166398-23-8

Basic information

• Product Name: 4-(3,4-dihydroisoquinolin-2(1H)-yl)cyclohexanone
• Synonyms: 4-(3,4-dihydroisoquinolin-2(1H)-yl)cyclohexanone;4-(3,4-Dihydro-2(1H)-isoquinolinyl)cyclohexanone;7,8-difluoro-2-methoxyquinoline-4-carbaldehyde;Cyclohexanone, 4-(3,4-dihydro-2(1H)-isoquinolinyl)-
• CAS NO: 166398-23-8
• Molecular Formula: C₁₅H₁₉NO
• Molecular Weight: 229.321
• Mol File: 166398-23-8.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.124
• CAS DataBase Reference: 4-(3,4-dihydroisoquinolin-2(1H)-yl)cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3,4-dihydroisoquinolin-2(1H)-yl)cyclohexanone(166398-23-8)
• EPA Substance Registry System: 4-(3,4-dihydroisoquinolin-2(1H)-yl)cyclohexanone(166398-23-8)

Safety Data

• Hazardous Substances Data: 166398-23-8(Hazardous Substances Data)

Usage

General Description

4-(3,4-dihydroisoquinolin-2(1H)-yl)cyclohexanone is a chemical compound that consists of a cyclohexanone ring with a 3,4-dihydroisoquinolin-2(1H)-yl group attached to it. It is a cyclic ketone that may have potential applications in the field of organic chemistry and pharmaceuticals. 4-(3,4-dihydroisoquinolin-2(1H)-yl)cyclohexanone may exhibit interesting reactivity and characteristics due to the presence of the 3,4-dihydroisoquinolin-2(1H)-yl moiety, which could make it valuable for medicinal purposes or as a building block for the synthesis of other complex compounds. Further research and evaluation of its properties and potential uses are necessary to fully understand the capabilities and limitations of this chemical.

Upstream product

• 166398-22-7 8-(Tetrahydroisoquinolin-2-yl)-1,4-dioxaspiro[4,5]decane 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 

Relevant articles and documents

On the bioactive conformation of NAN-190 (1) and MP3022 (2), 5-HT(1A) receptor antagonists

Structural modifications of 1, a postsynaptic 5-HT(1A) receptor antagonist, provided its flexible (8, 12) and rigid (7, 9, 11, 13) analogues. Compounds 7, 8, 9, and 11 showed high 5-HT(1A) receptor affinity (K(i) = 4-72 nM). They acted as 5-HT(1A) postsynaptic receptor antagonists, since, like 1, they inhibited the behavioral syndrome, i.e., flat body posture (FBP) and forepaw treading (FT), in reserpine-pretreated rats as well as the lower lip retraction (LLR) in rats, both induced by 8-hydroxy-2-(di-n- propylamino)tetralin hydrobromide (8-OH-DPAT), a 5-HT(1A) receptor agonist. Compound 12, which demonstrated high 5-HT(1A) receptor affinity (K(i) = 50 nM), revealed properties of a partial 5-HT(1A) receptor agonist: it induced LLR and, at the same time, inhibited FT in rats. Compound 13 (K(i) = 1600 nM) was not tested in a behavioral study. Restriction of the conformational freedom in 2, a full 5-HT(1A) receptor antagonist, yielded compound 14 with high 5-HT(1A) receptor affinity (K(i) = 47 nM) and partial agonist properties at postsynaptic 5-HT(1A) receptors in the above tests in vivo; i.e., it induced LLR and inhibited FBP and FT in rats. New constrained analogues of I and 2 (compounds 7 and 14, respectively) were also synthesized to recognize a bioactive conformation of those 5-HT(1A) receptor antagonists. On the basis of in vitro and in vivo investigations, binding and functional properties of compound 7 were found to reflect those of I at 5-HT(1A) receptors. On the other hand, compound 14, a rigid analogue of 2, showed a different activity in vivo in comparison with the parent compound. PM3 and MM calculations revealed the existence of three low-energy conformers of 7 and six of 14, all of them belonging to the extended family of conformations. The optimized structures of both analogues had a different angle between aromatic planes of terminal fragments; moreover, the heteroaromatic system of those molecules occupied various space regions. Our present study provides support to the hypothesis that the bioactive conformation of 1, responsible for its postsynaptic 5-HT(1A) receptor antagonism, is an extended linear structure represented by 7.