142382-42-1

Basic information

• Product Name: glyantrypine
• Synonyms: glyantrypine
• CAS NO: 142382-42-1
• Molecular Formula: C20H16 N4 O2
• Molecular Weight: 344.37
• Mol File: 142382-42-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.48g/cm³
• Refractive Index: 1.777
• CAS DataBase Reference: glyantrypine(CAS DataBase Reference)
• NIST Chemistry Reference: glyantrypine(142382-42-1)
• EPA Substance Registry System: glyantrypine(142382-42-1)

Safety Data

• Hazardous Substances Data: 142382-42-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H16N4O2/c25-19-17(9-12-10-21-15-7-3-1-5-13(12)15)24-18(11-22-19)23-16-8-4-2-6-14(16)20(24)26/h1-8,10,17,21H,9,11H2,(H,22,25)

Upstream product

• 4530-20-5 BOC-glycine 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 118-92-3 anthranilic acid 
• 2279-15-4 N-(benzyloxycarbonyl)-D-tryptophan 
• 264236-34-2 ethyl D-tryptophanylglycinate 
• 205042-94-0 N-(2-aminobenzoyl)-D-tryptophan methyl ester 
• 118-48-9 isatoic anhydride 
• 374114-83-7 2-(2-tert-butoxycarbonylamino-acetylamino)-3-(1H-indol-3-yl)-propionic acid methyl ester 
• 4299-70-1 D-Tryptophan methyl ester 
• 7451-73-2 c-(D-Trp-Gly) 
• 34897-85-3 o-azidobenzoyl chloride 
• 374114-79-1 (6R)-1-(o-Azidobenzoyl)-6-(3-indolylmethyl)-2,5-piperazinedione 
• 262590-37-4 N-{2-[(S)-1-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-aminoethyl]-4H-3,1-benzoxazin-4-ylidene}-D-tryptophan methyl ester 
• 264236-32-0 (4R)-2-acetyl-4-(1-acetyl-3-indolylmethyl)-1,2,3,4-tetrahydro-5H-pyrazino[2,1-b]quinazoline-3,6-dione 

Relevant articles and documents

Enzymatic processing of fumiquinazoline F: A tandem oxidative-acylation strategy for the generation of multicyclic scaffolds in fungal indole alkaloid biosynthesis

Aspergillus fumigatus Af293 is a known producer of quinazoline natural products, including the antitumor fumiquinazolines, of which the simplest member is fumiquinazoline F (FQF) with a 6-6-6 tricyclic core derived from anthranilic acid, tryptophan, and alanine. FQF is the proposed biological precursor to fumiquinazoline A (FQA) in which the pendant indole side chain has been modified via oxidative coupling of an additional molecule of alanine, yielding a fused 6-5-5 imidazoindolone. We recently identified fungal anthranilate-activating nonribosomal peptide synthetase (NRPS) domains through bioinformatics approaches. One domain previously identified is part of the trimodular NRPS Af12080, which we predict is responsible for FQF formation. We now show that two adjacent A. fumigatus ORFs, a monomodular NRPS Af12050 and a flavoprotein Af12060, are necessary and sufficient to convert FQF to FQA. Af12060 oxidizes the 2′,3′-double bond of the indole side chain of FQF, and the three-domain NRPS Af12050 activates l-Ala as the adenylate, installs it as the pantetheinyl thioester on its carrier protein domain, and acylates the oxidized indole for subsequent intramolecular cyclization to create the 6-5-5 imidazolindolone of FQA. This work provides experimental validation of the fumiquinazoline biosynthetic cluster of A. fumigatus Af293 and describes an oxidative annulation biosynthetic strategy likely shared among several classes of polycyclic fungal alkaloids.

Regioselective N-acylation of 3-arylmethylpiperazine-2,5-diones: Short synthesis of (-)-glyantrypine and (-)-fumiquinazoline F

The folded conformation of the 3-arylmethyl substituent in 2,5-bis-O-trimethylsilyl-3,6-dihydropyrazines derived from the corresponding piperazine-2,5-diones, shields the N(1)-position allowing monoacylation at the neighbouring nitrogen atom. This regioselectivity was used to develop a four-step total synthesis of (-)-glyantrypine and (-)-fumiquinazoline F starting from D-tryptophan methyl ester.

Total synthesis of the fumiquinazoline alkaloids: Solution-phase studies

Biomimetic total syntheses of glyantrypine, fumiquinazoline F, fumiquinazoline G, and fiscalin B were achieved in four steps from tryptophan methyl ester. In the key step, the anthranilamide residue in a linear tripeptide is dehydrated to a benzoxazine by reaction with triphenylphosphine, iodine, and a tertiary amine. The benzoxazines subsequently undergo rearrangement to the natural products via an amidine intermediate. This dehydrative oxazine to quinazoline route is applicable to a broad range of N-acylanthranilamides, including sterically hindered cases.