- Synthesis and Biological Evaluation of Sigma-1 (σ1) Receptor Ligands Based on Phenyl-1,2,4-oxadiazole Derivatives
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In this study, a series of phenyl-1,2,4-oxadiazole derivatives were synthesized and evaluated for anti-allodynic activity. Structure–activity relationship studies identified 1-{4-[3-(2,4-dichlorophenyl)-1,2,4-oxadiazol-5-yl]butyl}piperidine (39) with excellent affinity for the σ1 receptor and selectivity for the σ2 receptor, with poor activity to other central nervous system neurotransmitter receptors and transporters associated with pain. Compound 39 exhibited dose-dependent efficacy in suppressing the formalin-induced flinching and attenuating mechanical allodynia in chronic constriction injury-induced neuropathic rats. These results suggest that compound 39 exerts potent antihyperalgesic activity and could be considered as a promising candidate for treating neuropathic pain.
- Cao, Xudong,Yao, Zhongyuan,Dou, Fei,Zhang, Yifang,Qiu, Yinli,Zhao, Song,Xu, Xiangqing,Liu, Xin,Liu, Bi-Feng,Chen, Yin,Zhang, Guisen
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- Efficient and convenient protocol for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles using HClO4-SiO2 as a heterogeneous recyclable catalyst
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Silica-supported perchloric acid (HClO4SiO2) was found to be a new, highly efficient, inexpensive, and reusable catalyst for a rapid and efficient synthesis of various 1,2,4-oxadiazoles with good to excellent yields under solvent-free conditions. The present methodology has been effectively utilized for the synthesis of oxolamine, an anti-inflammatory drug.
- Tadikonda, Ramu,Nakka, Mangarao,Gajula, Mahaboob Basha,Rayavarapu, Srinuvasarao,Gollamudi, Padma Rao,Vidavalur, Siddaiah
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supporting information
p. 1978 - 1986
(2014/07/07)
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- Tuned methods for conjugate addition to a vinyl oxadiazole; Synthesis of pharmaceutically important motifs
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The addition of various nucleophiles to a vinyl 1,2,4-oxadiazole is described. Following optimisation, individual protocols tuned for the use of each specific class of reagent have been developed to allow the installation of nitrogen, sulfur, oxygen, and carbon nucleophiles, and leading to the preparation of a series of compounds containing the pharmaceutically important oxadiazole motif.
- Burns, Alan R.,Kerr, Jennifer H.,Kerr, William J.,Passmore, Joanna,Paterson, Laura C.,Watson, Allan J. B.
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experimental part
p. 2777 - 2783
(2010/08/20)
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