6288-99-9

Basic information

• Product Name: 6-chloro-1-phenyl-1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS NO: 6288-99-9
• Molecular Formula: C₁₁H₇ClN₄O
• Molecular Weight: 246.6525
• Mol File: 6288-99-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 394.9°C at 760 mmHg
• Flash Point: 192.7°C
• Density: 1.58g/cm³
• Vapor Pressure: 1.91E-06mmHg at 25°C
• Refractive Index: 1.761
• CAS DataBase Reference: 6-chloro-1-phenyl-1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-1-phenyl-1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one(6288-99-9)
• EPA Substance Registry System: 6-chloro-1-phenyl-1,2-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one(6288-99-9)

Safety Data

• Hazardous Substances Data: 6288-99-9(Hazardous Substances Data)

Upstream product

• 15973-83-8 C₁₁H₈N₄O₂ 
• 100-63-0 phenylhydrazine 
• 5334-43-0 5-Amino-4-cyano-1-phenylpyrazole 
• 15973-83-8 4,6-Dioxo-1-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo<3,4-d>pyrimidine 
• 50427-77-5 5-amino-1-phenyl-1H-pyrazole-4-carboxamide 
• 99971-84-3 4,6-dichloro-1-phenyl-1H-pyrazolo<3,4-d>pyrimidine 
• 59-88-1 phenylhydrazine hydrochloride 
• 50270-27-4 2,4,6-trichloropyrimidine-5-carbaldehyde 

Downstream Products

• 1351413-56-3 2-((4-hydroxy-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-6-yl)-amino)-N-(4-methoxyphenyl)propanamide 
• 1399821-48-7 2-((1-(2-chlorophenyl)-4-hydroxy-1H-pyrazolo[3,4-d]pyrimidin-6-yl)amino)-N-(4-isopropoxyphenyl)propanamide 
• 1219026-96-6 6-bis(prop-2-en-1-yl)amino-1-phenyl-1H-pyrazolo[3,4-d]-pyrimidin-4(5H)-one 
• 1331826-53-9 1-phenyl-6-(prop-2-en-1-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 1219026-92-2 1-phenyl-6-(prop-2-en-1-ylamino)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one 
• 1331826-62-0 8-methyl-1-phenyl-6-(prop-2-en-1-yl)-1H-imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-one 
• 1331826-61-9 8-methyl-1-phenyl-1H-imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(5H)-one 
• 1331826-59-5 8-methylidene-1-phenyl-6-(prop-2-en-1-yl)-7,8-dihydro-1H-imidazo[1,2-a]-pyrazolo[4,3-e]pyrimidin-4(6H)-one 
• 1331826-57-3 8-methylidene-1-phenyl-7,8-dihydro-1H-imidazo[1,2-a]-pyrazolo[4,3-e]pyrimidin-4(6H)-one 
• 1331826-54-0 8-iodomethylidene-1-phenyl-7,8-dihydro-1H-imidazo[1,2-a]-pyrazolo[4,3-e]pyrimidin-4(6H)-one 
• 1331826-52-8 8-iodomethyl-1-phenyl-6-(prop-2-en-1-yl)-7,8-dihydro-1H-imidazo[1,2-a]-pyrazolo[4,3-e]pyrimidin-4(6H)-one 

Relevant articles and documents

COMPOUNDS HAVING PDE9A INHIBITORY ACTIVITY, AND PHARMACEUTICAL USES THEREOF

The present invention provides a compound having a specific chemical structure and having PDE9A inhibitory activity, or a pharmaceutically acceptable salt thereof. The present invention provides a composition containing the compound or a pharmaceutically acceptable salt thereof. The present invention provides a pharmaceutical use, for treating or preventing PDE9A-related diseases, of the compound according to the present invention, a salt thereof, and a composition containing the compound or salt. The present invention also provides a method for treating or preventing PDE9A-related diseases, the method comprising administering an effective amount of the compound according to the present invention, a salt thereof, or a composition containing the compound or salt to a subject in need of treatment.

Structure-based discovery of highly selective phosphodiesterase-9A inhibitors and implications for inhibitor design

A new series of phosphodiesterase-9 (PDE9) inhibitors that contain a scaffold of 6-amino-pyrazolopyrimidinone have been discovered by a combination of structure-based design and computational docking. This procedure significantly saved the load of chemical synthesis and is an effective method for the discovery of inhibitors. The best compound 28 has an IC50 of 21 nM and 3.3 μM, respectively, for PDE9 and PDE5 and about 3 orders of magnitude of selectivity against other PDE families. The crystal structure of the PDE9 catalytic domain in complex with 28 has been determined and shows a hydrogen bond between 28 and Tyr424. This hydrogen bond may account for the 860-fold selectivity of 28 against PDE1B, in comparison with about 30-fold selectivity of BAY73-6691. Thus, our studies suggest that Tyr424, a unique residue of PDE8 and PDE9, is a potential target for improvement of selectivity of PDE9 inhibitors.