696-75-3

Usage

Uses

Used in Pharmaceutical Industry:
trans-1,2-Cyclopropanedicarboxylic acid is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into complex molecular structures, contributing to the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, trans-1,2-Cyclopropanedicarboxylic acid is utilized as a building block in the creation of agrochemicals, such as pesticides and herbicides, due to its reactivity and potential to form stable and effective compounds for agricultural applications.
Used in Specialty Chemicals Production:
trans-1,2-Cyclopropanedicarboxylic acid is employed in the production of specialty chemicals, where its unique cyclopropane ring and carboxylic acid groups allow for the development of high-value compounds used in various industrial applications.
Used in Research and Development:
trans-1,2-Cyclopropanedicarboxylic acid is also used in research and development across different industries as a versatile building block for the synthesis of a wide range of products, enabling the exploration of new chemical reactions and the creation of innovative materials.

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-/m1/s1

Upstream product

• 96149-00-7 (1S,2S)-cyclopropane-1,2-dicarboxylic acid bis-(1R,2S,5R)-(5-isopropyl-2-methyl-cyclohexyl) ester 
• 826-35-7 dimethyl trans-1,2-cyclopropanedicarboxylate 
• 3999-55-1 diethyl trans-cyclopropane-1,2-dicarboxylate 
• 35974-55-1 methyl (±)-trans-2-carbamoylcyclopropanecarboxylate 
• 702-28-3 1,2-cyclopropane dicarboxylic acid diester 
• 106-93-4 ethylene dibromide 
• 105-53-3 diethyl malonate 
• 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 
• 878-14-8 Aethylmethyl-1,2-cyclopropandicarboxylat 
• 5617-74-3 3-oxabicyclo[3.1.0]hexane-2,4-dione 
• 7732-18-5 water 

Downstream Products

• 89180-99-4 (1R,2R)-Cyclopropane-1,2-dicarbonyl dichloride 
• 5617-69-6 cis-cyclopropane-1,2-dicarboximide 
• 5617-74-3 3-oxabicyclo[3.1.0]hexane-2,4-dione 
• 58616-95-8 trans-1,2-cyclopropanedicarboxylic acid 
• 696-74-2 cis-1,2-cyclopropanedicarboxylic acid 
• 710-43-0 cis-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 52745-75-2 (-)-(1R,3R)-1,3-bis(hydroxymethyl)cyclopropane 
• 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 
• 889461-57-8 (+)-(S,S)-cyclopropane-1,2-dicarboxylic acid diethyl ester 
• 781658-85-3 1,2;3,4-(di-O-isopropylidene)-6-O-α-D-galactopyranosyl (1S,2S)-2-(3,4-dichlorobenzoyl)-cyclopropane-1-carboxylate 

Relevant academic research and scientific papers

HETEROCYCLIC COMPOUNDS AS ARGINASE INHIBITORS

The present invention relates to heterocyclic compounds as arginase inhibitors, in particular to a compound represented by Formula (I), or a pharmaceutically acceptable salt, stereoisomer or tautomer, or prodrug thereof and a pharmaceutical composition comprising said compound.

IMIDAZOLIDINONE DERIVATIVES AS INHIBITORS OF PERK

The invention is directed to substituted imidazolidinone derivatives. Specifically, the invention is directed to compounds according to Formula I (I) wherein R1, R2, R3, R4, R5, R6, R7, X, Y1, Y2 and Z are defined herein. The compounds of the invention are inhibitors of PERK and can be useful in the treatment of cancer, pre-cancerous syndromes, as Alzheimer's disease, neuropathic pain, spinal cord injury, traumatic brain injury, ischemic stroke, stroke, Parkinson disease, diabetes, metabolic syndrome, metabolic disorders, Huntington's disease, Creutzfeldt-Jakob Disease, fatal familial insomnia, Gerstmann-Str?ussler-Scheinker syndrome, and related prion diseases, amyotrophic lateral sclerosis, progressive supranuclear palsy, myocardial infarction, cardiovascular disease, inflammation, organ fibrosis, chronic and acute diseases of the liver, fatty liver disease, liver steatosis, liver fibrosis, chronic and acute diseases of the lung, lung fibrosis, chronic and acute diseases of the kidney, kidney fibrosis, chronic traumatic encephalopathy (CTE), neurodegeneration, dementias, frontotemporal dementias, tauopathies, Pick's disease, Neimann-Pick's disease, amyloidosis, cognitive impairment, atherosclerosis, ocular diseases, arrhythmias, in organ transplantation and in the transportation of organs for transplantation. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting PERK activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

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.

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

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.

Enantioselective bacterial hydrolysis of amido esters and diamides derived from (±)-trans-cyclopropane-1,2-dicarboxylic acid

Different optically active amido esters, mixed acid esters, amido acids, and diamides derived from trans-cyclopropane-1,2-dicarboxylic acid were prepared from the commercially available diethyl (±)-trans-cyclopropane-1,2- dicarboxylate. The key step was the Rhodococcus rhodochrous IFO 15564 catalyzed hydrolysis of the corresponding racemic amide. The amidase present in this microorganism showed moderate to high enantioselectivity towards these substrates. In addition a simple and efficient Curtius rearrangement of some of the enzymatically prepared cyclopropanecarboxylic acids allowed us to obtain optically active β-aminocyclopropanecarboxylic acid derivatives with high yields and enantiomeric excesses. The Royal Society of Chemistry.

COSMETIC USES AND METHODS FOR INDOLINE GRANZYME B INHIBITOR COMPOSITIONS

Cosmetic uses and methods for indoline granzyme B inhibitor compounds in compositions with a cosmetically acceptable carrier. Uses and methods for treating, reducing or inhibiting the appearance of ageing in the skin are provided. Also provided are compositions and formulation for cosmetic uses and methods of maintaining a youthful appearance, reducing an appearance of ageing, inhibiting an appearance of ageing, reducing a rate of an appearance of ageing, reducing a skin inelasticity, reducing a rate of increasing skin inelasticity, maintaining a skin elasticity, and increasing the density of hair follicles of a skin of a subjecl. The uses and methods comprise applying/administering an indoline granzyme B inhibitor to a skin, or a portion of a skin of the subject.

2-PYRIDYL CARBOXAMIDE-CONTAINING SPLEEN TYROSINE KINASE (SYK) INHIBITORS

The invention provides certain 2-pyridyl carboxamide-containing compounds of the Formula (I) or pharmaceutically acceptable salts thereof, wherein A and B are as defined herein. The invention also provides pharmaceutical compositions comprising such compounds, and methods of using the compounds for treating diseases or conditions mediated by Spleen Tyrosine Kinase (Syk) kinase.

Highly stereoselective cyclopropanation of α,β-unsaturated carbonyl compounds with methyl (diazoacetoxy)acetate catalyzed by a chiral ruthenium(II) complex

Tantalizing triangles: The title reaction gives bicarbonyl cyclopropane products that can lead to versatile intermediates with high yields and stereoselectivities. This system was also applied to the enantioselective total synthesis of spiro cyclopropane oxindole, an HIV-1 nonnucleoside reverse transcriptase inhibitor. Copyright

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.