64220-40-2

Usage

Uses

Used in Research and Scientific Experiments:
5-chloro-2-methyl-1-indanone is used as a research chemical for conducting scientific experiments. Its complex molecular structure and functional groups make it a valuable compound for studying various chemical reactions and processes.
Used in Pharmaceutical Development:
5-chloro-2-methyl-1-indanone is used as an intermediate in the development of pharmaceuticals. Its unique structure and reactivity can be utilized to synthesize new drug molecules with potential therapeutic applications.
Used in Chemical Synthesis:
5-chloro-2-methyl-1-indanone is used as a building block in the synthesis of other complex organic compounds. Its functional groups can be further modified or reacted with other molecules to create new chemical entities with specific properties and applications.
Safety Precautions:
As with all chemicals, appropriate safety measures should be employed when handling 5-chloro-2-methyl-1-indanone, due to its potentially harmful interactions. Exact details regarding its properties, uses, and safety precautions should be thoroughly checked from the databases of registered chemicals.

Upstream product

• 33000-64-5 2-bromo-1-(4-chlorophenyl)-2-methylpropan-1-one 
• 13222-26-9 2-chloroisobutyryl chloride 
• 108-90-7 chlorobenzene 
• 57-15-8 1,1,1-trichloro-2-methyl-2-propanol 
• 7446-70-0 aluminium trichloride 
• 18713-58-1 1-(4-chlorophenyl)-2-methylpropan-1-one 
• 1186047-99-3 ethyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 42348-86-7 5-chloro-1-indanone 

Relevant academic research and scientific papers

Design and discovery of a high affinity, selective and β-arrestin biased 5-HT7 receptor agonist

Compound 1c, 5-chloro-2-(2-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl)-2,3-dihydro-1H-inden-1-one was previously reported from our laboratory showing high affinity binding to the 5-HT7 receptor (Ki = 0.5 nM). However, compound 1c racemizes readily upon enantiomeric separation. To prevent racemization, we have redesigned and synthesized methyl and carboxyethyl analogs, compounds 2 and 3 respectively, whose binding affinities were similar to those of compound 1c. Compounds 2 and 3 cannot undergo racemization since tautomerism was no longer possible and thus, compound 2 was selected for enantiomeric separation and further evaluation. Upon enantiomeric separation, the levorotatory enantiomer, (?)2 or 2a demonstrated a higher affinity (Ki = 1.2 nM) than the (+)2 or 2b enantiomer (Ki = 93 nM) and a β-arrestin biased functional selectivity for the 5-HT7 receptor. Although 2a showed about 8 times less activity than 5-HT in the Gs pathway, it showed over 31 times higher activity than 5-HT in the β-arrestin pathway. This constitutes a significant β-arrestin pathway preference and shows 2a to be more potent and more efficacious than the recently published β-arrestin biased 3-(4-chlorophenyl)-1,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine, the N-debenzylated analog of JNJ18038683 (Compound 7). [Figure not available: see fulltext.]

New dual 5-HT1A and 5-HT7 receptor ligands derived from SYA16263

We have previously reported that dual 5-HT1A and 5-HT7 receptor ligands might find utility as treatment options for various CNS related conditions including cognitive and anxiolytic impairments. We have also more recently reported that SYA16263 has antipsychotic-like properties with an absence of catalepsy in animal models ascribed to its ability to recruit β-arrestin to the D2 receptor. However, SYA16263 also binds with very high affinity to 5-HT1AR (Ki = 1.1 nM) and a moderate affinity at 5-HT7R (Ki = 90 nM). Thus, it was of interest to exploit its pharmacophore elements in designing new dual receptor ligands. Using SYA16263 as the lead molecule, we have conducted a limited structure-affinity relationship (SAFIR) study by modifying various structural elements in the arylalkyl moiety, resulting in the identification of a new dual 5-HT1AR and 5-HT7R ligand, 6-chloro-2-methyl-2-(3-(4-(pyridin-2-yl)piperazin-1-yl)propyl)-2,3-dihydro-1H-inden-1-one (21), which unlike SYA16263, has a sub-nanomolar (5-HT1AR, Ki = 0.74 nM) and a low nanomolar (5-HT7R, Ki = 8.4 nM) affinity for these receptors. Interestingly, 21 is a full agonist at 5-HT1AR and antagonist at the 5-HT7R, functional characteristics which point to its potential as an antidepressant agent.

ALKYLATED TETRAHYDROISOQUINOLINES FOR BINDING TO CENTRAL NERVOUS SYSTEM RECEPTORS

Derivatives of 1,2,3,4-tetrahydroisoquinoline (THIQ) having the general formula A-(CH2)n—B are provided, wherein A is THIQ or a substituted derivative thereof and B is an aryl, cycloalkylaryl, or cycloalkyl group, wherein A and B are linked to each other by an alkyl or substituted alkyl chain. The compounds are useful as selective ligands (agonists or antagonists) of central nervous system receptors, and in particular of the seratonin receptors. The compounds or their salts can be formulated into pharmaceutical in need thereof by any route of administration suitable for a desired treatment protocol and especially for the treatment of psychiatric disorders.