139756-30-2

Basic information

• Product Name: 5-(2-Ethoxyphenyl)-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
• Synonyms: 5-(2-Ethoxyphenyl)-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
• CAS NO: 139756-30-2
• Molecular Formula: C₁₆H₁₈N₄O₂
• Molecular Weight: 298.33972
• Product Categories: Aromatics;Heterocycles;Inhibitors;Aromatics, Heterocycles, Inhibitors
• Mol File: 139756-30-2.mol

Chemical Properties

• Melting Point: 250-252°C
• Appearance: /
• Density: 1.323g/cm³
• Refractive Index: 1.655
• Storage Temp.: Refrigerator
• Solubility: Dichloromethane, DMF, DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 5-(2-Ethoxyphenyl)-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2-Ethoxyphenyl)-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one(139756-30-2)
• EPA Substance Registry System: 5-(2-Ethoxyphenyl)-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one(139756-30-2)

Safety Data

• Hazardous Substances Data: 139756-30-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-(2-Ethoxyphenyl)-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one is used as a potent PDE inhibitor scaffold for its in vivo activity, which can be utilized in the development of new drugs targeting various medical conditions.
Used as an Intermediate:
In the Pharmaceutical Industry, 5-(2-Ethoxyphenyl)-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one is used as an intermediate for the preparation of Desmethylsildenafil, contributing to the synthesis of compounds with potential therapeutic applications.
Chemical Properties:
The compound is described as a white solid, which is an important characteristic for its identification and handling in various applications.

InChI:InChI=1/C16H18N4O2/c1-3-7-11-13-14(20-19-11)16(21)18-15(17-13)10-8-5-6-9-12(10)22-4-2/h5-6,8-9H,3-4,7H2,1-2H3,(H,19,20)(H,17,18,21)

Upstream product

• 139756-10-8 4-(2-ethoxybenzamido)-3-n-propyl-1H-pyrazolo-5-carboxamide 
• 134-11-2 2-ethoxybenzoic acid 
• 1370409-61-2 C₉H₁₅N₃O₂ 
• 36983-31-0 ethyl 3-butyrylpyruvate 
• 76424-56-1 4-Amino-3-n-propyl-1H-pyrazole-5-carboxamide 
• 76424-47-0 3-n-propyl-1H-pyrazolo-5-carboxylic acid 
• 139756-08-4 4-Nitro-3-n-propyl-1H-pyrazole-5-carboxamide 
• 76424-48-1 4-Nitro-3-n-propyl-1H-pyrazole-5-carboxylic Acid 

Relevant articles and documents

Synthesis and evaluation of human phosphodiesterases (PDE) 5 inhibitor analogs as trypanosomal PDE inhibitors. Part 1. Sildenafil analogs

Parasitic diseases, such as African sleeping sickness, have a significant impact on the health and well-being in the poorest regions of the world. Pragmatic drug discovery efforts are needed to find new therapeutic agents. In this Letter we describe target repurposing efforts focused on trypanosomal phosphodiesterases. We outline the synthesis and biological evaluation of analogs of sildenafil (1), a human PDE5 inhibitor, for activities against trypanosomal PDEB1 (TbrPDEB1). We find that, while low potency analogs can be prepared, this chemical class is a sub-optimal starting point for further development of TbrPDE inhibitors.

Comparison of different heterocyclic scaffolds as substrate analog PDE5 inhibitors

Several different heterocyclic systems were compared as PDE5 inhibitor scaffolds. In addition to the known 3H-imidazo[5,1-f][1,2,4]triazin-4-ones and pyrazolopyrimidinones, isomeric imidazo[1,5-a][1,3,5]triazin-4(3H)-ones were also shown to be potent and selective PDE inhibitor scaffolds with in vivo activity. SAR trends were elucidated for sulfonamide derivatives with generality across different scaffolds.

Pyrazolopyrimidinones which inhibit type 5 cyclic guanosine 3',5'-monophosphate phosphodiesterase (cGMP PDE5) for the treatment of sexual dysfunction

Compounds of formulae (IA) and (IB) or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates of either entity, wherein R1 is C1 to C3 alkyl substituted with C3 to C6 cycloalkyl, CONR5R6 or a N-linked heterocyclic group; (CH2)nHet or (CH2)nAr; R2 is C1 to C6 alkyl; R3 is C1 to C6 alkyl optionally substituted with C1 to C4 alkoxy; R4 is SO2NR7R8; R5 and R6 are each independently selected from H and C1 to C4 alkyl optionally substituted with C1 to C4 alkoxy, or, together with the nitrogen atom to which they are attached, form a 5- or 6-membered heterocyclic group; R7 and R8, together with the nitrogen atom to which they are attached, form a 4-R10-piperazinyl group; R10 is H or C1 to C4 alkyl optionally substituted with OH, C1 to C4 alkoxy or CONH2; H is an optionally substituted C-linked 5- or 6-membered heterocyclic group; Ar is optionally substituted phenyl; and n is 0 or 1; are potent and selective cGMP PDE5 inhibitors useful in the treatment of, inter alia, male erectile dysfunction and female sexual dysfunction.

Method of treating a patient having precancerous lesions with phenyl purinone derivatives

Derivatives of Phenyl Purinone are useful for the treatment of patients having precancerous lesions. These compounds are also useful to inhibit growth of neoplastic cells.

PYRAZOLOPYRIMIDINONE ANTIANGINAL AGENTS

Compounds of the formula:wherein R1 is H, C1-C3 alkyl, C3-C5 cycloalkyl or C1-C3 perfluoroalkyl; R2 is H, C1-C6 alkyl optionally substituted by OH, C1-C3 alkoxy or C3-C6 cycloalkyl, or C1-C3 perfluoroalkyl; R3 is C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C7 cycloalkyl, C1-C6 perfluoroalkyl or (C3 -C6 cycloalkyl)C1-C6 alkyl; R4 taken together with the nitrogen atom to which it is attached completes a pyrrolidinyl, piperidino, morpholino, or 4-N-(R6)-piperazinyl group; R5 is H, C1-C4 alkyl, C1-C3 alkoxy, NR7 R8, or CONR7 R8 ; R6 is H, C1-C6 alkyl, (C1-C3 alkoxy) C2-C6 alkyl, hydroxy C2-C6 alkyl, (R7 R8 N)C2 -C6 alkyl, (R7 R8 NCO)C1-C6 alkyl, CONR7 R8, CSNR7 R8 or C(NH)NR7 R8 ; R7 and R8 are each independently H, C1-C4 alkyl, (C1-C3 alkoxy)C2-C4 alkyl or hydroxy C2-C4 alkyl; and pharmaceutically acceptable salts thereof, are selective cGMP PDE inhibitors useful in the treatment of cardiovascular disorders such as angina, hypertension, heart failure and atherosclerosis