Toyocamycin
Toyocamycin structure
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Common Name | Toyocamycin | ||
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| CAS Number | 606-58-6 | Molecular Weight | 291.26300 | |
| Density | 1.91g/cm3 | Boiling Point | 721.1ºC at 760 mmHg | |
| Molecular Formula | C12H13N5O4 | Melting Point | N/A | |
| MSDS | Chinese USA | Flash Point | 389.9ºC | |
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Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin.
Carbohydr. Res. 331(1) , 77-82, (2001) Syntheses of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides are reported. Treatment of pyranulose glycoside with aminoguanidine in acetic acid gave the corresponding semicarbazone in 96% yield. The ring transformation of the semicarbazone in dioxane afforded a 5... |
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Synthesis of 2'-beta-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors.
Bioorg. Med. Chem. Lett. 15(3) , 725-7, (2005) Coupling reaction of 2-beta-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'-beta-C-methyl toyocamycin in high yield. Based on this result, a series... |
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Cell cycle arrest and cytochrome c-mediated apoptotic induction in human lung cancer A549 cells by MCS-C2, an analogue of sangivamycin.
J. Microbiol. Biotechnol. 20(2) , 433-7, (2010) In the course of our screening for novel modulators on cell cycle progression and apoptosis as anticancer drug candidates, we generated an analogue of sangivamycin, MCS-C2, designated as 4-amino-6-bromo-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide.... |
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Synthesis of carbocyclic analogs of 2',3'-dideoxysangivamycin, 2',3'-dideoxytoyocamycin, and 2',3'-dideoxytriciribine.
Nucleosides Nucleotides Nucleic Acids 20(10-11) , 1823-30, (2001) Syntheses and antiviral activity of new carbocyclic analogs of 2', 3'-dideoxysangivamycin, 2',3'-dideoxytoyocamycin and 2',3'-dideoxytriciribine is described. The key intermediate, carbocyclic 4-chloro-5-iodopyrrolopyrimidine. was synthesized in good yield vi... |
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Deciphering deazapurine biosynthesis: pathway for pyrrolopyrimidine nucleosides toyocamycin and sangivamycin.
Chem. Biol. 15(8) , 790-8, (2008) Pyrrolopyrimidine nucleosides analogs, collectively referred to as deazapurines, are an important class of structurally diverse compounds found in a wide variety of biological niches. In this report, a cluster of genes from Streptomyces rimosus (ATCC 14673) i... |
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Convergence of ubiquitylation and phosphorylation signaling in rapamycin-treated yeast cells.
Nature Methods 13 , 237-40, (2016) The target of rapamycin (TOR) kinase senses the availability of nutrients and coordinates cellular growth and proliferation with nutrient abundance. Inhibition of TOR mimics nutrient starvation and leads to the reorganization of many cellular processes, inclu... |
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Cell cycle arrest and apoptotic induction in LNCaP cells by MCS-C2, novel cyclin-dependent kinase inhibitor, through p53/p21WAF1/CIP1 pathway.
Cancer Sci. 97(5) , 430-6, (2006) The purpose of the present study was to investigate the mechanisms involved in the antiproliferative and apoptotic effects of MCS-C2, a novel analog of the pyrrolo[2,3-d]pyrimidine nucleoside toyocamycin and sangivamycin, in human prostate cancer LNCaP cells.... |
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Induction of p16/INK4a gene expression and cellular senescence by toyocamycin.
Biol. Pharm. Bull. 25(10) , 1272-6, (2002) We constructed an assay system of a luciferase reporter with p16/lNK4a gene transcriptional regulatory domain to identify p16-inducing substances, and found toyocamycin to induce gene expression from the screening of culture fluids of Streptomyces. Toyocamyci... |
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A toyocamycin analogue with the sugar moiety in a syn conformation.
Acta Crystallogr. C 65(Pt 9) , o431-4, (2009) The title compound [systematic name: 4-amino-5-cyano-1-(beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine hemihydrate], C(12)H(13)N(5)O(4).0.5H(2)O, is a regioisomer of toyocamycin with the ribofuranosyl residue attached to the pyrimidine moiety of the hetero... |
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Studies on the glycosylation of pyrrolo[2,3-d] pyrimidines with 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose: the formation of regioisomers during toyocamycin and 7-deazainosine syntheses.
Nucleosides Nucleotides Nucleic Acids 28(5) , 678-94, (2009) 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-beta-D-ribofuranose (10) under "one-pot" glycosylation conditions (MeCN, TMSOTf) yielded the N-7 isomer 11 together with the N-1 compound 13... |