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

Uses

3-(7-Cyano-5-(2-nitropropyl)indolin-1-yl)propyl Benzoate is used in the preparation of Silodosin (S465000), an α1a-adrenoceptor antagonist. It is used in treatment of benign prostatic hypertophy.

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 

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.