Synthesis and biological evaluation of new 1,2-dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for treatment of autoimmune disorders:: Structure-activity relationship

被引：141

作者：

Jönsson, S ^{[1
]}

Andersson, G ^{[1
]}

Fex, T ^{[1
]}

Fristedt, T ^{[1
]}

Hedlund, G ^{[1
]}

Jansson, K ^{[1
]}

Abramo, L ^{[1
]}

Fritzson, I ^{[1
]}

Pekarski, O ^{[1
]}

Runström, A ^{[1
]}

Sandin, H ^{[1
]}

Thuvesson, I ^{[1
]}

Björk, A ^{[1
]}

机构：

[1] Active Biotech Res AB, SE-22007 Lund, Sweden

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2004年 / 47卷 / 08期

关键词：

D O I：

10.1021/jm031044w

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).

引用

页码：2075 / 2088

页数：14

共 50 条

[21] Synthesis and biological activities of truncated acridone: Structure-activity relationship studies of cytotoxic 5-hydroxy-4-quinolone
Chun, MW
Olmstead, KK
Choi, YS
Lee, CO
Lee, CK
Kim, JH
Lee, JW
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1997, 7 (07) : 789 - 792
[22] C-4 analogues of podophyllotoxin as tubulin inhibitors: synthesis, biological evaluation, and structure-activity relationship
Lu, Breanna
Xu, Lexi
Chen, Harriet
Yu, Grace
Khow, Kimberly
Yang, Stella
Dinker, Arushi
Njoo, Edward
NATURAL PRODUCT RESEARCH, 2024,
[23] Synthesis and structure of 3-(3-acetoxyalkylcarbamoyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-1-yl)propanoic acids
I. V. Ukrainets
O. V. Gorokhova
K. V. Andreeva
Russian Journal of Organic Chemistry, 2014, 50 : 63 - 65
[24] 4-hydroxy-2-quinolones. 149*. Synthesis, chemical transformations, and biological properties of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylic acids
Ukrainets, I. V.
Tkach, A. A.
Yang, Liu Yang
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (11) : 1347 - 1354
[25] 4-hydroxy-2-quinolones - 140. Synthesis and diuretic activity of arylalkylamides of 4-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid
Ukrainets, I. V.
Bereznyakova, N. L.
Parshikov, V. A.
Kravchenko, V. N.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (01) : 64 - 72
[26] 4-hydroxy-2-quinolones. 149*. Synthesis, chemical transformations, and biological properties of β-N-acylhydrazides of 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylic acids
I. V. Ukrainets
A. A. Tkach
Liu Yang Yang
Chemistry of Heterocyclic Compounds, 2008, 44 : 1347 - 1354
[27] Synthesis and structure of 3-(3-acetoxyalkylcarbamoyl-4-hydroxy-2-oxo-1,2-dihydroquinolin-1-yl)propanoic acids
Ukrainets, I. V.
Gorokhova, O. V.
Andreeva, K. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 50 (01) : 63 - 65
[28] 4-Hydroxy-2-quinolones 140. Synthesis and diuretic activity of arylalkylamides of 4-methyl-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid
I. V. Ukrainets
N. L. Bereznyakova
V. A. Parshikov
V. N. Kravchenko
Chemistry of Heterocyclic Compounds, 2008, 44 : 64 - 72
[29] 4-HYDROXY-2-QUINOLONES. 191.* SYNTHESIS, TAUTOMERISM AND BIOLOGICAL ACTIVITY OF BENZIMIDAZOL-2-YLAMIDES OF 1-R-4-HYDROXY-2-OXO-1,2-DIHYDROQUINOLINE-3-CARBOXYLIC ACIDS
Ukrainets, I. V.
Grinevich, L. A.
Tkach, A. A.
Gorokhova, O. V.
Kravchenko, V. N.
Sim, G.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2011, 46 (11) : 1364 - 1370
[30] 4-hydroxy-2-quinolones. 191.* synthesis, tautomerism and biological activity of benzimidazol-2-ylamides of 1-r-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids
I. V. Ukrainets
L. A. Grinevich
A. A. Tkach
O. V. Gorokhova
V. N. Kravchenko
G. Sim
Chemistry of Heterocyclic Compounds, 2011, 46 : 1364 - 1370

← 1 2 3 4 5 →