916995-51-2

Usage

Uses

Used in Medicinal Chemistry:
4-(4-Methyl-1-piperazinyl)-N-[1,4,5,6-tetrahydro-5-[(2S)-2-methoxy-2-phenylacetyl]pyrrolo[3,4-c]pyrazol-3-yl]benzamide is used as a compound of interest in medicinal chemistry for its potential to interact with biological targets in novel ways due to its complex structure. The presence of the piperazinyl and benzamide groups, along with the tetrahydro pyrrolopyrazol ring system, suggests that it could be a promising candidate for the development of new therapeutic agents.
Used in Drug Development:
In the field of drug development, 4-(4-Methyl-1-piperazinyl)-N-[1,4,5,6-tetrahydro-5-[(2S)-2-methoxy-2-phenylacetyl]pyrrolo[3,4-c]pyrazol-3-yl]benzamide is utilized as a starting point for the design and synthesis of new pharmaceuticals. Its unique structural features may allow for the creation of drugs with specific mechanisms of action, potentially leading to more effective treatments for various diseases and conditions.
Further research and studies are necessary to fully understand the properties and potential uses of this chemical compound, as its complex nature may offer new avenues for therapeutic intervention and drug discovery.

Upstream product

• 34713-98-9 2-methoxy-2-(phenyl)acetyl chloride 
• 7021-09-2 rac-methoxyphenylacetic acid 
• 55137-68-3 (S)-(+)-O-methylmandeloyl chloride 
• 26164-26-1 (S)-2-methoxy-2-phenylacetic acid 
• 761443-69-0 5-tert-butyl 1-ethyl 3-{[4-(4-methylpiperazin-1-yl)benzoyl]amino}-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate 
• 398495-65-3 3-amino-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester 
• 398491-59-3 3-amino-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester 
• 916995-48-7 5-(methoxy-phenyl-acetyl)-3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester 
• 44981-94-4 N-cyanoethyl glycine ethyl ester 
• 3088-42-4 N-(2-cyanoethyl)glycine 
• 761443-50-9 3-[4-(N-methylpiperazin-1-yl)benzamido]-1-ethoxycarbonyl-4,6-dihydropyrrolo[3,4-c]pyrazole 
• 3966-32-3 (R)-methoxyphenylacetic acid 
• 175463-32-8 3-cyano-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 266353-18-8 N-tert-butoxycarbonyl-2-(2-cyanoethyl)aminoacetic acid ethyl ester 

Relevant academic research and scientific papers

(R)- N - [5 - (2 - methoxy - 2 - phenyl-acetyl) - 1, 4, 5, 6 - tetrahydro-pyrrolo [3, 4 - c] pyrazole - 3 - yl] - 4 - (4 - methyl piperazine - 1 - yl) benzamide synthesis method

The invention belongs to the technical field of medicine and relates to a preparation method for PHA739358(Danusertib), i.e., (R)-N-[5-(2-methoxy-2-phenylacetyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-3-yl]-4-(4-methyl piperazine-1-yl)benzamide. According to the invention, altogether four reaction routes are designed, simple and easily available glycine is used as a raw material, reactions like addition, esterification, amino protection and cyclization are carried out so as to prepare (R)-N-[5-(2-methoxy-2-phenylacetyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-3-yl]-4-(4-methyl piperazine-1-yl)benzamide, yield of the route 1, 2 and 4 is more than 25%, respectively, and yield of the route 3 is more than 20%. The preparation method has the advantages of a few reaction steps, simple and convenient post-treatment operation, little time consumption, high yield and low total cost. Thus, a novel method is provided for preparation of the antitumor drug PHA739358.

The human Aurora kinase inhibitor danusertib is a lead compound for anti-trypanosomal drug discovery via target repurposing

New drugs for neglected tropical diseases such as human African trypanosomiasis (HAT) are needed, yet drug discovery efforts are not often focused on this area due to cost. Target repurposing, achieved by the matching of essential parasite enzymes to those human enzymes that have been successfully inhibited by small molecule drugs, provides an attractive means by which new drug optimization programs can be pragmatically initiated. In this report we describe our results in repurposing an established class of human Aurora kinase inhibitors, typified by danusertib (1), which we have observed to be an inhibitor of trypanosomal Aurora kinase 1 (TbAUK1) and effective in parasite killing in vitro. Informed by homology modeling and docking, a series of analogs of 1 were prepared that explored the scope of the chemotype and provided a nearly 25-fold improvement in cellular selectivity for parasite cells over human cells.

1,4,5,6-Tetrahydropyrrolo[3,4-c]pyrazoles: Identification of a potent aurora kinase inhibitor with a favorable antitumor kinase inhibition profile

The optimization of a series of 5-phenylacetyl 1,4,5,6-tetrahydropyrrolo[3, 4-c]pyrazole derivatives toward the inhibition of Aurora kinases led to the identification of compound 9d. This is a potent inhibitor of Aurora kinases that also shows low nanomol

PYRROLO[3,4-c]PYRAZOLE DERIVATIVES ACTIVE AS KINASE INHIBITORS

Pyrrolo[3,4-c]pyrazole derivatives of formula (1) and pharmaceutically acceptable salts thereof, as defined in the specification, process for their preparation and pharmaceutical compositions comprising them are disclosed; the compounds of the invention m