398495-65-3

Usage

Uses

Used in Medicinal Chemistry:
1-ETHYLOXYCARBONYL-5-BOC-3-AMINO-4,6-DIHYDRO-PYRROLO[3,4-C]PYRAZOLE is used as a key intermediate in the synthesis of various bioactive compounds due to its unique structure and functional groups. The presence of the BOC protected amino group allows for further chemical modifications, making it versatile in the development of new pharmaceutical agents.
Used in Drug Development:
In the pharmaceutical industry, 1-ETHYLOXYCARBONYL-5-BOC-3-AMINO-4,6-DIHYDRO-PYRROLO[3,4-C]PYRAZOLE is utilized as a precursor for the creation of potential anti-cancer, anti-inflammatory, and anti-viral agents. Its pyrrolopyrazole derivatives have been studied for these properties, indicating its importance in the discovery and synthesis of new therapeutics.
Used in Organic Synthesis:
1-ETHYLOXYCARBONYL-5-BOC-3-AMINO-4,6-DIHYDRO-PYRROLO[3,4-C]PYRAZOLE serves as a valuable building block in organic synthesis, particularly for the preparation of complex organic molecules and pharmaceuticals. Its ethyloxycarbonyl and BOC protected amino functionalities provide opportunities for a range of chemical reactions, facilitating the construction of diverse molecular architectures.

Upstream product

• 398491-59-3 3-amino-4,6-dihydro-1H-pyrrolo[3,4-c]pyrazole-5-carboxylic acid tert-butyl ester 
• 541-41-3 chloroformic acid ethyl ester 
• 44981-94-4 N-cyanoethyl glycine ethyl ester 
• 25544-75-6 ethyl hydrazinecarboxylate hydrochloride 
• 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 
• 44915-39-1 [(2-cyanoethyl)amino]acetic acid methyl ester 
• 3088-42-4 N-(2-cyanoethyl)glycine 
• 266353-19-9 [tert-butoxycarbonyl-(2-cyanoethyl)amino]acetic acid methyl ester 

Downstream Products

• 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 
• 877859-95-5 3-[2-(4-pyrrolidin-1-yl-phenyl)-acetylamino]-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester 
• 916995-51-2 danusertib 
• 916995-51-2 PHA₇₃₉₃₅₈ 
• 827318-78-5 5-((R)-2-methoxy-2-phenylacetyl)-3-[4-(4-methylpiperazin-1-yl)benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl 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 
• 916995-45-4 5-(fluoro-phenyl-acetyl)-3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester 
• 916995-46-5 3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-5-(2-phenyl-propionyl)-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester 
• 916995-47-6 3-[4-(4-methyl-piperazin-1-yl)-benzoylamino]-5-(2-phenyl-propionyl)-5,6-dihydro-4H-pyrrolo[3,4-c]pyrazole-1-carboxylic acid ethyl ester 
• 827318-96-7 5-[(2R)-2-hydroxy-2-phenylethanoyl]-3-{[4-(4-methylpiperazin-1-yl)benzoyl]amino}-5,6-dihydropyrrolo[3,4-c]pyrazole-1(4H)-carboxylate 

Relevant academic research and scientific papers

4,6 DIHYDROPYRROLO [3,4-C] PYRAZOLE-5 (1H)-CARBONITRILE DERIVATES FOR TRATING CANCER

The present invention relates to novel compounds and methods for the manufacture of inhibitors of deubiquitylating enzymes (DUBs) and/ or desumoylating enzymes. In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase 7 or

BCR-ABL DIPLOID INHIBITOR, PREPARATION METHOD THEREFOR, AND USES THEREOF

Disclosed are compounds or pharmaceutically acceptable salts thereof having the following general formula: R-Linker-R. The compounds or pharmaceutically acceptable salts thereof provided by the present invention are used as Bcr-Abl diploid inhibitors, whi

(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.

PYRAZOLOPYRIDINE PYRAZOLOPYRIMIDINE AND RELATED COMPOUNDS

In one aspect this invention relates generally to compounds of Formula: and sub-formulas thereof, or a tautomer of each thereof, a pharmaceutically acceptable salt of each thereof, or a pharmaceutically acceptable solvate of each of the foregoing, where X1, L1, L3, and R3 are described herein.

Design, synthesis and anticancer activity of 1-acyl-3-amino-1,4,5,6- tetrahydropyrrolo[3,4-c]pyrazole derivatives

A series of novel 1-acyl-3-amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole derivatives were designed and synthesized. These derivatives were initially evaluated for their in vitro anticancer activity against human colon carcinoma HCT-116 cell line, and com

Design and synthesis of 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and pyrazolo[3,4-b]pyridines for Aurora-A kinase inhibitors

Two series of 3-aminopyrazole compounds including 24 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles and 16 pyrazolo[3,4-b]pyridines were synthesized and evaluated against HCT116, A549, and A2780 tumor cell lines. Among them, three compounds were found to have the ideal anti-proliferative activities in vitro. Docking experiments showed that the novel pyrazolo[3,4-b]pyridines share the similar interaction mode with Aurora-A kinase as PHA739358.

3-Amino-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoles: A new class of CDK2 inhibitors

We have recently reported about a new class of Aurora-A inhibitors based on a bicyclic tetrahydropyrrolo[3,4-c]pyrazole scaffold. Here we describe the synthesis and early expansion of CDK2/cyclin A-E inhibitors belonging to the same chemical class. Synthe

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

Potent and selective aurora inhibitors identified by the expansion of a novel scaffold for protein kinase inhibition

Potent and selective Aurora kinase inhibitors were identified from the combinatorial expansion of the 1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole bi-cycle, a novel and versatile scaffold designed to target the ATP pocket of protein kinases. The most potent c

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