75638-72-1

Usage

Uses

Used in Pharmaceutical Industry:
Chalcostrobamine is used as a pharmaceutical compound for its potential therapeutic applications. Due to its tropane alkaloid structure, it may have various biological activities and can be further studied and developed for use in medicine.
Used in Research and Development:
Chalcostrobamine is used as a research compound for studying its chemical properties, structure, and potential applications in drug discovery and development. Its unique structure and occurrence in nature make it an interesting subject for scientific investigation.

InChI:InChI=1/C17H19NO2/c1-18-13-8-9-14(18)17(16(20)11-13)15(19)10-7-12-5-3-2-4-6-12/h2-7,10,13-14,19H,8-9,11H2,1H3/b10-7+,17-15-/t13?,14-/m1/s1

Upstream product

• 532-24-1 tropinone 
• 60299-77-6 cinnamoyl cyanide 

Relevant academic research and scientific papers

Enantioselective synthesis of strobamine and its analogues

(2S,5S,8R)-Strobamine (+)-1a was synthesized by adding cinnamoyl cyanide 6a to tropinone 3 lithium enolate generated by treatment of (S,S')-a,a- dimethyldibenzylamide with butyl lithium in the presence of lithium chloride to give (-)-chalcostrobamine (-)-7a, which yielded a one-to-one mixture of (+)-1a and its C-2 epimer (-)-2a on treatment with 2N sulfuric acid. Compounds (+)-1a and (-)-2a could be separated by column chromatography. (-)-Strobamine (-)-1a and (+)-2a were synthesized by a similar set of reactions using the tropinone 3 lithium enolate generated with butyl lithium in the presence of (R,R')-a,a'-dimethyldibenzylamide and lithium chloride. (+)-and (-)-p-Methylstrobamine (+)-and (-)-1b and (+)-and (-)-epi-p-methylstrobamine (+)-and (-)-2b were synthesized by a similar procedure. The absolute configuration of (+)-epi-pmethylstrobamine (+)-2b was determined by X-ray analysis to have the (2S,5R,8S) configuration. ARKAT USA, Inc.