- Beyond direct Nrf2 activation; reinvestigating 1,2,4-oxadiazole scaffold as a master key unlocking the antioxidant cellular machinery for cancer therapy
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Harnessing the antioxidant cellular machinery has sparked considerable interest as an efficient anticancer strategy. Activating Nrf2, the master switch of the cellular redox system, suppresses ROS, alleviates oxidative stress, and halts cancer progression
- Ayoup, Mohammed Salah,Abu-Serie, Marwa M.,Abdel-Hamid, Hamida,Teleb, Mohamed
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- Copper-Catalyzed Three-Component Cascade Reaction of Benzaldehyde with Benzylamine and Hydroxylamine or Aniline: Synthesis of 1,2,4-Oxadiazoles and Quinazolines
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The analogous three-component synthesis strategy for substituted 1,2,4-oxadiazole and quinazoline derivatives from readily available benzaldehyde, benzylamine and hydroxylamine or aniline has been developed. Both the cascade reaction sequences involves nucleophilic addition of C?N bond, introduction a halogen donor, nucleophilic substitution and Cu(II)-catalyzed aerobic oxidation. This synthesis methodology demonstrated good yields, broad substrate scope and oxygen as a green oxidant. Thus, this synthesis protocol provides strategies for the construction of substituted 1,2,4-oxadiazole and quinazolines from readily and simple starting materials. (Figure presented.).
- Wang, Chao,Rui, Xiyan,Si, Dongjuan,Dai, Rupeng,Zhu, Yueyue,Wen, Hongmei,Li, Wei,Liu, Jian
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supporting information
p. 2825 - 2833
(2021/04/26)
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- Convenient entry to N-pyridinylureas with pharmaceutically privileged oxadiazole substituents via the acid-catalyzed C[sbnd]H activation of N-oxides
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Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be C[sbnd]H functionalized via the acid-catalyzed reaction with dialkylcyanamides, providing access to hitherto undescribed pyridine-2-yl substituted ureas, which have potential as “lead-l
- Geyl, Kirill,Baykov, Sergey,Tarasenko, Marina,Zelenkov, Lev E.,Matveevskaya, Vladislava,Boyarskiy, Vadim P.
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supporting information
(2019/09/12)
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- One-pot synthesis of 3,5-diaryl substituted-1,2,4-oxadiazoles using gem -dibromomethylarenes
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1,2,4-Oxadiazole is one of the most promising heterocyclic ring systems in medicinal chemistry. In the present paper, we report the method for an efficient one-pot synthesis of 3,5-diaryl substituted 1,2,4-oxadiazoles using a two-component reaction of gem-dibromomethylarenes with amidoximes in good yields. In this method, gem-dibromomethylarenes are used as benzoic acid equivalents for the efficient synthesis of aryl-substituted 1,2,4-oxadiazoles. It is anticipated that this methodology will have versatile applications in the practical syntheses of various molecules of both medicinal and material chemistry importance.
- Vinaya, Kambappa,Chandrashekara, Ganganahalli K.,Shivaramu, Prasanna D.
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p. 690 - 696
(2019/09/06)
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- A convenient and mild method for 1,2,4-oxadiazole preparation: Cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO
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Herein, we reported a general, convenient, and efficient synthesis of 3,5-disubstituted-1,2,4-oxadiazoles via cyclodehydration of O-acylamidoximes in the superbase system MOH/DMSO (M = Li, Na, K). Excellent isolated yields (up to 98%) were attained within
- Baykov, Sergey,Sharonova, Tatyana,Osipyan, Angelina,Rozhkov, Sergey,Shetnev, Anton,Smirnov, Alexey
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supporting information
p. 2898 - 2900
(2016/06/14)
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- A facile approach to synthesize 3,5-disubstituted-1,2,4-oxadiazoles via copper-catalyzed-cascade annulation of amidines and methylarenes
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Various 3,5-disubstituted-1,2,4-oxadiazoles are smoothly formed via copper-catalyzed cascade annulation of amidines and methylarenes. This tandem oxidation-amination-cyclization transformation represents a straightforward protocol to prepare 1,2,4-oxadiazoles from easily available starting materials, with inexpensive copper catalysts and green oxidants. It has the advantages of atom- and step-economy, good functional group tolerance, as well as operational simplicity.
- Guo, Wei,Huang, Kunbo,Ji, Fanghua,Wu, Wanqing,Jiang, Huanfeng
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supporting information
p. 8857 - 8860
(2015/05/20)
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- Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: A highly efficient and fluoride-free ring closure reaction of O-acylamidoximes
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Tetrabutylammonium hydroxide (TBAH) is an efficient and mild alternative to tetrabutylammonium fluoride (TBAF) for base catalyzed cyclizations of 1,2,4-oxadiazoles from O-acylamidoximes. For most 3,5-substituted 1,2,4-oxadiazoles the reactions were dramatically accelerated by addition of 0.1 equiv of TBAH at room temperature. This method was also more generally applicable allowing for a wider range of substrates. Additionally, due to the absence of fluoride, TBAH will not result in corrosion of reactor vessels and therefore is better suited for large-scale synthesis.
- Otaka, Hiromichi,Ikeda, Junya,Tanaka, Daisuke,Tobe, Masanori
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p. 979 - 981
(2014/02/14)
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- Construction of 3,5-substituted 1,2,4-oxadiazole rings triggered by tetrabutylammonium hydroxide: A highly efficient and fluoride-free ring closure reaction of O-acylamidoximes
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Tetrabutylammonium hydroxide (TBAH) is an efficient and mild alternative to tetrabutylammonium fluoride (TBAF) for base catalyzed cyclizations of 1,2,4-oxadiazoles from O-acylamidoximes. For most 3,5-substituted 1,2,4-oxadiazoles the reactions were dramatically accelerated by addition of 0.1 equiv of TBAH at room temperature. This method was also more generally applicable allowing for a wider range of substrates. Additionally, due to the absence of fluoride, TBAH will not result in corrosion of reactor vessels and therefore is better suited for large-scale synthesis.
- Otaka, Hiromichi,Ikeda, Junya,Tanaka, Daisuke,Tobe, Masanori
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p. 979 - 981
(2015/02/02)
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- HNO made-easy from photochemical cycloreversion of novel 3,5-heterocyclic disubstituted 1,2,4-oxadiazole-4-oxides
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A variety of symmetric and asymmetric 3,5-heterocyclic disubstituted 1,2,4-oxadiazole-4-oxides have been prepared through cycloaddition of aromatic and heteroaromatic nitrile oxides to heteroaromatic amidoximes. A library of novel, fully characterized, 1,
- Memeo, Misal Giuseppe,Dondi, Daniele,Mannucci, Barbara,Corana, Federica,Quadrelli, Paolo
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p. 7387 - 7394
(2013/08/23)
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- Synthesis and anticancer activities of novel 3,5-disubstituted-1,2,4-oxadiazoles
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A series of 3,5-disubstituted-1,2,4-oxadiazoles were synthesized and evaluated for their in vitro anti-proliferative activities against various cancer cell lines. Formation of 1,2,4-oxadiazole ring was accomplished by the reaction of amidoxime with carbox
- Kumar, Dalip,Patel, Gautam,Johnson, Emmanuel O.,Shah, Kavita
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experimental part
p. 2739 - 2741
(2009/12/31)
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- NOVEL OXADIAZOLE COMPOUNDS
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Novel oxadiazole compounds, pharmaceutical compositions containing such compounds and the use of those compounds or compositions as agonists or antagonists of the S1P family of G protein-coupled receptors for treating diseases associated with modulation o
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Page/Page column 80
(2008/12/06)
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- PYRROLO-PYRIDINE DERIVATIVES
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A class of pyrrolo[2,3-b]pyridine derivatives, linked via the 3-position thereof by a methylene group to a tetrahydropyridinyl moiety, the latter moiety being substituted in turn by an aryl-or heteroaryl-substituted divalent monocyclic radical, are ligands for dopamine receptorsubtypes within the body, in particular the D 4 subtype, and are accordingly of use in the treatment and/or prevention of disorders of the dopamine system, including schizophrenia and depression.
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