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

Akahane, Atsushi; Katayama, Hirohito; Mitsunaga, Takafumi; Kato, Takeshi; Kinoshita, Takayoshi; Kita, Yasuhiro; Kusunoki, Takahiro; Terai, Takao; Yoshida, Keizo; Shiokawa, Youichi

doi:10.1021/jm980671w

Cited by 104 publications

(62 citation statements)

References 19 publications

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“…This type of reaction with pyrazole- 44,45 or imidazole- 46 fused ring systems had been reported earlier, with ethyl chloroformate as the favoured reagent for such transformations.…”

Section: Scheme 23supporting

confidence: 64%

New heteroatom-rich ring systems from N,N-dialkyl-N’-chlorosulfonyl chloroformamidines

Francis¹

2016

Arkivoc

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N,N-Dialkyl-N'-chlorosulfonyl chloroformamidines constitute a class of readily available and very versatile bis-electrophiles. This Account describes the application of these unusual + C=N-S + building blocks for construction of a cornucopia of previously unknown or uncommon heterocyclic ring systems. Regioselectivity encountered during heterocycle formation and some properties and chemistry of the newly-formed ring systems are also discussed.

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“…This type of reaction with pyrazole- 44,45 or imidazole- 46 fused ring systems had been reported earlier, with ethyl chloroformate as the favoured reagent for such transformations.…”

Section: Scheme 23supporting

confidence: 64%

New heteroatom-rich ring systems from N,N-dialkyl-N’-chlorosulfonyl chloroformamidines

Francis¹

2016

Arkivoc

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“…Although the initial lead compound FK 453 (13) already showed a good affinity coupled with a good selectivity over the A 2 receptor, there were vast improvements made with the dihydropyridazinyl group. Substitution with a carboxylic acid group (FK 838 (14)) [71] reduced the affinity for the A 1 receptor, and also increased the affinity for the A 2A receptor significantly. Further manipulation of the dihydropyridazinyl moiety with (2-substituted) cyclohexene derivatives (i.e., 15 ± 19) was in consequence to the six-membered (2-substituted) piperidine of FK 453 (13).…”

Section: The Adenosine a 1 Receptormentioning

confidence: 99%

Non‐Xanthine Antagonists for the Adenosine A₁ Receptor

Chang

Brussee

IJzerman

2004

Chemistry & Biodiversity

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“…Pyridazine compounds have been reported to possess varied biological activities such as anti-HIV 1 , anti-TMV 2 , antidepressant 3 , antihypertensive 4 , antithrombotic 5 , anticonvulsant 6 , cardiotonic 7 , anti-bacterial 8 , diuretic 9 and anticancer 10 . Antibacterial, antifungal, antituberculosis, antiviral, anti-inflammatory, anticancer and effectiveness against cardiovascular disorders have also been reported 11,12 .…”

Section: Introductionmentioning

confidence: 99%

New pyrano[2,3-c]pyridazine derivatives with antimicrobial activity synthesized using piperidine as the organocatalyst

Kandile

Zaky

2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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A simple and efficient method for the synthesis of highly diverse pyrano [2,3-c]pyridazines was achieved by a one pot multicomponent reaction using piperidine as the organocatalyst. The synthesis of a series of heterocyclic derivatives with varying functionality (e.g. thiazine, tetrazole and pyrimidine) incorporating the pyrano[2,3-c]pyridazine moiety were achieved via reaction of 2a-e with different reagents. The structures of the synthesized derivatives were elucidated by FTIR, MS, 1 H and 13 C NMR spectroscopy. A number of the newly synthesized targeted compounds 2b-e, 3a-c and 4a-c were evaluated for their in vitro antibacterial activity and were compared with chloramphenicol and nystatin as broad spectrum reference standard antibiotics. Tests were carried out against Staphylococcus aureus (MTCC3160) and Enterococcusi fecalis as Gram-positive bacteria, and Escherichia coli (MTCC1652) and Klebsiella pneumonia as Gram-negative bacteria. Antifungal potential against Candida albicans, and Aspergillus albicans strains were also evaluated. The results revealed that compounds 3a and 3c showed strong significant activity relative to the reference against these bacterial and fungal strains.

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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

Cited by 104 publications

References 19 publications

New heteroatom-rich ring systems from N,N-dialkyl-N’-chlorosulfonyl chloroformamidines

New heteroatom-rich ring systems from N,N-dialkyl-N’-chlorosulfonyl chloroformamidines

Non‐Xanthine Antagonists for the Adenosine A₁ Receptor

New pyrano[2,3-c]pyridazine derivatives with antimicrobial activity synthesized using piperidine as the organocatalyst

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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

Cited by 104 publications

References 19 publications

New heteroatom-rich ring systems from N,N-dialkyl-N’-chlorosulfonyl chloroformamidines

New heteroatom-rich ring systems from N,N-dialkyl-N’-chlorosulfonyl chloroformamidines

Non‐Xanthine Antagonists for the Adenosine A1 Receptor

New pyrano[2,3-c]pyridazine derivatives with antimicrobial activity synthesized using piperidine as the organocatalyst

Contact Info

Product

Resources

About

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

Non‐Xanthine Antagonists for the Adenosine A₁ Receptor