Unusual products of the aqueous chlorination of atenolol.
The reaction of the drug atenolol with hypochlorite under conditions that simulate wastewater disinfection was investigated. The pharmaceutical reacted in 1h yielding three products that were separated by chromatographic techniques and characterized by spectroscopic features. Two unusual products 2-(4-(3-(chloro(2-chloropropan-2-yl)amino)-2-hydroxypropoxy)phenyl) acetamide and 2-(4-(3-formamido-2-hydroxypropoxy)phenyl) acetamide were obtained along with 2-(4-hydroxyphenyl) acetamide. When the reaction was stopped at shorter times only 2-(4-(3-amino-2-hydroxypropoxy)phenyl) acetamide and the dichlorinated product were detected. Tests performed on the seeds of Lactuca sativa show that chlorinated products have phytotoxic activity.
DellaGreca
Marina
M
UDR Napoli 4 (Consorzio INCA), IC-REACH Dipartimento di Chimica Organica e Biochimica, Università Federico II, Complesso Universitario Monte Sant'Angelo, Via Cinthia 4, I-80126 Napoli, Italy.
Iesce
Maria Rosaria
MR
Pistillo
Paola
P
Previtera
Lucio
L
Temussi
Fabio
F
D001262:Atenolol / Q000031:analogs & derivatives / Q000737:chemistry*; D054879:Halogenation; D006997:Hypochlorous Acid / Q000737:chemistry*; D018545:Lactuca / Q000187:drug effects / Q000378:metabolism
C539325:2-(4-(3-(chloro(2-chloropropan-2-yl)amino)-2-hydroxypropoxy)phenyl)acetamide; C539326:2-(4-(3-formamido-2-hydroxypropoxy)phenyl)acetamide; C539327:2-(4-hydroxyphenyl)acetamide; D001262:Atenolol; D006997:Hypochlorous Acid