Thiolutin

Base Information

• Chemical Name: Thiolutin
• CAS No.: 87-11-6
• Molecular Formula: C₈H₈N₂O₂S₂
• Molecular Weight: 228.296
• Hs Code.: 29419090
• European Community (EC) Number: 635-840-2
• NSC Number: 3927
• UNII: 02C005Q20B
• DSSTox Substance ID: DTXSID0040624
• Nikkaji Number: J4.271D
• Wikipedia: Thiolutin
• Wikidata: Q7784674
• NCI Thesaurus Code: C64175
• Metabolomics Workbench ID: 46432
• ChEMBL ID: CHEMBL507026
• Mol file: 87-11-6.mol

Synonyms:acetopyrrothine;thiolutin

Chemical Property of Thiolutin

Chemical Property:

• Vapor Pressure: 2.53E-09mmHg at 25°C
• Melting Point: 273-276℃
• Refractive Index: 1.5690 (estimate)
• Boiling Point: 478.6°C at 760 mmHg
• PKA: 10.54±0.20(Predicted)
• Flash Point: 243.3°C
• PSA: 107.58000
• Density: 1.55g/cm³
• LogP: 1.64450
• Storage Temp.: −20°C
• Solubility.: DMSO: 5 mg/mL
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 228.00271985
• Heavy Atom Count: 14
• Complexity: 387

Purity/Quality:

98%,99%, ^*data from raw suppliers

Thiolutin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+,T
• Statements: 28
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1=C2C(=CSS2)N(C1=O)C
• Description: Thiolutin is a natural dithiol that reversibly inhibits bacterial and yeast RNA polymerases (IC50 = 3 μg/ml). Because of this, it can be used for the analysis of mRNA stability. Thiolutin also inhibits endothelial cell adhesion (IC50 < 1 μM) and S180 tumor-induced angiogenesis in mice by inhibiting Hsp27 interactions with cytoskeletal elements.
• Uses: Thiolutin is an antibiotic first described by Tanner and co-workers in 1950. Resurgent interest in this class of microbial metabolites was stimulated by the discovery of their selective antitumour activity. Thiolutin is a potent inhibitor of bacterial and yeast RNA polymerases, and also inhibits mannan and glucan formation in fungi. Thiolutin suppresses tumour cell-induced angiogenesis in vivo. Thiolutin is an antibiotic isolated from several strains of Streptomyces albus. Thiolutin is a natural dithiol that reversibly inhibits bacterial and yeast RNA polymerases. Thiolutin has been used as a polymerase II inhibitor:to study its effects on yeast cells to calculate transcript half-life to study its effects on transcription during germination in budding yeast to study its effects on cell adhesion in zebrafish

Technology Process of Thiolutin

There total 13 articles about Thiolutin 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: 73.0%

Methyl-6-acetamido-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo<4,3-b>pyrrol-3-carboxylat (139102-08-2) → thiolutin (87-11-6)

Guidance literature:

With lithium iodide; In pyridine; at 110 ℃; for 1h;

Reference yield: 72.0%

N-(5,6-Dihydro-5-methyl-6-oxo-2,2-diphenyl-1,3-dithiino<5,4-b>pyrrol-7-yl)acetamid (142705-66-6) → thiolutin (87-11-6)

Guidance literature:

With bromine; In dichloromethane; acetic acid; for 12h; Ambient temperature;

Reference yield:

Methyl-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo<4,3-b>pyrrol-3-carboxylat (139101-74-9) → thiolutin (87-11-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / Br₂ / acetic acid / 0.02 h / 100 °C

2: 85 percent / HNO₃ / acetic acid / 100 °C

3: 80 percent / Na₂S₂O₄ / H₂O / 2 h / Heating

4: 73 percent / LiI / pyridine / 1 h / 110 °C

With sodium dithionite; bromine; nitric acid; lithium iodide; In pyridine; water; acetic acid;

upstream raw materials:

Methyl-6-acetamido-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo<4,3-b>pyrrol-3-carboxylat

N-(5,6-Dihydro-5-methyl-6-oxo-2,2-diphenyl-1,3-dithiino<5,4-b>pyrrol-7-yl)acetamid

Methyl-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo<4,3-b>pyrrol-3-carboxylat

Methyl-6-brom-4,5-dihydro-4-methyl-5-oxo-1,2-dithiolo<4,3-b>pyrrol-3-carboxylat

Refernces