62175-49-9

Usage

Uses

Used in Agricultural Applications:
DIMBOA is used as a natural pesticide for crop protection, leveraging its antifungal, antibacterial, and antiviral properties to safeguard plants from various pathogens. This helps in reducing the reliance on synthetic chemicals, promoting sustainable agriculture.
Used in Insect Pest Management:
DIMBOA is employed as a feeding deterrent in integrated pest management strategies, reducing the need for chemical insecticides. Its ability to repel insect pests contributes to the protection of crops and the environment.
Used in Plant Defense Research:
DIMBOA is utilized in scientific studies to understand the mechanisms of plant defense against herbivores and pathogens. This research can lead to the development of new strategies for enhancing plant resistance and improving crop yields.
Used in Crop Enhancement:
DIMBOA is studied for its potential role in enhancing crop growth and productivity. By understanding how it contributes to plant health, researchers can potentially develop new approaches to improve agricultural outcomes.

Upstream product

• 2941-78-8 2-Amino-5-methylbenzoic acid 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 201230-82-2 carbon monoxide 
• 29289-13-2 2-iodo-4-methylaniline 
• 583-68-6 2-bromo-p-toluidine 
• 78-39-7 Triethyl orthoacetate 

Downstream Products

• 109981-06-8 4-(2,6-dimethyl-4-oxo-4H-quinazolin-3-yl)-benzenesulfonic acid-[2]pyridylamide 
• 107414-72-2 [4-(2,6-dimethyl-4-oxo-4H-quinazolin-3-yl)-benzenesulfonyl]-guanidine 
• 62175-52-4 5-(2-acetylamino-5-methyl-phenyl)-oxazole-4-carboxylic acid methyl ester 
• 872826-86-3 2,6-dimethyl-3-o-tolyl-3H-quinazolin-4-one 
• 18731-19-6 3,4-dihydro-2,6-dimethyl-4-oxoquinazoline 
• 93392-68-8 2-(2-acetamidophenyl)-6-methyl-4(3H)-quinazolinone 
• 63190-58-9 2,3,6-trimethylquinazolin-4(3H)-one 
• 1382052-19-8 C₂₀H₁₆N₄O₄ 
• 1382052-17-6 C₂₀H₁₆N₄O₃ 
• 1382052-15-4 C₂₀H₁₆N₄O₃ 
• 1382052-13-2 C₂₀H₁₅N₅O₄ 
• 1382052-11-0 C₂₀H₁₅ClN₄O₂ 
• 1382052-09-6 C₂₁H₁₈N₄O₂ 
• 1382052-07-4 2-cyano-N-(2,6-dimethyl-4-oxoquinazolin-3(4H)-yl)-3-phenylacrylamide 

Relevant academic research and scientific papers

Recyclable palladium-catalyzed carbonylative annulation of 2-iodoanilines with acid anhydrides: A practical synthesis of 2-alkylbenzoxazinones

A highly efficient heterogeneous palladium-catalyzed carbonylative annulation of 2-iodoanilines and acid anhydrides has been developed. The reaction proceeds effectively in toluene using N,N-diisopropylethylamine (DiPEA) as the base at 100 °C under 2 bar of CO and provides a novel, general, and practical method for the assembly of a wide variety of 2-alkylbenzoxazinones with high functional group tolerance and good to excellent yields. This supported palladium complex can be readily separated from the product and recovered by a simple filtration of the reaction solution and reused up to seven times with almost consistent catalytic efficiency.

Novel Hydroxamic Acid Incorporating Quinazolin-4(3H)-ones as Histone Deacetylase Inhibitors and Anticancer Composition Comprising the Same

The compound according HDAC(histone deacetylase) to the present -4(3H)- won invention can, be used as an active. ingredient of, a potent anticancer agent, HDAC since the compound according, to the present invention can be used. as, an active ingredient of a potent anticancer agent, since the compound. according to the present invention can be used as an active ingredient of a potent anticancer agent. (by machine translation)

4H-Benzo[d][1,3]oxazin-4-ones and Dihydro analogs from substituted anthranilic acids and orthoesters

A one-pot route to 2-alkyl and 2-aryl-4H-benzo[d][1,3]oxazin-4-ones (also known as 4H-3,1-benzoxazin-4-ones) has been developed and studied. The method involves the reaction of aryl-substitutedanthranilic acidswithorthoesters inethanol catalyzedby acetic acid. Additionally,wehave also investigated the reaction under microwave conditions. Not all of the substrates were successful in yielding the target heterocycles as some of the reactions failed to undergo the final elimination. This process led to the isolation of (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.

Quinazolin-4(3H)-one-Based Hydroxamic Acids: Design, Synthesis and Evaluation of Histone Deacetylase Inhibitory Effects and Cytotoxicity

The present article describes the synthesis and biological activity of various series of novel hydroxamic acids incorporating quinazolin-4(3H)-ones as novel small molecules targeting histone deacetylases. Biological evaluation showed that these hydroxamic acids were potently cytotoxic against three human cancer cell lines (SW620, colon; PC-3, prostate; NCI?H23, lung). Most compounds displayed superior cytotoxicity than SAHA (suberoylanilide hydroxamic acid, Vorinostat) in term of cytotoxicity. Especially, N-hydroxy-7-(7-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5b) and N-hydroxy-7-(6-methyl-4-oxoquinazolin-3(4H)-yl)heptanamide (5c) (IC50 values, 0.10–0.16 μm) were found to be approximately 30-fold more cytotoxic than SAHA (IC50 values of 3.29–3.67 μm). N-Hydroxy-7-(4-oxoquinazolin-3(4H)-yl)heptanamide (5a; IC50 values of 0.21–0.38 μm) was approximately 10- to 15-fold more potent than SAHA in cytotoxicity assay. These compounds also showed comparable HDAC inhibition potency with IC50 values in sub-micromolar ranges. Molecular docking experiments indicated that most compounds, as represented by 5b and 5c, strictly bound to HDAC2 at the active binding site with binding affinities much higher than that of SAHA.

A general palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones from 2-bromoanilines and acid anhydrides

(C), its (O)K! An efficient palladium-catalyzed carbonylative synthesis of 2-alkylbenzoxazinones has been developed (see scheme). By starting from 2-bromoanilines and acid anhydrides, the corresponding products were isolated in good yields. Copyright

Quinazoline-tyrphostin as a new class of antitumor agents, molecular properties prediction, synthesis and biological testing

A new series of substituted quinazolin-4-(3H)-one-tyrphostin derivatives was prepared and screened for their cytotoxic activity against three tumor cell lines, namely human breast cancer cell line (MCF-7), human cervical cancer cell line (HeLa) and human

Quinazolin-4-one derivatives: A novel class of noncompetitive NR2C/D subunit-selective N-methyl-D-aspartate receptor antagonists

We describe a new class of subunit-selective antagonists of N-methyl d-aspartate (NMDA)-selective ionotropic glutamate receptors that contain the (E)-3-phenyl-2-styrylquinazolin-4(3H)-one backbone. The inhibition of recombinant NMDA receptor function induced by these quinazolin-4-one derivatives is noncompetitive and voltage-independent, suggesting that this family of compounds does not exert action on the agonist binding site of the receptor or block the channel pore. The compounds described here resemble CP-465,022 ((S)-3-(2-chlorophenyl)-2-[2-(6-diethylaminomethyl-pyridin-2-yl)-vinyl] -6-fluoro-3H-quinazolin-4-one), a noncompetitive antagonist of AMPA-selective glutamate receptors. However, modification of ring substituents resulted in analogues with greater than 100-fold selectivity for recombinant NMDA receptors over AMPA and kainate receptors. Furthermore, within this series of compounds, analogues were identified with 50-fold selectivity for recombinant NR2C/D-containing receptors over NR2A/B containing receptors. These compounds represent a new class of noncompetitive subunit-selective NMDA receptor antagonists.

Analogues of 4-[(7-Bromo-2-methyl-4-oxo-3 H -quinazolin-6-yl)methylprop-2- ynylamino]- N -(3-pyridylmethyl)benzamide (CB-30865) as potent inhibitors of nicotinamide phosphoribosyltransferase (Nampt)

We have shown previously that the target of the potent cytotoxic agent 4-[(7-bromo-2-methyl-4-oxo-3H-quinazolin-6-yl)methyl-prop-2-ynylamino] -N-(3-pyridylmethyl)benzamide (CB38065, 1) is nicotinamide phosphoribosyltransferase (Nampt). With its cellular target known we sought to optimize the biochemical and cellular Nampt activity of 1 as well as its cytotoxicity. It was found that a 3-pyridylmethylamide substituent in the A region was critical to cellular Nampt activity and cytotoxicity, although other aromatic substitution did yield compounds with submicromolar enzymatic inhibition. Small unsaturated groups worked best in the D-region of the molecule, with 3,3-dimethylallyl providing optimal potency. The E region required a quinazolin-4-one or 1,2,3-benzotriazin-4-one group for activity, and many substituents were tolerated at C2 of the quinazolin-4-one. The best compounds showed subnanomolar inhibition of Nampt and low nanomolar cytotoxicity in cellular assays.

Synthesis, structure-activity relationships, and biological profiles of a quinazolinone class of histamine H3 receptor inverse agonists

A new series of quinazolinone derivatives was synthesized and evaluated as nonimidazole H3 receptor inverse agonists. 2-Methyl-3-(4-{[3-(1- pyrrolidinyl)propyl]oxy}phenyl)-5-(trifluoromethyl)-4(3H)-quinazolinone (1) was identified as a promising derivative for further evaluation following optimization of key parameters. Compound 1 has potent H3 inverse agonist activity and excellent selectivity over other histamine receptor subtypes and a panel of 115 unrelated diverse binding sites. Compound 1 also shows satisfactory pharmacokinetic profiles and brain penetrability in laboratory animals. Two hours after oral administration of 30 mg/kg of 1 to SD rats, significant elevation of brain histamine levels was observed where the brain H3 receptor was highly occupied (>90%). On the basis of species differences in P-glycoprotein (P-gp) susceptibility of 1 between human and rodent P-gps, the observed rodent brain permeability of 1 is significantly limited by P-gp mediated efflux in rodents, whereas the extent of P-gp mediated efflux in humans should be very small or negligible. The potential of 1 to be an efficacious drug was demonstrated by its excellent brain penetrability and receptor occupancy in P-gp-deficient CF-1 mice.

Synthesis of substituted benzylamino- and heterocyclylmethylamino carbodithioate derivatives of 4-(3H)-quinazolinone and their cytotoxic activity

A new series of substituted benzylamino- and heterocyclylmethylamino carbodithioate derivatives of 4-(3H)-quinazolinone were synthesized via four steps starting from 2-amino-5-methyl-benzoic acid and initially screened against A-549 (human non-small cell