133261-07-1

Basic information

• Product Name: 1-METHYL-3-PROPYL-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER
• Synonyms: 1-METHYL-3-PROPYL-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER;1-Methyl-3-propyl-1H-pyrazole-5-carboxylic acid ethyl ester ,97%;Ethyl 3-propyl-1H-pyrazole-5-carboxylate;Ethyl 1-Methyl-3-propyl-1H-pyrazole-5-carboxylate;Ethyl 2-methyl-5-propyl-pyrazole-3-carboxylate
• CAS NO: 133261-07-1
• Molecular Formula: C₁₀H₁₆N₂O₂
• Molecular Weight: 196.25
• EINECS: 604-604-1
• Mol File: 133261-07-1.mol

Chemical Properties

• Boiling Point: 302.042 °C at 760 mmHg
• Flash Point: 136.47 °C
• Appearance: /
• Density: 1.08 g/cm³
• Vapor Pressure: 0.00016mmHg at 25°C
• Refractive Index: 1.511
• PKA: 1.03±0.10(Predicted)
• CAS DataBase Reference: 1-METHYL-3-PROPYL-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-3-PROPYL-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER(133261-07-1)
• EPA Substance Registry System: 1-METHYL-3-PROPYL-1H-PYRAZOLE-5-CARBOXYLIC ACID ETHYL ESTER(133261-07-1)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 133261-07-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Methyl-3-propyl-1H-pyrazole-5-carboxylic acid ethyl ester is used as a chemical intermediate for the synthesis of Sildenafil (S435000), a medication that functions as a phosphodiesterase V inhibitor. This application is crucial for the development of treatments targeting erectile dysfunction and other related conditions, as it aids in enhancing blood flow to the affected areas.

InChI:InChI=1/C9H14N2O2/c1-3-5-7-6-8(11-10-7)9(12)13-4-2/h6H,3-5H2,1-2H3,(H,10,11)

Upstream product

• 77-78-1 dimethyl sulfate 
• 247583-69-3 2-Methyl-3-n-propyl-pyrazole-5-carboxylic Acid Ethyl Ester 
• 107-87-9 2-Pentanone 
• 95-92-1 oxalic acid diethyl ester 
• 60-34-4 methylhydrazine 
• 92945-27-2 ethyl 3-propyl-1H-pyrazole-5-carboxylate 
• 74-88-4 methyl iodide 
• 36983-31-0 ethyl 3-butyrylpyruvate 

Downstream Products

• 247583-69-3 2-Methyl-3-n-propyl-pyrazole-5-carboxylic Acid Ethyl Ester 
• 139756-22-2 5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one 
• 147676-70-8 5-(5-bromo-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]-pyrimidin-7-one 

Relevant articles and documents

NOVEL COMPOUNDS FOR USE IN COGNITION IMPROVEMENT

Novel compounds for use in cognition improvement It relates to certain compounds having a polycyclic structure and a -(C=O)NRaRb moiety, wherein the polycyclic structure comprises at least three ring systems, wherein one ring system is a polycyclic ring system comprising from 2 to 4 rings; at least one ring is an aromatic ring; and wherein the structure comprises at least 3 nitrogen atoms and 1 oxygen atom. It also relates to pharmaceutical compositions containing them, and to their use in medicine, in particular in the treatment and/or prevention of neurological disorders coursing with a cognition deficit or impairment, or neurodegenerative diseases.

Novel pyrazole-5-carboxamide and pyrazole-pyrimidine derivatives: Synthesis and anticancer activity

A series of novel pyrazole-5-carboxamide and pyrazole-pyrimidine derivatives were designed and synthesized. All compounds have been screened for their antiproliferative activity against MGC-803, SGC-7901 and Bcap-37 cell lines in vitro. The results revealed that compounds 8a, 8c and 8e exhibited strong inhibitory activity against MGC-803 cell line. The flow cytometric analysis result showed that compound 8e could inhibit MGC-803 proliferation. Some title compounds were tested against telomerase, and compound 8e showed the most potent inhibitory activity with IC50 value at 1.02 ± 0.08 μM. The docking simulation of compound 8e was performed to get the probable binding model, among them, LYS 189, LYS 372, LYS 249 and ASP 254 may be the key residues for the telomerase activity.

PYRAZOLOPYRIMIDINONES FOR THE TREATMENT OF IMPOTENCE AND PROCESS FOR THE PREPARATION THEREOF

The present invention relates to Pyrazolopyrimidinone compounds as PDE5 inhibitors with better IC50 value, good in vivo efficacy and PK profile and a process for the preparation thereof. The present invention covers the pyrazolo pyrimidinone based compounds that have been designed, synthesized and screened for PDE5 inhibitory activity and its PDE5 inhibitory potential is provided in this invention. These designer compounds have shown nanomolar potency when screened for PDE5 inhibitory activity and also shown better in vivo efficacy. These compounds can be used in the treatment of male erectile dysfunction or in the treatment of impotence.

NOVEL COMPOUNDS AS DUAL INHIBITORS OF PHOSPHODIESTERASES AND HISTONE DEACETYLASES

It relates to certain compounds having a polycyclic structure and a hydroxamic acid moiety, wherein the polycyclic structure comprises at least three ring systems, wherein one ring system is a polycyclic ring system comprising from 2 to 4 rings; at least one ring is an aromatic ring; and wherein the structure comprises at least 3 nitrogen atoms and 1 oxygen atom. It also relates to a process for their preparation, as well as to pharmaceutical compositions containing them, and to their use in medicine, in particular in the treatment and/or prevention of neurological disorders coursing with a cognition deficit or impairment, or neurodegenerative diseases. wherein B1 is a radical selected from the group consisting of formula (A"), formula (B"), formula (C"), and formula (D"):

HIGHLY SELECTIVE and LONG-ACTING PDE5 MODULATORS

Disclosed herein are substituted phosphodiesterase type 5 enzyme modulators of Formula I, processes of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

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.

Method for preparing 1-alkyl-pyrazol-5-carboxylic acid esters III

1-Alkyl-pyrazole-5-carboxylic esters are obtained with surprisingly low proportions of 1-alkyl-pyrazole-3-carboxylic esters if a 2,4-diketo ester and/or an enolate thereof is reacted with an alkylhydrazine and/or a corresponding alkylhydrazinium salt, if appropriate, in the presence of a solvent and/or of water, in such a manner that during at least about 90% of the reaction free alkylhydrazine is present.

Pyrazolopyrimidinone cGMP PDE5 inhibitors for the treatment of sexual dysfunction

Compounds of the formulae (IA) and (IB): wherein R1is C1to C3alkyl optionally substituted with phenyl, Het or a N-linked heterocyclic group selected from piperidinyl and morpholinyl; wherein said phenyl group is optionally substituted by one or more substitutents selected from C1to C4alkoxy; halo; CN; CF3; OCF3or C1to C4alkyl wherein said C1to C4alkyl group is optionally substituted by C1to C4haloalkyl or haloalkoxy either of which is substituted by one or more halo atoms; R2is C1to C6alkyl and R13is OR3or NR5R6, or pharmaceutically or veterinarily acceptable salts thereof, or pharmaceutically or veterinarily acceptable solvates of either entity are potent and selective inhibitors of type 5 cyclic guanosine 3′,5′-monophosphate phosphodiesterase (cGMP PDE5) and have utility in the treatment of, inter alia, male erectile dysfunction (MED) and female sexual dysfunction (FSD).

Method of preparing 1-alkyl-pyrazol-5-carboxylic acid esters

The invention relates to the preparation of 1-alkyl-pyrazole-5-carboxylic esters by reacting the enolate of a 2,4-diketocarboxylic ester in the presence of a solvent and water with an N-alkylhydrazinium salt. This process permits a particularly economical preparation of 1-alkyl-pyrazole-5-carboxylic esters in a simple manner and with only limited formation of undesirable isomers.

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.