35308-87-3

Usage

Uses

Used in Pharmaceutical Research:
4-(oxiranylmethoxy)-1H-indole is used as a research compound for its potential therapeutic applications. The presence of the oxiranylmethoxy group suggests that 4-(oxiranylmethoxy)-1H-indole may have unique biological activities, making it valuable for the development of new drugs and therapies.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-(oxiranylmethoxy)-1H-indole is used as a reactive intermediate in various chemical reactions. The epoxy group's reactivity allows for the synthesis of a wide range of chemical products, contributing to the advancement of chemical research and development.
Used in Chemical Research:
4-(oxiranylmethoxy)-1H-indole serves as a subject of interest in chemical research due to its unique structure and potential reactivity. Scientists are interested in exploring the compound's properties and behavior in different chemical environments, which can lead to a better understanding of its potential applications and interactions with other molecules.
Used in Drug Development:
In the pharmaceutical industry, 4-(oxiranylmethoxy)-1H-indole is used as a starting material or a building block in the development of new drugs. Its potential biological activity and reactivity make it a valuable component in the creation of novel therapeutic agents that could address various medical conditions.

InChI:InChI=1/C11H11NO2/c1-2-10-9(4-5-12-10)11(3-1)14-7-8-6-13-8/h1-5,8,12H,6-7H2

Upstream product

• 2380-94-1 1H-indol-4-ol 
• 106-89-8 epichlorohydrin 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 67843-74-7 (S)-epichlorohydrin 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 

Downstream Products

• 102573-78-4 1-(1H-Indol-4-yloxy)-3-[2-(4-nitro-phenyl)-ethylamino]-propan-2-ol 
• 102573-81-9 1-[2-(3,4-Dichloro-phenyl)-ethylamino]-3-(1H-indol-4-yloxy)-propan-2-ol 
• 102573-80-8 1-[2-(4-Fluoro-phenyl)-ethylamino]-3-(1H-indol-4-yloxy)-propan-2-ol 
• 77890-09-6 DL-iodoazidobenzylpindolol 
• 111794-53-7 3-{Benzyl-[2-hydroxy-3-(1H-indol-4-yloxy)-propyl]-amino}-N-[4-(4-methyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-propionamide 
• 126953-40-0 1-{4-[1-(2,4-Dinitro-phenylamino)-1-methyl-ethyl]-1-methyl-cyclohexylamino}-3-(1H-indol-4-yloxy)-propan-2-ol 
• 126953-41-1 1-{1-[4-(2,4-Dinitro-phenylamino)-4-methyl-cyclohexyl]-1-methyl-ethylamino}-3-(1H-indol-4-yloxy)-propan-2-ol 
• 102573-77-3 carvedilol 
• 102573-79-5 1-(1H-Indol-4-yloxy)-3-phenethylamino-propan-2-ol 
• 102573-83-1 1-(2-Fluoro-benzylamino)-3-(1H-indol-4-yloxy)-propan-2-ol 
• 106469-51-6 N⁸-(bromoacetyl)-N¹-<3-(4-indolyloxy)-2-hydroxypropyl>-(Z)-1,8-diamino-p-menthane 
• 106469-52-7 N¹-(bromoacetyl)-N⁸-<3-(4-indolyloxy)-2-hydroxypropyl>-(Z)-1,8-diamino-p-menthane 
• 102573-82-0 1-(4-Fluoro-benzylamino)-3-(1H-indol-4-yloxy)-propan-2-ol 
• 113854-62-9 1-[1-(p-toluenesulfonyl)indol-4-yloxy]-2,3-epoxypropane 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of (S)-Pindolol using lipases

A straightforward chemoenzymatic synthesis of (S)-Pindolol has been developed. The key step involved the enzymatic kinetic resolution of rac-2-acetoxy-1-(1H-indol-4-yloxy)-3-chloropropane with lipase from Pseudomonas fluorescens via hydrolytic process to obtain enantiomerically enriched halohydrin (2S)-1-(1H-indol-4-yloxy)-3-chloro-2-propanol (96% ee) and (2R)-2-acetoxy-1-(1H-indol-4-yloxy)-3-chloropropane (97% ee). The latter was subjected to a hydrolysis reaction catalyzed by Candida rugosa leading to (2R)-1-(1H-indol-4-yloxy)-3-chloro-2-propanol (97% ee), followed by a reaction with isopropylamine, producing (S)-Pindolol (97% ee) in quantitative yield.

Synthesis and pharmacological activity of a new series of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)-propan-2-ol analogs

β-Adrenergic receptor antagonists are important therapeutics for the treatment of cardiovascular disorders. In the group of β-blockers, much attention is being paid to the third-generation drugs that possess important ancillary properties besides inhibiting β-adrenoceptors. Vasodilating activity of these drugs is produced through different mechanisms, such as nitric oxide (NO) release, β2-agonistic action, α1-blockade, antioxidant action, and Ca2t entry blockade. Here, a study on evaluation of the cardiovascular activity of five new compounds is presented. Compound 3a is a methyl and four of the tested compounds (3b–e) are dimethoxy derivatives of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)-ethylamino)propan-2-ol. The obtained results confirmed that the methyl and dimethoxy derivatives of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propan-2-ol and their enantiomers possess α1- and β1-adrenolytic activities and that the antiarrhythmic and hypotensive effects of the tested compounds are related to their adrenolytic properties.

STORE OVERLOAD-INDUCED CALCIUM RELEASE INHIBITORS AND METHODS FOR PRODUCING AND USING THE SAME

The present invention provides compounds having store overload-induced Ca2+ release (SOICR) inhibitory activity and methods for producing and using the same. In particular, compounds of the invention is of the formula: R1-X1-L-X2-R2, wherein R1, X1, L, X2, and R2 are those defined herein.

Novel carvedilol analogues that suppress store-overload-induced Ca 2+ release

Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the β-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.

Synthesis and characterization of high-affinity 4,4-difluoro-4-bora-3a,4a- diaza-s-indacene-labeled fluorescent ligands for human β-adrenoceptors

The growing practice of exploiting noninvasive fluorescence-based techniques to study G protein-coupled receptor pharmacology at the single cell and single molecule level demands the availability of high-quality fluorescent ligands. To this end, this study evaluated a new series of red-emitting ligands for the human β-adrenoceptor family. Upon the basis of the orthosteric ligands propranolol, alprenolol, and pindolol, the synthesized linker-modified congeners were coupled to the commercially available fluorophore BODIPY 630/650-X. This yielded high-affinity β-adrenoceptor fluorescent ligands for both the propranolol and alprenolol derivatives; however, the pindolol-based products displayed lower affinity. A fluorescent diethylene glycol linked propranolol derivative (18a) had the highest affinity (log KD of -9.53 and -8.46 as an antagonist of functional β2- and β1-mediated responses, respectively). Imaging studies with this compound further confirmed that it can be employed to selectively label the human β2-adrenoceptor in single living cells, with receptor-associated binding prevented by preincubation with the nonfluorescent β2-selective antagonist 3-(isopropylamino)-1-[(7- methyl-4-indanyl)oxy]butan-2-ol (ICI 118551) (J. Cardiovasc. Pharmacol.1983, 5, 430-437.)

A vHTS approach for the identification of β-adrenoceptor ligands

Using a vHTS based on a pharmacophore alignment on known β3-adrenoceptor ligands, a set of intriguing β-adrenoceptor ligands was identified, optimization of which resulted in a selective and potent human β2-AR antagonist.

Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol and its enantiomers. Part 1

The synthesis of (2RS)-1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol ((RS)-9) and its enantiomers has been described and tested for electrocardiographic, antiarrhythmic, hypotensive and spasmolytic activities as well as for α1-, α2- and β1-adrenoceptors' binding affinities. All compounds significantly decrease systolic and diastolic blood pressure, and possess antiarrhythmic activity and affinity to α1-, α2- and β1-adrenoceptors. The results suggest that the antiarrhythmic and hypotensive effects of these compounds are related to their adrenolytic but not spasmolytic properties.

Indoloxypropanolamine analogues as 5-HT1A receptor antagonists

Analogues of pindolol, 1-(1H-indol-4-yloxy)-3-isopropylamino-propan-2-ol, were synthesized and evaluated as 5-HT1A receptor antagonists. The structural features required for optimal binding to the 5-HT1A receptor are as follows: S-2-propanol linker, 4-indoloxy substituent, and a large lipophilic cyclic amine substituent.

SMALL MOLECULE INHIBITORS OF HER2 EXPRESSION

Peptide mimetic small molecule inhibitors of Sur-2 are provided having the general formula (I).

Small molecule inhibitors of HER2 expression

Peptide mimetic small molecule inhibitors of Sur-2 are provided having the general formula: