82589-42-2

Usage

Structure

A pyrrolidine derivative with a naphthylmethyl moiety attached to the nitrogen atom

Usage

As a building block for the synthesis of various bioactive compounds in medicinal chemistry and drug development

Biological activities

Potential antiviral, anticancer, and antibacterial properties

Derivatives

Studied for their potential biological activities

Chiral auxiliary

Investigated for its potential application in asymmetric synthesis

Value

Unique structure and properties make it a valuable tool for researchers in the development of new pharmaceuticals and chemical substances.

Upstream product

• 108716-05-8 5-[1]naphthylmethyl-3,4-dihydro-2H-pyrrole 
• 82590-37-2 (Z)-5-Naphthalen-1-yl-4-nitro-pent-4-enoic acid ethyl ester 
• 82590-45-2 4-Amino-5-naphthalen-1-yl-pentan-1-ol 
• 66-77-3 1-naphthaldehyde 

Downstream Products

• 82589-56-8 7,9,10,11,11a,12-Hexahydrobenzopyrrolo<1,2-b>isoquinoline 

Relevant academic research and scientific papers

Synthesis of Hexahydropyrroloisoquinolines - Analogs of Phenanthroindolizidine Anticancer Alkaloids

A convenient preparative route has been developed for the synthesis of hexahydropyrroloisoquinolines involving condensation of an araldehyde with ethyl 4-nitrobutanoate followed by LAH reduction and subsequent cyclization with H2SO4 to 2-arylmethylpyrrolidines.The latter on formylation and Bischler-Napieralsky cyclization followed by NaBH4 reduction give the required pyrroloisoquinolines.Using this method, 8-methoxy-1,2,3,5,10,10a-hexahydropyrroloisoquinoline (IXa); 7,8-dimethoxy-1,2,3,5,10,10a-hexahydropyrroloisoquinoline (IXb); 7,9,10,11,11a,12-hexahydrobenzopyrroloisoquinoline (Xa); 3-methoxy-7,9,10,11,11a,12-hexahydrobenzopyrroloisoquinoline (Xb); 7,7a,8,9,10,12-hexahydrobenzopyrroloisoquinoline (XIa); 3-methoxy-7,7a,8,9,10,12-hexahydrobenzopyrroloisoquinoline (XIb) and 2,3-dimethoxy-7,7a,8,9,10,12-hexahydrobenzopyrroloisoquinoline (XIc) have been synthesized.None of these compounds has shown any noteworthy anticancer activity while few have exhibited interesting antihistaminic, β-blocking, hypertensive, antiinflammatory and antireserpine activities.