91189-24-1

Usage

Properties

1. Chemical Name: 2,7-Diazaspiro[4.4]nonane-1,3,8-trione, 2-methyl-
2. Molecular Formula: C8H11N3O3
3. Structure: Spirocyclic compound with two nitrogen atoms and a trione functional group
4. Aliases: Also known as Picrotoxin
5. Occurrence: Naturally occurring toxin found in certain plants
6. Historical Uses: Used as a pesticide and as a treatment for alcoholism
7. Biological Activity: Potent antagonist of the GABAA receptor
8. Role in Neurobiology and Pharmacology: Useful for research purposes
9. Toxicity: Considered toxic and has been largely replaced by safer alternatives

Structure

Spirocyclic with two nitrogen atoms and a trione functional group

Aliases

Picrotoxin

Occurrence

Naturally found in certain plants

Historical uses

Used as a pesticide and for treating alcoholism

Biological activity

Acts as a potent antagonist of the GABAA receptor

Role in research

Valuable for neurobiology and pharmacology studies

Toxicity

Considered toxic and replaced by safer alternatives in modern usage

InChI:InChI=1/C8H10N2O3/c1-10-6(12)3-8(7(10)13)2-5(11)9-4-8/h2-4H2,1H3,(H,9,11)

Upstream product

• 91189-23-0 ethyl 3-(ethoxycarbonyl)-5-oxo-3-pyrrolidineacetate 
• 20822-61-1 triethyl 2-cyano-1,2,3-propanetricarboxylate 
• 74-89-5 methylamine 

Downstream Products

• 135380-53-9 2-methyl-2,7-diazaspiro<4.4>nonane 
• 91189-25-2 2-Methyl-7-(phenylmethyl)-2,7-diazaspiro[4.4]-nonane-1,3,8-trione 
• 99735-27-0 2-methyl-7-(phenylmethyl)-2,7-diazaspiro<4.4>nonane 

Relevant academic research and scientific papers

Synthesis and differential functionalisation of pyrrolidine and piperidine based spirodiamine scaffolds

The synthesis and differential substitution/protection of a series of spirodiamine scaffolds are described. Methods for selective access to the two mono-N-methyl isomers based on 2,7-diazaspiro[4.5]decane are also described. Key precursors associated with this chemistry are prone to rearrangement and methods for circumventing this issue are reported. While direct mono-carbamoylation (Boc) was not efficient, selective deprotection of doubly Boc-protected derivatives derived from symmetrical diamines provided mono-Boc variants. N-Arylation, exemplified by a series of monosubstituted spirodiamines incorporating the 2-chloro-5-pyridyl moiety, which is a privileged nicotinic agonist substructure, has also been carried out to provide monoarylated secondary and tertiary spirodiamines variants.

Quinolone Antibacterial Agents Substituted at the 7-Position with Spiroamines. Synthesis and Structure-Activity Relationships

A series of fluoroquinolone antibacterials having the 7-position (10-position of pyridobenzoxazines) substituted with 2,7-diazaspirononane (4b), 1,7-diazaspirononane (5a), or 2,8-diazaspiroundecane (6b) was prepared, and their biological activities were compared with piperazine and pyrrolidine substituted analogues.Most exhibited potent Gram-positive and Gram-negative activity, especially when side chain 4b was N-alkylated.

4-oxo-1,4-dihydroquinoline-3-carboxylic acid derivative as antibacterial agents

Novel naphthyridine-, quinoline- and benzoxazinecarboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

Antibacterial agents

Novel quinoline-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

Antibacterial agents

Novel naphthyridine-, quinoline- and benzoxazine-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

Antibacterial agents III

Novel 1-amino-naphthyridine- and quinoline-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections.