title: Diastereoselective synthesis of substituted hexahydrobenzo[de]isochromanes and evaluation of their antileishmanial activity.
abstract: Hexahydrobenzo[de]isochromanes and hexahydropyrano[3,4,5-ij]isoquinolines can be efficiently synthesized via Friedel Crafts and oxa Pictet-Spengler reaction of acrylyl enol ethers mediated by triflic acid in good yields. The reaction is highly stereoselective. Two of the hexahydrobenzo[de]isochromanes are found to have moderate antileishmanial activity.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, Assam, India. asaikia@iitg.ernet.in.
authors.forename: Anil K
authors.initials: AK
authors.lastname: Saikia
authors.forename: Sabera
authors.initials: S
authors.lastname: Sultana
authors.forename: Ngangbam Renubala
authors.initials: NR
authors.lastname: Devi
authors.forename: Manash J
authors.initials: MJ
authors.lastname: Deka
authors.forename: Kartikeya
authors.initials: K
authors.lastname: Tiwari
authors.forename: Vikash K
authors.initials: VK
authors.lastname: Dubey
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D007893:Leishmania donovani / Q000187:drug effects*; D015394:Molecular Structure; D021261:Parasitic Sensitivity Tests; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000085:Acetates; D000981:Antiprotozoal Agents; D001578:Benzopyrans; C000611050:ethyl 2-(3-(4-methoxyphenyl)-3a,6,6-trimethyl-1,3,3a,4,5,6-hexahydro-benzo(de)isochroman-1-yl)acetate; C000611051:ethyl 2-(8-bromo-6,6-dimethyl-1,3,3a,4,5,6-hexahydrobenzo(de)isochroman-1-yl)acetate