Enantioseparation and plant virucidal bioactivity of new quinazoline derivatives with alpha-aminophosphonate moiety.
Enantiomers of some new quinazoline derivatives bearing alpha-aminophosphonate moiety were separated under normal-phase conditions on two immobilized polysaccharide-based chiral stationary phases (Chiralpak IA and Chiralpak IC). The role of two chiral stationary phases (CSPs), polar modifier and column temperature on retention time and separation factor was studied. Apparent thermodynamic parameters were deduced from Van't Hoff plots and plausible mechanism of chiral recognition has been discussed. The semi-preparative separation of some compounds was executed successfully in n-hexane/isopropyl alcohol (IPA) on the Chiralpak IA column. The preliminary bioassay showed that both the enantiomers of the investigated series of compounds possessed similar anti-tobacco mosaic virus (TMV) activities.
Zhang
Yuping
Y
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
Bai
Song
S
Song
Baoan
B
Bhadury
Pinaki S
PS
Hu
Deyu
D
Yang
Song
S
Zhang
Xiaoyan
X
Fan
Huitao
H
Lu
Ping
P
D019840:2-Propanol / Q000737:chemistry; D000688:Amylose / Q000737:chemistry; D000998:Antiviral Agents; D002219:Carbamates / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid / Q000379:methods*; D006586:Hexanes / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry; D011799:Quinazolines / Q000737:chemistry* / Q000494:pharmacology*; D015203:Reproducibility of Results; D013237:Stereoisomerism; D013696:Temperature; D013816:Thermodynamics; D014027:Tobacco Mosaic Virus / Q000187:drug effects*
D000998:Antiviral Agents; D002219:Carbamates; D006586:Hexanes; D063065:Organophosphonates; D011799:Quinazolines; C026385:n-hexane; D000688:Amylose; D019840:2-Propanol