156329-62-3

Usage

Uses

Used in Pharmaceutical Industry:
Bicyclo[1.1.1]pentane-1-carboxylic acid, 3-cyano-, methyl ester (9CI) is used as a building block for the synthesis of pharmaceutical compounds. Its unique structure and functional groups make it a valuable component in the development of new drugs, potentially contributing to the creation of novel therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, Bicyclo[1.1.1]pentane-1-carboxylic acid, 3-cyano-, methyl ester (9CI) is utilized as a precursor in the synthesis of agrochemicals. Its properties may be harnessed to develop new pesticides, herbicides, or other agricultural chemicals that can improve crop protection and yield.
Used in Materials Science:
Bicyclo[1.1.1]pentane-1-carboxylic acid, 3-cyano-, methyl ester (9CI) is employed as a component in the development of new materials. Its structural and functional attributes can be leveraged to create innovative materials with specific properties for various applications, such as in coatings, adhesives, or polymers.
Used as a Reagent in Organic Chemistry:
Bicyclo[1.1.1]pentane-1-carboxylic acid, 3-cyano-, methyl ester (9CI) serves as a reagent in various organic chemistry reactions. Its versatility allows it to participate in a range of chemical processes, facilitating the synthesis of other complex organic compounds for research and industrial purposes.

Upstream product

• 156329-77-0 methyl 3-carbamoylbicyclo<1.1.1>pentane-1-carboxylate 
• 115913-30-9 1,1′-(bicyclo[1.1.1]pentane-1,3-diyl)bis(ethan-1-one) 
• 115913-32-1 dimethyl bicyclo<1.1.1>pentane-1,3-dicarboxylate 
• 115913-31-0 1,3-bis(chlorocarbonyl)bicyclo<1.1.1>pentane 
• 110371-22-7 methyl 3-(chlorocarbonyl)bicyclo<1.1.1>pentane-1-carboxylate 
• 83249-10-9 3‐(methoxycarbonyl)bicyclo[1.1.1]pentane‐1‐carboxylic acid 
• 56842-95-6 bicyclo<1.1.1>pentane-1,3-dicarboxylic acid 

Downstream Products

• 83249-02-9 3-cyanobicyclo<1.1.1>pentane-1-carboxylic acid 
• 156329-61-2 3-bromobicyclo<1.1.1>pentane-1-carbonitrile 
• 1370705-39-7 3-(hydroxymethyl)bicyclo[1.1.1]pentane-1-carbonitrile 
• 1370705-40-0 (R)-2-{4-chloro-N-[(3-cyanobicyclo[1.1.1]pentan-1-yl)methyl]phenylsulfonamide}-5,5,5-trifluoropentanamide 
• 1370705-38-6 (R)-2-{N-{[3-(1,2,4-oxadiazol-3-yl)bicyclo[1.1.1]pentan-1-yl]-methyl}-4-chlorophenylsulfonamido}-5,5,5-trifluoropentanamide 

Relevant academic research and scientific papers

Quinuclidine derivative, method for preparing same and application of quinuclidine derivative

The invention relates to a quinuclidine derivative, a pharmaceutically acceptable salt, pro-drug and solvent compound of the quinuclidine derivative, a method for preparing the quinuclidine derivative, a drug composition with the quinuclidine derivative and the pharmaceutically acceptable salt, pro-drug and solvent compound and pharmaceutical application of the quinuclidine derivative. The quinuclidine derivative, the pharmaceutically acceptable salt, pro-drug and solvent compound, the method, the drug composition and the pharmaceutical application have the advantage that the compound is excellent in M3 receptor antagonist activity and accordingly can be used as a novel efficient drug for chronic obstructive pulmonary diseases.

Application of the bicyclo[1.1.1]pentane motif as a nonclassical phenyl ring bioisostere in the design of a potent and orally active γ-secretase inhibitor

Replacement of the central, para-substituted fluorophenyl ring in the γ-secretase inhibitor 1 (BMS-708,163) withthe bicyclo[1.1.1]pentane motif led to the discovery of compound 3, an equipotent enzyme inhibitor with significant improvements in passive permeability and aqueous solubility. The modified biopharmaceutical properties of 3 translated into excellent oral absorption characteristics (～4-fold Cmax and AUC values relative to 1) in a mouse model of γ-secretase inhibition. In addition, SAR studies into other fluorophenyl replacements indicate the intrinsic advantages of the bicyclo[1.1.1]pentane moiety over conventional phenyl ring replacements with respect to achieving an optimal balance of properties (e.g., γ-secretase inhibition, aqueous solubility/permeability, in vitro metabolic stability). Overall, this work enhances the scope of the [1.1.1]-bicycle beyond that of a mere spacer unit and presents a compelling case for its broader application as a phenyl group replacement in scenarios where the aromatic ring count impacts physicochemical parameters and overall drug-likeness.

Synthesis and biological evaluation of 2-(3′-(1H-tetrazol-5-yl)bicyclo[1.1.1]pent-1-yl)glycine (S-TBPG), a novel mGlu1 receptor antagonist

The design and synthesis of 2-(3′-(1H-tetrazol-5-yl)bicyclo[1.1.1]pent-1-yl)glycine (S-TBPG), a novel mGluR1 antagonist is reported. S-TBPG is characterized by the bioisosteric replacement of the distal carboxy group of 2-(3′-carboxybicyclo[1.1.1]pent-1-yl)glycine (S-CBPG) by a tetrazolyl moiety. Despite a moderate reduction in potency, S-TBPG is a selective mGluR1 antagonist (69 μM), with no activity at other mGluR subtypes. The interesting biological profile of S-TBPG, coupled with its peculiar chemical structure, is discussed in terms of the structure-activity relationship (SAR) of mGluR1 antagonists.

Synthesis of Some Bridgehead-Bridgehead-Disubstituted Bicyclopentanes

The synthesis of a wide variety of 1,3-disubstituted bicyclopentanes is described, with particular emphasis on the generation of a series of 3-X-substituted bicyclopentyl bromides required for solvolytic studies.Functional group manipulation at the bridgehead was readily accomplished in the majority of cases by radical processes; in some instances, transformations were effected via carbanionic-type intermediates.