1221818-81-0

Basic information

• Product Name: (1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
• Synonyms: 7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid
• CAS NO: 1221818-81-0
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.28356
• Mol File: 1221818-81-0.mol

Chemical Properties

• Boiling Point: 371.0±25.0 °C(Predicted)
• Appearance: /
• Density: 1.232±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 4.50±0.20(Predicted)
• CAS DataBase Reference: (1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid(1221818-81-0)
• EPA Substance Registry System: (1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid(1221818-81-0)

Safety Data

• Hazardous Substances Data: 1221818-81-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid is used as a pharmaceutical intermediate for the synthesis of various drugs due to its unique bicyclic structure and carboxylic acid functional group. The specific stereochemistry of this compound may contribute to the development of new drugs with improved efficacy and selectivity.
Used in Organic Synthesis:
(1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid is used as a building block in organic synthesis for the preparation of complex organic molecules. Its unique structure and functional groups make it a valuable component in the synthesis of natural products, pharmaceuticals, and other specialty chemicals.
Used as a Protecting Group in Chemical Reactions:
(1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid is used as a protecting group in chemical reactions to temporarily mask functional groups, preventing unwanted side reactions. The tert-butoxycarbonyl group can be selectively removed under mild conditions, allowing for the controlled synthesis of complex molecules with multiple functional groups.

Upstream product

• 1260981-47-2 7-(tert-butyloxycarbonyl)-2-endo-carbethoxy-7-azabicyclo<2.2.1>heptane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 197080-73-2 (+/-) endo-7-tert-butyl 2-methyl 7-azabicyclo[2.2.1]heptane-2,7-dicarboxylate 
• 181873-33-6 3-bromo-7-aza-bicyclo[2.2.1]hepta-2,5-diene-2,7-dicarboxylic acid 7-tert-butyl ester 2-methyl ester 
• 197080-73-2 (+/-)-methyl endo-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylate 
• 918411-42-4 (1S,2S,4R)-2-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 163458-37-5 (1R,2R,4S)-7-(tert-Butoxycarbonyl)-2-(methoxycarbonyl)-7-azabicyclo<2.2.1>heptane 
• 918411-41-3 (1R,2R,4S)-2-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-7-aza-bicyclo[2.2.1]heptane-7-carboxylic acid tert-butyl ester 
• 1251009-93-4 (1S,4R)-7-Aza-bicyclo[2.2.1]heptane-2-carboxylic acid ethyl ester 
• 197080-73-2 (+/-) endo-7-tert-butyl 2-methyl 7-azabicyclo[2.2.1]heptane-2,7-dicarboxylate 
• 1221818-81-0 endo-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid 

Downstream Products

• 1260981-47-2 7-(tert-butyloxycarbonyl)-2-exo-carbethoxy-7-azabicyclo<2.2.1>heptane 
• 188895-96-7 (+/-)-epiboxidine 
• 163458-37-5 (1R,2R,4S)-7-(tert-Butoxycarbonyl)-2-(methoxycarbonyl)-7-azabicyclo<2.2.1>heptane 
• 918411-43-5 (1R,2R,4S)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid 
• 918411-46-8 (1S,2S,4R)-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid 
• 197080-73-2 (+/-)-methyl endo-7-(tert-butoxycarbonyl)-7-azabicyclo[2.2.1]heptane-2-carboxylate 
• 500556-90-1 (+)-(1S,2R,4R)-tert-butyl 2-amino-7-azabicyclo[2.2.1]heptane-7-carboxylate 

Relevant articles and documents

Design, synthesis, structure-activity relationship, and in vivo activity of azabicyclic aryl amides as α7 nicotinic acetylcholine receptor agonists

A novel set of azabicyclic aryl amides have been identified as potent and selective agonists of the α7 nAChR. A two-pronged approach was taken to improve the potential hERG liability of previously disclosed α7 nAChR agonist, PNU-282,987, while maintaining the compound's other desirable pharmacological properties. The first approach involved further exploration of the aryl carboxylic acid fragment of PNU-282,987, while the second approach focused on modification of the azabicyclic amine portion of PNU-282,987. The best compounds from each series are characterized by rapid brain penetration, good oral bioavailability in rat, and demonstrate in vivo efficacy in a rat P50 auditory sensory gating assay. At least one analog from each series (1h, 1o, 2a, 9a, and 18a) shows an improved hERG safety profile over PNU-282,987.

SUBSTITUTED 7-AZABICYCLES AND THEIR USE AS OREXIN RECEPTOR MODULATORS

The present invention is directed to compounds of Formula I: wherein ring A is phenyl, naphihalenyl, pyridyl, quinolinyl, isoquinolinyl, imidazopyridyl, furanyi, tlisazolyl, isoxazolvl, pyrazolyl, imidazothiazolyi, benzimidazolyl, or indazolyi; R1 is H, alky], aikoxy, hydroxyalkylene, OH, halo, phenyl, triazolyl, oxazolyl, isoxazofyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazmyl, piperazinyl, pyrazolyl, oxadiazolvl, pyrrolidinyl, thiophenyi, morpholinyl, or dialkyiamino; R2 is H, alkyl, aikoxy, hydroxyalkylene, or halo; Z is NH, N-alkyl, or O; R5 is pyridyl, pyrimidinyl, pyrazinyl, pyridazmyl, qumazolinyi, quinoxalinyl, pyrazolyl, benzoxazolyl, imidazopyrazinyl, triazolopyrazinyl, optionally substituted with a one or two substituents independently selected from the group consisting of alkyl, aikoxy, or halo; and n is 0 or 1, Methods of making the compounds of Formula 1 are also described. The invention also relates to pharmaceutical compositions comprising compounds of Formula I. Methods of using the compounds of the invention are also within the scope of the invention.

BICYCLIC HETEROCYCLE DERIVATIVES AND METHODS OF USE THEREOF

The present invention relates to Bicyclic Heterocycle Derivatives, compositions comprising a Bicyclic Heterocycle Derivative, and methods of using the Bicyclic Heterocycle Derivatives for treating or preventing obesity, diabetes, a metabolic disorder, a cardiovascular disease or a disorder related to the activity of a GPCR in a patient.

Structure-activity relationships of adenosines with heterocyclic N6-substituents

Two series of N6-substituted adenosines with monocyclic and bicyclic N6 substituents containing a heteroatom were synthesized in good yields. These derivatives were assessed for their affinity ([3H]CPX), potency, and intrinsic activity (cAMP accumulation) at the A1 adenosine receptor in DDT1 MF-2 cells. In the monocyclic series, the N6-tetrahydrofuran-3-yl and thiolan-3-yl adenosines (1 and 26, respectively) were found to possess similar activities, whereas the corresponding selenium analogue 27 was found to be more potent. A series of nitrogen containing analogues showed varying properties, N6-((3R)-1-benzyloxycarbonylpyrrolidin-3-yl)adenosine (30) was the most potent at the A1AR; IC50 = 3.2 nM. In the bicyclic series, the effect of a 7-azabicyclo[2.2.1]heptan-2-yl substituent in the N6-position was explored. N6-(7-Azabicyclo[2.2.1]heptan-2-yl)adenosine (38) proved to be a reasonably potent A1 agonist (Ki = 51 nM, IC50 = 35 nM) while further substitution on the 7″-nitrogen with tert-butoxycarbonyl (31, IC50 = 2.5 nM) and 2-bromobenzyloxycarbonyl (34, IC50 = 9.0 nM) gave highly potent A1AR agonists.

Oligomers of β-amino acid bearing non-planar amides form ordered structures

In this report, we explore the feasibility of using bicyclic chiral β-amino acids, (1R,2R,4S)- and (1S,2S,4R)-7-azabicyclo[2.2.1]heptane-2-carboxylic acid (R-Ah2c and S-Ah2c, respectively), to prepare novel peptides with unique properties. Facile cis-trans isomerization of the non-planar amide bonds of these β-amino acids should result in great flexibility of the backbone structure of β-peptides containing them. Indeed, oligomers of these amino acids showed thermostability and characteristic CD absorptions, which were not concentration-dependent, suggesting that the oligomers remained monomeric. The results indicated the formation of self-organized monomeric structures with chain-length-dependent stabilization. Energy calculations suggested that the peptides can take helical structures in which the energy barriers to cis-trans isomerization are greater for the central amide bonds than for the terminal amides.

1H-PYRAZOLE AND 1H-PYRROLE-AZABICYCLIC COMPOUNDS WITH ALFA-7 NACHR ACTIVITY

The invention provides compounds of Formula (I), wherein Azabicyclo is Formula (I, II, III, IV, V, VI, VII); W is Formula (m); where the variables have the definitions discussed herein. These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals to treat a disease or condition in which α7 is known to be involved.

COMPOUNDS AS RADIOLIGANDS FOR THE DIAGNOSIS OF DISEASE

Radiolabeled ligands useful as probes for determining the relative abundance, receptor occupancy, and/or function of nicotinic acetylcholine receptors. The compounds of Formula I as described herein are labeled with a radioactive isotopic moiety such as 11C, 18F, 76Br, 123I or 125I. Disorders are diagnosed by administering to a mammal a detectably labeled compound and detecting the binding of that compound to the nAChR. The compounds that have been administered are detected using methods including, but not limited to, position emission topography and single-photon to emission computed tomography. The present invention is useful in diagnosing a wide variety of diseases and disorders as discussed herein.

EXO-(T-BUTYL 2R(+))-2-AMINO-7-AZABICYCLO[2.2.1]HEPTANE-7-CARBOXYLATE, INTERMEDIATES, AND PROCESS TO PREPARE AND ISOLATE THEM

The present invention relates to exo-(t-butyl 2R(+))-2-amino-7-azabicyclo[2.2.1]heptane-7-carboxylate (formula 1) a novel compound, and the process for the preparation thereof, and novel intermediates therein.

COMPOUNDS HAVING BOTH α7 NICOTINIC AGONIST ACTIVITY AND 5HT3 ANTAGONIST ACTIVITY FOR TREATMENT OF CNS DISEASES

The invention discloses compounds that are selective α7 nAChR agonists and 5-HT3 antagonists. The compounds are useful for treating many CNS diseases.

Fused bicyclic-N-bridged-heteroaromatic carboxamides for the treatment of disease

The invention provides compounds of Formula I: 1These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals to treat conditions or diseases in which α7 is known to be involved.