152062-96-9

Basic information

• Product Name: 3-AMINO-2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE
• Synonyms: 3-AMINO-2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE;AKOS B028875;3-amino-2-(trifluoromethyl)-3,4-dihydroquinazolin-4-one
• CAS NO: 152062-96-9
• Molecular Formula: C₉H₆F₃N₃O
• Molecular Weight: 229.16
• Mol File: 152062-96-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-AMINO-2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE(152062-96-9)
• EPA Substance Registry System: 3-AMINO-2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE(152062-96-9)

Safety Data

• Hazardous Substances Data: 152062-96-9(Hazardous Substances Data)

Upstream product

• 31385-12-3 methyl 2-[(trifluoroacetyl)amino] benzoate 
• 134-20-3 2-carbomethoxyaniline 
• 118-92-3 anthranilic acid 
• 16062-71-8 2-trifluoromethyl-4H-3,1-benzoxazin-4-one 
• 152063-00-8 3-(7-Aza-bicyclo[4.1.0]hept-7-yl)-2-trifluoromethyl-3H-quinazolin-4-one 

Relevant articles and documents

Design, Synthesis, and Structure-Activity Relationship of Quinazolinone Derivatives as Potential Fungicides

Plant diseases caused by phytopathogenic fungi reduce the yield and quality of crops. To develop novel antifungal agents, we designed and synthesized eight series of quinazolinone derivatives and evaluated their anti-phytopathogenic fungal activity. The bioassay results revealed that compounds KZL-15, KZL-22, 5b, 6b, 6c, 8e, and 8f exhibited remarkable antifungal activity in vitro. Especially, compound 6c displayed the highest bioactivity against Sclerotinia sclerotiorum, Pellicularia sasakii, Fusarium graminearum, and Fusarium oxysporum, displaying appreciable IC50 values (50% inhibitory concentration) of 2.46, 2.94, 6.03, and 11.9 μg/mL, respectively. A further mechanism interrogation revealed abnormal mycelia, damaged organelles, and changed permeability of cell membranes in S. sclerotiorum treated with compound 6c. In addition, the in vivo bioassay indicated that compound 6c possessed comparable curative and protective effects (87.3 and 90.7%, respectively) to the positive control azoxystrobin (89.5 and 91.2%, respectively) at 100 μg/mL concentration against S. sclerotiorum. This work validated the potential of compound 6c as a new and promising fungicide candidate, contributing to the exploration of potent antifungal agents.

Quinazolinone compounds and application in preparing drug for preventing agricultural plant diseases

The invention discloses application of quinazolinone compounds KZL-01-KZL-34 in preventing or resisting agricultural plant fungal diseases. Antimicrobial activity testing results show that the compounds have inhibition activity on the plant fungal diseases caused by sclerotinia sclerotiorum, rhizoctonia solani, fusarium graminearum Sehw. and botrytis cinerea, and especially have higher inhibitionactivity on the rhizoctonia solani, the inhibition activity of part of the compounds on the germs is higher than that of azoxystrobin, and the quinazolinone compounds can be used as lead compounds ofan agricultural fungicide to be developed.

Identification of novel quinazolin-4(3H)-ones as inhibitors of thermolysin, the prototype of the M4 family of proteinases

A combinatorial series of novel quinazolin-4(3H)-ones were synthesised and their structures were established based on spectroscopic data (IR, NMR, EI-MS, and FAB-MS). The compounds were tested for inhibition of the zinc metalloproteinase thermolysin (TLN) utilizing a chemical array-based approach. Some of the compounds were found to inhibit TLN, with IC50 values ranging from 0.0115 μM (compound 3) to 122,637 μM (compound 29). Compound 3 [3-phenyl-2-(trifluoromethyl) quinazolin-4(3H)-one] (IC50 = 0.0115 μM) and compound 35 [3-(isopropylideneamino)-2,2-dimethyl-2,3-dihydroquinazolin-4 (1H)-one] (IC50 = 0.2477 μM) were found to be the most potent inhibitors.

The stereodivergent aziridination of allylic carbamates, amides and sulfonamides

A stereodivergent protocol for the aziridination of a range of cyclic allylic amine derivatives has been developed. syn-Products can be obtained in >99:1 dr under H-bonded control and anti-products are obtained in >99:1 dr under steric control by judiciou

Aziridination of alkenes using 3-acetoxyamino-2-trifluoromethylquinazolin-4(3H)-one

Oxidation of 3-amino-2-trifluoromethylquinazolin-4(3H)-one 6 with lead tetraacetate in dichloromethane gives the title 3-acetoxyamino derivative 7 which is isolable at room temperature and considerably more stable than the corresponding 2-alkyl substituted analogues. Compound 7 aziridinates alkenes in yields which are consistently higher than those from the 2-alkyl substituted analogues. Aziridinations using 3-acetoxyaminoquinazolinones bearing other electron-withdrawing groups on the 2-position of the quinazolinone ring have been examined.

3-Acetoxyamino-2-trifluoromethylquinazolin-4(3H)one as an Aziridinating Agent for Alkenes

The title compound 4, prepared by lead tetraacetate oxidation of 5, is stable at room temperature and aziridinates alkenes in better yield and higher diastereoselectivity than, e.g. the 2-ethyl compound 1; hydrazinolysis of the quinazolinone ring in 20 gives the corresponding N-aminoaziridine 21 in 64percent yield.