New Pyrazolo[1′,5′:1,6]pyrimido[4,5-d]pyridazin-4 (3H)-ones Fluoroderivatives as Human A1 Adenosine Receptor Ligands

被引：0

作者：

Graziano, Alessia ^{[1
]}

Giovannoni, Maria Paola ^{[1
]}

Cilibrizzi, Agostino ^{[1
]}

Crocetti, Letizia ^{[1
]}

Dal Piaz, Vittorio ^{[1
]}

Vergelli, Claudia ^{[1
]}

Trincavelli, Maria Letizia ^{[2
]}

Martini, Claudia ^{[2
]}

Giacomelli, Chiara ^{[2
]}

机构：

[1] Dipartimento Sci Farmaceut, I-50019 Sesto Fiorentino, Italy

[2] Univ Pisa, Dipartimento Psichiatria Neurobiol Farmacol & Bio, I-56126 Pisa, Italy

来源：

ACTA CHIMICA SLOVENICA | 2012年 / 59卷 / 03期

关键词：

Adenosine receptors; A(1) subtype; Ligands; Pyrazolo[1 ',5 ':1,6]pyrimido[4,5-d]pyridazin-4(3H)-ones; BEARING POLAR SUBSTITUENTS; POTENT; PHARMACOLOGY; DESIGN;

D O I：

暂无

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this paper we report the synthesis and biological evaluation of a new series of pyrazolo[1',5': 1,6] pyrimido[4,5-d]pyridazin-4(3H)-ones as human A(1) adenosine receptor ligands. The tricyclic scaffold was modified at position 6 and 9 by introducing small alkyl chains and substituted phenyls. The most interesting compounds showed Ki for A(1) in the submicromolar range (0.105-0.244 mu M) and the most interesting term (compound 4c) combined an appreciable affinity for A(1) (Ki = 0.132 mu M) with a good selectivity toward A(2A) (43% inhibition at 10 mu M) and A(3) (46% inhibition at 10 mu M).

引用

页码：648 / 655

页数：8

共 50 条

[21] Synthesis and Antimicrobial Evaluation. of Some New Pyrazole, Fused Pyrazolo[1,5-a]-pyrimidine and Pyrazolo[1,5-d]pyrimido[4,5-d][1,2,3]triazine Derivatives
Darwish, Elham S.
Mahmoud, Fivian F.
Altalbawy, Farag M. A.
ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (07) : 2997 - 3002
[22] HETEROCYCLIC STUDIES .34. SOME 5H-PYRIMIDO[4,5-B][1,4]THIAZINE-6(7H)-ONES,5H-PYRIMIDO[4,5-B][1,4]THIAZINE-4,6(3H,7H)-DIONES AND 5H-PYRIMIDO[4,5-B][1,4]THIAZINE-2,4,6(1H,3H,7H)-TRIONES
CLARK, J
SOUTHON, IW
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (15): : 1814 - 1818
[23] Synthesis and Ca2+-desensitizing Activity of 2-methyl-7-aryl(alpha-furyl)-[1,3]thiazolo[4,5-d]pyridazin-4(5H)-ones
Soloviev, Anatoly
Demchenko, Sergey
Bobkova, Ludmyla
Panchenko, Valentyn
Zelenskyi, Sergey
Demchenko, Anatoly
JOURNAL OF PHARMACEUTICAL RESEARCH INTERNATIONAL, 2018, 21 (01)
[24] PYRIMIDO[4,5-D]PYRIMIDINES, PYRIMIDO[4',5'-4,5]PYRIMIDO[6,1-A]-AZEPINES, AND AN IMIDAZO[5,1-F][1,2,4]TRIAZINE BY 3 COMPONENT REACTION
WAMHOFF, H
SCHMIDT, A
HETEROCYCLES, 1993, 35 (02) : 1055 - 1066
[25] Reactions of uracils, 2.3.: Subsequent reactions of 7-ethoxypyrimido[4,5-d]pyrimidines:: Nucleophilic exchange, pyrimido[4,5:4′,5′]pyrimido[1,2-a]quinazolines, benzo[f]pyrimido[4,5:4′,5′] pyrimido[1,2-d][1,3,4]triazepine
Wamhoff, H
Muhr, J
Horn, M
Sohár, P
Csámpai, A
HETEROCYCLIC COMMUNICATIONS, 1999, 5 (04) : 365 - 376
[26] Synthesis and reactivity of 1-amino-4-methyl-3,4-dihydro-5H-pyrazolo[3′,4′:4,5]pyrimido[1,6-a]benzoimidazolo-5-one
Abdelhamid, Abdou O.
Awad, Ahmed A.
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2007, 44 (03) : 701 - 705
[27] Reactions of tetrahydropyrido[4,5-d][1,2,4]triazolo[1,5-a]-pyrimidin-4-ones with activated alkynes. Synthesis of [1,2,4]triazolo[1',5':1,2]pyrimido[4,5-d]azocines
Voskressensky, L. G.
Borisova, T. N.
Ovcharov, M. V.
Sorokina, E. A.
Khrustalev, V. N.
Varlamov, A. V.
RUSSIAN CHEMICAL BULLETIN, 2012, 61 (08) : 1603 - 1608
[28] Reactions of tetrahydropyrido[4,5-d][1,2,4]triazolo[1,5-a]-pyrimidin-4-ones with activated alkynes. Synthesis of [1,2,4]triazolo[1′,5′:1,2]pyrimido[4,5-d]azocines
L. G. Voskressensky
T. N. Borisova
M. V. Ovcharov
E. A. Sorokina
V. N. Khrustalev
A. V. Varlamov
Russian Chemical Bulletin, 2012, 61 : 1603 - 1608
[29] Green Synthesis of Pyrimido[4,5-b]quinolin-2,4(1H,3H)-ones
Nadaraj, Vetrivel
Selvi, Senniappan Thamarai
Abirami, Maharajan
Thangadurai, Thangaian Daneil
RESEARCH JOURNAL OF PHARMACEUTICAL BIOLOGICAL AND CHEMICAL SCIENCES, 2015, 6 (03): : 901 - 904
[30] 1,6-DIMETHYLTETRAHYDROIMIDAZO[4,5-D]IMIDAZOLE-2,5(1H,6H)-DIONE MONOHYDRATE
DEKAPRILEVICH, PO
SUVOROVA, LI
KHMELNITSKII, LI
STRUCHKOV, YT
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1994, 50 : 2056 - 2058

← 1 2 3 4 5 →