180-44-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Azaspiro[5.5]undecane is used as a key intermediate in the synthesis of various drug molecules. Its unique ring structure and functional groups make it a valuable component in the development of new medications with improved efficacy and selectivity.
Used in Agrochemical Industry:
3-Azaspiro[5.5]undecane is utilized as a structural element in the design of novel agrochemicals, such as insecticides and herbicides. Its incorporation into these compounds can enhance their target specificity, reducing the environmental impact and improving their overall performance.
Used in Organic Synthesis:
3-Azaspiro[5.5]undecane serves as a versatile building block in organic synthesis, allowing for the creation of a wide range of complex molecules with diverse applications. Its unique spiro-connected azaspiro ring system provides opportunities for the development of innovative synthetic routes and methodologies.
As an M2 Proton Channel Blocker:
3-Azaspiro[5.5]undecane is used as a salt-free form of 4,4-Pentamethylenepiperidine Hydrochloride (P271760), which is an M2 proton channel blocker. This application is particularly relevant in the development of treatments for neurological disorders and conditions where modulation of proton channels is beneficial.

Biological Activity

M2 proton channel blocker (IC 50 = 0.92 μ M). Inhibits influenza virus M2 protein (AM2).

InChI:InChI=1/C10H19N/c1-2-4-10(5-3-1)6-8-11-9-7-10/h11H,1-9H2

Upstream product

• 1130-32-1 3-azaspiro[5.5]undecane-2,4-dione 
• 1075-89-4 tetramethylene glutarimide 
• 4375-49-9 3-benzyl-3-azaspiro[5.5]undecane 

Downstream Products

• 137795-82-5 (R)-5-(3-Aza-spiro[5.5]undec-3-yl)-4-benzyloxycarbonylamino-5-oxo-pentanoic acid benzyl ester 
• 291544-99-5 2-(3-Azaspiro[5.5]undec-3-yl)benzophenon 
• 137795-48-3 (R)-5-(3-Aza-spiro[5.5]undec-3-yl)-4-(3-chloro-benzoylamino)-5-oxo-pentanoic acid 
• 137822-88-9 (R)-5-(3-Aza-spiro[5.5]undec-3-yl)-4-(3,4-dichloro-benzoylamino)-5-oxo-pentanoic acid 
• 1162762-63-1 3-(pyridin-2-ylmethyl)-3-azaspiro[5.5]undecane 
• 1162762-56-2 3-(thiophen-3-ylmethyl)-3-azaspiro[5.5]undecane 
• 1162762-60-8 3-((1-methyl-1H-pyrazol-4-yl)methyl)-3-azaspiro[5.5]undecane 
• 1162762-61-9 3-(3-azaspiro[5.5]undecan-3-ylmethyl)-5-methylisoxazole 
• 1162762-54-0 3-(cyclopentylmethyl)-3-azaspiro[5.5]undecane 
• 1162762-65-3 3-((1H-imidazol-4-yl)methyl)-3-azaspiro[5.5]undecane 
• 1162762-73-3 3-azaspiro[5.5]undecane-3-carboxamide 
• 1125-01-5 3-azaspiro[5.5]undecane hydrochloride 
• 1162762-66-4 3-((1H-imidazol-2-yl)methyl)-3-azaspiro[5.5]undecane 
• 1206822-01-6 3-(cyclopropylmethyl)-3-azaspiro[5,5]undecane hydrochloride 

Relevant academic research and scientific papers

C-H/C-C Functionalization Approach to N-Fused Heterocycles from Saturated Azacycles

Herein we report the synthesis of substituted indolizidines and related N-fused bicycles from simple saturated cyclic amines through sequential C-H and C-C bond functionalizations. Inspired by the Norrish-Yang Type II reaction, C-H functionalization of azacycles is achieved by forming α-hydroxy-β-lactams from precursor α-ketoamide derivatives under mild, visible light conditions. Selective cleavage of the distal C(sp2)-C(sp3) bond in α-hydroxy-β-lactams using a Rh-complex leads to α-acyl intermediates which undergo sequential Rh-catalyzed decarbonylation, 1,4-addition to an electrophile, and aldol cyclization, to afford N-fused bicycles including indolizidines. Computational studies provide mechanistic insight into the observed positional selectivity of C-C cleavage, which depends strongly on the groups bound to Rh trans to the phosphine ligand.

Compound as potassium channel modulator

The invention relates to a compound as a potassium channel modulator, which is a compound of a formula (I) or a pharmaceutically acceptable salt thereof. The compound or the pharmaceutically acceptable salt thereof is effective for curing and preventing diseases and symptoms influenced by the activity of potassium ion channels.

Discovery of spiro-piperidine inhibitors and their modulation of the dynamics of the M2 proton channel from influenza A virus

Amantadine has been used for decades as an inhibitor of the influenza A virus M2 protein (AM2) in the prophylaxis and treatment of influenza A infections, but its clinical use has been limited by its central nervous system (CNS) side effects as well as emerging drug-resistant strains of the virus. With the goal of searching for new classes of M2 inhibitors, a structure-activity relation study based on 2-[3-azaspiro(5,5)undecanol]-2-midazoline (BL-1743) was initiated. The first generation BL-1743 series of compounds has been synthesized and tested by two-electrode voltage-clamp (TEV) assays. The most active compound from this library, 3-azaspiro[5,5]undecane hydrochloride (9), showed an IC50 as low as0.92 ± 0.11 μM against AM2, more than an order of magnitude m ore potent than amantadine (IC50 = 16 μM). 15N and 13C solid-state NMR was employed to determine the effect of compound 9 on the structure and dynamics of the transmembrane domain of AM2 (AM2-TM) in phospholipid bilayers. Compared to amantadine, spiro-piperidine 9 (1) induces a more homogeneous conformation of the peptide,(2) reduces the dynamic disorder of the G34-I35 backbone near the water -filled central cavity of the helical bundle, and (3) influences the dynamics and magnetic environment of more residues within the transmembranehelices. These data suggest that spiro-piperidine 9 binds more extensiv ely with the AM2 channel, thus leading to stronger inhibitory potency.

SPIROPIPERIDINE COMPOUND AND MEDICINAL USE THEREOF

The present invention relates to a CXCR3 antagonist comprising a compound represented by formula (I) (wherein all the symbols have the same meaning as defined in the description), a salt thereof, a quaternary ammonium salt thereof, an N-oxide form thereof or a solvate thereof, or a prodrug thereof. This antagonist is useful as a preventive, therapeutic and/or progression-suppressing agent for a CXCR3-mediated disease such as an immune or an allergic disease [e.g., an atopic disease, an autoimmune disease (e.g., multiple sclerosis, rheumatoid arthritis, systemic lupus erythematosus, type I diabetes, glomerulonephritis, Sjogren's syndrome and the like), systemic inflammatory response syndrome (SIRS), a rejection response to transplanted organ, tissue and/or cell or the like], a gastrointestinal disease [e.g., an inflammatory bowel disease or the like], or a respiratory disease [e.g., asthma, a chronic obstructive pulmonary disease or the like].

Substituted benzothiazole amide derivatives

A compound of formula I and a method of treatment of diseases, related to modulation of the adenosine A2 receptor system comprising administering a compound of formula 1to a person in need of such treatment.