606-58-6

Basic information

• Product Name: 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE
• Synonyms: NSC 63701;NSC 99843;TOYOCAMYCIN;3-d)pyrimidine-5-carbonitrile,4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(;4-amino-5-cyano-7-(d-ribofuranosyl)-7h-pyrrolo(2,3-d)pyrimidine;4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine-5-carbonitrile;a-399-y4;ahygroscopin-b
• CAS NO: 606-58-6
• Molecular Formula: C₁₂H₁₃N₅O₄
• Molecular Weight: 291.26
• Mol File: 606-58-6.mol

Chemical Properties

• Melting Point: 243°; mp 239-243°
• Boiling Point: 433.28°C (rough estimate)
• Flash Point: 389.9°C
• Appearance: /
• Density: 1.3067 (rough estimate)
• Vapor Pressure: 7.93E-22mmHg at 25°C
• Refractive Index: 1.7000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble0.90 - 1.10mg/mL, clear, colorless
• PKA: 12.31±0.70(Predicted)
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE(606-58-6)
• EPA Substance Registry System: 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE(606-58-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 606-58-6(Hazardous Substances Data)

Usage

Uses

Used in Anticancer Applications:
Toyocamycin is used as an anticancer agent, particularly in the study of IRE1α action in the endoplasmic reticulum stress response. It prevents IRE1α-induced mRNA cleavage and inhibits the constitutive activation of XBP1 in multiple myeloma cell lines. Toyocamycin also demonstrates synergistic effects with bortezomib and induces apoptosis in pancreatic cancer cells.
Used in Antibiotic Production and Silent Gene Activation:
Toyocamycin is used to improve antibiotic production and activate silent genes in Streptomyces diastatochromogenes through ribosome engineering.
Used in Inhibiting Enzyme Activity:
Toyocamycin is used as an inhibitor of phosphatidylinositol kinase in vitro, although it does not inhibit the enzyme in cells. It also blocks the ribosomal RNA-processing kinase Rio1.
Used in Drug Delivery Systems:
While not explicitly mentioned in the provided materials, Toyocamycin's potential applications in drug delivery systems could be explored, similar to the development of drug delivery systems for gallotannin to enhance its delivery, bioavailability, and therapeutic outcomes against cancer cells.

Biochem/physiol Actions

Studies have implicated that toyocamycin blocks the replication of fowl plague virus.

References

1) Yen?et al. (2006),?Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries; RNA,?12?797 2) Ri?et al.?(2012),?Identification of Toyocamycin, an agent cytotoxic for multiple myeloma cells, as a potent inhibitor of ER stress-induced XBP1 mRNA splicing; Blood Cancer J.,?2?e79 3) Chien?et al.?(2014),?Selective inhibition of unfolded protein response induces apoptosis in pancreatic cancer cells; Oncotarget,?5?4881

InChI:InChI=1/C12H13N5O4/c13-1-5-2-17(11-7(5)10(14)15-4-16-11)12-9(20)8(19)6(3-18)21-12/h2,4,6,8-9,12,18-20H,3H2,(H2,14,15,16)/t6-,8-,9-,12-/m1/s1

Upstream product

• 13035-61-5 1,2,3,5-tetraacetylribose 
• 74112-93-9 4-amino-6-bromo-5-cyano-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 141232-17-9 6-bromo-5-cyano-4-tritylaminopyrrolo<2,3-d>pyrimidine 
• 141232-18-0 5-cyano-4-tritylaminopyrrolo<2,3-d>pyrimidine 
• 102690-94-8 2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride 
• 24391-41-1 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 
• 151707-53-8 (2R,3R,4R,5R)-2-(4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-((benzoyloxy)methyl)tetrahydrofuran-3,4-diyl dibenzoate 
• 19393-83-0 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine 
• 6974-32-9 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose 
• 151707-54-9 4-amino-5-cyano-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 20201-56-3 6-Bromosangivamycin 
• 20201-55-2 4-Amino-5-cyan-6-brom-7-<β-D-ribofuransoyl>-7H-pyrrolo<2,3-d>pyrimidin 
• 74098-09-2 4-amino-5-cyano-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 57071-52-0 4-chloro-5-cyano-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 

Downstream Products

• 115044-83-2 4-Amino-5-cyano-7-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 22242-90-6 thiosangivamycin 
• 22242-96-2 3,4-dihydro-4-oxo-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine-5-carbonitrile 
• 1256339-56-6 ((3S,4R,5R)-5-(4-amino-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl 4-nitrophenyl hydrogen phosphate 
• 20201-55-2 4-Amino-5-cyan-6-brom-7-<β-D-ribofuransoyl>-7H-pyrrolo<2,3-d>pyrimidin 
• 119483-98-6 4-amino-5-cyano-7-(3-O-methyl-5-(O-nitrophenylselenide)-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine 
• 98890-73-4 mycalisine A 
• 117175-59-4 4-amino-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carboxy-Nε-Z-L-lysine methyl ester 
• 117175-51-6 4-amino-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carboxy-L-phenylalanine methyl ester 
• 117175-52-7 4-amino-7-(β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine-5-carboxy-L-phenylalanine amide 
• 105582-76-1 3'-deoxytoyocamycin 
• 83379-31-1 3'-Deoxysangivamycin 
• 115044-81-0 2',3'-dideoxytoyocamycin 
• 65562-55-2 5'-deoxytoyocamycin 

Relevant articles and documents

New small molecule inhibitors of histone methyl transferase DOT1L with a nitrile as a non-traditional replacement for heavy halogen atoms

A number of new nucleoside derivatives are disclosed as inhibitors of DOT1L activity. SARs established that DOT1L inhibition could be achieved through incorporation of polar groups and small heterocycles at the 5-position (5, 6, 12) or by the application of alternative nitrogenous bases (18). Based on these results, CN-SAH (19) was identified as a potent and selective inhibitor of DOT1L activity where the polar 5-nitrile group was shown by crystallography to bind in the hydrophobic pocket of DOT1L. In addition, we show that a polar nitrile group can be used as a non-traditional replacement for heavy halogen atoms.

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

Glycosylation of silylated 4-amino-6-bromo-5-cyano-7H-pyrrolo[2,3-d] pyrimidine (9) with 1-O-acetyl-2,3,5-tri-O-benzoyl - d-ribofuranose (10) under "one-pot" glycosylation conditions (MeCN, TMSOTf) yielded the N-7 isomer 11 together with the N-1 compound 13 (ratio = 2:1). When the same conditions were applied to 4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine (21) the N-3 isomer 22 was the only glycosylation product formed in almost quantitative yield.

Phosphazole compounds

A class of substituted and unsubstituted nucleo-base analogs and related azoles, designated as "phosphazoles," is disclosed, certain preferred embodiments having the basic structure of STR1 Also disclosed are methods of making and using the new compounds.

Total synthesis of the naturally occurring antibiotic toyocamycin using new and improved synthetic procedures

Starting with commercially available tetracyanoethylene, we describe a more efficient and higher yielding synthesis of toyocamycin with regards to convenience, overall yield, and total reaction time than those syntheses previously reported.

A SYNTHESIS AND AN X-RAY ANALYSIS OF 2'-C-, 3'-C- AND 5'-C-METHYLSANGIVAMYCINS

3'-C-, 5'(R)-C- and 5'(S)-C-Methylsangivamycins (3-5) were synthesized by the trimethylsilyl triflate mediated coupling reaction of the methyl substituted ribose derivatives (7), (9) and (10) with the base moiety (11) and the successive functional group m