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
• Description: Toyocamycin (606-58-6) is an adenosine analog which inhibits ribozyme self cleavage in mammalian cells, EC50?= 0.4 μM (for expression of a luciferase reporter).1?A potent inhibitor of ER stress-induced XBP1 mRNA splicing.2?It suppresses thapsigargin-, tunicamycin- and 2-deoxyglucose-induced XBP1 mRNA splicing in HeLa cells without affecting ATF6 and PERK activation. Although unable to inhibit IRE1α phosphorylation, toyocamycin prevented IRE1α-induced XBP1 mRNA cleavage in vitro.?It inhibits not only ER stress-induced but also constitutive activation of XBP1 expression in multiple myeloma cell lines as well as in primary patient samples.2?Displays synergistic effects with bortezomib. Toyocamycin inhibits unfolded protein response and induces apoptosis in pancreatic cancer cells.3
• Uses: Toyocamycin is a pyrrolopyrimidine nucleoside isolated from Streptomyces toyocaensis in 1956. Toyocamycin, like other members of pyrrolopyrimidine class, is an adenosine nucleotide antimetabolite, with a broad spectrum of action against bacteria, fungi, protozoans and mammalian cell lines. Toyocamycin is a natural adenosine analog first isolated from Streptomyces and shown in early studies to be cytotoxic to bacteria, fungi, and cancer cells and to have antiviral activities. Toyocamycin prevents IRE1α-induced mRNA cleavage (IC50 = 80 nM) and inhibits constitutive activation of XBP1 in multiple myeloma cell lines. It is used to study IRE1α action in the endoplasmic reticulum stress response, particularly in the context of cancer. It also inhibits phosphatidylinositol kinase in vitro (IC50 = 3.3 μg/ml), but not in cells, and blocks the ribosomal RNA-processing kinase Rio1 (IC50 = ~30 nM).[Cayman Chemical] Toyocamycin Improves antibiotic production and silent gene activation in streptomyces diastatochromogenes by ribosome engineering, Preparation of tricyclic chromenone-based inhibitors of IRE-1 RNase activity.

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:

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

4-amino-3-oxy-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

3,4-dihydro-4-oxo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile

5-cyano-2,4-dichloro-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine

Refernces

• 1、 Leonard, Peter,Ingale, Sachin A.,Ding, Ping,Ming, Xin,Seela, Frank. "Studies on the glycosylation of pyrrolo[2,3-d] pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl -β-D-ribofuranose: The formation of regioisomers during toyocamycin and 7-deazainosine syntheses". experimental part. p. 678 - 694. Retrieved 2010/08/06.
• 2、 Porcari, Anthony R.,Townsend, Leroy B.. "Total synthesis of the naturally occurring antibiotic toyocamycin using new and improved synthetic procedures". . p. 153 - 159. Retrieved 2007/10/03.