Toyocamycin

Base Information

• Chemical Name: Toyocamycin
• CAS No.: 606-58-6
• Molecular Formula: C12H13 N5 O4
• Molecular Weight: 291.30
• UNII: L7995C4D7F
• DSSTox Substance ID: DTXSID801031395
• Nikkaji Number: J9.455B
• Wikidata: Q27282806
• Metabolomics Workbench ID: 112902
• ChEMBL ID: CHEMBL99668
• Mol file: 606-58-6.mol

Synonyms:Deazacyanoadenosine;Toyocamycin;Toyokamycin

Chemical Property of Toyocamycin

Chemical Property:

• Vapor Pressure: 7.93E-22mmHg at 25°C
• Melting Point: 243°; mp 239-243°
• Refractive Index: 1.7000 (estimate)
• Boiling Point: 721.1°C at 760 mmHg
• PKA: 12.31±0.70(Predicted)
• Flash Point: 389.9°C
• PSA: 150.44000
• Density: 1.91g/cm³
• LogP: -0.92212
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble0.90 - 1.10mg/mL, clear, colorless
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 291.09675391
• Heavy Atom Count: 21
• Complexity: 443

Purity/Quality:

98%, ^*data from raw suppliers

Toyocamycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C2=C(N=CN=C2N1C3C(C(C(O3)CO)O)O)N)C#N
• Isomeric SMILES: C1=C(C2=C(N=CN=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)N)C#N
• General Description: **4-Amino-5-cyano-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (Toyocamycin)** is a nucleoside antibiotic analog with demonstrated antibacterial, antiviral, and antineoplastic properties. As part of a broader class of bioactive nucleosides, it serves as a structural template for the development of synthetic isosteres, such as pyrrolo[2,1-f][1,2,4]triazine C-nucleosides, aimed at enhancing therapeutic potential. Its biological activities and structural versatility make it a valuable scaffold for antimicrobial and anticancer research.

Technology Process of Toyocamycin

There total 17 articles about Toyocamycin 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: 82.0%

4-amino-5-cyano-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine (151707-54-9) → Vengicide (606-58-6)

Guidance literature:

With methanol; ammonia; for 8h; Ambient temperature;

DOI:10.1080/15257779908043063

Reference yield: 76.4%

4-amino-5-cyano-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine (74098-09-2) → Vengicide (606-58-6)

Guidance literature:

With ammonia; at 5 ℃; for 2h;

DOI:10.1021/jo01308a025

Reference yield: 53.0%

4-chloro-5-cyano-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine (57071-52-0) → Vengicide (606-58-6)

Guidance literature:

With ammonia; at 110 ℃; for 8h;

upstream raw materials:

4-chloro-5-cyano-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

4-amino-5-cyano-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

4-Amino-5-cyan-6-brom-7-<β-D-ribofuransoyl>-7H-pyrrolo<2,3-d>pyrimidin

6-Bromosangivamycin

Downstream raw materials:

sangivamycic acid

2-amino-5-cyano-3,4-dihydro-7-β-D-ribofuranosyl-7H-pyrrolo<2,3-d>pyrimidin-4-one

sangivamycin

4-Amino-5-cyano-7-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)pyrrolo<2,3-d>pyrimidine

Refernces

Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin

10.1016/S0008-6215(01)00017-9

The research involves the synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides, which are isosteres of nucleoside antibiotics such as sangivamycin, tubercidin, and toyocamycin. These compounds have shown potential in combating bacteria, viruses, and cutaneous neoplasms. The study aimed to develop a general synthetic method for these C-nucleosides, starting from an intermediate, 6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3(2H,6H)one. The study successfully synthesized the target C-nucleosides and is currently examining their biological activities.