112244-38-9

Usage

Uses

Used in Pharmaceutical Industry:
5-(2-Aminopropyl)-2-methoxybenzenesulfonamide is used as a key intermediate compound for the synthesis of various pharmaceuticals targeting α1-adrenoceptor related diseases. Its unique structure allows it to interact with specific receptors in the body, modulating their activity and providing therapeutic benefits.
Used in Research and Development:
In the field of research and development, 5-(2-Aminopropyl)-2-methoxybenzenesulfonamide serves as a valuable building block for the creation of novel compounds with potential applications in medicine, particularly in the treatment of α1-adrenoceptor related conditions. Its versatility in chemical reactions makes it a useful tool for exploring new therapeutic strategies and advancing our understanding of receptor biology.
Used in Drug Delivery Systems:
Similar to gallotannin, 5-(2-Aminopropyl)-2-methoxybenzenesulfonamide can also be incorporated into drug delivery systems to enhance its bioavailability and therapeutic efficacy. By employing various carriers such as organic and metallic nanoparticles, the compound can be more effectively delivered to target tissues, improving its overall performance in treating α1-adrenoceptor related diseases.

InChI:InChI=1/C10H16N2O3S/c1-7(11)5-8-3-4-9(15-2)10(6-8)16(12,13)14/h3-4,6-7H,5,11H2,1-2H3,(H2,12,13,14)

Upstream product

• 116091-63-5 2-methoxy-5-(2-oxopropyl)benzenesulfonamide 
• 944395-49-7 5-(2-hydroxyiminopropyl)-2-methoxybenzenesulfonamide 

Downstream Products

• 863666-27-7 (R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide D-tartrate 
• 1262059-09-5 C₂₁H₃₄N₂O₅S 
• 1262059-08-4 C₂₁H₃₄N₂O₅S 
• 1210430-94-6 5-[(2R)-2-aminopropyl]-2-methoxybenzenesulfonamide D-mandelate 
• 94666-07-6 5-[2-[2-(2-ethoxyphenoxy)-ethylamino]-2-methylethyl]-2-methoxybenzenesulfonamide 
• 106133-20-4 tamsulosin hydrochloride 
• 521301-00-8 (S)-tamsarocin (+)-camphor-10-sulfonate 
• 521300-99-2 (R)-tamsarocin (-)-camphor-10-sulfonate 
• 106133-20-4 (R)-tamsulosin 
• 119714-13-5 (S)-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide 
• 112101-81-2 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide 

Relevant academic research and scientific papers

Synthesis and α1-adrenoceptor antagonist activity of tamsulosin analogues

Tamsulosin (-)-1 is the most utilized α1-adrenoceptor antagonist in the benign prostatic hyperplasia therapy owing to its uroselective antagonism and capability in relieving both obstructive and irritative lower urinary tract symptoms. Here we report the synthesis and pharmacological study of the homochiral (-)-1 analogues (-)-2-(-)-5, bearing definite modifications in the 2-substituted phenoxyethylamino group in order to evaluate their influence on the affinity profile for α1-adrenoceptor subtypes. The benzyl analogue (-)-3, displaying a preferential antagonist profile for α1A-than α1D-and α1B- adrenoceptors, and a 12-fold higher potency at α1A- adrenoceptors with respect to the α1B subtype, may have improved uroselectivity compared to (-)-1.

PROCESS FOR MANUFACTURING OPTICALLY PURE (R) OR (S)-5-(2-AMINOPROPYL)-2-METHOXYBENZENE SULFONAMIDE

The invention relates to an improved process for the manufacture of enantiomerically pure R-(+) or S-(+)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide by resolution of (R,S)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide with D-(-) or L-(+)-tartaric acid to form a mixture of diastereomeric salts, separating the diastereomeric salts by kinetic resolution in a mixture of solvent systems of the kind such as herein described, in the specified time and temperature range to provide said R-(-)-5-(2-aminopropyl)-2-methoxybenzene sulfonamide or S-(+)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide with excellent chiral purity more than 99.9 %.

A PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY PURE (R) OR (S)-5-(2-AMINOPROPYL)-2-METHOXYBENZENESULFONAMIDE

The invention relates to a process for the manufacture of optically pure (R) or (S)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide with D-i.e. (2S, 3S) or L-i.e. (2R, 3R)-tartaric acid to form a mixture of diastereomeric salts, separating the diastereomeric salts by fractional crystallization in a mixture of solvent systems and at the specified temperature range and contacting the individual salts so separated with a base to provide said R-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide or S-(+)-5-(2-amino propyl)-2-methoxybenzenesulfonamide.