1639431-05-2

Basic information

• Product Name: C₂₂H₂₄ClNO₃
• Synonyms: C₂₂H₂₄ClNO₃
• CAS NO: 1639431-05-2
• Molecular Weight: 385.89
• Mol File: 1639431-05-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₂H₂₄ClNO₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₂H₂₄ClNO₃(1639431-05-2)
• EPA Substance Registry System: C₂₂H₂₄ClNO₃(1639431-05-2)

Safety Data

• Hazardous Substances Data: 1639431-05-2(Hazardous Substances Data)

Upstream product

• 104-86-9 4-chlorobenzylamine 
• 18409-93-3 (+)-1,2-dihydro-α-santonin 

Relevant articles and documents

Structure-Activity relationship study of sesquiterpene lactones and their semi-synthetic amino derivatives as potential antitrypanosomal products

Sesquiterpene lactones (STLs) are natural products that have potent antitrypanosomal activity in vitro and, in the case of cynaropicrin, also reduce parasitemia in the murine model of trypanosomiasis. To explore their structure-Antitrypanosomal activity relationships, a set of 34 natural and semi-synthetic STLs and amino-STLs was tested in vitro against T. b. rhodesiense (which causes East African sleeping sickness) and mammalian cancer cells (rat bone myoblast L6 cells). It was found that the a-methylene-?- lactone moiety is necessary for both antitrypanosomal effects and cytotoxicity. Antitrypanosomal selectivity is facilitated by 2-(hydroxymethyl)acrylate or 3,4-dihydroxy-2- methylenebutylate side chains, and by the presence of cyclopentenone rings. Semi-synthetic STL amines with morpholino and dimethylamino groups showed improved in vitro activity over the native STLs. The dimethylamino derivative of cynaropicrin was prepared and tested orally in the T. b. rhodesiense acute mouse model, where it showed reduced toxicity over cynaropicrin, selectivity is facilitated by 2-(hydroxymethyl)acrylate or 3,4-dihydroxy-2-methylenebutylate side chains, and by the presence of cyclopentenone rings. Semi-synthetic STL amines with morpholino and dimethylamino groups showed improved in vitro activity over the native STLs. The dimethylamino derivative of cynaropicrin was prepared and tested orally in the T. b. rhodesiense acute mouse model, where it showed reduced toxicity over cynaropicrin, but also lost antitrypanosomal activity.