Preparation and antimalarial activity of semisynthetic lycorenine derivatives

被引：14

作者：

Cedron, Juan C. ^{[1
,2
,3
]}

Gutierrez, David ^{[4
]}

Flores, Ninoska ^{[4
]}

Ravelo, Angel G. ^{[1
,2
]}

Estevez-Braun, Ana ^{[1
,2
]}

机构：

[1] Inst Univ Bioorgan Antonio Gonzalez, San Cristobal la Laguna 38206, Tenerife, Spain

[2] ICIC, Madrid, Spain

[3] Univ Ingn & Tecnol UTEC, Lima 43, Peru

[4] Univ Mayor San Andres, Fac Ciencias Farmaceut & Bioquim, Inst Invest Farm Bioquim, La Paz, Bolivia

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2013年 / 63卷

关键词：

Lycorenine; Antiplasmodial activity; Amaryllidaceae alkaloids; Hippeastrine; LYCORINE DERIVATIVES; N-DEMETHYLATION; CLIVIA-MINIATA; ALKALOIDS; AMARYLLIDACEAE; OXIDATION; ALCOHOLS;

D O I：

10.1016/j.ejmech.2013.03.018

中图分类号：

R914 [药物化学];

学科分类号：

100705 [微生物与生化药学];

摘要：

A set of twenty one lycorenine derivatives has been prepared from the alkaloid hippeastrine (1). The modifications performed on hippeastrine included some functional group transformations, structural simplification and preparation of dimers. All alkaloids were tested as potential antimalarial agents, being the hippeastrine dimers the most active compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

引用

页码：722 / 730

页数：9

共 27 条

[1]

N-DEMETHYLATION OF MORPHINE AND STRUCTURALLY RELATED COMPOUNDS WITH CHLOROFORMATE ESTERS [J].

ABDELMONEM, MM ;

PORTOGHESE, PS .

JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (02) :208-+

[2]

CLIVONIDINE, A NEW ALKALOID FROM CLIVIA-MINIATA [J].

ALI, AA ;

ROSS, SA ;

ELMOGHAZY, AM ;

ELMOGHAZY, SA .

JOURNAL OF NATURAL PRODUCTS, 1983, 46 (03) :350-352

[3]

CYTOTOXICITY OF HYMENOCALLIS-EXPANSA ALKALOIDS [J].

ANTOUN, MD ;

MENDOZA, NT ;

RIOS, YR ;

PROCTOR, GR ;

WICKRAMARATNE, DBM ;

PEZZUTO, JM ;

KINGHORN, AD .

JOURNAL OF NATURAL PRODUCTS, 1993, 56 (08) :1423-1425

[4]

Manganese dioxide can oxidise unactivated alcohols under in situ oxidation-Wittig conditions [J].

Blackburn, L ;

Wei, XD ;

Taylor, RJK .

CHEMICAL COMMUNICATIONS, 1999, (14) :1337-1338

[5]

Synthesis and antimalarial activity of new haemanthamine-type derivatives [J].

Cedron, Juan C. ;

Gutierrez, David ;

Flores, Ninoska ;

Ravelo, Angel G. ;

Estevez-Braun, Ana .

BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (18) :5464-5472

[6]

Synthesis and antiplasmodial activity of lycorine derivatives [J].

Cedron, Juan C. ;

Gutierrez, David ;

Flores, Ninoska ;

Ravelo, Angel G. ;

Estevez-Braun, Ana .

BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (13) :4694-4701

[7]

Cedrón JC, 2010, ALKALOIDS-CHEM BIOL, V68, P1, DOI 10.1016/S1099-4831(10)06801-X

[8]

Pancratium canariense as an Important Source of Amaryllidaceae Alkaloids [J].

Cedron, Juan C. ;

Oberti, Juan C. ;

Estevez-Braun, Ana ;

Ravelo, Angel G. ;

Del Arco-Aguilar, Marcelino ;

Lopez, Matias .

JOURNAL OF NATURAL PRODUCTS, 2009, 72 (01) :112-116

[9]

COREY EJ, 1975, TETRAHEDRON LETT, P2647

[10]

A convenient and chemoselective one-pot oxidation/Wittig reaction for the C2-homologation of carbohydrate-derived glycols [J].

Crisóstomo, FRP ;

Carrillo, R ;

Martín, T ;

García-Tellado, F ;

Martín, VS .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (24) :10099-10101

← 1 2 3 →