24303-61-5

Usage

Uses

Used in Pharmaceutical Industry:
2,2,3,3-Tetramethyl cyclopropane carboxynyl chloride is used as a synthetic reagent for the preparation of potential 4-Hydroxy-5-fluoropentyl side-chain metabolites. These metabolites are of significant interest in the development of synthetic cannabinoids, which have potential applications in the treatment of various medical conditions, including chronic pain, nausea, and appetite stimulation.
The compound's unique structure and reactivity make it a valuable building block in the synthesis of complex organic molecules, particularly in the pharmaceutical sector. Its ability to form meta-depside bonds and interact with biopolymers and macromolecules further enhances its utility in drug development.

Upstream product

• 86246-72-2 (3-bromo-2,6-dimethylphenyl)methanol 
• 15641-58-4 2,2,3,3-tetramethylcyclopropane-1-carboxylic acid 

Downstream Products

• 68428-99-9 2,2,3,3-Tetramethyl-cyclopropanecarboxylic acid 2-(2,4-dimethyl-phenyl)-5,5-dimethyl-3-oxo-cyclohex-1-enyl ester 
• 208251-94-9 2,2,3,3-Tetramethyl-cyclopropanecarboxylic acid cyano-[3-(4-nitro-phenoxy)-phenyl]-methyl ester 
• 208252-00-0 benzyl 3-[cyano-(2,2,3,3-tetramethylcyclopropanecarbonyloxy)methyl]phenoxyacetate 
• 208251-98-3 2,2,3,3-Tetramethyl-cyclopropanecarboxylic acid [3-(5-benzyloxycarbonyl-pentyloxy)-phenyl]-cyano-methyl ester 
• 208251-90-5 2,2,3,3-Tetramethyl-cyclopropanecarboxylic acid {3-[4-(2-benzyloxycarbonyl-ethyl)-phenoxy]-phenyl}-cyano-methyl ester 
• 171722-69-3 N-methyl-2,2,3,3-tetramethylcyclopropane carboxamide 
• 39515-41-8 fenpropathrin 
• 85418-08-2 (S) cyano-(4-fluoro-3-phenoxy-phenyl)-methyl 2,2,3,3-tetramethyl-cyclopropane-1-carboxylate 
• 928649-17-6 4-[(2,2,3,3-tetramethyl-cyclopropanecarbonyl)-amino]-benzonitrile 
• 895157-31-0 1-[(2,2,3,3-tetramethylcyclopropyl)carbonyl]-1H-indole 
• 895152-66-6 (1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone 
• 1043455-61-3 C₁₄H₂₀ClN₃O₅S₂ 
• 1043455-54-4 C₁₇H₂₅NO 
• 1043455-59-9 C₁₅H₂₀N₂O₂ 

Relevant academic research and scientific papers

Simple sulfinate synthesis enables C-H trifluoromethylcyclopropanation

A simple method to convert readily available carboxylic acids into sulfinate salts by employing an interrupted Barton decarboxylation reaction is reported. A medicinally oriented panel of ten new sulfinate reagents was created using this method, including a key trifluoromethylcyclopropanation reagent, TFCS-Na. The reactivity of six of these salts towards C-H functionalization was field-tested using several different classes of heterocycles.

Tetramethylcyclopropyl analogue of a leading antiepileptic drug, valproic acid. Synthesis and evaluation of anticonvulsant activity of its amide derivatives

Although valproic acid (VPA) is an extensively used antiepileptic drug for treatment of various kinds of epilepsies, it has been proven to possess two life-threatening side effects: hepatotoxicity and teratogenicity. Amide and urea derivatives of 2,2,3,3-tetramethylcyclopropanecarboxylic acid (TMCA) were prepared to discover lead compounds with clinical potential. In the amide and alkylamide series of TMCA derivatives, N-methoxy-2,2,3,3- tetramethylcyclopropanecarboxamide (21) was one of the most active compounds, having the subcutaneous metrazol test (scMet) ED50 values of 35 mg/kg in rats and 74 mg/kg in mice. In the maximal electroshock-induced seizure test (MES), this compound had ED50 values of 108 mg/kg in rats and 115 mg/ kg in mice. Compound 21 was 18.5 and 4.5 times more potent than VPA in the corresponding rat tests. The most active compound in the series of urea derivatives was 2,2,3,3-tetramethylcyclopropanecarbonylurea (25), possessing MES ED50 values of 29 mg/kg in rats and 90 mg/ kg in mice. In the scMet test this compound had ED50 values of 92 mg/kg in rats and 125 mg/kg in mice. The median toxic dose (TD50) in rats was 538 mg/kg, providing compound 25 with a wide safety margin and a protective index (TD 50/ED50) of 18.5 in the MES test, which is about 12 times greater than that of VPA. Compounds 21 and 25 have the potential for development as novel potent and safe central nervous system active drugs with a broad spectrum of antiepileptic activity.

Synthesis of gibberellic acid derivatives and their effects on plant growth

A series of novel C-3-OH substituted gibberellin derivatives bearing an amide group were designed and synthesized from the natural product gibberellic acid (GA3). Their activities on the plant growth regulation of rice and Arabidopsis were evaluated in vivo. Among these compounds, 10d and 10f exhibited appreciable inhibitory activities on rice (48.6% at 100 μmol/L) and Arabidopsis (41.4% at 100mol/L), respectively. These results provide new insights into the design and synthesis of potential plant growth regulators.

Synthesis of 2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazoles via the cyclopropyliminium rearrangement of substituted 2-cyclopropylbenzimidazoles

2-Cyclopropylbenzimidazole derivatives with various substituents in the small ring undergo cyclopropyliminium rearrangement into 2,3- dihydropyrrolobenzimidazoles substituted at positions 1, 2 or 3. The substrates containing a functional group in position 1 of the cyclopropane ring form products substituted at position 3. Substituents at position 2 in most cases lead to the formation of a mixture of isomers. The reaction can be directed to yield one of the isomers predominantly by varying the solvent polarity.

Discovery of GW870086: A potent anti-inflammatory steroid with a unique pharmacological profile

Background and Purpose Glucocorticoids are highly effective therapies for a range of inflammatory diseases. Advances in the understanding of the diverse molecular mechanisms underpinning glucocorticoid action suggest that anti-inflammatory molecules with reduced side effect liabilities can be discovered. Here we set out to explore whether modification of the 17α position of the steroid nucleus could generate molecules with a unique pharmacological profile and to determine whether such molecules would retain anti-inflammatory activity. Experimental Approach The pharmacological properties of GW870086 were compared with fluticasone propionate (FP) using a range of cellular and in vivo model systems, including extensive gene expression profiling. Key Results GW870086 repressed inflammatory cytokine release from lung epithelial cells in a similar manner to FP but antagonized the effect of dexamethasone on MMTV-driven reporter gene transactivation. GW870086 had a strong effect on the expression of some glucocorticoid-regulated genes (such as PTGS2), while having minimal impact on the expression of other known target genes (such as SGK). GW870086 retained the ability to strengthen tight junctions in epithelial cell culture but, unlike FP, was unable to protect the culture from elastase-mediated damage. In murine models of irritant-induced contact dermatitis and ovalbumin-induced allergic inflammation, GW870086 showed comparable anti-inflammatory efficacy to FP. Conclusion and Implications GW870086 is a potent anti-inflammatory compound with a unique ability to regulate only a subset of those genes that are normally affected by classical glucocorticoids. It has the potential to become a new topical steroid with a different safety profile to existing therapies.

Synthesis and characterization of chrysanthemic acid esters

A short and convenient synthesis for a series of novel chrysanthemic acid esters from aldehyde and chrysanthemic acid is reported.

Indol-3-ylcycloalkyl ketones: Effects of N1 substituted indole side chain variations on CB2 cannabinoid receptor activity

Several 3-acylindoles with high affinity for the CB2 cannabinoid receptor and selectivity over the CB1 receptor have been prepared. A variety of 3-acyl substituents were investigated, and the tetramethylcyclopropyl group was found to lead to high affinity CB2 agonists (5, 16). Substitution at the N1-indole position was then examined. A series of aminoalkylindoles was prepared and several substituted aminoethyl derivatives were active (23-27, 5) at the CB2 receptor.Astudy of N1 nonaromatic side chain variants provided potent agonists at the CB2 receptor (16, 35-41, 44-47, 49-54, and 57-58). Several polar side chains (alcohols, oxazolidinone) were well-tolerated for CB2 receptor activity (41, 50), while others (amide, acid) led to weaker or inactive compounds (55 and 56). N1 aromatic side chains also afforded several high affinity CB2 receptor agonists (61, 63, 65, and 69) but were generally less potent in an in vitro CB2 functional assay than were nonaromatic side chain analogues.

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS

The present application relates to cannabinoid receptor ligands containing compounds of formula (I) wherein A, R1, R2, and R3 are as defined in the specification. The present application also relates to compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF

The present invention relates to compounds of formula (I), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, formula (I). wherein R1, R2, R3, R4, and L1 are defined in the specfication, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions. The present invention also relates to compounds of formula (II), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, formula (II). wherein R1a, R2a, Rx, and n are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.

NOVEL COMPOUNDS AS CANNABINOID RECEPTOR LIGANDS AND USES THEREOF

The present invention relates to compounds of formula (I), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R1, R2, R3, and L1 are defined in the specfication, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions. The present invention also relates to compounds of formula (II), or pharmaceutical salts, prodrugs, salts of prodrugs, or combinations thereof, wherein R1a, R2a and (Rx)n are as defined in the specification, compositions comprising such compounds, and methods of treating conditions and disorders using such compounds and compositions.