PHA-543613

Modify Date: 2024-01-11 15:00:17

PHA-543613 Structure
PHA-543613 structure
 Common Name PHA-543613
CAS Number 478149-53-0 Molecular Weight 271.31
Density N/A Boiling Point N/A
Molecular Formula C15H17N3O2 Melting Point N/A
MSDS USA Flash Point N/A

 Use of PHA-543613


PHA-543613 is a potent, orally active, brain-penetrant and selective α7 nAChR agonist with a Ki of 8.8 nM. PHA-543613 displays selectivity for α7-nAChR over α3β4, α1β1γδ, α4β2 and 5-HT3 receptors[1]. PHA-543613 can be used for the cognitive deficits of Alzheimer's disease and schizophrenia research[2].

 Names

Name N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide
Synonym More Synonyms

 PHA-543613 Biological Activity

Description PHA-543613 is a potent, orally active, brain-penetrant and selective α7 nAChR agonist with a Ki of 8.8 nM. PHA-543613 displays selectivity for α7-nAChR over α3β4, α1β1γδ, α4β2 and 5-HT3 receptors[1]. PHA-543613 can be used for the cognitive deficits of Alzheimer's disease and schizophrenia research[2].
Related Catalog
Target

Ki: 8.8 nM (α7 nAChR)[1]

In Vivo PHA-543613 (0.3 mg/kg) successfully reverses Scopolamine-induced short-term memory deficits in rats[2].
References

[1]. Donn G Wishka, et al. Discovery of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]furo[2,3-c]pyridine-5-carboxamide, an agonist of the alpha7 nicotinic acetylcholine receptor, for the potential treatment of cognitive deficits in schizophrenia: synthesis and structure--activity relationship. J Med Chem. 2006 Jul 13;49(14):4425-36.

[2]. Nóra Bruszt, et al. Potentiation of cognitive enhancer effects of Alzheimer's disease medication memantine by alpha7 nicotinic acetylcholine receptor agonist PHA-543613 in the Morris water maze task. Psychopharmacology (Berl). 2021 Nov;238(11):3273-3281.

 Chemical & Physical Properties

Molecular Formula C15H17N3O2
Molecular Weight 271.31
Exact Mass 307.10900
PSA 58.37000
LogP 2.78260

 Safety Information

RIDADR NONH for all modes of transport

 Synthetic Route

Furo[2,3-c]pyridine-5-carboxylic acid structure

Furo[2,3-c]pyri...

CAS#:478148-62-8

(R)-AUINUCLIDIN-3-AMINE HYDROCHLORIDE structure

(R)-AUINUCLIDIN...

CAS#:137661-31-5

~66%

PHA-543613 Structure

PHA-543613

CAS#:478149-53-0

Literature: Toray Industries, Inc.; Hayashi, Kenichi Patent: US2014/128606 A1, 2014 ; Location in patent: Paragraph 0190; 0191; 0192; 0193; 0194; 0195 ;
Furo[2,3-c]pyridine-5-carboxylic acid structure

Furo[2,3-c]pyri...

CAS#:478148-62-8

3-Aminoquinuclidine dihydrochloride structure

3-Aminoquinucli...

CAS#:6530-09-2

~%

PHA-543613 Structure

PHA-543613

CAS#:478149-53-0

Literature: Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4425 - 4436
Furo[2,3-c]pyridine-5-carbaldehyde structure

Furo[2,3-c]pyri...

CAS#:478148-61-7

~%

PHA-543613 Structure

PHA-543613

CAS#:478149-53-0

Literature: Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4425 - 4436
Furo[2,3-c]pyridin-5-ylmethanol structure

Furo[2,3-c]pyri...

CAS#:478148-60-6

~%

PHA-543613 Structure

PHA-543613

CAS#:478149-53-0

Literature: Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4425 - 4436
2-chlorpyridin-3-ol structure

2-chlorpyridin-3-ol

CAS#:6636-78-8

~%

PHA-543613 Structure

PHA-543613

CAS#:478149-53-0

Literature: Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4425 - 4436
2-Chloro-6-(hydroxymethyl)-3-pyridinol structure

2-Chloro-6-(hyd...

CAS#:208519-41-9

~%

PHA-543613 Structure

PHA-543613

CAS#:478149-53-0

Literature: Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4425 - 4436
(7-Chlorofuro[2,3-c]pyridin-5-yl)methanol structure

(7-Chlorofuro[2...

CAS#:208519-39-5

~%

PHA-543613 Structure

PHA-543613

CAS#:478149-53-0

Literature: Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4425 - 4436
2-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol structure

2-Chloro-6-(hyd...

CAS#:208519-37-3

~%

PHA-543613 Structure

PHA-543613

CAS#:478149-53-0

Literature: Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4425 - 4436
2-Chloro-6-methoxy-4-[2-(trimethylsilyl)ethynyl]-3-pyridinol structure

2-Chloro-6-meth...

CAS#:208519-38-4

~%

PHA-543613 Structure

PHA-543613

CAS#:478149-53-0

Literature: Wishka, Donn G.; Walker, Daniel P.; Yates, Karen M.; Reitz, Steven C.; Jia, Shaojuan; Myers, Jason K.; Olson, Kirk L.; Jacobsen, E. Jon; Wolfe, Mark L.; Groppi, Vincent E.; Hanchar, Alexander J.; Thornburgh, Bruce A.; Cortes-Burgos, Luz A.; Wong, Erik H. F.; Staton, Brian A.; Raub, Thomas J.; Higdon, Nicole R.; Wall, Theron M.; Hurst, Raymond S.; Walters, Rodney R.; Hoffmann, William E.; Hajos, Mihaly; Franklin, Stanley; Carey, Galen; Gold, Lisa H.; Cook, Karen K.; Sands, Steven B.; Zhao, Sabrina X.; Soglia, John R.; Kalgutkar, Amit S.; Arneric, Stephen P.; Rogers, Bruce N. Journal of Medicinal Chemistry, 2006 , vol. 49, # 14 p. 4425 - 4436

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 Synonyms

N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide,hydrochloride
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