350797-56-7

Basic information

• Product Name: 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile
• Synonyms: 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile;3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl benzoate
• CAS NO: 350797-56-7
• Molecular Formula: C₂₂H₂₃N₃O₄
• Molecular Weight: 393
• EINECS: 1592732-453-0
• Mol File: 350797-56-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 608.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.27
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 7.80±0.13(Predicted)
• CAS DataBase Reference: 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile(350797-56-7)
• EPA Substance Registry System: 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile(350797-56-7)

Safety Data

• Hazardous Substances Data: 350797-56-7(Hazardous Substances Data)

Usage

Description

1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile is a complex organic compound with a unique molecular structure. It is characterized by its benzoyloxypropyl group, dihydroindole framework, and nitropropyl and carbonitrile functional groups. 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile is known for its potential applications in various fields due to its chemical properties and reactivity.

Uses

1. Pharmaceutical Industry:
1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile is used as an intermediate in the synthesis of Silodosin (S465000), an α1a-adrenoceptor antagonist. It plays a crucial role in the development of medications for the treatment of benign prostatic hyperplasia (BPH), a common condition in aging men that affects the prostate gland and can cause urinary problems.
2. Chemical Research:
Due to its unique structure and functional groups, 1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile can be utilized in chemical research for the development of new compounds with potential applications in various industries, such as pharmaceuticals, materials science, and agrochemicals.
3. Material Science:
1-[3-(Benzoyloxy)propyl]-2,3-dihydro-5-(2-nitropropyl)-1H-indole-7-carbonitrile may also find applications in the field of material science, where its unique properties could be harnessed to create novel materials with specific characteristics, such as improved stability, reactivity, or selectivity in various chemical processes.

InChI:InChI=1S/C22H23N3O4/c1-16(25(27)28)12-17-13-19-8-10-24(21(19)20(14-17)15-23)9-5-11-29-22(26)18-6-3-2-4-7-18/h2-4,6-7,13-14,16H,5,8-12H2,1H3

Upstream product

• 76699-29-1 1-(3-chloropropyl)indoline 
• 582-25-2 Potassium benzoate 
• 350797-52-3 1-(3-benzoyloxypropyl)-5-formyl-2,3-dihydroindole 
• 350797-51-2 1-(3-benzoyloxypropyl)-2,3-dihydroindole hydrochloride 
• 350797-55-6 1-(3-benzoyloxypropyl)-7-formyl-5-(2-nitropropyl)-2,3-dihydroindole 
• 350797-54-5 1-(3-benzoyloxypropyl)-5-(2-nitropropyl)-2,3-dihydroindole 
• 350797-53-4 1-(3-benzoyloxypropyl)-5-(2-nitro-1-propenyl)-2,3-dihydroindole 
• 65-85-0 benzoic acid 
• 496-15-1 1-indoline 

Downstream Products

• 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 
• 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 
• 1401991-17-0 (R)-5-(2-aminopropyl)-1-(3-hydroxypropyl)indoline-7-carbonitrile 

Relevant articles and documents

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.