7501-38-4

Usage

Chemical class

Benzoxazinoids

Occurrence

Found in various plants, including cereals (wheat, rye, and maize), grasses, and weeds

Allelopathic properties

Inhibits the growth of competing plants by releasing toxic substances into the soil

Potential uses

Natural herbicide, defense compound against herbivores, antimicrobial and insecticidal activities

Derivatives

Synthesized for potential pharmacological and agricultural applications

Upstream product

• 68506-37-6 2-(2-nitrobenzamido)benzoic acid 
• 108-24-7 acetic anhydride 
• 118-92-3 anthranilic acid 
• 610-14-0 2-nitrobenzyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 37960-65-9 potassium anthranilate 
• 72367-10-3 2-(2-nitrobenzoylamino)benzoic acid methyl ester 
• 134-20-3 2-carbomethoxyaniline 
• 88116-43-2 N-(2'-formylphenyl)-2-nitrobenzamide 

Downstream Products

• 316142-99-1 2-nitro-N-(2-(phenylcarbamoyl)phenyl)benzamide 
• 67718-36-9 N-[2-(aminocarbonyl)phenyl]-2-nitrobenzamide 
• 7265-24-9 2-(2'-amino-phenyl)-benzo[d][1,3]oxazin-4-one 
• 68506-37-6 2-(2-nitrobenzamido)benzoic acid 
• 96609-67-5 [2-(2-Nitro-benzoylamino)-benzoylamino]-acetic acid benzyl ester 
• 54987-33-6 3-amino-2-(2'-aminophenyl)-quinazolin-4(3H)-one 
• 612-34-0 N-anthraniloyl-anthranilic acid 
• 432543-93-6 2-(2-nitrophenyl)-3-hydroxy-quinazoline-4(3H)-one 
• 1404368-86-0 (S)-methyl 1-(2-(2-nitrobenzamido)benzoyl)pyrrolidine-2-carboxylate 
• 1404368-87-1 (R)-benzyl 1-(2-(2-nitrobenzamido)benzoyl)pyrrolidine-2-carboxylate 
• 1404368-84-8 (S)-N-(4-bromophenyl)-1-(2-(2-nitrobenzamido)benzoyl)pyrrolidine-2-carboxamide 
• 875017-11-1 2-nitro-N-(2-(pyrrolidine-1-carbonyl)phenyl)benzamide 
• 1448441-17-5 (R)-methyl 2-(2-(1-(2-(2-nitrobenzamido)benzoyl)pyrrolidine-2 carboxamido)benzamido)benzoate 
• 1448441-18-6 (R)-1-(2-(2-aminobenzamido)benzoyl)-N-(2-((2-(methylcarbamoyl)phenyl)carbamoyl)phenyl)pyrrolidine-2-carboxamide 

Relevant academic research and scientific papers

Structural Insights into the Hydrogen-Bonding and Folding Pattern in Ant-Ant-Pro-Gly Tetrapeptides

In this paper, we provide structural insights into the hydrogen-bonding and folding pattern in Ant-Ant-Pro-Gly tetrapeptides (Ant: anthranilic acid; Pro: proline; and Gly: glycine). Comparison of the C-terminal esters and their amide analogs revealed strikingly different H-bonding networks. Whereas the ester analogs displayed an open structure without terminal H-bonding interactions, the amide analogs showed a completely folded structure. Structural details were revealed by using a combination of X-ray crystal structure studies and NOE-based molecular dynamics (MD) simulation studies.

TBHP/CoCl2-mediated intramolecular oxidative cyclization of N-(2-formylphenyl)amides: An approach to the construction of 4H-3,1-benzoxazin-4-ones

The intramolecular oxidative cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as an oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives and features readily available starting materials and mild reaction conditions. The intramolecular cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as the oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives.

BCL-3 INHIBITORS

The present application relates to compounds of any one of Formulae I, Ia, Ib, Ic, Id, Ie, and If. Compounds of Formula (I) have the structure, wherein A, B, Y, Z, R2, R4, R5, R6, Rq and q are as defined herein. The compounds can be used as inhibitors of Bcl-3 and can be used for the treatment of cancer, particularly metastatic cancer.

2-BENZOYLAMINOBENZAMIDE DERIVATIVES AS BCL-3 INHIBITORS

The invention relates to a compound of general formula (I): wherein R1, R2, R3, R4, Q, m and n are as defined herein. The compounds are inhibitors of Bcl3 and are useful for the treatment of cancer, particularly

Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors

Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structureactivity relationship were tested against α-chymotrypsin. Majority of synthesized compounds showed significant in vitro α-chymotrypsin inhibitory properties having IC50values in the range of 5.42 ± 1.66 - 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1- benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3, 1-benzoxazin-4-one (3t) with IC50values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.

A synthetic zipper peptide motif orchestrated via co-operative interplay of hydrogen bonding, aromatic stacking, and backbone chirality

Here, we report on a new class of synthetic zipper peptide which assumes its three-dimensional zipper-like structure via a co-operative interplay of hydrogen bonding, aromatic stacking, and backbone chirality. Structural studies carried out in both solid- and solution-state confirmed the zipper-like structural architecture assumed by the synthetic peptide which makes use of unusually remote inter-residual hydrogen-bonding and aromatic stacking interactions to attain its shape. The effect of chirality modulation and the extent of noncovalent forces in the structure stabilization have also been comprehensively explored via single-crystal X-ray diffraction and solution-state NMR studies. The results highlight the utility of noncovalent forces in engineering complex synthetic molecules with intriguing structural architectures.

Facile synthesis and herbicidal evaluation of 2-Aryl-4H-3, 1-benzoxazin-4-ones

The present work deals with the synthesis of 4H-3,1-benzoxazin-4-ones carrying an aryl functional group at position-2. Synthesized compounds tested for herbicidal activity at three different doses (500 μg/mL, 50 μg/mL and 5μg/mL). Most of the compounds exhibited significant herbicidal activity against Lemna aequinocitalis welv. at higher dose (500 μg/mL). Among the tested compounds 2-phenyl-4H-3,1-benzoxazin-4-one (3a) and 2-(3-chlorophenyl)- 4H-3,1-benzoxazin-4- one (3l) completely inhibited the plant growth at 500 and 50 μg/mL concentrations. All the synthetic compounds were characterized by FT-IR, 1H NMR, EI-MS and elemental analysis.

Synthesis and antimicrobial activity of 2-Aryl-4H-3,1-benzoxazin-4-ones

Twenty derivatives of 2-aryl-4H-3,1-benzoxazin-4-one synthesized and their potential therapeutically significance tested against two strains of Gram positive bacteria (Staphylococcus aureus and Bacillus subtilis) and four strains of Gram negative bacteria (Shigella flexnari, Escherichia coli, Salmonella typhi and Pseudomonas aeruginsoa) by agar well diffusion method. The 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one (3f) recorded significant antibacterial activity against Bacillus subtilis whereas 2-(4-bromophenyl)-4H-3, 1-benzoxazin-one (3o) exhibited weak antibacterial activity against Staphylococcus aureus. Further 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one (3b) showed significant activity against Shigella Flexnari, Escherichia coli, Pseudomonas aeruginsoa and Salmonella typhi. The antibacterial activity of synthesized derivatives of 2-aryl-4H-3,1-benzoxazin-4-one was compared to reference standard antibiotics amoxycillin, streptomycin, kanamycin and ciprofloxacin. The present study revealed that 2-aryl-4H-3,1-benzoxazin-4-ones possess good bactericidal activity against a panel of bacteria causing common bacterial diseases and therefore opens the possibility of finding latest clinically useful antibacterial compounds. The synthesized compounds were characterized by 1H NMR, EI, FT-IR and elemental analysis.

Multifaceted folding in a foldamer featuring highly cooperative folds

Herein, we report on the folding pattern observed in a synthetic peptide featuring two highly mutually dependent, yet strikingly dissimilar, closed networks of hydrogen-bonded rings that work in a cumulative fashion to stabilize the entire folded architec

2-Chloro-1,3-dimethylimidazolinium chloride. 2. Its application to the construction of heterocycles through dehydration reactions

2-Chloro-1,3-dimethylimidazolinium chloride (DMC) (1) can act as a powerful dehydrating equivalent to DCC (2) under nearly neutral conditions. Its application to the construction of heterocycles through dehydration reactions is described.