88722-24-1

Usage

Molecular structure

The compound has an isoindole structure with a sulfonyl and oxyethyl side chain.

Chirality

The compound exists in its (S)form, indicating its asymmetric properties.

Use as a chiral auxiliary

The compound is commonly used in asymmetric synthesis to produce stereochemically-pure compounds.

Potential applications

The compound has potential applications in the pharmaceutical industry for the synthesis of chiral drugs and active pharmaceutical ingredients.

Upstream product

• 85-44-9 phthalic anhydride 
• 4192-28-3 Phth-L-Ala-OH 
• 70058-19-4 2-((2S)-1-hydroxypropan-2-yl)-1H-isoindole-1,3(2H)-dione 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 934987-50-5 2-((1S)-2-{[1-(4-fluorophenyl)-1H-indazol-4-yl]oxy}-1-methylethyl)-1H-isoindole-1,3(2H)-dione 
• 1035342-76-7 2-[(2S)-1-[6-chloro-1-(4-fluorophenyl)indazo-5-yl]oxypropan-2-yl]isoindole-1,3-dione 

Relevant academic research and scientific papers

The discovery of potent and selective non-steroidal glucocorticoid receptor modulators, suitable for inhalation

We report the discovery of highly potent and selective non-steroidal glucocorticoid receptor modulators with PK properties suitable for inhalation. A high throughput screen of the AstraZeneca compound collection identified sulfonamide 3 as a potent non-steroidal glucocorticoid receptor ligand. Further optimization of this lead generated indazoles 30 and 48 that were progressed to characterization in in vivo models. X-ray crystallography was used to gain further insight into the binding mode of selected ligands.

INDAZOLYL SULPHONAMIDE DERIVATIVES FOR THE TREATMENT OF GLUCOCORTICOID RECEPTOR MEDIATED DISORDERS

Compounds of formula (I): [Chemical formula should be inserted here. Please see paper copy] or a pharmaceutically acceptable salt thereof; compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating the glucocorticoid receptor in a warm blooded animal)

NOVEL BICYCLIC SULFONAMIDES FOR USE AS GLUCOCORTICOID RECEPTOR MODULATORS IN THE TREATMENT OF INFLAMMATORY DISEASES

Compounds of formula (I): or a pharmaceutically acceptable salt thereof; compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating the glucocorticoid receptor in a warm blooded animal).

NOVEL SULPHONAMIDE DERIVATIVES AS GLUCOCORTICOID RECEPTOR MODULATORS FOR THE TREATMENT OF INFLAMMATORY DISEASES

Compounds of formula (I) or a pharmaceutically acceptable salt thereof; compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating the glucocorticoid receptor in a warm blooded animal).

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.

OPTICALLY ACTIVE ISOCARBOSTYRIL DERIVATIVES AND A METHOD OF PREPARING THE SAME

Four different optical isomers of a new compound, 1-2'-(o-methoxyphenoxy)-1'-methylethylamino!-3-(4"-isocarbostyriloxy)-2-propa nol are now provided as new substances. These four optical isomers are now named as (2R, 1'S)-1-2'-(o-methoxyphenoxy)-1'-methylethylamino!-3-(4"-isocarbostyriloxy)-2-propa nol, (2S, 1'S)-1-2'-(o-methoxyphenoxy)-1'-methylethylamino!-3-(4"-isocarbostyriloxy)-2-propa nol, (2S, 1'R)-1-2'-(o-methoxyphenoxy)-1'-methylethylamino!-3-(4"-isocarbostyriloxy)-2-propa nol, and (2R, 1'R)-1-2'-(o-methoxyphenoxy)-1'-methylethylamino!-3-(4"-isocarbostyriloxy)-2-propa nol, respectively. These four optical isomers have different activities for their β-adrenergic-blocking effect and α-adrenergic-blocking effect and are useful as valuable agents for therapeutic treatment of various cardiovascular diseases, as compared to an optically inactive racemic mixture of said isomer compounds. These four optical isomers may be produced and isolated from each other by chromatographing (1'S)-or (1'R)-N-2'-(o-methoxyphenoxy)-1'-methylethyl!-5-(4"-isocarbostyriloxymethyl)-2-oxaz olidones to isolate either its (5R, 1'S)-isomer and its (5S, 1'S)-isomer, or its (5S, 1'R)-isomer and its (5R, 1'R)-isomer therefrom separately and then hydrolyzing each of these isolated isomers under alkaline conditions to obtain separately (2R, 1'S)-, (2S, 1'S)-, (2S, 1'R)-and (2R, 1'R)-1-2'-(o-methoxyphenoxy)-1'-methylethylamino!-3-(4"-isocarbostyriloxy)-2-propa nols. "

Stereospecific Synthesis of (2R,5R)-Hept-6-yne-2,5-diamine: A Potent and Selective Enzyme-activated Irreversible Inhibitor of Ornithine Decarboxylase (ODC)

Hept-6-yne-2,5-diamine (2) and 2-methylhept-6-yne-2,5-diamine (3), while structurally related to the potent ornithine decarboxylase (ODC) inhibitor hex-5-yne-1,4-diamine (1), are stable to in vivo oxidation by monoamine oxidase (MAO).Although the methyl substitution is at a carbon relatively remote from the site of metabolic attack by ornithine decarboxylase (ODC), it has a critical influence on the potencies of these compounds as inhibitors of the enzyme.Of the four stereoisomers, (2R,5R)-(2) is the most active.Unambiguous syntheses of each isomer of (2) from the dianion of 3-trimethylsilyl-N-butoxycarbonylprop-2-ynylamine (5) are presented.