BIS(METHYLTHIO)GLIOTOXIN

Base Information

• Chemical Name: BIS(METHYLTHIO)GLIOTOXIN
• CAS No.: 74149-38-5
• Molecular Formula: C15H20N2O4S2
• Molecular Weight: 356.467
• Mol file: 74149-38-5.mol

Synonyms:Pyrazino[1,2-a]indole-1,4-dione,2,3,5a,6,10,10a-hexahydro-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylthio)-,[3R-(3a,5ab,6b,10aa)]-;Bisdethiobis(methylthio)gliotoxin;Dimethylgliotoxin;FR 49175;

Chemical Property of BIS(METHYLTHIO)GLIOTOXIN

Chemical Property:

• Appearance/Colour: Colorless oil
• Vapor Pressure: 8.57E-21mmHg at 25°C
• Refractive Index: 1.701
• Boiling Point: 669.6 °C at 760 mmHg
• PKA: 12.69±0.60(Predicted)
• Flash Point: 358.8 °C
• PSA: 131.68000
• Density: 1.49 g/cm³
• LogP: -0.09690
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

Bis(methylthio)gliotoxin(FR-49175) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Description: Bis(methylthio)gliotoxin is a fungal metabolite originally isolated from G. deliquescens that has diverse biological activities. It inhibits PAF- and collagen-induced platelet aggregation in rabbit platelet-rich plasma (IC50s = 8.4 and 84.2 μM, respectively) but has no effect on arachidonic acid- or ADP-induced platelet aggregation (IC50s = >400 μM). Bis(methylthio)gliotoxin inhibits growth of HCT116 colon cancer cells (IC50 = 23.56 μM). It inhibits PAF-induced bronchoconstriction in guinea pigs when administered at a dose of 0.1 mg/kg and is less toxic to mice (LD50 = >500 mg/kg) than gliotoxin . Bis(methylthio)gliotoxin has been used as a serum biomarker in patients infected with invasive aspergillosis.
• Uses: Bis(methylthio)gliotoxin (FR-49175) is an antiphagocytic metabolite.

Technology Process of BIS(METHYLTHIO)GLIOTOXIN

There total 2 articles about BIS(METHYLTHIO)GLIOTOXIN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.4%

Gliotoxin → bisdethiobis(methylthio)gliotoxin (74149-38-5)

Guidance literature:

With sodium tetrahydroborate; S-Adenosyl-L-methionine; In isopropyl alcohol; at 0 ℃; for 0.5h;

DOI:10.1021/ja5033106

Reference yield:

gliotoxin (67-99-2) + methyl iodide (74-88-4) → bisdethiobis(methylthio)gliotoxin (74149-38-5)

Guidance literature:

With pyridine; sodium tetrahydroborate; Yield given. Multistep reaction; 1.) 0 deg C, 2.) methanol, room temperature, 4 h;

DOI:10.1039/P19800000119

Reference yield:

bisdethiobis(methylthio)gliotoxin (74149-38-5) → C28H22Br2N2O6S2

Guidance literature:

Multi-step reaction with 2 steps

1: 204 mg / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CHCl₃ / 6 h / Heating

2: pyridine

With pyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In chloroform;

DOI:10.1039/P19800000119

upstream raw materials:

gliotoxin

methyl iodide