- A KHSO4 mediated facile synthesis of 2-amino-1,3,4-oxadiazole derivatives
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A novel, efficient and mild KHSO4 mediated synthesis for 2-amino-1,3,4-oxadiazoles has been established via the cyclodesulfurization of benzoylhydrazine and isothiocyanate derivatives in one pot. The reactions proceeded smoothly at room tempera
- Gan, Zongjie,Han, Lei,Hu, Xiangnan,Long, Binyu,Tang, Qiang,Tian, Binghua,Wang, Chenyu,Wang, Zifan,Wu, Yue,Yu, Yu
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- 2-Amino-substituted oxadiazole derivatives and pharmaceutical composition comprising the same
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The present invention provides: a novel 2-amino-substituted oxadiazole derivative represented by Chemical Formula 1 and having an excellent Wnt gene expression controlling activity; a pharmaceutically allowable salt of the same; a method for producing the
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Paragraph 0127; 0129; 0148; 0149
(2016/11/21)
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- Regioselective synthesis of 2-amino-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives via reagent-based cyclization of thiosemicarbazide intermediate
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A regioselective, reagent-based method for the cyclization reaction of 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole core skeletons is described. The thiosemicarbazide intermediate 3 was reacted with EDC·HCl in DMSO or p-TsCl, triethylamine in N-
- Yang, Seung-Ju,Lee, Seok-Hyeong,Kwak, Hyun-Jung,Gong, Young-Dae
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p. 438 - 444
(2013/04/10)
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- Oxadiazoles in medicinal chemistry
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Oxadiazoles are five-membered heteroaromatic rings containing two carbons, two nitrogens, and one oxygen atom, and they exist in different regioisomeric forms. Oxadiazoles are frequently occurring motifs in druglike molecules, and they are often used with the intention of being bioisosteric replacements for ester and amide functionalities. The current study presents a systematic comparison of 1,2,4- and 1,3,4-oxadiazole matched pairs in the AstraZeneca compound collection. In virtually all cases, the 1,3,4-oxadiazole isomer shows an order of magnitude lower lipophilicity (log D), as compared to its isomeric partner. Significant differences are also observed with respect to metabolic stability, hERG inhibition, and aqueous solubil ity, favoring the 1,3,4-oxadiazole isomers. The difference in profile between the 1,2,4 and 1,3,4 regioisomers can be rationalized by their intrinsically different charge distributions (e.g., dipole moments). To facilitate the use of these heteroaromatic rings, novel synthetic routes for ready access of a broad spectrum of 1,3,4-oxadiazoles, under mild conditions, are described.
- Bostr?m, Jonas,Hogner, Anders,Llinàs, Antonio,Wellner, Eric,Plowright, Alleyn T.
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p. 1817 - 1830
(2012/05/05)
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- O -iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles
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A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.
- Chaudhari, Pramod S.,Pathare, Sagar P.,Akamanchi, Krishnacharaya G.
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experimental part
p. 3716 - 3723
(2012/06/16)
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