7795-52-0

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-1-(1H-INDOL-3-YL)PROPAN-2-AMINE is used as a pharmaceutical agent for its potential therapeutic applications. As a non-selective serotonin receptor agonist, it acts as a relatively balanced releasing agent of serotonin, norepinephrine, and dopamine. This makes it a promising candidate for the development of drugs targeting various neurological and psychiatric disorders, such as depression, anxiety, and addiction.
Used in Research Applications:
In the field of scientific research, (2R)-1-(1H-INDOL-3-YL)PROPAN-2-AMINE serves as a valuable tool for studying the mechanisms of neurotransmitter release and receptor interactions. Its ability to modulate multiple neurotransmitter systems allows researchers to investigate the complex interplay between these systems and their role in various physiological and pathological processes.
Used in Drug Development:
(2R)-1-(1H-INDOL-3-YL)PROPAN-2-AMINE can be employed as a lead compound in the development of novel drugs with improved efficacy and selectivity. Its unique chemical structure and biological properties provide a foundation for the design of new molecules with tailored pharmacological profiles, potentially leading to the discovery of more effective treatments for various conditions.
Used in Neuropharmacology:
In neuropharmacology, (2R)-1-(1H-INDOL-3-YL)PROPAN-2-AMINE is used to explore the effects of indole alkaloids on the central nervous system. Its ability to act as a psychedelic, stimulant, and entactogenic substance provides insights into the molecular mechanisms underlying these psychoactive effects, which can contribute to the development of safer and more effective psychopharmacological agents.
Overall, (2R)-1-(1H-INDOL-3-YL)PROPAN-2-AMINE is a versatile and promising compound with a wide range of potential applications in various industries, particularly in the pharmaceutical and research sectors. Its unique properties and ability to modulate neurotransmitter systems make it an attractive candidate for further investigation and development.

Upstream product

• 299-26-3 1-(1H-indol-3-yl)propan-2-amine 
• 371-27-7 2,2,2-trifluoroethylbutyrate 
• 1100753-75-0 N-octanoylglycine 2,2,2-trifluoroethyl ester 
• 615-36-1 2-bromoaniline 
• 847199-90-0 tert-butyl (R)-(1-(1H-indol-3-yl)propan-2-yl)carbamate 
• 1384127-07-4 N-octanoyl dimethyl glycine trifluoroethyl ester 
• 61587-85-7 (S)-2-(((benzyloxy)carbonyl)amino)-3-(1H-indol-3-yl)propyl 4-methylbenzenesulfonate 
• 1039646-91-7 2,3-bis(4-methylbenzoic acid)succinic acid 
• 4771-72-6 α-methyl-β-(3-indolyl)-1-nitroethane 
• 1201-26-9 3-(1H-indolyl)acetone 
• 113997-61-8 (S,R)-N-α-phenetyl-1-indol-3-yl-2-aminopropane 
• 113997-58-3 (R)-1-(1H-indol-3-yl)-N-((R)-1-phenylethyl)propan-2-amine 

Downstream Products

• 820216-46-4 thiophene-2-sulfonic acid (3-{1-(tert-butyl-dimethyl-silanyloxy)-2-[2-(1H-indol-3-yl)-1-methyl-ethylamino]-ethyl}-phenyl)-amide 
• 847199-90-0 tert-butyl (R)-(1-(1H-indol-3-yl)propan-2-yl)carbamate 
• 1193314-22-5 (1S,3R)-5'-chloro-3-methyl-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-indol]-2'(1'H)-one 

Relevant academic research and scientific papers

PROCESSES FOR MAKING SERD TRICYCLIC COMPOUNDS HAVING A SUBSTITUTED PHENYL OR PYRIDINYL MOIETY

Provided herein are processes for the preparation of compounds useful in the treatment of cancer.

Efficient Manufacturing Process for the Selective Estrogen Receptor Degrader GDC-9545 (Giredestrant) via a Crystallization-Driven Diastereoselective Pictet-Spengler Condensation

GDC-9545 is a selective estrogen receptor degrader that is being developed as a treatment for ER+/HER2- breast cancer. A robust, convergent manufacturing process for GDC-9545 was developed. The process features a Wenker aziridine synthesis to produce the key starting material tryptamine 11, a highly efficient C-N coupling between aminoazetidine 9 and 2,6-difluoro-4-bromobenzaldehyde diethyl acetal (33) to construct key intermediate 10, and a crystallization-driven diastereoselective Pictet-Spengler reaction to furnish the active pharmaceutical ingredient GDC-9545·tartrate.

REGIMENS OF ESTROGEN RECEPTOR ANTAGONISTS

Provided herein are methods of administering estrogen receptor antagonists for use in treatment of cancer. The antagonists (such as a hexahydro pyrido[3,4-b]indole, AZD9496, RAD-1901, ARN-810, endoxifen, or fulvestrant) may be an inhibitor of both activating function 1 and activating function 2 of the estrogen receptor. Also provided are combinations of above inhibitors with a secondary agent, which is a CDK 4/6 inhibitor (such as, palbocociclib, ribociclib, abemaciclib, lerociclib, and trilaciclib).

METHODS OF TREATING ESTROGEN RECEPTOR-ASSOCIATED DISEASES

The present disclosure provides methods of treating estrogen receptor-associated diseases, disorders, and conditions.

Preparation method of chiral alpha-methyl arylethylamine

The invention provides a preparation method of chiral alpha-methyl arylethylamine, and relates to the technical field of organic synthesis medicines. Boc-amino acid methyl ester is used as an initial raw material, Boc-amino alcohol is obtained through reduction, Boc-amino alcohol reacts with thionyl chloride and is oxidized through sodium periodate to obtain a sulfonamide compound, and then the sulfonamide compound is reduced through sodium borohydride promoted by lewis acid and a protecting group is removed under the acidic condition to obtain a target compound. According to the method, raw materials are cheap and easy to obtain, a single optical isomer product is obtained by using chiral raw materials, the problem of column chromatography resolution is solved, generation of a large amount of solid wastes and isomers is avoided, atom economy is improved, the product purity is high, the yield is high, and the production cost is effectively reduced. In addition, the mild reduction system is used for replacing the original high-pressure hydrogenation reaction, the process operation is relatively simple, and the method is more suitable for large-scale industrial production.

SOLID FORMS OF 3-((1R,3R)-1-(2,6-DIFLUORO-4-((1-(3-FLUOROPROPYL)AZETIDIN-3-YL)AMINO)PHENYL)-3-METHYL-1,3,4,9-TETRAHYDRO-2H-PYRIDO[3,4-B]INDOL-2-YL)-2,2-DIFLUOROPROPAN-1-OL AND PROCESSES FOR PREPARING FUSED TRICYCLIC COMPOUNDS COMPRISING A SUBSTITUTED PHENYL OR PYRIDINYL MOIETY, INCLUDING METHODS OF THEIR USE

Provided herein are solid forms, salts such as compound B, and formulations of 3-((lR,3R)-l-(2,6-difluoro-4-((l-(3-fluoropropyl) azetidin-3-yl)amino)phenyl)-3-methyl-l,3,4,9-tetrahydro-2H- pyrido[3,4-b]indol-2-yl)-2,2-difluoropropan-l-ol, processes and synthesis thereof, and methods of their use in the treatment of cancer.

ESTROGEN RECEPTOR MODULATORS

Compounds of Formula (I) are estrogen receptor alpha modulators, where the variables in Formula (I) are described in the disclosure. Such compounds, as well as pharmaceutically acceptable salts and compositions thereof, are useful for treating diseases or conditions that are estrogen receptor alpha dependent and/or estrogen receptor alpha mediated, including conditions characterized by excessive cellular proliferation, such as breast cancer.

TETRAHYDRO-1H-PYRIDO[3,4-b]INDOLE ANTI-ESTROGENIC DRUGS

The present disclosure provides tetrahydro-1H-pyrido[3,4-b]indole compounds or a pharmaceutically acceptable salt, solvate, hydrate, prodrug, stereoisomer, tautomer, rotamer, N-oxide and/or substituted derivative or, optionally in a pharmaceutical composition, for the modulation of disorders mediated by estrogen, or other disorders as more fully described herein.

Stereoselective Cascade to C3-Methylated Strictosidine Derivatives Employing Transaminases and Strictosidine Synthases

(S)-Strictosidine represents the first key intermediate in the biosynthesis of several pharmaceutically relevant monoterpenoid indole alkaloids. Optically pure C3-methyl-substituted strictosidine derivatives were prepared by setting up the two stereogenic centers at the β-carboline core via two enzymatic steps catalyzed by the enzymes transaminase and strictosidine synthase in a one-pot cascade fashion. The two enzymatic steps were performed simultaneously as well as in a stepwise fashion. The amination of the prochiral ketones led to optically pure amines with up to >98% enantiomeric excess. Depending on the enzyme used, the (S)- and (R)-enantiomers were prepared in most cases. Selected amines were then condensed with secologanin in a Pictet-Spengler reaction catalyzed by strictosidine synthase leading to diastereomerically pure products (>98% diastereomeric excess).

N-octanoyldimethylglycine trifluoroethyl ester, an acyl donor leading to highly enantioselective protease-catalysed kinetic resolution of amines

The use of N-octanoyldimethylglycine trifluoroethyl ester as acyl donor in the kinetic resolution of aliphatic amines catalysed by proteases led to enantiomeric ratios >200 in most cases. The resolutions mediated by Protex 6L were shown to be much faster