83012-13-9Relevant articles and documents
New hybrid trifluoromethylquinolines as antiplasmodium agents
da Silva, Renata M.R.J.,Gandi, Marilia O.,Mendon?a, Jorge S.,Carvalho, Alcione S.,Coutinho, Julia Penna,Aguiar, Anna C.C.,Krettli, Antoniana U.,Boechat, Nubia
, p. 1002 - 1008 (2019/02/13)
Malaria remains a major public health problem worldwide, and it is responsible for high rates of morbidity and mortality. Resistance to current antimalarial drugs has been identified, and new drugs are urgently needed. In this study, we designed and synthesized seventeen novel quinolines based on the structures of mefloquine ((2,8-bis(trifluoromethyl)quinolin-4-yl)(piperidin-2-yl)methanol) and amodiaquine (4-((7-chloroquinolin-4-yl)amino)-2-((diethylamino)methyl)phenol) using ring bioisosteric replacement and molecular hybridization of the functional groups. The compounds were evaluated in vitro against Plasmodium falciparum and in vivo in mice infected with P. berghei. All derivatives presented anti-P. falciparum activity with IC50 values ranging from 0.083 to 33.0 μM. The compound with the best anti-P. falciparum activity was N-(5-methyl-4H-1,2,4-triazol-3-yl)-2,8-bis(trifluoromethyl)quinolin-4-amine (12) which showed an IC50 of 0.083 μM. The three most active compounds were selected for antimalarial activity tests against P. berghei-infected mice. Compound 12 was the most active on the 5th day after infection, reducing parasitemia by 66%, which is consistent with its in vitro activity. This is an important result as 12, a simpler molecule than mefloquine, does not contain the stereogenic center, and consequently, its synthesis in the laboratory is easier and less expensive. This system proved promising for the design of potential antimalarial compounds.
Application of 2,8-bis(trifluoromethyl)quinoline 4-modified derivatives in prevention and treatment of plant diseases
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Paragraph 0022-0024, (2019/09/14)
The invention discloses 2,8-bis(trifluoromethyl)quinoline 4-modified derivatives, a preparation method thereof and an application of the derivatives in prevention and treatment of plant diseases. Thetest results show that the compounds have excellent control effect on sclerotiniasclerotiorum, rhizoctonia solani, wheat phytoalexin, pyriculariaoryzae, phyllostictazeae, botrytis cinerea, watermelongummy stem blight and cotton fusarium wilt. The derivatives of the invention are simple in preparation process, low in price and easy to obtain raw materials, high in product purity and wide in bactericidal spectrum, and are expected to be developed into a new bactericide.
Investigations into the flexibility of the 3D structure and rigid backbone of quinoline by fluorine addition to enhance its blue emission
Alapour,Zamisa,Silva,Alves,Omondi,Ramjugernath,Koorbanally
, p. 2316 - 2323 (2018/04/30)
Achieving the desired structures of organic molecules for targeted applications is vital. Folding caused by weak intermolecular forces plays an important part in their 3D structure. Powerful tools which enable us to do this are currently under investigation by researchers across the globe. On this account, quinoline was chosen as a model scaffold because of its rigid 3D structure. Addition of fluorine was found to result in increased flexibility of the structure with a decrease in the number of intermolecular interactions. This resulted in improvement of their photophysics and blue emission. A total of 19 novel fluoroquinoline molecules were synthesised in order to carry out this study. Of these, grown crystals of 10 compounds were successfully achieved and used. In addition, characterisation techniques such as NMR, HRMS, UV-vis and computational techniques were used to explore the 3D structure of these molecules.
