1668-07-1

Usage

Uses

Used in Pharmaceutical Industry:
(3R)-2,3-Dihydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3α,10aα-epidithiopyrazino[1,2-a]indole-1,4-dione is used as a pharmaceutical compound for its potential biological activity. (3R)-2,3-Dihydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3α,10aα-epidithiopyrazino[1,2-a]indole-1,4-dione's unique structure and functional groups may contribute to its interaction with biological targets, offering opportunities for the development of new drugs and therapies.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (3R)-2,3-Dihydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-10H-3α,10aα-epidithiopyrazino[1,2-a]indole-1,4-dione serves as a valuable target for synthetic studies. Its chemical properties and potential reactivity make it an interesting subject for exploring novel synthetic pathways and developing new chemical entities with potential therapeutic applications.

InChI:InChI=1/C13H12N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,16-17H,5-6H2,1H3/t12?,13-/m1/s1

Upstream product

• 67-99-2 gliotoxin 
• 79247-67-9 C₂₁H₂₀N₂O₅S₂ 
• 79247-67-9 C₂₁H₂₀N₂O₅S₂ 
• 5625-52-5 1-methylpiperazin-2,5-dione 
• 50627-31-1 2-iodo-3-methoxybenzoic acid 
• 50627-32-2 3-methoxy-2-(4-methyl-2,5-dioxo-piperazin-1-yl)-benzoic acid methyl ester 
• 79247-64-6 C₂₁H₂₀N₂O₄S₂ 
• 79247-66-8 C₂₉H₂₈N₂O₅S₂ 
• 79247-66-8 C₂₉H₂₈N₂O₅S₂ 
• 49593-04-6 (1R,3S,5R)-6-(2-Chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione 
• 49593-04-6 (1R,3R,5R)-6-(2-Chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione 
• 79247-65-7 (1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione 
• 50627-34-4 3-methoxy-2-[3ξ-(4-methoxy-phenyl)-8-methyl-7,9-dioxo-2,4-dithia-6,8-diaza-bicyclo[3.2.2]non-6-yl]-benzoic acid methyl ester 
• 79247-64-6 C₂₁H₂₀N₂O₄S₂ 

Relevant academic research and scientific papers

The Biosynthetic Incorporation of Phenylalanine into Gliotoxin

When mixtures of DL--m-tyrosine and DL-phenylalanine were fed to cultures of Gliocladium deliquescens good incorporation (4.9 and 1.6percent in separate experiments) of (14)C and negligible incorporation (ca. 0.04percent) of (3)H into the derived gliotoxin (2) was observed.Incorporation of DL--, DL--, and L--phenylalanine into gliotoxin occured without loss of tritium.Degradation of the gliotoxin gave, in each case, bis(anhydro-dethio)gliotoxin (3) and dehydrogliotoxin (4) having a tritium content indicating that the incorporation of phenylalanine had occured without migration of tritium.These results, taken together, show that neither m-tyrosine (3'-hydroxyphenylalanine) nor any other hydroxybenzene derivative can be an obligatory intermediate on the biosynthetic pathway from phenylalanine to gliotoxin.The possible involvement of arene oxides in gliotoxin biosyhthesis is discussed.

TOTAL SYNTHESIS OF GLIOTOXIN, DEHYDROGLIOTOXIN AND HYALODENDRIN

Two general methods, Method A and Method B in Scheme 19, to synthesize epidithiapiperazinediones, are described.A total synthesis of racemic and optically active gliotoxin (1) and of racemic dehydrogliotoxin (53) was achieved by using Method A, whereas a total synthesis of racemic hyalodendrin (52) was completed by using Method B.