as Translational Readthrough-Inducing Drugs (TRIDs)

Synthesis of 5-arylacetylenyl-1,2,4-oxadiazoles and their transformations under superelectrophilic activation conditions

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