50886-63-0

Basic information

• Product Name: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione
• Synonyms: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione;Benzyl-3,4-dihydro-4-Methyl-1H-1,4-benzodiazepine-2,5-dione;(S)-cyclopeptine
• CAS NO: 50886-63-0
• Molecular Formula: C₁₇H₁₆N₂O₂
• Molecular Weight: 280.32
• Mol File: 50886-63-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 514.3°Cat760mmHg
• Flash Point: 264.8°C
• Appearance: /
• Density: 1.206g/cm³
• Vapor Pressure: 1.1E-10mmHg at 25°C
• Refractive Index: 1.599
• PKA: 13.20±0.40(Predicted)
• CAS DataBase Reference: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione(50886-63-0)
• EPA Substance Registry System: (4S)-4-benzyl-5-methyl-2,5-diazabicyclo[5.4.0]undeca-7,9,11-triene-3,6-dione(50886-63-0)

Safety Data

• Hazardous Substances Data: 50886-63-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 50886-63-0 differently. You can refer to the following data:
1. Cyclopeptine is a benzodiazepine metabolite produced by a number of species of Penicillium. While there is little literature about the metabolite, there is considerable interest in the enzymes responsible for the biosynthesis of the benzodiazepine nucleus, cyclopeptine synthetase.
2. Cyclopeptine is a benzodiazepine Penicillium species metabolite.

Definition

ChEBI: An optically active form of cyclopeptine having S-configuration.

InChI:InChI=1/C17H16N2O2/c1-19-15(11-12-7-3-2-4-8-12)16(20)18-14-10-6-5-9-13(14)17(19)21/h2-10,15H,11H2,1H3,(H,18,20)/t15-/m0/s1

Upstream product

• 211567-41-8 (3S)-3,4-dihydro-2-methoxy-N-methyl-3-phenylmethyl-[1,4]benzodiazepin-5(5H)one 
• 150256-42-1 2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)benzoic acid 
• 2439-60-3 N-methyl-L-phenylalanine methyl ester 
• 34897-85-3 o-azidobenzoyl chloride 
• 196928-07-1 N-(2-azidobenzoyl)-N-methyl-L-phenylalanine methyl ester 
• 31162-13-7 2-azidobenzoic acid 
• 201230-82-2 carbon monoxide 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 615-36-1 2-bromoaniline 
• 615-43-0 2-iodophenylamine 
• 19460-86-7 (N-methyl)-L-phenylalanine methyl ester hydrochloride 
• 118-48-9 isatoic anhydride 

Downstream Products

• 129-24-8 4-phenyl-3-hydroxyquinolin-2(1H)-one 
• 31965-37-4 3-benzylidene-4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione 
• 157047-96-6 (-)-benzomalvin A 
• 196928-08-2 (3S)-[1-(2-azidobenzoyl)]-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione 

Relevant articles and documents

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.

Structure of the Dioxygenase AsqJ: Mechanistic Insights into a One-Pot Multistep Quinolone Antibiotic Biosynthesis

Multienzymatic cascades are responsible for the biosynthesis of natural products and represent a source of inspiration for synthetic chemists. The FeII/α-ketoglutarate-dependent dioxygenase AsqJ from Aspergillus nidulans is outstanding because it stereoselectively catalyzes both a ferryl-induced desaturation reaction and epoxidation on a benzodiazepinedione. Interestingly, the enzymatically formed spiro epoxide spring-loads the 6,7-bicyclic skeleton for non-enzymatic rearrangement into the 6,6-bicyclic scaffold of the quinolone alkaloid 4′-methoxyviridicatin. Herein, we report different crystal structures of the protein in the absence and presence of synthesized substrates, surrogates, and intermediates that mimic the various stages of the reaction cycle of this exceptional dioxygenase.

The first total synthesis of (-)-benzomalvin A via intramolecular Aza-Wittig reactions

The first total synthesis of (-)-benzomalvin A 1, which possesses quinazolin-4(3H)-one moiety and 1,4-benzodiazepin-5-one moiety, was described. Both of 6- and 7-membered ring skeletons were efficiently constructed by intramolecular aza-Wittig reactions as the key reactions.