The Beckmann Rearrangement Applied to Ursolic Acid with Antimalarial Activity in Medicinal Chemistry Studies

被引：8

作者：

Dalla-Vechia, Luciana ^{[1
]}

Dassonville-Klimpt, Alexandra ^{[2
]}

Grellier, Philippe ^{[3
]}

Sonnet, Pascal ^{[2
]}

Gosmann, Grace ^{[1
]}

Gnoatto, Simone C. B. ^{[1
,2
]}

机构：

[1] Univ Fed Rio Grande do Sul, Fac Farm, BR-90610000 Porto Alegre, RS, Brazil

[2] Univ Picardie Jules Verne, Fac Med & Pharm, DMAG, EA 3901, F-80037 Amiens 1, France

[3] Museum Natl Hist Nat, CNRS, Dept RDDM, FRE 3206, F-75231 Paris 05, France

来源：

LETTERS IN ORGANIC CHEMISTRY | 2012年 / 9卷 / 02期

关键词：

Antimalarial; Beckmann rearrangement; Beckmann fragmentation; triterpene; ursolic acid; OLEANOLIC ACID; DERIVATIVES;

D O I：

10.2174/157017812800221708

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The A ring-expanded derivative of ursolic acid and the corresponding fragmentation product were obtained through the Beckmann rearrangement under optimized reaction conditions. A mechanistic approach was taken in order to explain both the specificity of the rearrangement and the fragmentation of the cycle. The intermediates and the final products of the route were evaluated for antimalarial activity.

引用

页码：92 / 95

页数：4

共 35 条

[1] Evolution in medicinal chemistry of ursolic acid derivatives as anticancer agents
Chen, Haijun
Gao, Yu
Wang, Ailan
Zhou, Xiaobin
Zheng, Yunquan
Zhou, Jia
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 92 : 648 - 655
[2] Medicinal Chemistry Studies Applied to Protein Targets
Scotti, Luciana
Scotti, Marcus T.
[J]. CURRENT PROTEIN & PEPTIDE SCIENCE, 2019, 20 (12) : 1132 - 1134
[3] Consensus Analyses in Molecular Docking Studies Applied to Medicinal Chemistry
Maia, Mayara dos Santos
Soares Rodrigues, Gabriela Cristina
Silva Cavalcanti, Andreza Barbosa
Scotti, Luciana
Scotti, Marcus Tullius
[J]. MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2020, 20 (14) : 1322 - 1340
[4] Antimalarial Imidazopyridines Incorporating an Intramolecular Hydrogen Bonding Motif: Medicinal Chemistry and Mechanistic Studies
Attram, Henrietta D.
Korkor, Constance M.
Taylor, Dale
Njoroge, Mathew
Chibale, Kelly
[J]. ACS INFECTIOUS DISEASES, 2023, 9 (04): : 928 - 942
[5] A MEDICINAL CHEMISTRY PROGRAM FOR THE DISCOVERY OF PLASMODIUM FALCIPARUM DIHYDROOROTATE DEHYDROGENASE INHIBITORS WITH ANTIMALARIAL ACTIVITY
Patel, Vishal
Booker, Michael L.
Celatka, Cassandra
Kramer, Martin L.
Liu, Hanlan
Cortese, Joseph
Lillie, James
Wiegand, Roger
Clardy, Jon
Wirth, Dyann F.
[J]. AMERICAN JOURNAL OF TROPICAL MEDICINE AND HYGIENE, 2008, 79 (06): : 172 - 172
[6] RECENT STUDIES ON URSOLIC ACID AND ITS BIOLOGICAL AND PHARMACOLOGICAL ACTIVITY
Lee, Sook Young
Kim, Yong Joo
Chung, Sun Ok
Park, Sang Un
[J]. EXCLI JOURNAL, 2016, 15 : 221 - 228
[7] Medicinal chemistry updates on quinoline- and endoperoxide-based hybrids with potent antimalarial activity
Uddin, Amad
Chawla, Meenal
Irfan, Iram
Mahajan, Shubhra
Singh, Shailja
Abid, Mohammad
[J]. RSC MEDICINAL CHEMISTRY, 2021, 12 (01): : 24 - 42
[8] BECKMANN REARRANGEMENT IN CONCENTRATED SULFURIC-ACID - STUDIES BY MEANS OF NMR AND KINETIC ISOTOPE EFFECT
KIM, SG
KAWAKAMI, T
ANDO, T
YUKAWA, Y
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (04) : 1115 - 1120
[9] CHEMICAL STUDIES ON PENTACYCLIC TRI-TERPENES .1. BENZILIC ACID REARRANGEMENT OF RING A IN URSOLIC ACID
OSMAN, AM
ELGARBYYOUNES, M
SHETA, AE
[J]. EGYPTIAN JOURNAL OF CHEMISTRY, 1972, 15 (03): : 269 - 272
[10] Influence of Amodiaquine on the Antimalarial Activity of Ellagic Acid: Crystallographic and Biological Studies
Zeslawska, Ewa
Oleksyn, Barbara
Fabre, Aude
Benoit-Vical, Francoise
[J]. CHEMICAL BIOLOGY & DRUG DESIGN, 2014, 84 (06) : 669 - 675

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