6-氧代-3-(2-苯基吡唑并[1,5-a]吡啶-3-基)-1(6H)-哒嗪丁酸（FK 838）的发现：一种具有强效利尿活性的新型非黄嘌呤腺苷A1受体拮抗剂。 - Suppr

Discovery of 6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1(6H)- pyridazinebutanoic acid (FK 838): a novel non-xanthine adenosine A1 receptor antagonist with potent diuretic activity.

作者信息

Akahane A, Katayama H, Mitsunaga T, Kato T, Kinoshita T, Kita Y, Kusunoki T, Terai T, Yoshida K, Shiokawa Y

机构信息

Medicinal Chemistry Research Laboratories, Fujisawa Pharmaceutical Company, Ltd., 1-6, 2-chome, Kashima, Yodogawa-ku, Osaka 532-8514, Japan.

出版信息

J Med Chem. 1999 Mar 11;42(5):779-83. doi: 10.1021/jm980671w.

DOI:10.1021/jm980671w

PMID:10072675

Abstract

摘要

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Discovery of 6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1(6H)- pyridazinebutanoic acid (FK 838): a novel non-xanthine adenosine A1 receptor antagonist with potent diuretic activity.6-氧代-3-(2-苯基吡唑并[1,5-a]吡啶-3-基)-1(6H)-哒嗪丁酸（FK 838）的发现：一种具有强效利尿活性的新型非黄嘌呤腺苷A1受体拮抗剂。

J Med Chem. 1999 Mar 11;42(5):779-83. doi: 10.1021/jm980671w.

General pharmacology of the new non-xanthine adenosine A1 receptor antagonist (+)-(R)-[(E)-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2- piperidine ethanol.新型非黄嘌呤腺苷A1受体拮抗剂(+)-(R)-[(E)-3-(2-苯基吡唑并[1,5-a]吡啶-3-基)丙烯酰基]-2-哌啶乙醇的一般药理学

Arzneimittelforschung. 1996 Feb;46(2):185-91.

Novel adenosine A1 receptor antagonists. Synthesis and structure-activity relationships of a novel series of 3-(2-cyclohexenyl-3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5 -a]pyridines.新型腺苷A1受体拮抗剂。新型系列3-(2-环己烯基-3-氧代-2,3-二氢哒嗪-6-基)-2-苯基吡唑并[1,5-a]吡啶的合成与构效关系

Bioorg Med Chem. 2000 Jan;8(1):55-64. doi: 10.1016/s0968-0896(99)00258-8.

Synthesis and structure-activity relationship of pyrazolo[3,4-d]pyrimidines: potent and selective adenosine A1 receptor antagonists.吡唑并[3,4-d]嘧啶的合成及其构效关系：强效且选择性的腺苷A1受体拮抗剂

J Med Chem. 1996 Oct 11;39(21):4156-61. doi: 10.1021/jm960052s.

New pyrazolo[3,4-b]pyridones as selective A(1) adenosine receptor antagonists: synthesis, biological evaluation and molecular modelling studies.新型吡唑并[3,4 - b]吡啶酮类化合物作为选择性A(1)腺苷受体拮抗剂：合成、生物学评价及分子模拟研究

Org Biomol Chem. 2005 Jun 21;3(12):2262-70. doi: 10.1039/b502831k. Epub 2005 May 19.

A novel non-xanthine adenosine A1 receptor antagonist.一种新型非黄嘌呤腺苷A1受体拮抗剂。

Eur J Pharmacol. 1995 Jun 12;279(2-3):217-25. doi: 10.1016/0014-2999(95)00165-h.

Discovery of 3-{5-[(6-amino-1H-pyrazolo[3,4-b]pyridine-3-yl)methoxy]-2-chlorophenoxy}-5-chlorobenzonitrile (MK-4965): a potent, orally bioavailable HIV-1 non-nucleoside reverse transcriptase inhibitor with improved potency against key mutant viruses.3-{5-[(6-氨基-1H-吡唑并[3,4-b]吡啶-3-基)甲氧基]-2-氯苯氧基}-5-氯苯甲腈（MK-4965）的发现：一种强效、口服生物可利用的HIV-1非核苷逆转录酶抑制剂，对关键突变病毒具有更高的活性。

J Med Chem. 2008 Oct 23;51(20):6503-11. doi: 10.1021/jm800856c. Epub 2008 Oct 1.

Pyrazolopyridines with potent activity against herpesviruses: effects of C5 substituents on antiviral activity.对疱疹病毒具有强效活性的吡唑并吡啶：C5取代基对抗病毒活性的影响。

Bioorg Med Chem Lett. 2008 Feb 1;18(3):1157-61. doi: 10.1016/j.bmcl.2007.11.120. Epub 2007 Dec 4.

CVT-124, a novel adenosine A1 receptor antagonist with unique diuretic activity.CVT - 124，一种具有独特利尿活性的新型腺苷A1受体拮抗剂。

J Pharmacol Exp Ther. 1998 Sep;286(3):1191-6.

Synthesis and 3D QSAR of new pyrazolo[3,4-b]pyridines: potent and selective inhibitors of A1 adenosine receptors.

J Med Chem. 2005 Nov 17;48(23):7172-85. doi: 10.1021/jm050407k.

引用本文的文献

Three successive and regiocontroled palladium cross-coupling reactions to easily synthesize novel series of 2,4,6-tris(het)aryl pyrido[1',2':1,5]pyrazolo[3,4-]pyrimidines.通过三步连续且区域可控的钯交叉偶联反应，轻松合成新型系列的2,4,6-三（杂）芳基吡啶并[1',2':1,5]吡唑并[3,4-]嘧啶。

RSC Adv. 2018 Jan 2;8(2):732-741. doi: 10.1039/c7ra12246b.

Synthesis, spectroscopy, crystal structure, TGA/DTA study, DFT and molecular docking investigations of ()-4-(4-methylbenzyl)-6-styrylpyridazin-3()-one.（）-4-（4-甲基苄基）-6-苯乙烯基哒嗪-3（）-酮的合成、光谱学、晶体结构、热重/差示热分析研究、密度泛函理论及分子对接研究

J Mol Struct. 2021 Mar 15;1228:129435. doi: 10.1016/j.molstruc.2020.129435. Epub 2020 Oct 10.

Synthetic Strategy for Pyrazolo[1,5-]pyridine and Pyrido[1,2-]indazole Derivatives through AcOH and O-Promoted Cross-dehydrogenative Coupling Reactions between 1,3-Dicarbonyl Compounds and -Amino-2-iminopyridines.通过乙酸和氧促进的1,3-二羰基化合物与α-氨基-2-亚氨基吡啶之间的交叉脱氢偶联反应合成吡唑并[1,5-a]吡啶和吡啶并[1,2-a]吲唑衍生物的策略

ACS Omega. 2019 Sep 4;4(12):15289-15303. doi: 10.1021/acsomega.9b02430. eCollection 2019 Sep 17.

Scalable Sonochemical Synthetic Strategy for Pyrazolo[1,5-]pyridine Derivatives: First Catalyst-Free Concerted [3 + 2] Cycloaddition of Alkyne and Alkene Derivatives to 2-Imino-1-pyridin-1-amines.吡唑并[1,5 - ]吡啶衍生物的可扩展声化学合成策略：炔烃和烯烃衍生物与2 - 亚氨基 - 1 - 吡啶 - 1 - 胺的首例无催化剂协同[3 + 2]环加成反应

ACS Omega. 2019 Apr 19;4(4):7182-7193. doi: 10.1021/acsomega.9b00562. eCollection 2019 Apr 30.

Regioselective Synthesis of New 2,4-(Het)aryl-3H-pyrido[1',2':1,5]pyrazolo[4,3-d]pyrimidines Involving Palladium-Catalyzed Cross-Coupling Reactions.新型 2,4-(杂)芳基-3H-吡啶并[1',2':1,5]吡唑并[4,3-d]嘧啶的区域选择性合成涉及钯催化的交叉偶联反应。

Molecules. 2018 Oct 23;23(11):2740. doi: 10.3390/molecules23112740.

Pyrazolo derivatives as potent adenosine receptor antagonists: an overview on the structure-activity relationships.作为强效腺苷受体拮抗剂的吡唑并衍生物：构效关系概述

Int J Med Chem. 2011;2011:480652. doi: 10.1155/2011/480652. Epub 2011 Mar 7.

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Discovery of 6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1(6H)- pyridazinebutanoic acid (FK 838): a novel non-xanthine adenosine A1 receptor antagonist with potent diuretic activity.

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