CYLINDROSPERMOPSIN

Base Information

• Chemical Name: CYLINDROSPERMOPSIN
• CAS No.: 143545-90-8
• Molecular Formula: C₁₅H₂₁N₅O₇S
• Molecular Weight: 415.427
• Mol file: 143545-90-8.mol

Synonyms:2,4(1H,3H)-Pyrimidinedione,6-[hydroxy[2,2a,3,4,5,5a,6,7-octahydro-3-methyl-4-(sulfooxy)-1H-1,8,8b-triazaacenaphthylen-7-yl]methyl]-,[2aS-[2aa,3a,4a,5aa,7b(S*)]]-; 1H-1,8,8b-Triazaacenaphthylene,2,4(1H,3H)-pyrimidinedione deriv.; Cylindrospermopsin; Cylindrospermopsine

Chemical Property of CYLINDROSPERMOPSIN

Chemical Property:

• Refractive Index: 1.6460 (estimate)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 185.56000
• Density: 2.03g/cm³
• LogP: -1.12180
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble

Purity/Quality:

99% ^*data from raw suppliers

Cylindrospermopsin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Cylindrospermopsin, a tricyclic uracil derivative, is a cyanobacterial toxin that was first discovered in an algal bloom contaminating a local drinking supply on Palm Island in Queensland, Australia after an outbreak of a mysterious disease. Cylindrospermopsin targets protein and glutathione synthesis in hepatocytes (IC50s = 1.3 and 2.4 μM, respectively), leading to cell death. It has been shown to inhibit the activity of the uridine monophosphate synthase complex with a Ki value of 10 μM. Cylindrospermopsin is genotoxic, inducing DNA damage as evidenced by double strand breaks and reducing cell viability in HepG2 cells at 0.1-0.5 μg/ml.
• Uses: Cylindrospermopsin is a cyanotoxin produced by cyanobacterial species and found in many bodies of water.

Technology Process of CYLINDROSPERMOPSIN

There total 31 articles about CYLINDROSPERMOPSIN 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: 76.0%

C15H21N4(15)NO4*C2HF3O2 → cylindrospermopsin (265652-18-4,143545-90-8) + cylindrospermopsine (143545-90-8)

Guidance literature:

With sulfur trioxide pyridine complex; In N,N-dimethyl-formamide; at 0 - 23 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.8b03071

Reference yield: 76.0%

C15H21N4(15)NO4*C2HF3O2 → cylindrospermopsin (265652-18-4,143545-90-8) + cylindrospermopsine (143545-90-8)

Guidance literature:

With sulfur trioxide pyridine complex; In N,N-dimethyl-formamide; at 0 - 23 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jacs.8b03071

Reference yield: 63.0%

pyridine (110-86-1) + 6-[(S)-Hydroxy-((2aS,3R,4S,5aS,7R)-4-hydroxy-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triaza-acenaphthylen-7-yl)-methyl]-1H-pyrimidine-2,4-dione; hydrochloride → cylindrospermopsin (265652-18-4,143545-90-8) + Sulfuric acid mono-{(2aS,3R,4S,5aS,7R)-7-[(S)-(2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-sulfooxy-methyl]-3-methyl-2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triaza-acenaphthylen-4-yl} ester; compound with pyridine

Guidance literature:

With sulfur trioxide; sodium sulfate; In N,N-dimethyl-formamide; at 24 ℃; for 0.5h;

DOI:10.1021/jo0486387

upstream raw materials:

pyridine

(3S,4R)-5-(4-bromobenzyloxy)-4-hydroxy-3-methylpent-1-ene

(3S,4S)-4-amino-5-(4-bromobenzyloxy)-3-methylpent-1-ene

(3S,4S)-5-(4-bromobenzyloxy)-4-hydroxylamino-3-methylpent-1-ene

Refernces

• 1、 Looper, Ryan E.,Runnegar, Maria T.C.,Williams, Robert M.. "Syntheses of the cylindrospermopsin alkaloids". . p. 4549 - 4562. Retrieved 2007/10/03.