https://scholars.lib.ntu.edu.tw/handle/123456789/416067
標題: | Substituent and solvent effects in the 1,3-dipolar cycloadditions for synthesis of anti-influenza agent peramivir and its analog | 作者: | Chen, C.-L. Chiu, T.-W. Chen, Y.-W. Fang, J.-M. |
關鍵字: | Cycloaddition; Influenza; Nitrile oxide; Organic synthesis; Peramivir | 公開日期: | 2019 | 來源出版物: | Tetrahedron | 摘要: | Influenza remains a health problem to humans. Peramivir is a FDA approved anti-influenza drug targeting the virus neuraminidase. The (3 + 2) cycloaddition reaction of 2-ethylbutanenitrile oxide with the cyclopentene dipolarophile derived from Vince lactam is a key step in the conventional synthesis of peramivir. Our study showed that conducting the (3 + 2) cycloaddition reactions with either aliphatic or aromatic nitrile oxide in hexane solution provided high percentage of the desired regioisomer, and the N-substituent having electron-withdrawing property is also beneficial to the regioselectivity. This study also demonstrated an alternative synthetic pathway of (?)-peramivir and the analog having a phenyl group in place of the 3-pentyl moiety. ? 2019 Elsevier Ltd |
URI: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85068040386&doi=10.1016%2fj.tet.2019.06.023&partnerID=40&md5=aacd8756abf5cc3ea3fb021c1c68f0f2 https://scholars.lib.ntu.edu.tw/handle/123456789/416067 |
DOI: | 10.1016/j.tet.2019.06.023 | SDG/關鍵字: | 2 ethyl n hydroxybutanimidoyl chloride; antivirus agent; methyl 3 (pentan 3 yl) 4 (2,2,2 trifluoroacetamido) 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 6 carboxylate; methyl 3 (pentan 3 yl) 4 [(trifluoromethyl)sulfonamido]3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 6 carboxylate; methyl 3 (pentan 3 yl) 4 [[(2,2,2 trichloroethoxy) carbonyl]amino] 3a,5,6,6a tetrahydro 4h cyclopent[d]isoxazole 6 carboxylate; methyl 3 (pentan 3 yl) 6 (2,2,2 trifluoroacetamido) 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 4 carboxylate; methyl 3 (pentan 3 yl) 6 [(trifluoromethyl) sulfonamido] 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 4 carboxylate; methyl 3 (pentan 3 yl) 6 [[(2,2,2 trichloroethoxy)carbonyl]amino] 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 4 carboxylate; methyl 3 phenyl 4 [[(2,2,2 trichloroethoxy)carbonyl] amino] 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 6 carboxylate; methyl 3 phenyl 6 [[(2,2,2 trichloroethoxy) carbonyl]amino] 3a,5,6,6a tetrahydro 4h cyclopent[d]isoxazole 4 carboxylate; methyl 4 (1,3 dioxoisoindolin 2 yl) 3 (pentan 3 yl) 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 6 carboxylate; methyl 4 (1,3 dioxoisoindolin 2 yl)cyclopent 2 ene 1 carboxylate; methyl 4 (2,2,2 trifluoroacetamido)cyclopent 2 ene 1 carboxylate; methyl 4 acetamido 3 (pentan 3 yl) 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 6 carboxylate; methyl 4 acetamidocyclopent 2 ene 1 carboxylate; methyl 4 tert butoxycarbonylamino 3 (1 ethylpropyl) 4,5,6,6a tetrahydro 3aH cyclopenta[d]isoxazole 6 carboxylate; methyl 4 [(2 nitrophenyl)sulfonamido] 3 (pentan 3 yl) 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 6 carboxylate; methyl 4 [(2 nitrophenyl)sulfonamido]cyclopent 2 ene 1 carboxylate; methyl 4 [(tert butoxycarbonyl)amino] 3 phenyl 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 6 carboxylate; methyl 4 [(tert butoxycarbonyl)amino]cyclopent 2 ene 1 carboxylate; methyl 4 [(trifluoromethyl)sulfonamido]cyclopent 2 ene 1 carboxylate; methyl 4 [[(2,2,2 trichloroethoxy)carbonyl]amino]cyclopent 2 ene 1 carboxylate; methyl 6 (1,3 dioxoisoindolin 2 yl) 3 (pentan 3 yl) 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 4 carboxylate; methyl 6 acetamido 3 (pentan 3 yl) 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 4 carboxylate; methyl 6 [(2 nitrophenyl)sulfonamido] 3 (pentan 3 yl) 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 4 carboxylate; methyl 6 [(tert butoxycarbonyl)amino] 3 (pentan 3 yl) 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 4 carboxylate; methyl 6 [(tert butoxycarbonyl)amino] 3 phenyl 3a,5,6,6a tetrahydro 4h cyclopenta[d]isoxazole 4 carboxylate; n hydroxybenzimidoyl chloride; peramivir; unclassified drug; unindexed drug; antiviral activity; Article; concentration response; cycloaddition; drug structure; drug synthesis; isomer; priority journal; regioselectivity; solvent effect; substitution reaction |
顯示於: | 化學系 |
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