31965-37-4

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-4-methyl-3-(phenylmethylene)-1H-1,4-benzodiazepine-2,5-dione is used as a benzodiazepine metabolite responsible for the biosynthesis of cyclopeptine synthetase. It has potential applications in the development of new pharmaceuticals and therapeutic agents.
Used in Cosmetics Industry:
3,4-Dihydro-4-methyl-3-(phenylmethylene)-1H-1,4-benzodiazepine-2,5-dione is used in vitro evaluation of the photoprotective potential of quinolinic alkaloids isolated from Antarctic marine fungus Penicillium echinulatum for topical use. It can be utilized in the development of sunscreens and other skincare products to protect the skin from harmful UV radiation.
Used in Research and Development:
3,4-Dihydro-4-methyl-3-(phenylmethylene)-1H-1,4-benzodiazepine-2,5-dione is used as a research compound to study the biosynthesis of benzodiazepine alkaloids and the enzymes involved in their production. This can contribute to the advancement of knowledge in the field of organic chemistry and drug discovery.

InChI:InChI=1/C17H14N2O2/c1-19-15(11-12-7-3-2-4-8-12)16(20)18-14-10-6-5-9-13(14)17(19)21/h2-11H,1H3,(H,18,20)

Upstream product

• 118-48-9 isatoic anhydride 
• 100-52-7 benzaldehyde 
• 3415-35-8 4-methyl-3H-1,4-benzodiazepine-2,5-(1H,4H)-dione 
• 150256-42-1 2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)benzoic acid 
• 50886-63-0 (3S)-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione 

Downstream Products

• 19357-57-4 (-)-cyclopenin 
• 129-24-8 4-phenyl-3-hydroxyquinolin-2(1H)-one 
• 19357-57-4 4-methyl-3'c-phenyl-(2'rN)-1H-spiro[benzo[e][1,4]diazepine-3,2'-oxirane]-2,5-dione 
• 19357-57-4 4-methyl-3'-phenylspiro[benzo[e][1,4]diazepine-3,2'-oxirane]-2,5(1H,4H)-dione 

Relevant academic research and scientific papers

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

Mechanistic Investigation of a Non-Heme Iron Enzyme Catalyzed Epoxidation in (-)-4′-Methoxycyclopenin Biosynthesis

Mechanisms have been proposed for α-KG-dependent non-heme iron enzyme catalyzed oxygen atom insertion into an olefinic moiety in various natural products, but they have not been examined in detail. Using a combination of methods including transient kinetics, M?ssbauer spectroscopy, and mass spectrometry, we demonstrate that AsqJ-catalyzed (-)-4′-methoxycyclopenin formation uses a high-spin Fe(IV)-oxo intermediate to carry out epoxidation. Furthermore, product analysis on 16O/18O isotope incorporation from the reactions using the native substrate, 4′-methoxydehydrocyclopeptin, and a mechanistic probe, dehydrocyclopeptin, reveals evidence supporting oxo? hydroxo tautomerism of the Fe(IV)-oxo species in the non-heme iron enzyme catalysis.