210644-32-9

Basic information

• Product Name: futalosine
• Synonyms: futalosine;3-[1,5,6-Trideoxy-1-(1,6-dihydro-6-oxo-9H-purin-9-yl)-β-D-ribo-heptofuranuronoyl]benzoic Acid
• CAS NO: 210644-32-9
• Molecular Formula: C₁₉H₁₈N₄O₇
• Molecular Weight: 414.36882
• Product Categories: Aromatics;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Aromatics, Nucleotides, Bases & Related Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 210644-32-9.mol

Chemical Properties

• Boiling Point: 890.2±65.0 °C(Predicted)
• Appearance: /
• Density: 1.73±0.1 g/cm3(Predicted)
• PKA: 3.85±0.10(Predicted)
• CAS DataBase Reference: futalosine(CAS DataBase Reference)
• NIST Chemistry Reference: futalosine(210644-32-9)
• EPA Substance Registry System: futalosine(210644-32-9)

Safety Data

• Hazardous Substances Data: 210644-32-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Futalosine is used as an antibiotic and cancer inhibitor for its ability to target and inhibit the growth of cancer cells. Its unique nucleoside analog structure allows it to interfere with essential cellular processes in cancer cells, leading to their inhibition or destruction.
Used in Anticancer Applications:
Futalosine is employed as an anticancer agent, particularly in the treatment of various types of cancer. Its mode of action involves targeting specific cellular pathways and processes, making it a promising candidate for cancer therapy.
Used in Drug Development:
Futalosine's unique properties also make it a valuable compound in the development of new drugs and therapies. Its potential as an antibiotic and cancer inhibitor can be further explored and optimized through drug development processes, potentially leading to the creation of more effective treatments for various diseases.

Upstream product

• 210424-87-6 futalosine methyl ester 

Relevant articles and documents

Deamination of 6-aminodeoxyfutalosine in menaquinone biosynthesis by distantly related enzymes

Proteins of unknown function belonging to cog1816 and cog0402 were characterized. Sav2595 from Steptomyces avermitilis MA-4680, Acel0264 from Acidothermus cellulolyticus 11B, Nis0429 from Nitratiruptor sp. SB155-2 and Dr0824 from Deinococcus radiodurans R1 were cloned, purified, and their substrate profiles determined. These enzymes were previously incorrectly annotated as adenosine deaminases or chlorohydrolases. It was shown here that these enzymes actually deaminate 6-aminodeoxyfutalosine. The deamination of 6-aminodeoxyfutalosine is part of an alternative menaquinone biosynthetic pathway that involves the formation of futalosine. 6-Aminodeoxyfutalosine is deaminated by these enzymes with catalytic efficiencies greater than 10 5 M-1 s-1, Km values of 0.9-6.0 μM, and kcat values of 1.2-8.6 s-1. Adenosine, 2′-deoxyadenosine, thiomethyladenosine, and S-adenosylhomocysteine are deaminated at least an order of magnitude slower than 6-aminodeoxyfutalosine. The crystal structure of Nis0429 was determined and the substrate, 6-aminodeoxyfutalosine, was positioned in the active site on the basis of the presence of adventitiously bound benzoic acid. In this model, Ser-145 interacts with the carboxylate moiety of the substrate. The structure of Dr0824 was also determined, but a collapsed active site pocket prevented docking of substrates. A computational model of Sav2595 was built on the basis of the crystal structure of adenosine deaminase and substrates were docked. The model predicted a conserved arginine after β-strand 1 to be partially responsible for the substrate specificity of Sav2595.

An efficient synthesis of futalosine

Futalosine is a naturally occurring nucleoside comprised of an inosine core with a 3-carboxyphenyl methylene ketone functionality replacing the C-5′ hydroxyl. Recent studies have shown that it is a key intermediate in an alternative biosynthetic pathway that generates menaquinone in a variety of bacterial species. Here we report the first synthesis of futalosine in seven steps from inosine in an overall 17% yield. This work will enable further studies on menaquinone biosynthesis in pathogenic bacteria.