350797-52-3

Usage

Uses

Used in Pharmaceutical Research and Development:
1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-Indole-5-carboxaldehyde is used as a starting material for the synthesis of biologically active molecules, contributing to the development of new drugs and pharmaceutical products.
Used in Organic Synthesis:
BPI is employed as a key intermediate in the synthesis of complex organic compounds, facilitating the creation of novel chemical entities with potential applications in various fields.
Used in Cancer Treatment Research:
1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-Indole-5-carboxaldehyde is used as a potential therapeutic agent in the treatment of various types of cancer, due to its pharmacological properties that may target cancer cells and inhibit their growth.
Used in Neurological Disorders Research:
BPI is utilized in the study and potential treatment of neurological disorders, leveraging its pharmacological properties to explore its effects on the nervous system and the mitigation of disease symptoms.
Used in Drug Discovery:
1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-Indole-5-carboxaldehyde is used as a lead compound in drug discovery processes, where its chemical structure and properties are further optimized to enhance its therapeutic potential and safety profile.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 65-85-0 benzoic acid 
• 496-15-1 1-indoline 
• 350797-51-2 1-(3-benzoyloxypropyl)-2,3-dihydroindole hydrochloride 

Downstream Products

• 350797-53-4 1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole 
• 160970-54-7 silodosin 
• 239463-72-0 5-[(2R)-2-aminopropyl]-2,3-dihydro-1-[3-(benzoyloxy)propyl]-1H-indole-7-carbonitrile 
• 885340-11-4 2,3-dihydro-1-[3-(benzoyloxy)propyl]-5-[(2R)-2-[[2-[(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile 
• 885340-13-6 1-(3-hydroxypropyl)-5-[(2R)-2-({2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl}amino)propyl]-2,3-dihydro-1H-indole-7-carbonitrile 
• 350797-54-5 1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole 
• 350797-55-6 1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole 
• 350797-56-7 1-(3-benzoyloxypropyl)-7-cyano-5-(2-nitropropyl)-2,3-dihydroindole 
• 1338365-54-0 5-(2-aminopropyl)-1-[3-(benzoyloxy)propyl]-2,3-dihydro-7-cyano-1H-indole 
• 239463-85-5 5-[(2R)-2-aminopropyl]-1-[3-(benzoyloxy)propyl]-2,3-dihydro-1H-indol-7-carbonitrile (2R,3R)-2,3-dihydroxybutanedioate salt 

Relevant academic research and scientific papers

Preparation method of indoline derivative for synthesizing silodosin

The invention provides a preparation method of an indoline derivative for synthesizing silodosin. Indoline is taken as a starting raw material and reacts with benzoic acid and 1-chloro-3-bromopropane to prepare a compound (1); a reaction is carried out in a Vilsmeier agent, and a formyl group in introduced to the 5th position to prepare a compound (2); the compound (2) and nitroethane undergoes an asymmetric Henry reaction in the catalysis of quinidine-copper acetate to prepare a compound (3); the compound (3) is subjected to acetylation through acetic anhydride to prepare a compound (4); a cyano group is introduced to the 7th position to prepare a compound (6); and two functional groups are reduced through palladium-on-carbon hydrogenation in one step to obtain a high-chiral-purity target compound: (R)-1-[1-(3-benzoyloxypropyl)-5-(2-aminopropyl)-7-cyano]indoline. In the early stage of the method, cheap quinidine is used to perform an asymmetric Henry reaction for introduction of chiral centers, thereby avoiding resolution in the latter stage. The method is reasonable in design, simple to operate, effectively improved in yield and reduced in cost, and therefore is suitable for massive production.

Design, Synthesis, and Biological Evaluation of Indoline and Indole Derivatives as Potent and Selective α1A-Adrenoceptor Antagonists

A series of indoline and indole derivatives were designed, synthesized, and evaluated as selective α1A-adrenergic receptor (α1A-AR) antagonists for the treatment of benign prostatic hyperplasia (BPH). In this study, two highly selective and potent α1A-AR antagonists, compounds (R)-14r (IC50 = 2.7 nM, α1B/α1A = 640.1, α1D/α1A = 408.2) and (R)-23l (IC50 = 1.9 nM, α1B/α1A = 1506, α1D/α1A = 249.6), which exhibited similar activities and better selectivities in cell-based calcium assays as compared with the marketed drug silodosin (IC50 = 1.9 nM, α1B/α1A = 285.9, α1D/α1A = 14.4), were identified. In the functional assays with isolated rat tissues, compounds (R)-14r and (R)-23l also showed high potency and uroselectivity. Most importantly, (R)-14r and (R)-23l can significantly decrease the micturition frequency and increase the mean voided volume of the BPH rats in a dose-dependent manner, making them worthy of further investigation for the development of anti-BPH agents.

METHOD FOR PREPARING SILODOSIN

The present invention relates to a process for preparing silodosin with high optical purity up to 99.9% enantiomeric excess (e.e.) or above. The process makes use of a method step, in which the enantiomers contained in a racemic mixture of a compound represented by the general formula V: wherein * denotes the asymmetric center, R1 is a protecting group, and R2 is cyano or carbamoyl, are separated.

PROCESS FOR PREPARING AN INTERMEDIATE FOR SILODOSIN

The present invention provides a process for preparing a compound of formula (I), wherein R1 is a hydroxyl-protecting group and R2 is a cyano group or a carbamoyl group, wherein the process comprises the direct hydrogenation of the corresponding achiral nitro compound and the resolution of the racemic amino compound. The compound of formula (I) can easily be further transferred to silodosin.