18417-89-5

Basic information

• Product Name: SANGIVAMYCIN
• Synonyms: ski27013;NSC-65346;SANGIVAMYCIN;7-DEAZAADENOSINE-7-CARBOXAMIDE;7-DEAZA-7-CARBAMOYLADENOSINE;4-AMINO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE-5-CARBOXAMIDE;sangivamycin hydrate from streptomyces rimosus;Antibiotic BA-90912
• CAS NO: 18417-89-5
• Molecular Formula: C₁₂H₁₅N₅O₅
• Molecular Weight: 309.28
• Mol File: 18417-89-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 260°C
• Boiling Point: 449.56°C (rough estimate)
• Flash Point: 486.4°C
• Appearance: /
• Density: 1.3120 (rough estimate)
• Vapor Pressure: 3.3E-33mmHg at 25°C
• Refractive Index: 1.6500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 0.5 M HCl: complete5 mg/ml
• CAS DataBase Reference: SANGIVAMYCIN(CAS DataBase Reference)
• NIST Chemistry Reference: SANGIVAMYCIN(18417-89-5)
• EPA Substance Registry System: SANGIVAMYCIN(18417-89-5)

Safety Data

• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 36/37/39-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: UY9355000
• Hazardous Substances Data: 18417-89-5(Hazardous Substances Data)

Usage

Definition

ChEBI: A nucleoside analogue that is adenosine in which the nitrogen at position 7 is replaced by a carbamoyl-substituted carbon. It is a potent inhibitor of protein kinase C.

InChI:InChI=1/C12H15N5O5.H2O/c13-9-6-4(10(14)21)1-17(11(6)16-3-15-9)12-8(20)7(19)5(2-18)22-12;/h1,3,5,7-8,12,18-20H,2H2,(H2,14,21)(H2,13,15,16);1H2/t5-,7-,8-,12-;/m1./s1

Upstream product

• 57071-59-7 6-Aminosangivamycin 
• 73210-47-6 6-Chloro-4-amino>-5-(N-formylcarboxamido)-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 73210-46-5 5-Amino-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-v-triazino<4,5-b>pyrimido<4,5-d>pyrrol-4-one 
• 73210-48-7 5'-O-Acetyl-6-chlorosangivamycin 
• 73210-45-4 5-Amino-9-(β-D-ribofuranosyl)-v-triazino<4,5-b>pyrimido<4,5-d>pyrrol-4-one 
• 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 
• 57071-52-0 4-chloro-5-cyano-7-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 24391-41-1 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 
• 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 
• 19393-83-0 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine 
• 74098-09-2 4-amino-5-cyano-7-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine 

Downstream Products

• 20201-56-3 6-Bromosangivamycin 
• 65562-56-3 5'-deoxysangivamycin 
• 115044-82-1 4-Amino-5-carboxamido-7-(2,3-dideoxy-β-D-glycero-pentofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 115044-80-9 4-Amino-5-carboxamido-7-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl)pyrrolo<2,3-d>pyrimidine 
• 83379-32-2 5'-deoxy-5'-(phenylthio)sangivamycin 

Related news

Antiviral activities of 2′-deoxyribofuranosyl and arabinofuranosyl analogs of SANGIVAMYCIN (cas 18417-89-5) against retro- and DNA viruses09/07/2019

Eight sugar-modified pyrrolopyrimidine nucleoside analogs related to the antibiotic sangivamycin were evaluated in cell culture against herpes simplex types 1 (HSV-1) and 2 (HSV-2), cytomegalovirus (CMV), adenovirus, and visna virus. Five of the compounds were highly active against most of the v...detailed

Effect of SANGIVAMYCIN (cas 18417-89-5) and xylosyladenine on the synthesis and methylation of polysomal ribonucleic acid in Ehrlich ascites cells in vitro09/06/2019

The pyrrolopyrimidine, sangivamycin, and the adenosine analog, xylosyladenine, were examined for their effects on the synthesis and methylation of polysomal RNA in Ehrlich ascites tumor cells in vitro. The synthesis of non-polyriboadenylic acid (non-poly (A) −) and poly(A)-containing RNA was inh...detailed

Comparison between the inhibitory activities of SANGIVAMYCIN (cas 18417-89-5) and thioSANGIVAMYCIN (cas 18417-89-5) on nuclear ribonucleic acid synthesis in L1210 cells in vitro09/05/2019

The molecular effects of the pyrrolopyrimidine analogs, sangivamycin and thiosangivamycin, on RNA and DNA synthesis were examined in L1210 cells in vitro. Pretreatment of cells for 30 min with either sangivamycin or thiosangivamycin resulted in a median inhibitory dose of 1 × 10−5 M and 2 × 10...detailed

Design, synthesis and activity against human cytomegalovirus of non-phosphorylatable analogs of toyocamycin, SANGIVAMYCIN (cas 18417-89-5) and thioSANGIVAMYCIN (cas 18417-89-5)☆09/04/2019

A number of 7-alkyl 4-aminopyrrolo[2,3-dpyrimidine derivatives related to toyocamycin, sangivamycin and thiosangivamycin have been prepared and tested for their activity against human cytomegalovirus (HCMV). Only the thioamide substituted derivatives demonstrated biological activity.detailed

In vivo and enzymatic conversion of toyocamycin to SANGIVAMYCIN (cas 18417-89-5) by Streptomyces rimosus☆09/03/2019

The pyrrolopyrimidine nucleosides, toyocamycin, sangivamycin, and tubercidin are isolated from the culture filtrates of 14 species of the Streptomyces. Although earlier experiments showed that the biosynthesis of the pyrrolopyrimidine nucleosides require GTP as the common precursor, there was no...detailed

Synthesis of 2′-β-C-methyl toyocamycin and SANGIVAMYCIN (cas 18417-89-5) analogues as potential HCV inhibitors09/01/2019

Coupling reaction of 2-β-C-methyl-1,2,3,4-tetra-O-benzoyl-d-ribofuranose with 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine, followed by debromination and debenzoylation, gave the 2′-β-C-methyl toyocamycin in high yield. Based on this result, a series of 2′-β-C-methyl-4-substituted toyoca...detailed

SANGIVAMYCIN (cas 18417-89-5) induces apoptosis by suppressing Erk signaling in primary effusion lymphoma cells08/30/2019

Sangivamycin, a structural analog of adenosine and antibiotic exhibiting antitumor and antivirus activities, inhibits protein kinase C and the synthesis of both DNA and RNA. Primary effusion lymphoma (PEL) is an aggressive neoplasm caused by Kaposi’s sarcoma-associated herpesvirus (KSHV) in imm...detailed

Relevant articles and documents

Pyrrolo[2,3-d]pyrimidine nucleoside antibiotics. Total synthesis and structure of toyocamycin, unamycin B, vengicide, antibiotic E-212, and Sangivamycin (BA-90912).

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COMPOUNDS, COMPOSITIONS AND METHODS FOR TREATING VIRAL INFECTION

The present invention describes compounds of formulae I and II and methods for treating viral infection, such as Flaviviridae virus infection, including Hepatitis C infection (HCV).

Synthesis of 5'-fluoro-5'-deoxy- and 5'-amino-5'-deoxytoyocamycin and sangivamycin and some related derivatives

A series of 5'-substituted analogs of toyocamycin were prepared by condensation of silylated 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine with protected 5-azido-5-deoxy- or 5-fluoro-5-deoxyribofuranose followed by debromination and deblocking. Alternatively, 5'-azido-5'-deoxytoyocamycin was prepared by azidation of toyocamycin. Conversion of the 5-nitrile function of the toyocamycin derivatives into a carboxamide or a thiocarboxamide gave the corresponding analogs of sangivamycin or thiosangivamycin while reduction of the 5'-azido-5'-deoxy nucleosides provided 5'-amino-5'-deoxy derivatives.

2' AND 3'-KETONUCLEOSIDES AND THEIR ARABINO AND XYLO REDUCTION PRODUCTS CONVENIENT ACCESS VIA SELECTIVE PROTECTION AND OXIDATION OF RIBONUCLEOSIDES

A number of 2',5'- or 3',5'-diprotected ribonucleosides and 5'-protected 2'- or 3'-deoxy-β-D-erythro-pentofuranosyl nucleosides have been oxidized to the corresponding 3' or 2'-ketonucleoside derivatives using chromium trioxide/pyridine/acetic anhydride or dimethyl sulfoxide/acetic anhydride.Reduction of the carbonyl functions with sodium borohydride gave the inverted arabino, xylo, or deoxy-threo isomers as predominant products by attack at the less hindered α-face of the sugar ring.Parallel reductions using sodium borodeuteride corroborated the epimeric ratios by demonstrating that complete oxidation of the original hydroxyl groups had occured.The deuterium labeling also aided in making NMR spectral assignments.