53348-47-3

Basic information

• Product Name: (3R)-2,3,5aβ,6α-Tetrahydro-6β-hydroxy-3β-(hydroxymethyl)-2-methyl-10H-3α,10aα-epitetrathiopyrazino[1,2-a]indole-1,4-dione
• Synonyms: (3R)-2,3,5aβ,6α-Tetrahydro-6β-hydroxy-3β-(hydroxymethyl)-2-methyl-10H-3α,10aα-epitetrathiopyrazino[1,2-a]indole-1,4-dione;(5R)-7aβ,8-Dihydro-8β-hydroxy-5-(hydroxymethyl)-14-methyl-12H-5β,12aβ-(iminomethano)[1,2,3,4,6]tetrathiazocino[6,5-a]indole-6,13(5H)-dione;Gliotoxin G
• CAS NO: 53348-47-3
• Molecular Formula: C₁₃H₁₄N₂O₄S₄
• Molecular Weight: 390.52126
• Mol File: 53348-47-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R)-2,3,5aβ,6α-Tetrahydro-6β-hydroxy-3β-(hydroxymethyl)-2-methyl-10H-3α,10aα-epitetrathiopyrazino[1,2-a]indole-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-2,3,5aβ,6α-Tetrahydro-6β-hydroxy-3β-(hydroxymethyl)-2-methyl-10H-3α,10aα-epitetrathiopyrazino[1,2-a]indole-1,4-dione(53348-47-3)
• EPA Substance Registry System: (3R)-2,3,5aβ,6α-Tetrahydro-6β-hydroxy-3β-(hydroxymethyl)-2-methyl-10H-3α,10aα-epitetrathiopyrazino[1,2-a]indole-1,4-dione(53348-47-3)

Safety Data

• Hazardous Substances Data: 53348-47-3(Hazardous Substances Data)

Upstream product

• 1402592-74-8 C₂₅H₄₂N₂O₇Si 
• 1402592-70-4 C₁₅H₂₁NO₅ 
• 1402592-87-3 C₂₄H₄₁NO₅Si 
• 1402592-69-1 C₂₅H₄₁NO₇SSi 
• 1402592-96-4 C₂₄H₄₃NO₇Si 
• 1402592-68-0 C₁₅H₂₃NO₇ 
• 1402592-66-8 C₁₅H₂₁NO₇ 
• 1402592-65-7 C₁₅H₂₁NO₅ 
• 1402592-63-5 C₁₇H₂₅NO₇ 
• 1402592-72-6 C₁₄H₁₉NO₅ 
• 1402592-61-3 C₁₅H₂₃NO₆ 
• 144534-57-6 (2S,3aR,7aR)-3a-Hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 67-99-2 gliotoxin 

Relevant articles and documents

Synthesis and biological evaluation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines: Synthetic methodology, enantioselective total synthesis of epicoccin G, 8,8′-epi-ent-rostratin B, gliotoxin, gliotoxin G, emethallicin E, and haematocin and discovery of new antiviral and antimalarial agents

An improved sulfenylation method for the preparation of epidithio-, epitetrathio-, and bis-(methylthio)diketopiperazines from diketopiperazines has been developed. Employing NaHMDS and related bases and elemental sulfur or bis[bis(trimethylsilyl)amino]trisulfide (23) in THF, the developed method was applied to the synthesis of a series of natural and designed molecules, including epicoccin G (1), 8,8′-epi-ent-rostratin B (2), gliotoxin (3), gliotoxin G (4), emethallicin E (5), and haematocin (6). Biological screening of selected synthesized compounds led to the discovery of a number of nanomolar antipoliovirus agents (i.e., 46, 2,2′-epi-46, and 61) and several low-micromolar anti-Plasmodium falciparum lead compounds (i.e., 46, 2,2′-epi-46, 58, 61, and 1).

Partial synthesis of gliotoxin G, an epitetrathiodioxopiperazine

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