166398-22-7

Basic information

• Product Name: 2-(1,4-dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroisoquinoline
• Synonyms: 2-(1,4-Dioxaspiro[4.5]dec-8-yl)-1,2,3,4-tetrahydroisoquinoline;Isoquinoline, 2-(1,4-dioxaspiro[4.5]dec-8-yl)-1,2,3,4-tetrahydro-;2-(1,4-dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 166398-22-7
• Molecular Formula: C₁₇H₂₃NO₂
• Molecular Weight: 273.37
• Mol File: 166398-22-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.17
• CAS DataBase Reference: 2-(1,4-dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,4-dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroisoquinoline(166398-22-7)
• EPA Substance Registry System: 2-(1,4-dioxaspiro[4.5]decan-8-yl)-1,2,3,4-tetrahydroisoquinoline(166398-22-7)

Safety Data

• Hazardous Substances Data: 166398-22-7(Hazardous Substances Data)

Usage

Molecular structure

A unique structure consisting of a spirocyclic ring system and a tetrahydroisoquinoline ring.

Stability and rigidity

The spirocyclic ring system is known for its stability and rigidity, making it a valuable scaffold for designing drug-like molecules.

Medicinal chemistry interest

The compound may have potential applications in medicinal chemistry, particularly in the development of new pharmaceuticals.

Presence in natural products

The tetrahydroisoquinoline ring is of interest due to its presence in various natural products and biologically active molecules.

Need for further research

Further research is needed to explore the potential pharmacological properties and synthetic applications of this compound.

Upstream product

• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 4746-97-8 cyclohexanedione monoethylene ketal 

Downstream Products

• 166398-23-8 4-[2-(1,2,3,4-tetrahydroisoquinolinyl)]cyclohexanone 

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.