95093-95-1

Usage

Uses

Used in Organic Synthesis:
(S)-(+)-4-(2,3-EPOXYPROPOXY)CARBAZOLE is used as a key intermediate in organic synthesis for the development of new chemical compounds and materials. Its epoxypropoxy group allows for a wide range of chemical reactions, making it a valuable building block for creating complex organic molecules with specific properties and functions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-(+)-4-(2,3-EPOXYPROPOXY)CARBAZOLE is used as a starting material for the synthesis of various drug candidates. Its unique structure and reactivity enable the development of novel therapeutic agents with potential applications in treating a variety of diseases and medical conditions.
Used in Chemical Research:
(S)-(+)-4-(2,3-EPOXYPROPOXY)CARBAZOLE is also utilized in chemical research as a model compound to study the properties and behavior of epoxy-containing organic molecules. This helps researchers gain insights into the fundamental chemistry of such compounds and contributes to the advancement of organic chemistry as a whole.

InChI:InChI=1/C15H13NO2/c1-2-5-12-11(4-1)15-13(16-12)6-3-7-14(15)18-9-10-8-17-10/h1-7,10,16H,8-9H2/t10-/m0/s1

Upstream product

• 52602-39-8 9H-carbazol-4-ol 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 591-20-8 3-Bromophenol 
• 51594-55-9 (R)-(-)-epichlorohydrin 

Downstream Products

• 204593-21-5 (S)-4-[2-Hydroxy-3-{2-[2-methoxyphenoxy]ethylamino}propoxy]carbazole hydrochloride salt 
• 1160961-98-7 (S)-4'-(2-{[2-hydroxy-3-(carbazol-4-yloxy)propyl]-amino}ethyl)-2-(2-pyridyl)acetanilide hydrochloride 
• 392690-75-4 (+)-(S)-1-bromo-4-(oxiran-2-ylmethoxy)carbazole 
• 78859-34-4 NSC 305336 
• 95094-00-1 (-)-Carvedilol 
• 143412-40-2 1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol 

Relevant academic research and scientific papers

Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

Starting from the β-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gαs, while they only show weak or even no β-arrestin-2 recruitment at both β1- and β2-AR. Molecular dynamics simulations suggest that the difference in G protein efficacy and β-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the β2-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser5.46 and Asn6.55, and the aromatic head group of the ligands.

Synthesis of Glycoborine, Glybomine A and B, the Phytoalexin Carbalexin A and the β-Adrenoreceptor Antagonists Carazolol and Carvedilol

We describe a regioselective synthesis of 4- or 5-substituted carbazoles by oxidative cyclisation of meta-oxygen-substituted N-phenylanilines. Using the regiodirecting effect of a pivaloyloxy group, we prepared 4-hydroxycarbazole, a precursor for the enantiospecific synthesis of the β-adrenoreceptor antagonists (?)-(S)-carazolol (5) and (?)-(S)-carvedilol (6). Regioselective palladium(II)-catalysed cyclisation of different diarylamines led to total synthesis of glycoborine (7) and the first total syntheses of the phytoalexin carbalexin A (8), glybomine A (9) and glybomine B (10). For glybomine B (10), a 5-hydroxycarbazole was converted into the corresponding triflate and utilized for introduction of a prenyl substituent.

BETA-3 RECEPTOR LIGANDS AND THEIR USE IN THERAPY

The present invention relates to new compounds, ligands of the beta-3 adrenergic receptor, their preparation and their use in therapy or as research tools for said receptor; the invention also relates to a process for the preparation of the compounds of the invention and the use of inverse agonists of the beta-3 adrenergic receptor as medicaments.

BRIDGED ARYL PIPERAZINES DERIVATIVES USEFUL FOR THE TREATMENT OF CNS, GI-URINARY AND REPRODUCTIVE DISORDERS

The present invention is directed to bridged aryl piperazine derivatives, pharmaceutical compositions containing them and their use in the treatment of depression and related disorders. The compounds of the present invention are serotonin transport inhibi

NOVEL HETEROCYCLIC COMPOUNDS AS PSTAT3/IL-6 INHIBITORS

The present invention relates to novel heterocyclic compounds of the general formula (I), as IL-6 inhibitors, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their hydrates, their solvates, their pharmaceutically acceptable salts and compositions, their metabolites and prodrugs thereof. The present invention more particularly provides novel heterocyclic compounds of the general formula (I). Also included is a method for treatment of cancer, cancer cachexia and inflammatory diseases including immunological diseases, particularly those mediated by cytokines such as IL-6, through pSTAT3 inhibition, in a mammal comprising administering an effective amount of a compound of formula (I) as described above.

Novel heterocyclic compounds as pSTAT3/IL-6 inhibitors

The present invention relates to novel heterocyclic compounds of the general formula (I), as IL-6 inhibitors, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their hydrates, their solvates, their pharmaceutically acceptable salts and compositions, their metabolites and prodrugs thereof. The present invention more particularly provides novel heterocyclic compounds of the general formula (I). Also included is a method for treatment of cancer, cancer cachexia and inflammatory diseases including immunological diseases, particularly those mediated by cytokines such as IL-6, through pSTAT3 inhibition, in a mammal comprising administering an effective amount of a compound of formula (I) as described above.

CARDIOTONIC COMPOUNDS WITH INHIBITORY ACTIVITY AGAINST BETA-ADRENERGIC RECEPTORS AND PHOSPHODIESTERASE

The present invention provides compounds possessing inhibitory activity against ? adrenergic receptors and phosphodiesterase (PDE), including type 3 phosphodiesterase (PDE-3). The present invention further provides pharmaceutical compositions comprising s

Synthesis of β3 adrenergic receptor agonist LY377604 and its metabolite 4-hydroxycarbazole, labeled with carbon-14 and deuterium

Synthesis of 14C-radiolabeled 4-hydroxycarbazole was accomplished starting from aniline-[U-14C], based on zinc chloride initiated Fischer cyclization of the phenylhydrazone prepared from phenylhydrazine-[U-14C] and cyclohexane-1,3-dione. The resulting tetrahydrooxocarbazole was subjected to dehydrogenation-aromatization using palladium on carbon. The aromatized 4-hydroxycarbazole-[4b,5,6,7,8,8a- 14C] was then used for the synthesis of 14C-labeled β3 adrenergic receptor agonist LY377604. The introduction of four deuteria in the carbazole fragment of LY377604 accomplished by its initial bromination and subsequent catalytic deuteration of the resulting tetrabromide. A similar approach was used for the conversion of 4-hydroxycarbazole into its tetradeutero-isotopomer. Copyright

2- ( (2, 3-DIHYDROXYPROPYL) AMINOMETHYL) CHROMANE DERIVATIVES FOR USE AS BETA-3 ADRENORECEPTOR AGONISTS IN THE TREATMENT OF UROLOGICAL AND INFLAMMATORY DISORDERS

This invention relates to chroman derivatives of formula (I) and salts thereof which are useful as active ingredients of pharmaceutical preparations. The chroman derivatives of the present invention have an excellent activity as BETA 3 antagonists and are useful for the prophylaxis and treatment of diseases associated with BETA 3 activity, in particular for the treatment of urological disorder or disease, such as detrusor overactivity (overactive bladder), urinary incontinence, neurogenic detrusor overactivity (detrusor hyperflexia), idiopathic detrusor overactivity (detrusor instability), benign prostatic hyperplasia, and lower urinary tract symptoms; and inflammatory disorders, such as asthma and COPD.

Novel substituted 4-aminomethylpiperidines as potent and selective human β3-agonists. Part 1: Aryloxypropanolaminomethylpiperidines

The synthesis and SAR of a series of human β3 adrenoreceptor agonists based on a template derived from a common pharmacophore coupled with 4-aminomethylpiperidine is described. Potent and selective agents were identified such as 26 that was in vitro active in CHO cells expressing human β3-AR (EC50=49 nM, IA=1.1), and in vivo active in a transgenic mouse model.