Synthesis, antimalarial properties and 2D-QSAR studies of novel triazole-quinine conjugates.
Click chemistry technique led to novel 1,2,3-triazole-quinine conjugates 8a-g, 10a-o, 11a-h and 13 utilizing benzotriazole-mediated synthetic approach with excellent yields. Some of the synthesized analogs (11a, 11d-h) exhibited antimalarial properties against Plasmodium falciparum strain 3D7 with potency higher than that of quinine (standard reference used) through in vitro standard procedure bio-assay. Statistically significant BMLR-QSAR model describes the bio-properties, validates the observed biological observations and identifies the most important parameters governing bio-activity.
Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia.
Hassan M
HM
Faidallah
Department of Chemistry & Physics, Augusta University, Augusta, GA 30912, USA. Electronic address: sspanda12@gmail.com.
Siva S
SS
Panda
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
Juan C
JC
Serrano
Pesticide Chemistry Department, National Research Centre, Dokki, Giza 12622, Egypt.
Adel S
AS
Girgis
Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia.
Khalid A
KA
Khan
Department of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia.
Khalid A
KA
Alamry
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
Tanya
T
Therathanakorn
Center for World Health & Medicine, Saint Louis University, Saint Louis, MO 63104, USA.
Marvin J
MJ
Meyers
Center for World Health & Medicine, Saint Louis University, Saint Louis, MO 63104, USA.
Francis M
FM
Sverdrup
Center for World Health & Medicine, Saint Louis University, Saint Louis, MO 63104, USA.
Christopher S
CS
Eickhoff
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
Stephen G
SG
Getchell
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA.
Alan R
AR
Katritzky
D000818:Animals; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001681:Biological Assay; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D015195:Drug Design; D020128:Inhibitory Concentration 50; D010963:Plasmodium falciparum / Q000187:drug effects; D066244:Proton Magnetic Resonance Spectroscopy; D021281:Quantitative Structure-Activity Relationship; D011803:Quinine / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D014230:Triazoles / Q000737:chemistry*
D000962:Antimalarials; D014230:Triazoles; D011803:Quinine
Antimalarial; Click chemistry; QSAR; Quinine; Triazole