180-44-9

Basic information

• Product Name: 3-AZASPIRO[5.5]UNDECANE
• Synonyms: 3-AZASPIRO[5.5]UNDECANE;4,4-Pentamethylenepiperidine hydrochloride;3-Azaspiro[5.5]undecane hydrochloride salt
• CAS NO: 180-44-9
• Molecular Formula: C₁₀H₁₉N
• Molecular Weight: 153.26456
• EINECS: 214-404-1
• Mol File: 180-44-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 223.2 °C at 760 mmHg
• Flash Point: 86.7 °C
• Appearance: /
• Density: 0.93 g/cm³
• Vapor Pressure: 0.0973mmHg at 25°C
• Refractive Index: 1.494
• Storage Temp.: Desiccate at RT
• PKA: 11.17±0.20(Predicted)
• CAS DataBase Reference: 3-AZASPIRO[5.5]UNDECANE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AZASPIRO[5.5]UNDECANE(180-44-9)
• EPA Substance Registry System: 3-AZASPIRO[5.5]UNDECANE(180-44-9)

Safety Data

• Hazardous Substances Data: 180-44-9(Hazardous Substances Data)

Usage

Uses

4,4-Pentamethylenepiperidine is an M2 proton channel blocker. It is salt free form of 4,4-Pentamethylenepiperidine Hydrochloride (P271760).

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

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

Downstream Products

• 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 
• 1443121-77-4 4-{3-azaspiro[5.5]undecan-3-ylmethyl}benzene-1,3-diol 
• 56953-38-9 3-(2-chloro-ethyl)-3-aza-spiro[5.5]undecane 
• 1452808-85-3 6-(3-azaspiro[5.5]undecan-3-yl)-9H-purine 
• 1206822-01-6 3-(cyclopropylmethyl)-3-azaspiro[5,5]undecane hydrochloride 

Relevant articles and documents

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.

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.

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.