Title:
ALKYNYL AMINO ACID ESTER DERIVATIVE PREPARATION METHOD USING PHOTOCATALYTIC REACTION, AND USES THEREOF
Document Type and Number:
WIPO Patent Application WO/2024/085386
Kind Code:
A1
Abstract:
It has been identified that an alkynyl amino acid ester derivative preparation method using a photocatalytic reaction, according to the present invention, is simple and enables a linear, cyclic or chiral alkynyl amino acid ester derivative to be effectively prepared under simple and eco-friendly conditions. In addition, it has been identified that the alkynyl amino acid ester derivative prepared in the present invention exhibits anti-inflammatory and neuroprotective effects, and thus can be effectively used in an inflammatory composition.
Inventors:
LEE ANSOO (KR)
LEE SANGHEE (KR)
KIM JUYEONG (KR)
SON JUNHYEOK (KR)
LEE SANGHEE (KR)
KIM JUYEONG (KR)
SON JUNHYEOK (KR)
Application Number:
PCT/KR2023/011341
Publication Date:
April 25, 2024
Filing Date:
August 02, 2023
Export Citation:
Assignee:
KOREA INST SCI & TECH (KR)
International Classes:
C07C303/40; A23L33/10; A61K8/46; A61K8/49; C07C307/04; C07D207/16; C07D211/96; C07D223/06; C07D333/06; C07F7/08
Other References:
CRUCIANELLI, M. ET AL. SYNTHESIS OF ENANTIOMERICALLY PURE Α-ETHYL: "α-vinyl and α-ethynyl 3", 3, vol. 125, 3-trifluoro alaninates. Journal of fluorine chemistry. 2004, pages 573 - 577, XP004507061, DOI: 10.1016/j.jfluchem.2003.11.034
LU ZHANG: "Redox deracemization of β,γ-alkynyl α-amino esters", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 11, no. 17, 6 May 2020 (2020-05-06), United Kingdom , pages 4444 - 4449, XP093160505, ISSN: 2041-6520, DOI: 10.1039/D0SC00944J
ISAO MIZOTA: "Regioselective Tandem N -Alkylation/ C -Acylation of β,γ-Alkynyl α-Imino Esters", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 15, no. 16, 16 August 2013 (2013-08-16), US , pages 4206 - 4209, XP093160508, ISSN: 1523-7060, DOI: 10.1021/ol401934x
QIANG KANG: "Asymmetric Transfer Hydrogenation of β,γ-Alkynyl α-Imino Esters by a Brønsted Acid", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 10, no. 10, 1 May 2008 (2008-05-01), US , pages 2031 - 2034, XP093160509, ISSN: 1523-7060, DOI: 10.1021/ol800494r
JIAN‐XIN JI; TERRY T.‐L. AU‐YEUNG; JING WU; CHIU WING YIP; ALBERT S. C. CHAN: "Efficient Synthesis of β,γ‐Alkynyl α‐Amino Acid Derivatives by Ag(I)‐Catalyzed Alkynylation of α‐Imino Esters", ADVANCED SYNTHESIS AND CATALYSIS, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 346, no. 1, 16 February 2004 (2004-02-16), Hoboken, USA, pages 42 - 44, XP072354974, ISSN: 1615-4150, DOI: 10.1002/adsc.200303148
JUYEONG KIM: "Photocatalytic Alkyl Addition to Access Quaternary Alkynyl α-Amino Esters", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 24, no. 48, 9 December 2022 (2022-12-09), US , pages 8870 - 8874, XP093160514, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.2c03669
LU ZHANG: "Redox deracemization of β,γ-alkynyl α-amino esters", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 11, no. 17, 6 May 2020 (2020-05-06), United Kingdom , pages 4444 - 4449, XP093160505, ISSN: 2041-6520, DOI: 10.1039/D0SC00944J
ISAO MIZOTA: "Regioselective Tandem N -Alkylation/ C -Acylation of β,γ-Alkynyl α-Imino Esters", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 15, no. 16, 16 August 2013 (2013-08-16), US , pages 4206 - 4209, XP093160508, ISSN: 1523-7060, DOI: 10.1021/ol401934x
QIANG KANG: "Asymmetric Transfer Hydrogenation of β,γ-Alkynyl α-Imino Esters by a Brønsted Acid", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 10, no. 10, 1 May 2008 (2008-05-01), US , pages 2031 - 2034, XP093160509, ISSN: 1523-7060, DOI: 10.1021/ol800494r
JIAN‐XIN JI; TERRY T.‐L. AU‐YEUNG; JING WU; CHIU WING YIP; ALBERT S. C. CHAN: "Efficient Synthesis of β,γ‐Alkynyl α‐Amino Acid Derivatives by Ag(I)‐Catalyzed Alkynylation of α‐Imino Esters", ADVANCED SYNTHESIS AND CATALYSIS, JOHN WILEY & SONS, INC., HOBOKEN, USA, vol. 346, no. 1, 16 February 2004 (2004-02-16), Hoboken, USA, pages 42 - 44, XP072354974, ISSN: 1615-4150, DOI: 10.1002/adsc.200303148
JUYEONG KIM: "Photocatalytic Alkyl Addition to Access Quaternary Alkynyl α-Amino Esters", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 24, no. 48, 9 December 2022 (2022-12-09), US , pages 8870 - 8874, XP093160514, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.2c03669
Attorney, Agent or Firm:
PADO IP LAW PLLC (KR)
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