696-74-2

Usage

Uses

Used in Pharmaceutical Research:
cis-1,2-Cyclopropane dicarboxylic acid is used as a chemical probe for the identification and biological study of non-metabolite agonists for the succinate receptor GPR9. Its unique structure allows it to interact with the receptor, providing valuable insights into the receptor's function and potential therapeutic applications.
Used in Chemical Synthesis:
Due to its reactive carboxylic acid groups and cyclopropane ring, cis-1,2-Cyclopropane dicarboxylic acid can be used as a building block or intermediate in the synthesis of various complex organic molecules. This makes it a valuable compound in the field of organic chemistry and pharmaceutical development.
Used in Material Science:
The unique properties of cis-1,2-Cyclopropane dicarboxylic acid, such as its rigid cyclic structure and functional groups, may also find applications in the development of new materials with specific properties. For example, it could be used in the design of novel polymers or as a component in the creation of advanced materials with tailored characteristics.

InChI:InChI=1/C5H6O4/c6-4(7)2-1-3(2)5(8)9/h2-3H,1H2,(H,6,7)(H,8,9)/t2-,3+

Upstream product

• 292638-85-8 acrylic acid methyl ester 
• 140-88-5 ethyl acrylate 
• 3120-05-6 N-Phenylimide of cis-1,2-cyclopropanedicarboxylic acid 
• 826-34-6 dimethyl cis-cyclopropane-1,2-dicarboxylate 
• 699-23-0 cis-racemic ethyl 2-cyanocyclopropane-1-carboxylate 
• 878-14-8 Aethylmethyl-1,2-cyclopropandicarboxylat 
• 5617-74-3 3-oxabicyclo[3.1.0]hexane-2,4-dione 
• 7732-18-5 water 
• 87387-81-3 4-methoxycarbonyl-pyrazoline-3-carboxylic acid methyl ester 
• 19255-80-2 5-methoxycarbonyl-pyrazoline-3-carboxylic acid methyl ester 
• 7209-00-9 diethyl 2-bromoglutarate 
• 857792-97-3 2,3-dibromo-glutaric acid 
• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 710-43-0 cis-cyclopropane-1,2-dicarboxylic acid diethyl ester 

Downstream Products

• 710-43-0 cis-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 5617-74-3 cis-1,2-cyclopropanedicarboxylic acid anhydride 
• 102586-93-6 1,2,3,4-tetrahydroquinoline-4-propanoic acid 
• 3187-76-6 cis-cyclopropane-1,2-diamine dihydrochloride 
• 463-49-0 1,2-propanediene 
• 5617-74-3 3-oxabicyclo[3.1.0]hexane-2,4-dione 
• 116669-26-2 9-<<(Z)-2-<(benzoyloxy)methyl>cyclopropyl>methyl>adenine 
• 116664-01-8 (Z)-1-<(benzoyloxy)methyl>-2-(chloromethyl)cyclopropane 
• 116663-99-1 (Z)-2-<(benzoyloxy)methyl>cyclopropanemethanol 
• 116664-03-0 1-<<(Z)-2-<(benzoyloxy)methyl>cyclopropyl>methyl>thymine 
• 659736-80-8 3-benzyl-4-hydroxy-4-methyl-3-azabicyclo[3.1.0]hexane-2-one 
• 73799-63-0 3-benzyl-3-aza-bicyclo[3.1.0]hexane-2,4-dione 
• 70110-45-1 3-benzyl-3-aza-bicyclo[3.1.0]hexane 
• 659736-81-9 3-benzyl-2-methyl-3-azabicyclo[3.1.0]hexane 

Relevant academic research and scientific papers

Oxidative and hydrolytic cleavage of cyclopropane and spirocyclobutane derivatives of 6,8-dioxabicyclo[3.2.1]octane, the products of transformation of levoglucosenone

A new method for the synthesis of (1R,4S,5S)-4-hydroxymethyl-3- oxabicyclo[3.1.0]hexan-2-one, the cyclopropane analog of (S)-5-hydroxypent-2-en- 4-olide, has been suggested based on oxidation of (1S,2S,4R,6R)-7,9- dioxatricyclo[4.2.1.02,4]nonan-5-one. Oxidation of cyclobutanones, spirojoined with the fragments of 6,8-dioxabicyclo[3.2.1]oct-2-ene, 6,8-dioxabicyclo[3.2.1]octane (at position 4), or 7,9-dioxatricyclo[4.2.1.0 2,4]nonane (at position 5), upon the action of m-chloroperoxybenzoic acid or the KMnO4-H2SO4-H2O system leads to the corresponding spirojoined butanolides in 73-85% yields. The same cyclobutanones easily undergo the four-membered ring opening upon the action of dilute H2SO4 at 50-90 °C to form 6,8-dioxabicyclo[3.2. 1]octane-4-or 7,9-dioxatricyclo[4.2.1.02,4]nonane-5-propionic acid.

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.

An efficient and improved process for the scale-up preparation of cis-cyclopropanediamine dihydrochloride

An effective and improved process for the preparation of cis-cyclopro panediamine dihydrochloride was developed in a 100 g scale. The key step in the process is the preparation of ciscyclopropane-1, 2-dicarboxylic acid from a mixture of cis- and transisomers by the formation of cyclic acidic anhydride. The whole process and all of the procedures are economical, industrially reliable and easily scaled up.

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.

Design and Synthesis of Novel Dimeric Morphinan Ligands for κ and μ Opioid Receptors

A novel series of morphinans were synthesized, and their binding affinity at and functional selectivity for μ, δ, and κ opioid receptors were evaluated. These dimeric ligands can be viewed as dimeric morphinans, which were formed by coupling two identical

Benzamides derived from 1,2-diaminocyclopropane as novel ligands for human D2 and D3 dopamine receptors

Benzamides (3a-f) derived from 4-amino-5-chloro-2-methoxybenzoic acid and either cis or trans 1,2-diaminocyclopropane were synthesised and were evaluated in binding assays employing, bovine striatal D2 receptors, recombinant human hD2/sub

Synthesis of racemic carbocyclic cyclopropanoid nucleoside analogues

As further representatives of a novel class of carbocyclic nucleoside analogues (±)-cis- and (±)-trans-(2-hydroxymethylcyclopropyl)-uracil, -thymine, and -inosine were synthesized from the corresponding dialkyl 1,2-cyclopropane dicarboxylates.

Synthesis of Cyclopropyl Carbocyclic Nucleosides

As representatives of a novel class of carboxylic nucleoside analogues (+/-)-cis-, (-)-cis and (+/-)-trans 9-(2-hydroxymethylcyclopropyl)-adenine (= -methanol) were synthesized from the corresponding dialkyl 1,2-cyclopropane dicarboxylates.

Aragusterol A: A Potent Antitumor Marine Steroid from the Okinawan Spronge of the Genus, Xestospongia

Aragusterol A, a new marine steroid possesing antitumor activity , was isolated from Okinawan sponge of the genus Xestospongia and its structure was determined by spectroscopic analysis and chemical evidence.The compoumd strongly inhibited the cell proliferation of KB, HeLaS3, P388 and LoVo cells in vitro, and also showed potent in vivo antitumor activity toward P388 in mice and L1210 in mice.