223761-83-9

Basic information

• Product Name: 2-[(1S,2S)-2-Fluorocyclopentyl]-isoindole-1,3-dione
• Synonyms: 2-[(1S,2S)-2-Fluorocyclopentyl]-isoindole-1,3-dione
• CAS NO: 223761-83-9
• Molecular Formula: C13H12FNO2
• Molecular Weight: 233.2382832
• Product Categories: Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 223761-83-9.mol

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane, Ethanol, Ethyl Acetate, Methanol
• CAS DataBase Reference: 2-[(1S,2S)-2-Fluorocyclopentyl]-isoindole-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(1S,2S)-2-Fluorocyclopentyl]-isoindole-1,3-dione(223761-83-9)
• EPA Substance Registry System: 2-[(1S,2S)-2-Fluorocyclopentyl]-isoindole-1,3-dione(223761-83-9)

Safety Data

• Hazardous Substances Data: 223761-83-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-[(1S,2S)-2-Fluorocyclopentyl]-isoindole-1,3-dione is used as a key intermediate in the synthesis of adenosine A1 receptor modulators. Adenosine A1 receptors play a crucial role in various physiological processes, including cardiovascular function, neuroprotection, and immune response. The chiral nature of 2-[(1S,2S)-2-Fluorocyclopentyl]-isoindole-1,3-dione allows for the development of enantiomerically pure drugs, which can exhibit improved selectivity and reduced side effects compared to their racemic counterparts.
In the preparation of adenosine A1 receptor modulators, 2-[(1S,2S)-2-Fluorocyclopentyl]-isoindole-1,3-dione serves as a valuable building block for the design and synthesis of novel therapeutic agents. These agents can be used to treat a wide range of conditions, such as heart failure, arrhythmias, neurodegenerative diseases, and inflammatory disorders, by modulating the activity of adenosine A1 receptors.

Upstream product

• 136918-14-4 phthalimide 
• 1214921-47-7 (S,S)-(+)-2-fluorocyclopentanol 
• 1755-12-0 2-fluorocyclopentanone 
• 285-67-6 Cyclopentene oxide 
• 1993-91-5 (1R,2R)-2-fluorocyclopentan-1-ol 

Relevant articles and documents

Synthesis of optically active vicinal fluorocyclopentanols and fluorocyclopentanamines by enzymatic deracemization

All possible stereoisomers of cis- and trans-2-fluorocyclopentan-1-ols were obtained by kinetically controlled deracemization in the presence of lipases in organic media. High enantioselectivities and good yields of stereomers were obtained for all substrates. Optically pure 1,2-fluorocyclopentan-1-ols were converted to 2-fluoro-cyclopentan-1-amines using the Mitsunobu reaction. The absolute configurations were determined using the Kazlauskas rule and chemical correlation. The interaction of substrates with enzymes has considered using Koshland induced fit theory.

ARYL-SUBSTITUTED NITROGEN-CONTAINING HETEROCYCLIC COMPOUND

Disclosed is an aryl-substituted nitrogen-containing heterocyclic compound represented by the formula (I) below or a pharmaceutically acceptable salt thereof. This compound serves as a nociceptin receptor antagonist and is useful as a pharmaceutical agent for treating diseases associated with a nociceptin receptor. (I) [In the formula, A1, A2 and A3 independently represent a carbon atom or a nitrogen atom, and one or two of A1, A2 and A3 represent a carbon atom; R1 represents a lower alkyl group or the like; R2 represents a phenyl group which may be substituted by a halogen atom or the like; R3 represents a hydrogen atom, a lower alkyl group or the like; and R4 represents a lower alkyl group or the like.]

Adenosine analogues and related method of treatment

A compound of formula (I) wherein R2represents C1-3alkyl, halogen or hydrogen; R3represents a fluorinated straight or branched alkyl group of 1-6 carbon atoms; and salts and solvates thereof, in particular, physiologically acceptable solvates and salts thereof. These compounds are agonists of the Adenosine A1 receptor.