73323-91-8

Usage

Uses

Used in Pharmaceutical Industry:
2-[(1R)-2-HYDROXY-1-METHYLETHYL]-1H-ISOINDOLE-1,3(2H)-DIONE is used as a building block and intermediate for the synthesis of various pharmaceuticals. Its unique structure and properties make it a valuable component in the development of new drugs and medicinal compounds.
Used in Organic Synthesis:
In the field of organic synthesis, 2-[(1R)-2-HYDROXY-1-METHYLETHYL]-1H-ISOINDOLE-1,3(2H)-DIONE serves as a key intermediate for the creation of a wide range of organic compounds. Its versatility in chemical reactions allows for the production of various molecules with potential applications in different industries.

Upstream product

• 85-44-9 phthalic anhydride 
• 35320-23-1 (R)-2-aminopropan-1-ol 

Downstream Products

• 211501-32-5 (R)-2-[2-(2,5-difluorophenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione 
• 545376-11-2 (+)-(R)-2-phthalimido-1-(4-chlorophenoxy)propane 
• 868609-64-7 (R)-2-[2-(4-iodo-phenoxy)-1-methyl-ethyl]-isoindol-1,3-dione 
• 1152595-43-1 O-[(2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl] 4-chlorophenylthiocarbamate 
• 1152595-82-8 2-({[(1R)-2-({[(4-chlorophenyl)amino]carbonothioyl}oxy)-1-methylethyl]amino}carbonyl)benzoic acid 
• 1152595-41-9 O-[(2R)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl] 4-methylphenylthiocarbamate 
• 1152595-79-3 2-({[(1R)-1-methyl-2-({[(4-methylphenyl)amino]carbonothioyl}oxy)ethyl]amino}carbonyl)benzoic acid 
• 1297539-49-1 (R)-4-(1-(2-(1,3-dioxoisoindolin-2-yl)propyl)-1H-pyrazol-3-yl)-2-(trifluoromethyl)benzonitrile 
• 1252084-90-4 (+)-(R)-2-[2-(3-methoxyphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione 
• 265994-88-5 (-)-(R)-2-[2-(2,6-dimethylphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione 

Relevant academic research and scientific papers

Searching for new antiarrhythmic agents: Evaluation of meta- hydroxymexiletine enantiomers

Mexiletine is a very well-known class IB antiarrhythmic drug, whose enantiomers differ in both pharmacodynamic and pharmacokinetic properties, the (R)-isomer being the eutomer on experimental arrhythmias and in binding studies on cardiac voltage-gated sodium channels. meta-Hydroxymexiletine (MHM) is a minor metabolite of mexiletine, which has demonstrated to be more potent than the parent compound. Herein we report the synthesis and biological evaluation of MHM enantiomers for their potential antiarrhythmic activity. The same stereoselectivity pattern observed for mexiletine was found for MHM: the (R)-enantiomer of MHM was the eutomer on ac-arrhythmia also showing a negative inotropism higher than the one displayed by mexiletine and, at the same time, a decreased vasorelaxant activity on guinea-pig left atrium and guinea-pig ileum longitudinal smooth muscle.

ISOINDOLYL COMPOUNDS

Compounds of the formula I: or pharmaceutically acceptable salts thereof, wherein the variables are as defined herein. Also disclosed are methods of making the compounds and using the compounds for treatment of diseases associated with the P2X7 purinergic receptor

ANDROGEN RECEPTOR MODULATING COMPOUNDS

Compounds of formula (I) wherein R1 to R16, A. B and E are as defined in the claims and pharmaceutically acceptable salts and esters thereof, are disclosed. The compounds of formula (I) possess utility as tissue-selective androgen receptor modulators (SARM) and are particularly useful as medicaments in the treatment of prostate cancer and other AR dependent conditions and diseases where AR antagonism is desired.

Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists.

Novel modifications in the series of O-(2-phthalimidoethyl)-N-substituted thiocarbamates and their ring-opened congeners as non-nucleoside HIV-1 reverse transcriptase inhibitors

The structure-activity relationships (SARs) of N-aryl-O-(2-phthalimidoethyl)thiocarbamates (C-TCs) and their imide ring-opened congeners (O-TCs) as non-nucleoside HIV-1 reverse transcriptase inhibitors were further investigated. The SAR strategy involved

3-SUBSTITUTED-[1,2,3]BENZOTRIAZINONE COMPOUNDS FOR ENHANCING GLUTAMATERGIC SYNAPTIC RESPONSES

This invention relates to the prevention and treatment of cerebral insufficiency, including enhancement of receptor functioning in synapses in brain networks responsible for higher order behaviors. These brain networks are involved in cognitive abilities related to memory impairment, such as is observed in a variety of dementias and in imbalances in neuronal activity between different brain regions, as is suggested in disorders such as Parkinson's disease, schizophrenia and affective disorders. In a particular aspect, the present invention relates to compounds useful for treatment of such conditions, and methods of using these compounds for such treatment.

Synthesis of chiral 1-[ω(4-chlorophenoxy)alkyl]-4-methylpiperidines and their biological evaluation at σ1, σ2, and sterol δ8-δ7 isomerase sites

Sumitomo's patented σ ligand 1-[3-(4-chlorophenoxy)propyl]-4-methylpiperidine (15), which has been claimed as agent for CNS disorders and neuropathies, and its lower homologue 12 were prepared along with related chiral (4-chlorophenoxy)alkylpiperidines. They were tested at σ1, σ2, and sterol Δ8-Δ7 isomerase (SI) sites by in vitro radioligand binding assays, to evaluate the influence of a chiral center in the alkyl chain on the selective σ1 binding relative to other σ family sites. Generally high σ1-site affinities were found, so that the chirality introduced by a methyl substitution resulted in slight differences. Nevertheless, the shorter oxyethylenic chain was beneficial to increase σ1 selectivity. However, the (-)-(S)-4-methyl-1-[2-(4-chlorophenoxy)1-methylethyl]piperidine ((-)-(S)-17) reached the highest σ1 affinity (Ki = 0.34 nM) and the best selectivity relative to the σ2 site (547-fold). Compound (-)-(S)-17 displayed also a moderate selectivity (11-fold) relative to the SI site.

Diastereoselective access to chiral non-racemic [1,3]oxazolo-[2,3-a] isoindol-5-one ring systems via o-cationic cyclization

The title compounds 4 have been prepared from suitable β-amino-alcohol 2 and phthalic anhydride (5) in a three-step sequence in moderate to good yields (58-94%). The key step of this methodology is based on an intramolecular O-cationic cyclization involving N-acyliminium species. The high levels of the observed chemoselectivity during the intermolecular or intramolecular cyclization were also discussed.

Stereospecific synthesis of mexiletine and related compounds: Mitsunobu versus Williamson reaction

Mexiletine [1-(2,6-dimethylphenoxy)-2-propanamine], a chiral, orally effective antiarrhythmic agent, and several analogues substituted on either the stereogenic centre or the xylyloxy moiety, were prepared in both, highly enriched, optically active forms. According to the 'chiral pool' approach, the appropriate amino alcohols, protected as the corresponding phthalimide derivatives, were condensed with the desired phenols under either Mitsunobu (method A) or Williamson (method B) conditions. Generally, method A provided the most efficient route, both in terms of yields and number of steps necessary. Only when an isopropyl group was present on the stereogenic centre, i.e. when 2-amino-3-methylbutanol was used as the starting alcohol, method B proved to be the only available route, method A giving no product other than the starting phthalimide derivative. Regardless of the method used, enantiomeric excesses ranged from 91 to 99%. Given the availability of both variously substituted phenols and optically active amino alcohols, the two methods described herein, taken together, may serve as a versatile approach, useful to meet the needs of new chiral, optically active mexiletine analogues, possibly endowed with higher potency in exerting a use-dependent block on sodium channels and/or more resistant to biotransformations. Copyright (C) 2000 Elsevier Science Ltd.