RU2011121184A - NEW Bicyclic pyrrolidine derivatives with antioxidant activity and a method for their preparation - Google Patents

NEW Bicyclic pyrrolidine derivatives with antioxidant activity and a method for their preparation Download PDF

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RU2011121184A
RU2011121184A RU2011121184/04A RU2011121184A RU2011121184A RU 2011121184 A RU2011121184 A RU 2011121184A RU 2011121184/04 A RU2011121184/04 A RU 2011121184/04A RU 2011121184 A RU2011121184 A RU 2011121184A RU 2011121184 A RU2011121184 A RU 2011121184A
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hal
hoph
meoph
naphthalene
noph
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RU2472794C1 (en
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Константин Викторович Кудрявцев
Надежда Титовна Берберова
Виктория Павловна Осипова
Наталья Александровна Антонова
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Федеральное государственное образовательное учреждение высшего профессионального образования Астраханский государственный технический университет (ФГОУ ВПО АГТУ)
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Abstract

1. Средство, обладающее пролонгированной антиоксидантной активностью, представляющее собой производные пирролидинов, содержащих фрагмент пространственно-затрудненного фенола, общей формулы:где R=H, Me, Et, Bn; R=H, Me, Et, i-Pr, i-Bu, Bn, 4-HOPhCH, CHCHSMe; Ar=Ph, 2-Hal (Hal=F, Cl, Br, I), 3-Hal, 4-Hal, 2,6-diMePhN, 2,3,5,6-tetraFPh, 2-MeOPh, 3-MeOPh, 4-MeOPh, 2-HOPh, 3-HOPh, 4-HOPh, (нафталин-1-ил), (нафталин-2-ил), 2-NOPh, 3-NOPh, 4-NOPh.2. Способ получения новых бициклических производных пирролидина, обладающих антиоксидантной активностью, общей формулы:где R=H, Me, Et, Bn; R=H, Me, Et, i-Pr, i-Bu, Bn, 4-HOPhCH, CHCHSMe; Ar=Ph, 2-Hal (Hal=F, Cl, Br, I), 3-Hal, 4-Hal, 2,6-diMePhN, 2,3,5,6-tetraFPh, 2-MeOPh, 3-MeOPh, 4-MeOPh, 2-HOPh, 3-HOPh, 4-HOPh, (нафталин-1-ил), (нафталин-2-ил), 2-NOPh, 3-NOPh, 4-NOPh, при котором растворы азометина и N-замещенного малеимида смешивают на воздухе и индуцируют их взаимодействие каталитическими количествами N-трет-бутоксикарбонильных производных альфа-аминокислот (глицина, аланина, фенилаланина) с последующим концентрированием органической фазы при пониженном давлении, и очисткой остатка при помощи хроматографии на силикагеле с использованием CHCl/MeOH в качестве элюента.1. A tool with prolonged antioxidant activity, which is a derivative of pyrrolidines containing a fragment of spatially hindered phenol, of the general formula: where R = H, Me, Et, Bn; R = H, Me, Et, i-Pr, i-Bu, Bn, 4-HOPhCH, CHCHSMe; Ar = Ph, 2-Hal (Hal = F, Cl, Br, I), 3-Hal, 4-Hal, 2,6-diMePhN, 2,3,5,6-tetraFPh, 2-MeOPh, 3-MeOPh 4-MeOPh, 2-HOPh, 3-HOPh, 4-HOPh, (naphthalen-1-yl), (naphthalene-2-yl), 2-NOPh, 3-NOPh, 4-NOPh. 2. A method of obtaining new bicyclic pyrrolidine derivatives having antioxidant activity, of the general formula: where R = H, Me, Et, Bn; R = H, Me, Et, i-Pr, i-Bu, Bn, 4-HOPhCH, CHCHSMe; Ar = Ph, 2-Hal (Hal = F, Cl, Br, I), 3-Hal, 4-Hal, 2,6-diMePhN, 2,3,5,6-tetraFPh, 2-MeOPh, 3-MeOPh , 4-MeOPh, 2-HOPh, 3-HOPh, 4-HOPh, (naphthalene-1-yl), (naphthalene-2-yl), 2-NOPh, 3-NOPh, 4-NOPh, in which solutions of azomethine and N-substituted maleimide is mixed in air and their reaction is induced by catalytic amounts of N-tert-butoxycarbonyl derivatives of alpha amino acids (glycine, alanine, phenylalanine), followed by concentration of the organic phase under reduced pressure, and purification of the residue by silica gel chromatography using CHCl / MeOH as eluent.

Claims (2)

1. Средство, обладающее пролонгированной антиоксидантной активностью, представляющее собой производные пирролидинов, содержащих фрагмент пространственно-затрудненного фенола, общей формулы:1. A tool with prolonged antioxidant activity, which is a derivative of pyrrolidines containing a fragment of spatially hindered phenol, of the general formula:
Figure 00000001
Figure 00000001
 где R1=H, Me, Et, Bn; R2=H, Me, Et, i-Pr, i-Bu, Bn, 4-HOPhCH2, CH2CH2SMe; Ar=Ph, 2-Hal (Hal=F, Cl, Br, I), 3-Hal, 4-Hal, 2,6-diMePhN, 2,3,5,6-tetraFPh, 2-MeOPh, 3-MeOPh, 4-MeOPh, 2-HOPh, 3-HOPh, 4-HOPh, (нафталин-1-ил), (нафталин-2-ил), 2-NO2Ph, 3-NO2Ph, 4-NO2Ph.where R 1 = H, Me, Et, Bn; R 2 = H, Me, Et, i-Pr, i-Bu, Bn, 4-HOPhCH 2 , CH 2 CH 2 SMe; Ar = Ph, 2-Hal (Hal = F, Cl, Br, I), 3-Hal, 4-Hal, 2,6-diMePhN, 2,3,5,6-tetraFPh, 2-MeOPh, 3-MeOPh , 4-MeOPh, 2-HOPh, 3-HOPh, 4-HOPh, (naphthalene-1-yl), (naphthalene-2-yl), 2-NO 2 Ph, 3-NO 2 Ph, 4-NO 2 Ph . 2. Способ получения новых бициклических производных пирролидина, обладающих антиоксидантной активностью, общей формулы:2. A method for producing new bicyclic pyrrolidine derivatives having antioxidant activity, of the general formula:
Figure 00000001
Figure 00000001
 где R1=H, Me, Et, Bn; R2=H, Me, Et, i-Pr, i-Bu, Bn, 4-HOPhCH2, CH2CH2SMe; Ar=Ph, 2-Hal (Hal=F, Cl, Br, I), 3-Hal, 4-Hal, 2,6-diMePhN, 2,3,5,6-tetraFPh, 2-MeOPh, 3-MeOPh, 4-MeOPh, 2-HOPh, 3-HOPh, 4-HOPh, (нафталин-1-ил), (нафталин-2-ил), 2-NO2Ph, 3-NO2Ph, 4-NO2Ph, при котором растворы азометина и N-замещенного малеимида смешивают на воздухе и индуцируют их взаимодействие каталитическими количествами N-трет-бутоксикарбонильных производных альфа-аминокислот (глицина, аланина, фенилаланина) с последующим концентрированием органической фазы при пониженном давлении, и очисткой остатка при помощи хроматографии на силикагеле с использованием CHCl3/MeOH в качестве элюента. where R 1 = H, Me, Et, Bn; R 2 = H, Me, Et, i-Pr, i-Bu, Bn, 4-HOPhCH 2 , CH 2 CH 2 SMe; Ar = Ph, 2-Hal (Hal = F, Cl, Br, I), 3-Hal, 4-Hal, 2,6-diMePhN, 2,3,5,6-tetraFPh, 2-MeOPh, 3-MeOPh , 4-MeOPh, 2-HOPh, 3-HOPh, 4-HOPh, (naphthalene-1-yl), (naphthalene-2-yl), 2-NO 2 Ph, 3-NO 2 Ph, 4-NO 2 Ph in which solutions of azomethine and N-substituted maleimide are mixed in air and their interaction is induced by catalytic amounts of N-tert-butoxycarbonyl derivatives of alpha amino acids (glycine, alanine, phenylalanine), followed by concentration of the organic phase under reduced pressure, and purification of the residue by chromatography on silica gel using CHCl 3 / MeOH as eluent.
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