121564-88-3

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl exo-1-azabicyclo[2.2.1]heptane-3-carboxylate serves as a key precursor in the creation of various pharmaceuticals, leveraging its unique structure to form the backbone of multiple medicinal compounds. Its reactivity in chemical reactions enables the development of new drugs with distinct therapeutic properties.
Used in Organic Compounds Synthesis:
In the realm of organic chemistry, Methyl exo-1-azabicyclo[2.2.1]heptane-3-carboxylate is utilized as an intermediate for synthesizing a wide array of organic compounds. Its ability to undergo various chemical transformations makes it a versatile building block for creating complex organic molecules with specific functionalities.
Used in Medicinal Chemistry:
Methyl exo-1-azabicyclo[2.2.1]heptane-3-carboxylate is applied in medicinal chemistry for its potential to contribute to the development of new drugs. Its unique structural features and reactivity are harnessed to design and synthesize compounds with novel biological activities and therapeutic potentials.
Used in Drug Development:
In the field of drug development, Methyl exo-1-azabicyclo[2.2.1]heptane-3-carboxylate plays a pivotal role as a precursor in the synthesis of biologically active compounds. Its involvement in the formation of diverse derivatives with different properties is crucial for the advancement of new pharmaceutical entities that address unmet medical needs.
Used in Organic Synthesis Research:
Methyl exo-1-azabicyclo[2.2.1]heptane-3-carboxylate is also utilized in research settings to explore new methods and pathways in organic synthesis. Its unique reactivity provides opportunities for scientists to investigate novel synthetic routes and mechanisms, potentially leading to more efficient and innovative chemical processes.

InChI:InChI=1/C8H13NO2/c1-11-8(10)7-5-9-3-2-6(7)4-9/h6-7H,2-5H2,1H3

Upstream product

• 67-56-1 methanol 
• 114704-10-8 (1R,3R,4R)-1-Aza-bicyclo[2.2.1]heptane-3-carboxylic acid ethyl ester 
• 118796-92-2 Hexahydro-furo[3,4-c]pyridin-3-one 
• 72726-63-7 4-(Hydroxymethyl)nicotinic acid 
• 133745-58-1 (1R,3S,4S)-1-Benzyl-3-ethoxycarbonyl-1-azonia-bicyclo[2.2.1]heptane; bromide 
• 133745-56-9 (3S,4S)-1-Benzyl-4-bromomethyl-piperidine-3-carboxylic acid ethyl ester 
• 133745-54-7 cis-5-benzyl-3a,4,5,6,7,7a-hexahydrofuro<3,4-c>pyridin-3(1H)-one 
• 4664-08-8 cinchomeronic anhydride 
• 5657-52-3 1,3-dihydrofuro<3,4-c>pyridin-3-one 
• 121564-86-1 methyl 1-(2-methoxy-2-oxoethyl)-5-oxopyrrolidine-3-carboxylate 
• 121564-87-2 methyl 1-(2-methoxy-2-oxoethyl)pyrrolidine-3-carboxylate 
• 21472-89-9 1-azabicyclo[2.2.1]heptan-3-one 
• 114704-09-5 3-(1,3-dithian-2-ylidene)-1-azabicylo<2.2.1>heptane 

Downstream Products

• 121564-89-4 exo-3-(3-methyl-1,2,4-oxadiazol-5-yl)-1-azabicyclo<2.2.1>heptane 

Relevant academic research and scientific papers

Ester Bio-isosteres: Synthesis of Oxadiazolyl-1-azabicycloheptanes as Muscarinic Agonists

The methyl ester functionality in arecoline and related esters has been replaced by 1,2,4-oxadiazole to generate the most potent and efficacious muscarinic agonists known.

Comparison of Azabicyclic Esters and Oxadiazoles as Ligands for the Muscarinic Receptor

The link between the cognitive deficit associated with Alzheimer type dementia and the loss of cholinergic function in the disease provides a basis for examining muscarinic agonists as potential therapeutic agents.This paper describes the design and synthesis of novel azabicyclic methyl esters as ligands for the muscarinic receptor.Replacement of the methyl ester by a 3-methyl-1,2,4-oxadiazole ring produces potent metabolically more stable muscarinic agonists capable of penetrating the central nervous system.These compounds generally show improved affinity relativeto the corresponding methyl esters. 3-Methyl-1,2,4-oxadiazole 7b has an affinity 4 times that of acetylcholine.Receptor affinity is discussed in relation to the size and geometry of the azabicyclic ring and the electronic properties of the heteroaromatic ring.

Synthesis and biological activity of 1,2,4-oxadiazole derivatives: Highly potent and efficacious agonists for cortical muscarinic receptors

The synthesis and biochemical evaluation of novel 1,2,4-oxadiazole-based muscarinic agonists which can readily penetrate into the CNS is reported. Efficacy and binding of these compounds are markedly influenced by the structure and physicochemical properties of the cationic head group. In a series of azabicyclic ligands efficacy and affinity are influenced by the size of the surface area presented to the receptor, at the active site, and the degree of conformational flexibility. The exo-1-azanorbornane 16a represents the optimum arrangement, and this compound is one of the most efficacious and potent muscarinic agonists known. In a series of isoquinuclidine based muscarinic agonists efficacy and are influenced by the geometry between the cationic head group and hydrogen bond acceptor pharmacophore and steric bulk in the vicinity of the base. The anti configuration represented by 22a is optimal for muscarinic activity. Ligands with pK(a) below 6.5 show poor binding to the muscarinic receptor as exemplified by the diazabicyclic derivative 42.