934278-66-7

Upstream product

• 35853-41-9 2,8-bis(trifluoromethyl)quinolin-4-ol 
• 934278-64-5 2-[[2,8-bis(trifluoromethyl)-4-quinolinyl]oxy]acetic acid ethyl ester 

Relevant academic research and scientific papers

Application of 2, 8-bis (trifluoromethyl)-4-hydroxyquinoline derivative in preparation and prevention and treatment of agricultural diseases

The invention discloses application of a 2, 8-bis (trifluoromethyl)-4-hydroxyquinoline derivative in preparation and prevention and treatment of agricultural diseases. Activity test results show that the compound has potential inhibitory activity on four plant pathogenic fungi including sclerotinia sclerotiorum, botrytis cinerea, fusarium graminearum and rhizoctonia solani, and can be developed as a bactericide.

Antifungal Exploration of Quinoline Derivatives against Phytopathogenic Fungi Inspired by Quinine Alkaloids

Enlightened from our previous work of structural simplification of quinine and innovative application of natural products against phytopathogenic fungi, lead structure 2,8-bis(trifluoromethyl)-4-quinolinol (3) was selected to be a candidate and its diversified design, synthesis, and antifungal evaluation were carried out. All of the synthesized compounds Aa1-Db1 were evaluated for their antifungal activity against four agriculturally important fungi, Botrytis cinerea, Fusarium graminearum, Rhizoctonia solani, and Sclerotinia sclerotiorum. Results showed that compounds Ac3, Ac4, Ac7, Ac9, Ac12, Bb1, Bb10, Bb11, Bb13, Cb1. and Cb3 exhibited a good antifungal effect, especially Ac12 had the most potent activity with EC50 values of 0.52 and 0.50 μg/mL against S. sclerotiorum and B. cinerea, respectively, which were more potent than those of the lead compound 3 (1.72 and 1.89 μg/mL) and commercial fungicides azoxystrobin (both >30 μg/mL) and 8-hydroxyquinoline (2.12 and 5.28 μg/mL). Moreover, compound Ac12 displayed excellent in vivo antifungal activity, which was comparable in activity to the commercial fungicide boscalid. The preliminary mechanism revealed that compound Ac12 might cause an abnormal morphology of cell membranes, an increase in membrane permeability, and release of cellular contents. These results indicated that compound Ac12 displayed superior in vitro and in vivo fungicidal activities and could be a potential fungicidal candidate against plant fungal diseases.

Structure-Activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating mycobacterium tuberculosis

Tuberculosis (TB) remains as a global pandemic that is aggravated by a lack of health care, the spread of HIV, and the emergence of multidrug-resistant TB (MDR-TB) and extensively drug-resistant TB (XDRTB) strains. New anti-TB drugs are urgently required to shorten the long 6-12 month treatment regimen and to battle drug-resistant Mtb strains. We have identified several potent quinoline-based anti-TB compounds, bearing an isoxazole containing side-chain. The most potent compounds, 7g and 13, exhibited submicromolar activity against the replicating bacteria (R-TB), with minimum inhibitory concentrations (MICs) of 0.77 and 0.95 μM, respectively. In general, these compounds also had micromolar activity against the nonreplicating persistent bacteria (NRP-TB) and did not show toxicity on Vero cells up to 128 μM concentration. Compounds 7g and 13 were shown to retain their anti-TB activity against rifampin, isoniazid, and streptomycin resistant Mtb strains. The results suggest that quinoline-isoxazole-based anti-TB compounds are promising leads for new TB drug development.

Synthesis of novel substituted/unsubstituted- (2,8-bis-trifluoromethyl- quinolin-4-yloxy)-acetic acid: Derivatives of cephalosporin and their antibacterial activity

Substituted/unsubstituted-(2,8-bis-trifluoromethyl-quinolin-4-yloxy)-acetic acid derivatives of cephalosporin have been synthesized by condensation of acid chlorides of substituted/unsubstituted - (2,8-bis-trifluoromethyl-quinolin-4- yloxy)-acetic acid with various silylated (6R,7R)-7-amino-3-substituted cephalosporanic acids. The products have been tested for their antibacterial activity.