324741-99-3

Usage

Uses

Used in Pharmaceutical Industry:
(4R)-3-[((1S,2S)-2-Hydroxy-3-cyclopenten-1-yl)carbonyl]-4-(phenylMethyl)-1,3-oxazolidin-2-one is used as a key intermediate in the enantioselective synthesis of carbocyclic ribavirin, its analogs, and other antiviral agents. (4R)-3-[((1S,2S)-2-Hydroxy-3-cyclopenten-1-yl)carbonyl]-4-(phenylMethyl)-1,3-oxazolidin-2-one's chiral centers and unique structure enable the development of enantiomerically pure compounds, which are crucial for the effectiveness and safety of pharmaceuticals, as different enantiomers can exhibit distinct biological activities.
In the synthesis of carbocyclic ribavirin and its analogs, (4R)-3-[((1S,2S)-2-Hydroxy-3-cyclopenten-1-yl)carbonyl]-4-(phenylMethyl)-1,3-oxazolidin-2-one serves as a building block that can be further modified and functionalized to create new antiviral agents. These agents can potentially target a wide range of viral infections, offering new treatment options for patients suffering from viral diseases.
Furthermore, the oil-like nature of (4R)-3-[((1S,2S)-2-Hydroxy-3-cyclopenten-1-yl)carbonyl]-4-(phenylMethyl)-1,3-oxazolidin-2-one may also be advantageous in the formulation of pharmaceutical products, as it can facilitate the compound's incorporation into various dosage forms, such as capsules, tablets, or liquid formulations.
Overall, the unique properties and potential applications of (4R)-3-[((1S,2S)-2-Hydroxy-3-cyclopenten-1-yl)carbonyl]-4-(phenylMethyl)-1,3-oxazolidin-2-one make it a valuable compound in the field of pharmaceutical chemistry, with the potential to contribute to the development of new and effective antiviral therapies.

Upstream product

• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 1297139-24-2 (4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 155399-10-3 (4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 324741-98-2 (R)-3-((2S,3S)-2-Allyl-3-hydroxy-pent-4-enoyl)-4-benzyl-oxazolidin-2-one 

Downstream Products

• 1297139-25-3 (4R)-3-{[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]carbonyl}-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 1297139-27-5 (4R)-3-[((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy} bicyclo[3.1.0]hex-3-yl)carbonyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 1297139-33-3 N₁-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl) silyl]oxy}bicyclo [3.1.0]hex-3-yl)-N₂-[(4-nitrophenyl)sulfonyl]glycinamide 
• 1297139-34-4 1-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}bicyclo[3.1.0]hex-3-yl)-4-[(4-nitrophenyl)sulfonyl]-2-piperazinone 
• 324742-01-0 1-((1R,2S,3R,4R)-3-Benzyloxy-4-benzyloxymethyl-2-hydroxy-cyclopentyl)-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester 
• 324742-00-9 (1S,2R,3R,5S)-2-Benzyloxy-3-benzyloxymethyl-6-oxa-bicyclo[3.1.0]hexane 
• 1297139-59-3 4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyI)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-((1S,2S,3S,5S)-2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}bicyclo[3.1.0]hex-3-yl)-2-piperazinone 
• 1297139-58-2 4-{[3-chloro-5-cyclopropyl-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-2-yl]carbonyl}-1-[(1S,2S,3S,5S)-2-hydroxybicyclo[3.1.0]hex-3-yl]-2-piperazinone 

Relevant academic research and scientific papers

Identification of Novel Carbocyclic Pyrimidine Cyclic Dinucleotide STING Agonists for Antitumor Immunotherapy Using Systemic Intravenous Route

Stimulator of Interferon Genes (STING) plays an important role in innate immunity by inducing type I interferon production upon infection with intracellular pathogens. STING activation can promote increased T-cell activation and inflammation in the tumor microenvironment, resulting in antitumor immunity. Natural and synthetic cyclic dinucleotides (CDNs) are known to activate STING, and several synthetic CDN molecules are being investigated in the clinic using an intratumoral administration route. Here, we describe the identification of STING agonist 15a, a cyclic dinucleotide structurally diversified from natural ligands with optimized properties for systemic intravenous (iv) administration. Our studies have shown that STING activation by 15a leads to an acute innate immune response as measured by cytokine secretion and adaptive immune response via activation of CD8+ cytotoxic T-cells, which ultimately provides robust antitumor efficacy.

STING MODULATOR COMPOUNDS, AND METHODS OF MAKING AND USING

The present disclosure provides STING modulators/agonists, and methods of synthesis and methods for using for the prophylaxis or treatment of cancer and other STING-related diseases. The present disclosure relates to a compound represented by the Formula (I): wherein each symbol is as defined in the description, or a pharmaceutically acceptable salt thereof.

INHIBITORS OF THE FIBROBLAST GROWTH FACTOR RECEPTOR

Described herein are inhibitors of FGFR-4, pharmaceutical compositions including such compounds, and methods of using such compounds and compositions.

Hepatitis C replication inhibitors that target the viral NS4B protein

We describe the preclinical development and in vivo efficacy of a novel chemical series that inhibits hepatitis C virus replication via direct interaction with the viral nonstructural protein 4B (NS4B). Significant potency improvements were realized through isosteric modifications to our initial lead 1a. The temptation to improve antiviral activity while compromising physicochemical properties was tempered by the judicial use of ligand efficiency indices during lead optimization. In this manner, compound 1a was transformed into (+)-28a which possessed an improved antiviral profile with no increase in molecular weight and only a modest elevation in lipophilicity. Additionally, we employed a chimeric "humanized" mouse model of HCV infection to demonstrate for the first time that a small molecule with high in vitro affinity for NS4B can inhibit viral replication in vivo. This successful proof-of-concept study suggests that drugs targeting NS4B may represent a viable treatment option for curing HCV infection.

BENZIMIDAZOLE ANTIVIRAL AGENTS

Provided are compounds of Formula (I) and (II) and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

PYRAZOLYLPYRIDINE ANTIVIRAL AGENTS

Provided are compounds of Formula (I) and/or Formula (II) and pharmaceutically acceptable salts thereof, their pharmaceutical compositions, their methods of preparation, and their use for treating viral infections mediated by a member of the Flaviviridae family of viruses such as hepatitis C virus (HCV).

Enantioselective syntheses of carbocyclic ribavirin and its analogs: Linear versus convergent approaches

The first enantioselective syntheses of carbocyclic ribavirin by both convergent and linear approaches are described. The linear approach from chiral nonracemic 2-azabicyclo[2.2.1]hept-5-en-3-one proves to be a highly efficient route to carbocyclic analog