title: Amino- and hydroxy-functionalized 11-azaartemisinins and their derivatives.
abstract: An efficient conversion of artemisinin 1 into three new amino- and hydroxy-functionalized 11-aza prototypes 9, 11, and 12 has been achieved on a multigram scale by reaction with hydrazine, hydroxylamine, and 2-amino ethanol, respectively. Of these, 9 has been further diversified into a wide range of derivatives including imines, amines, amides, and linker based dimers. Prototypes 11 and 12 have been converted into the corresponding ethers in high yields. Some of these compounds have shown a high order of activity against multidrug-resistant malaria in mice by oral route.
authors.affiliation: Division of Medicinal and Process Chemistry, Central Drug Research Institute, Lucknow-226001, India.
authors.forename: Ajit Shankar
authors.initials: AS
authors.lastname: Singh
authors.forename: Ved Prakash
authors.initials: VP
authors.lastname: Verma
authors.forename: Mohammad
authors.initials: M
authors.lastname: Hassam
authors.forename: Naikade Niraj
authors.initials: NN
authors.lastname: Krishna
authors.forename: Sunil K
authors.initials: SK
authors.lastname: Puri
authors.forename: Chandan
authors.initials: C
authors.lastname: Singh
mesh_terms: D000284:Administration, Oral; D000818:Animals; D000981:Antiprotozoal Agents / Q000008:administration & dosage / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D037621:Artemisinins / Q000008:administration & dosage / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001372:Aza Compounds / Q000737:chemistry*; D018432:Drug Resistance, Multiple; D008288:Malaria / Q000188:drug therapy; D051379:Mice; D010967:Plasmodium yoelii / Q000187:drug effects
chemical_list: D000981:Antiprotozoal Agents; D037621:Artemisinins; D001372:Aza Compounds; C031327:artemisinin