65562-55-2

Basic information

• Product Name: 5'-deoxytoyocamycin
• Synonyms: 5'-deoxytoyocamycin;4-Amino-7-(5-deoxy-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• CAS NO: 65562-55-2
• Molecular Formula: C12H13N5O3
• Molecular Weight: 275.2633
• Mol File: 65562-55-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 644.3°Cat760mmHg
• Flash Point: 343.5°C
• Appearance: /
• Density: 1.78g/cm³
• Vapor Pressure: 1.75E-17mmHg at 25°C
• Refractive Index: 1.817
• CAS DataBase Reference: 5'-deoxytoyocamycin(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-deoxytoyocamycin(65562-55-2)
• EPA Substance Registry System: 5'-deoxytoyocamycin(65562-55-2)

Safety Data

• Hazardous Substances Data: 65562-55-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H13N5O3/c1-5-8(18)9(19)12(20-5)17-3-6(2-13)7-10(14)15-4-16-11(7)17/h3-5,8-9,12,18-19H,1H3,(H2,14,15,16)/t5-,8-,9-,12-/m1/s1

Upstream product

• 65562-54-1 4-amino-5-cyano-7-(5-chloro-5-deoxy-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 1054719-24-2 4-amino-5-cyano-7-(5-deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 37076-71-4 5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose 
• 19393-83-0 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine 
• 288388-08-9 Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(4-amino-6-bromo-5-cyano-pyrrolo[2,3-d]pyrimidin-7-yl)-5-methyl-tetrahydro-furan-3-yl ester 
• 606-58-6 Vengicide 
• 110089-43-5 2-bromo-5-(ethoxymethyleneamino)pyrrole-3,4-dicarbonitrile 
• 98130-58-6 2-amino-5-bromo-1H-pyrrole-3,4-dicarbonitrile 
• 670-54-2 ethenetetracarbonitrile 

Relevant articles and documents

An expeditious total synthesis of 50-Deoxy-toyocamycin and 50-Deoxysangivamycin

In present paper, an expeditious total synthesis of naturally occurring 50-deoxytoyocamycin and 50-deoxysangivamycin was accomplished. Because of the introduction of a benzoyl group at N-6 of 4-amino-5-cyano-6-bromo-pyrrolo[2,3-d]pyrimidine, a Vorbrüggen glycosylation with 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose afforded a completely regioselective N-9 glycosylation product, which is unambiguously confirmed by X-ray diffraction analysis. All of the involved intermediates were well characterized by various spectra.

Synthesis and cytokine modulation properties of pyrrolo[2,3.d]-4- pyrimidone nucleosides

A series of pyrrolo[2,3-d]pyrimidone nucleosides were synthesized and evaluated for their ability to enhance Type 2 cytokines and to suppress Type 1 cytokines in human T cells activated in vitro. Compounds 16b, 16c, 16d, 18c, and 19b induced substantial enhancement of IL-4 (a Type 2 cytokine) levels while three compounds (16b, 16c, and 16f) showed significant suppression of IFNγ (a Type 1 cytokine) levels. The results revealed a strict structural requirement for the nucleoside-mediated enhancement of IL- 4. Modifications of the ribofuranose moiety of the nucleosides either abolished or dramatically reduced the activity. Both the 5'-hydroxy and 5- carboxamidine are crucial for the activity. Of the few nucleoside analogues that demonstrated enhancement on Type 2 cytokine production, 7-(β-D- ribofuranosyl)pyrrolo[2,3d]-4-pyrimidone-5-carboxamidine (16c) showed a dramatic enhancement (> 200%) of IL-4 levels and a significant enhancement (36%) of IL-5 levels. Moreover, this compound showed substantial suppression of the Type 1 cytokines, IFNγ (42%), IL-2 (54%), and TNFα (55%). Similarly, compound 16b showed a substantial enhancement of IL-4 (46%) and suppression of IL-2 (35%), IFNγ (30%), and TNFα (26%). To our knowledge, these are the first nucleoside analogues that induce a Type 2 cytokine bias in T cells. The cytokine modulation property of 16c and 16b merits the therapeutic evaluation of these compounds in treating diseases in which immunopathology is associated with polarized Type 1 cytokine responses.