96149-00-7

Usage

Uses

Used in Pharmaceutical Industry:
1,2-Cyclopropanedicarboxylic Acid Bis [(1R, 2S, 5R)]-5-Methyl-2-(1-Methylethyl) is used as a key intermediate in the synthesis of complex organic molecules and pharmaceutical compounds. Its unique cyclopropane ring and stereochemistry make it a valuable building block for the development of new drugs with specific therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, 1,2-Cyclopropanedicarboxylic Acid Bis [(1R, 2S, 5R)]-5-Methyl-2-(1-Methylethyl) serves as a versatile reagent for the creation of various organic compounds. Its ability to form stable bonds with other molecules allows for the development of new chemical entities with potential applications in various industries.
Used in the Synthesis of Callipeltoside A:
1,2-Cyclopropanedicarboxylic Acid Bis [(1R, 2S, 5R)]-5-Methyl-2-(1-Methylethyl) is specifically used in the synthesis of Callipeltoside A, a compound known for its inhibitory effects on the proliferation of KB and P388 cells. This application highlights the potential of 1,2-Cyclopropanedicarboxylic Acid Bis [(1R, 2S, 5R)]-5-Methyl-2-(1-Methylethyl) in contributing to the development of anti-cancer agents and other bioactive molecules.

Upstream product

• 2216-51-5 (-)-menthol 
• 1501-56-0 (trans)-cyclopropane-1,2-dicarbonyl dichloride 
• 3999-55-1 diethyl trans-cyclopropane-1,2-dicarboxylate 
• 58616-95-8 trans-1,2-cyclopropanedicarboxylic acid 
• 74-97-5 chlorobromomethane 
• 34212-59-4 bis(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl butanedioate 

Downstream Products

• 781658-85-3 1,2;3,4-(di-O-isopropylidene)-6-O-α-D-galactopyranosyl (1S,2S)-2-(3,4-dichlorobenzoyl)-cyclopropane-1-carboxylate 
• 178684-64-5 (1S,2S)-2-[(R)-4-(2,2-Diphenyl-ethyl)-1-(4-methoxy-benzyl)-2,5-dioxo-imidazolidin-4-yl]-cyclopropanecarboxylic acid 4-methoxy-benzyl ester 
• 178898-44-7 (1S,2S)-2-[(S)-1-(4-Methoxy-benzyl)-2,5-dioxo-4-(2-m-tolyl-ethyl)-imidazolidin-4-yl]-cyclopropanecarboxylic acid 4-methoxy-benzyl ester 
• 201851-10-7 (1S,2S)-2-(2-9H-Xanthen-9-yl-acetyl)-cyclopropanecarboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 178684-63-4 (1S,2S)-2-(3,3-Diphenyl-propionyl)-cyclopropanecarboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 201851-15-2 (1S,2S)-2-[(R)-1-Amino-1-carboxy-2-(9H-xanthen-9-yl)-ethyl]-cyclopropanecarboxylic acid 
• 178898-39-0 5R-5-(1S,2S-2-carboxycyclopropan-1-yl)-5-(2,2-(diphenyl)ethyl)imidazolidine-2,4-dione 
• 201851-27-6 (5SR)-5-((1S,2S)-2-carboxycycloprop-1-yl)-5-(2,2-diphenylethyl)imidazolidine-2,4-dione 
• 178684-67-8 (1S,2S)-2-(3-m-Tolyl-propionyl)-cyclopropanecarboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 203208-44-0 (1S,2S)-2-(2-9H-Xanthen-9-yl-acetyl)-cyclopropanecarboxylic acid 
• 201851-22-1 (5SR)-5-((1S,2S)-2-carboxycycloprop-1-yl)-5-[2-(3-methylphenyl)ethyl]imidazolidine-2,4-dione 
• 178898-37-8 (1S,2S-2-carboxycycloprop-1-yl) (2,2-(diphenyl)ethyl) ketone 
• 178898-43-6 (1S,2S-2-carboxycycloprop-1-yl) (2-(3-methylphenyl)ethyl) ketone 
• 203209-15-8 (1S,2S)-2-[(R)-1-(4-Methoxy-benzyl)-2,5-dioxo-4-(9H-xanthen-9-ylmethyl)-imidazolidin-4-yl]-cyclopropanecarboxylic acid 4-methoxy-benzyl ester 

Relevant academic research and scientific papers

Development of effective bidentate diphosphine ligands of ruthenium catalysts toward practical hydrogenation of carboxylic acids

Hydrogenation of carboxylic acids (CAs) to alcohols represents one of the most ideal reduction methods for utilizing abundant CAs as alternative carbon and energy sources. However, systematic studies on the effects of metal-to-ligand relationships on the catalytic activity of metal complex catalysts are scarce. We previously demonstrated a rational methodology for CA hydrogenation, in which CA-derived cationic metal carboxylate [(PP)M(OCOR)]+ (M = Ru and Re; P = one P coordination) served as the catalyst prototype for CA self-induced CA hydrogenation. Herein, we report systematic trial- and-error studies on how we could achieve higher catalytic activity by modifying the structure of bidentate diphosphine (PP) ligands of molecular Ru catalysts. Carbon chains connecting two P atoms as well as Ar groups substituted on the P atoms of PP ligands were intensively varied, and the induction of active Ru catalysts from precatalyst Ru(acac)3 was surveyed extensively. As a result, the activity and durability of the (PP)Ru catalyst substantially increased compared to those of other molecular Ru catalyst systems, including our original Ru catalysts. The results validate our approach for improving the catalyst performance, which would benefit further advancement of CA self-induced CA hydrogenation.

RADIOLABELED CANNABINOID RECEPTOR 2 LIGAND

The present invention relates to a compound of formula (I) wherein R1, R2, and R3 are defined as in the description and in the claims. The compound of formula (I) can be used as a radiolabeled ligand.

Identification and Preclinical Development of a 2,5,6-Trisubstituted Fluorinated Pyridine Derivative as a Radioligand for the Positron Emission Tomography Imaging of Cannabinoid Type 2 Receptors

Despite the broad implications of the cannabinoid type 2 receptor (CB2) in neuroinflammatory processes, a suitable CB2-targeted probe is currently lacking in clinical routine. In this work, we synthesized 15 fluorinated pyridine derivatives and tested their binding affinities toward CB2 and CB1. With a sub-nanomolar affinity (Ki for CB2) of 0.8 nM and a remarkable selectivity factor of >12,000 over CB1, RoSMA-18-d6 exhibited outstanding in vitro performance characteristics and was radiofluorinated with an average radiochemical yield of 10.6 ± 3.8% (n = 16) and molar activities ranging from 52 to 65 GBq/μmol (radiochemical purity > 99%). [18F]RoSMA-18-d6 showed exceptional CB2 attributes as demonstrated by in vitro autoradiography, ex vivo biodistribution, and positron emission tomography (PET). Further, [18F]RoSMA-18-d6 was used to detect CB2 upregulation on postmortem human ALS spinal cord tissues. Overall, these results suggest that [18F]RoSMA-18-d6 is a promising CB2 PET radioligand for clinical translation.

PYRIDINE AND PYRAZINE DERIVATIVES AS PREFERENTIAL CANNABINOID 2 AGONISTS

The invention relates to a compound of formula (I), wherein A1, A2 and R1-R5 are as defined in the description and in the claims. The compound of formula (I) can be used as cannabinoid 2 preferential agonist.

Cyclopropane PNA: Observable triplex melting in a PNA constrained with a 3-membered ring

The first peptide nucleic acid (PNA) with a cyclopropane in the backbone has been synthesized, and the effects of the ring on DNA/RNA binding properties of the PNA have been examined. Well-defined triplex to duplex melting transitions of PNA2 DNA complexes is clearly observed by variable temperature UV absorbance with the cyclopropane-constrained PNA.

Glycoside derivatives of 2-(3,4-dichlorobenzoyl)-cycopropane-1-carboxylic acid

The compounds of formula I: ???wherein R is a glycoside residue optionally having one or more hydroxy groups alkylated or acylated by C1-C4 alkyl or acyl groups, are long lasting inhibitors of kynurenine 3-monooxygenase (KMO) and potent glutamate (GLU) re

Callipeltoside A: Total synthesis, assignment of the absolute and relative configuration, and evaluation of synthetic analogues

The total synthesis of the novel antitumor agent callipeltoside A, as well as several analogues, is accomplished and allows assignment of the stereochemistry not previously established. A convergent strategy is employed wherein the target is dissected into three units - the core macrolactone, the sugar callipeltose, and a cyclopropyl bearing chain. The strategy for the synthesis of the macrolactone derives from employment of diastereoselective aldol reactions that emanate from an 11 carbon piece. The stereochemistry of the latter derives from the chiral pool and two asymmetric reactions - a ketone reduction using CBS-oxazaborolidine and a Pd catalyzed asymmetric allylic alkylation (AAA). The novelty of the latter protocol is its control of regioselectivity as well as absolute configuration. The trisubstituted olefin is generated using an alkene-alkyne coupling to create a trisubustituted olefin with complete control of geometry. The excellent chemo- and regioselectivity highlights the synthetic potential of this new ruthenium catalyzed process. The macrolactonization employs in situ formation of an acylketene generated by the thermolysis of a m-dioxolenone. Two strategies evolved for attachment of the side chain-one based upon olefination and a second upon olefin metathesis. The higher efficiency of the latter makes it the method of choice. A novel one pot olefin metathesis-Takai olefination protocol that should be broadly applicable is developed. The sugar is attached by a glycosylation by employing the O-trichloroacetimidate. This route provided both C-13 epimers of the macrolactone by using either enantiomeric ligand in the Pd AAA reaction. It also provided both trans-chlorocyclopropane diastereomers of callipeltoside A which allows the C-20 and C-21 configuration to be established as S and R, respectively. The convergent nature of the synthesis in which the largest piece, the macrolatone, require only 16 linear steps imparts utility to this strategy for the establishment of the structure-activity relationship. Initial biological testing demonstrates the irrelevance of the chloro substituent and the necessity of the sugar.

Photodecarbonylation of chiral cyclobutanones

Triplet photosensitized irradiation of 2(S),3(R)-bis[(benzoyloxy)methyl]cyclobutanone gave optically pure (-)E-1(S),2(S)-bis(benzoyloxymethyl)cyclopropaneas a major product in the nonpolar fraction along with its stereoisomer and cycloelimination products. The absolute stereochemistry of the chiral cyclopropane was established by independent synthesis and X-ray crystal structure determination of a synthetic precursor. The distribution of decarbonylation and cycloelimination products was inversely dependent on the concentration of the substrate. Irradiation of the same ketone in tetrahydrofuran or benzene gave mostly cycloelimination products. Addition of Michler's ketone increased the ratio of photodecarbonylation, suggesting a triplet state pathway for this process. This was corroborated by the addition of dicyanoethylene, which showed significant quenching of photodecarbonylation. Irradiation of 2(S)-[(benzoyloxy)methyl]cyclobutane in acetone gave the corresponding cyclopropane as the principal product.