1H-Pyrrole-2,5-dione, 3-beta-D-ribofuranosyl-

Base Information

• Chemical Name: 1H-Pyrrole-2,5-dione, 3-beta-D-ribofuranosyl-
• CAS No.: 16755-07-0
• Molecular Formula: C₉H₁₁NO₆
• Molecular Weight: 229.189
• NSC Number: 93047
• Wikidata: Q104994540
• ChEMBL ID: CHEMBL1705403
• Mol file: 16755-07-0.mol

Synonyms:16755-07-0;MLS002695166;1H-Pyrrole-2,5-dione, 3-beta-D-ribofuranosyl-;3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrrole-2,5-dione;NSC93047;3-BETA-D-RIBOFURANOSYLPYRROLE-2,5-DIONE;1H-Pyrrole-2,5-dione, 3-.beta.-D-ribofuranosyl-;NSC-93047;SCHEMBL2391572;CHEMBL1705403;FFLUMYXAPXARJP-UHFFFAOYSA-N;ZINC01482170;Maleimide, 2-.beta.-D-ribofuranosyl-;Maleimide, 5-.beta.-D-ribofuranosyl-;NCGC00246900-01;NCI60_042070;SMR001561078;1H-Pyrrole-2, 3-.beta.-D-ribofuranosyl-;3-Pyrroline-2,5-dione, 3-.beta.-D-ribofuranosyl-

Chemical Property of 1H-Pyrrole-2,5-dione, 3-beta-D-ribofuranosyl-

Chemical Property:

• Vapor Pressure: 5.47E-15mmHg at 25°C
• Melting Point: 153-154°
• Refractive Index: 1.648
• Boiling Point: 562.4°Cat760mmHg
• PKA: 8.08±0.40(Predicted)
• Flash Point: 293.9°C
• PSA: 116.09000
• Density: 1.697g/cm³
• LogP: -2.62050
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 229.05863707
• Heavy Atom Count: 16
• Complexity: 365

Purity/Quality:

99% ^*data from raw suppliers

SHOWDOMYCIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC1=O)C2C(C(C(O2)CO)O)O
• General Description: 3-Beta-D-ribofuranosylpyrrole-2,5-dione, also known as Showdomycin, is a biologically active C-nucleoside exhibiting antibacterial, antitumor, and enzyme inhibitory properties. Its structure features a β-D-ribofuranosyl moiety attached to a maleimide (pyrrole-2,5-dione) core, which is critical for its activity. The compound has been the subject of structural modifications, such as the synthesis of Apioshowdomycin, where the ribosyl unit is replaced with a D-apio-β-D-furanosyl group to explore altered bioactivity. Showdomycin and its analogues are of interest due to their potential therapeutic applications and unique mechanism of action.

Technology Process of 1H-Pyrrole-2,5-dione, 3-beta-D-ribofuranosyl-

There total 80 articles about 1H-Pyrrole-2,5-dione, 3-beta-D-ribofuranosyl- 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: 95.0%

3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione (170897-53-7) → showdomycin (16755-07-0)

Guidance literature:

With trifluoroacetic acid; at 18 ℃; for 1.5h;

DOI:10.1055/s-2003-41026

Reference yield: 92.0%

showdomycin acetonide (19254-15-0) → showdomycin (16755-07-0)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 10h;

DOI:10.1246/bcsj.57.2515

Reference yield: 85.0%

3-<2,3-O-isopropylidene-5-O-(t-butyldimethylsilyl-β-D-ribofuranosyl)>maleimide (66149-72-2) → showdomycin (16755-07-0)

Guidance literature:

With trifluoroacetic acid; at 25 ℃; for 10h;

DOI:10.1246/bcsj.57.2515

upstream raw materials:

3-<2,3-O-isopropylidene-5-O-(t-butyldimethylsilyl-β-D-ribofuranosyl)>maleimide

Phenylselenyl chloride

D-ribose

2-(2,3-O-isopropylidene-5-O-trityl-β-D-ribofuranosyl)maleimide

Downstream raw materials:

3-(5-iodo-β-D-5-deoxy-ribofuranosyl)-pyrrole-2,5-dione

Refernces

Synthesis of D-Apio-β-D-furanosyl Maleimide, an Analogue of Showdomycin with Transposed Hydroxymethyl Group

10.1007/BF00807307

The research involves the synthesis of Apioshowdomycin, a C-nucleoside analogue of Showdomycin, which is an antibiotic with known antibacterial, antitumor, and enzyme inhibitory activities. The purpose of the study was to create a derivative of Showdomycin by replacing the β-D-ribosyl unit with a D-apio-β-D-furanosyl part, which involves a structural difference in the location of the hydroxymethyl group. The synthesis was achieved in eight steps, starting from 2,3-O-isopropylidene-D-apio-β-D-furanose, with an overall yield of 5%. Key chemicals used in the process included 2,3-O-isopropylidene-D-apio-β-D-furanose, acetylated and cyanide derivatives, sodium methoxide, methyl ester, and various protecting groups such as tert-butyldiphenylsilyl. The final product, Apioshowdomycin, was obtained after deprotection with aqueous trifluoroacetic acid, demonstrating a successful synthetic route to this Showdomycin analogue. The study concluded with the detailed NMR data of the synthesized compounds, confirming their structures and providing insights into the conformational changes that occurred during the synthesis.