129-24-8

Basic information

• Product Name: viridicatin
• Synonyms: viridicatin;2,3-Dihydroxy-4-phenylquinoline
• CAS NO: 129-24-8
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.25
• Mol File: 129-24-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 268°
• Boiling Point: 476.7°Cat760mmHg
• Flash Point: 242.1°C
• Appearance: /
• Density: 1.323g/cm³
• Vapor Pressure: 6.79E-10mmHg at 25°C
• Refractive Index: 1.677
• CAS DataBase Reference: viridicatin(CAS DataBase Reference)
• NIST Chemistry Reference: viridicatin(129-24-8)
• EPA Substance Registry System: viridicatin(129-24-8)

Safety Data

• Hazardous Substances Data: 129-24-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 129-24-8 differently. You can refer to the following data:
1. Viridicatin is a fungal metabolite produced by several species of Penicillium and formed by the rearrangement of the benzodiazepine, cyclopenin. Viridicatin exhibits potent selective activity against Mycobacterium tuberculosis, but is inactive against most other bacteria.
2. Viridicatin is a?Penicillium?metabolite active against?Mycobacterium tuberculosis. Isolated from deep-sea Penicillium griseofulvum alleviates anaphylaxis and has anti-?allergic properties.

InChI:InChI=1/C15H11NO2/c17-14-13(10-6-2-1-3-7-10)11-8-4-5-9-12(11)16-15(14)18/h1-9,17H,(H,16,18)

Upstream product

• 2835-77-0 (2-aminophenyl)(phenyl)methanone 
• 3526-43-0 N-(4-methoxybenzyl)aniline 
• 100-52-7 benzaldehyde 
• 19357-57-4 4-methyl-3'c-phenyl-(2'rN)-1H-spiro[benzo[e][1,4]diazepine-3,2'-oxirane]-2,5-dione 
• 31965-37-4 3-benzylidene-4-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione 
• 50886-63-0 (3S)-3,4-dihydro-4-methyl-3-phenylmethyl-[1,4]benzodiazepin-2,5(1H)-dione 
• 150256-42-1 2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)benzoic acid 
• 91-56-5 indole-2,3-dione 
• 118-48-9 isatoic anhydride 
• 2566-30-5 N-Methyl-L-phenylalanine 
• 14933-29-0 4-hydroxy-3-phenyl-2(1H)-quinolone 
• 28565-95-9 3-hydroxy-3-phenylquinoline-2,4(1H,3H)-dione 
• 93002-02-9 ethyl 3-hydroxy-2-oxo-1,2-dihydro-quinoline-4-carboxylate 
• 21267-23-2 ethyl diazo(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate 

Downstream Products

• 40357-47-9 3-methoxy-1-methyl-4-phenylquinolin-2(1H)-one 
• 113843-74-6 bis(4-phenyl-3-hydroxy-2-quinolone)copper 

Related news

Determination of viridicatin (cas 129-24-8) inPenicillium cyclopiumby Capillary Gas Chromatography09/28/2019

A sensitive gas chromatographic method for the determination of the quinoline alkaloid viridicatin, a fungal metabolite isolated from severalPenicilliumspecies and presumably a biogenetic precursor to naturally occurring diazepam-like 1,4-benzo-diazepines, has been developed. Prior to conversion...detailed

Viridicatol and viridicatin (cas 129-24-8) isolated from a shark-gill-derived fungus Penicilliumpolonicum AP2T1 as MMP-2 and MMP-9 inhibitors in HT1080 cells by MAPKs signaling pathway and docking studies09/27/2019

Matrix metalloproteinases (MMPs), the key enzymes in extracellular matrix degradation, seemed to increase in tumorigenesis, which has a relationship with metastasis and invasions. In this study, we investigated the MMP inhibitory effect of viridicatol and viridicatin, two compounds extracted fro...detailed

Pinacol Rearrangement of 3,4‐Dihydro‐3,4‐dihydroxyquinolin‐2(1H)‐ones: An Alternative Pathway to viridicatin (cas 129-24-8) Alkaloids and Their Analogs09/26/2019

3‐Alkyl/aryl‐3‐hydroxyquinoline‐2,4‐diones were reduced with NaBH4 to give cis‐3‐alkyl/aryl‐3,4‐dihydro‐3,4‐dihydroxyquinolin‐2(1H)‐ones. These compounds were subjected to pinacol rearrangement by treatment with concentrated H2SO4, resulting in 4‐alkyl/aryl‐3‐hydroxyquinolin‐2(1...detailed

Ring‐Expansion Reaction of Isatins with Ethyl Diazoacetate Catalyzed by Dirhodium(II)/DBU Metal‐Organic System: En Route to viridicatin (cas 129-24-8) Alkaloids09/25/2019

We present here the NHC‐dirhodium(II)/DBU‐catalyzed ring expansion reaction of isatins with ethyl diazoacetate. This new one‐pot protocol yields the ethyl 3‐hydroxy‐2(1H)‐oxoquinoline‐4‐carboxylate core, regioselectively and in good to excellent yields. A DFT mechanistic study indicates ...detailed

Relevant articles and documents

Synthesis and Mechanistic Insights of the Formation of 3-Hydroxyquinolin-2-ones including Viridicatin from 2-Chloro- N,3-diaryloxirane-2-carboxamides under Acid-Catalyzed Rearrangements

N-Benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides, easily obtained from aromatic aldehydes and anilides of dichloroacetic acid under Darzens condensation conditions, proved to be excellent starting compounds for the synthesis of 3-hydroxyindolin-2-ones, cyclohepto[b]pyrrole-2,3-diones, and 1-azaspiro[4.5]deca-3,6,9-triene-2-ones via the C(sp2)-C(sp2) bond formation in the first case and C(sp2)-C(sp3) bond formation in the second and third cases. Under optimized reaction conditions, 3-hydroxyindolin-2-ones are obtained in a one-pot process, which involves the treatment of N-benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides with CF3CO2H or AcOH/H2SO4. In the case of intramolecular cyclization, the detailed reaction channels depend strongly on the substituents present in the anilide component and in the aromatic ring of the aldehyde component of N-benzyl-2-chloro-N,3-diaryloxirane-2-carboxamides, as well as the temperature and duration of the reaction. A combined experimental and DFT mechanistic study of the formation of 1-benzyl-3-hydroxy-4-arylquinolin-2(1H)-ones showed that there are three competing reaction channels: (a) ring-closure via the ipso site, (b) ring-closure via the 1,2-Cl shift, and (c) ring-closure via the ortho site. Such mechanistic insights enabled an effective one-pot gram-scale synthesis of viridicatin from benzaldehyde and 2,2-dichloro-N-(4-methoxybenzyl)-N-phenylacetamide.

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.

Regioselective Ring Expansion of Isatins with in Situ Generated α-Aryldiazomethanes: Direct Access to Viridicatin Alkaloids

A novel efficient one-pot regioselective ring-expansion reaction of isatins with in situ generated α-aryl/heteroaryldiazomethanes for the construction of viridicatin alkaloids has been described under metal-free conditions. The utility of this protocol is further demonstrated in the synthesis of naturally occurring viridicatin, viridicatol, and substituted 3-O-methyl viridicatin and their scale up.