699-49-0

Upstream product

• 17639-93-9 2-chloro-propionic acid methyl ester 
• 97-63-2 methyl methacrylate 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 61168-38-5 (1R,2S)-1,2-Dimethyl-cyclopropane-1,2-dicarboxylic acid monomethyl ester 
• 714-79-4 (+/-)-(1R,2S)-diethyl 1,2-dimethylcyclopropane-1,2-dicarboxylate 
• 6914-83-6 1,2-Dimethyl-r-1,t-2-cyclopropandicarbonsaeure-dimethylester 
• 6914-70-1 1,2-Dimethyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester 

Downstream Products

• 884-79-7 3-phenyl-1,5-dimethyl-3-azabicyclo-<3.1.0>hexane-2,4-dione 
• 6914-67-6 1,2-dimethyl-cyclopropane-1r,2c-dicarboxylic acid anhydride 
• 119908-77-9 c-2-Chlorformyl-1,2-dimethyl-r-1-cyclopropancarbonsaeure 
• 119908-74-6 (1R,2S)-1,2-Dimethyl-cyclopropane-1,2-dicarbonyl dichloride 
• 412281-37-9 cis-1,2-Dimethyl-2-acetyl-cyclopropan-carbonsaeure-⁽¹⁾-methylester 
• 852359-90-1 3-benzyl-1,5-dimethyl-3-aza-bicyclo[3.1.0]hexane 
• 852359-85-4 3-benzyl-1,5-dimethyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 6914-67-6 1,2-dimethyl-cyclopropane-1,2-dicarboxylic acid anhydride 
• 6914-70-1 1,2-Dimethyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester 

Relevant academic research and scientific papers

Cyclopropane-1,2-dicarboxylic acids as new tools for the biophysical investigation of O-acetylserine sulfhydrylases by fluorimetric methods and saturation transfer difference (STD) NMR

Cysteine is a building block for many biomolecules that are crucial for living organisms. O-Acetylserine sulfhydrylase (OASS), present in bacteria and plants but absent in mammals, catalyzes the last step of cysteine biosynthesis. This enzyme has been dee

Cyclopropane derivatives as potential human serine racemase inhibitors: Unveiling novel insights into a difficult target

d-Serine is the co-agonist of NMDA receptors and binds to the so-called glycine site. d-Serine is synthesized by human serine racemase (SR). Over activation of NMDA receptors is involved in many neurodegenerative diseases and, therefore, the inhibition of SR might represent a novel strategy for the treatment of these pathologies. SR is a very difficult target, with only few compounds so far identified exhibiting weak inhibitory activity. This study was aimed at the identification of novel SR inhibitor by mimicking malonic acid, the best-known SR inhibitor, with a cyclopropane scaffold. We developed, synthesized, and tested a series of cyclopropane dicarboxylic acid derivatives, complementing the synthetic effort with molecular docking. We identified few compounds that bind SR in high micromolar range with a lack of significant correlation between experimental and predicted binding affinities. The thorough analysis of the results can be exploited for the development of more potent SR inhibitors.

Design, synthesis and activity of novel derivatives of Oxybutynin and Tolterodine

Novel derivatives of Tolterodine (1) and Oxybutynin (2) have been designed using conformationally restricted azabicyclics as replacement for open-chain amines. The synthesis and structure-activity relationships are presented.

Cyclopropanediamines, 3. - Pure Diastereomers of 1,2-Cyclopropanedicarboxylic Acids and Derivatives

Efficient preparations of pure diastereomers of dimethyl 1,2-cyclopropanedicarboxylates 2, dicarboxylic acids 3, dicarbonyl dichlorides 4, and dihydrazides 5 are reported.Mixtures of diastereomers of dimethyl dicarboxylates 2a, b, d, e are obtained from α,β-unsaturated methyl carboxylates 7 and methyl α-chlorocarboxylates 8 as well as from 7c, d and the sulfur ylide 10 (2c, d).The diastereomers are separated by fractionating distillations (2a, b, c, e) or crystallization (2d) on a 100-g to 1-kg scale (d.e. >99percent).Only low yields of 2c are obtained in the reaction of methyl crotonate (7c) with methyl α-chloroacetate (8a), since 7c predominantly dimerizes to afford 12.The diesters 2 are converted into the pure diastereomeric diacids 3, dicarbonyl dichlorides 4, and dihydrazides 5. 3,3-Dimethyl-cis-1,2-cyclopropanedicarboxylic acid (cis-3f) is obtained by trans-->cis isomerization of trans-3f with the help of acetic anhydride and sodium acetate as catalyst.The configurations of 2-6 and 12 are confirmed by 1H NMR spectroscopy.Derivatives of cis-1,2-dimethyl-1,2-cyclopropanedicarboxylic acid tend to form bicyclic products.Thus, the reaction of cis-3e with phosphorus pentachloride yields mainly the cyclic anhydride 6e and only small amounts of the dicarbonyl dichloride cis-4e.Furthermore, the dihydrazide cis-5e slowly cyclizes in the solid state to give the N-aminoimide 13 and hydrazine, a reaction which is fast in solution.Pure 13 is obtained by thermolysis of cis-5e at 60-65 deg C under high vacuum.