128656-25-7

Upstream product

• 16666-80-1 triphenylphosphonio-1-methylethanide 
• 23110-15-8 fumagillin 
• 132746-88-4 Fumaginone 
• 851764-31-3 (R)-4-hydroxy-1,4-dioxa-spiro[4.5]decan-8-one 
• 877052-52-3 4-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-cyclohex-2-enone 
• 877052-59-0 (3R,4S,5S)-5-Hydroxy-4-[(2R,3R)-2-methyl-3-(3-methyl-but-2-enyl)-oxiranyl]-1-oxa-spiro[2.5]octan-6-one 
• 877052-51-2 (7R,8R)-7,8-Bis-trimethylsilanyloxy-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde 
• 877052-54-5 (2S,3S,4R)-3-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-2,4-dihydroxy-4-hydroxymethyl-cyclohexanone 
• 877052-50-1 (7R,8S)-7,8-Bis-trimethylsilanyloxy-1,4-dioxa-spiro[4.5]decane-8-carbonitrile 
• 877052-53-4 (1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((E)-1,5-dimethyl-hexa-1,4-dienyl)-4-trimethylsilanyloxy-cyclohex-3-enol 
• 877052-55-6 Toluene-4-sulfonic acid (1R,2S,3S)-2-((E)-1,5-dimethyl-hexa-1,4-dienyl)-1,3-dihydroxy-4-oxo-cyclohexylmethyl ester 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 682746-13-0 (R)-7-(N-phenyl-aminooxy)-2,3-dioxa-spiro[4.5]decan-8-one 
• 192931-94-5 (3R,4S,5S,6R)-4-((E)-hexa-2,5-dien-2-yl)-5-methoxy-1-oxaspiro[2.5]octan-6-ol 

Downstream Products

• 94462-96-1 (1R)-2c-((1S,2Ξ)-1,2-epoxy-1,5-dimethyl-hexyl)-3t-methoxy-1-methyl-cyclohexane-1r,4t-diol 
• 129298-89-1 6-O-(2-carboxybenzoyl)fumagillol 
• 129299-11-2 (3R,4S,5S,6R)-4-((2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl)-5-(oxo-λ⁶-methyl)-1-oxaspiro[2.5]octan-6-yl acetylcarbamate 
• 129298-91-5 6-O-chloroacetylcarbamoylfumagillol 
• 129299-18-9 6-O-(2,4-difluorophenylcarbamoyl)fumagillol 
• 140629-84-1 6-O-benzoylfumagillol 
• 129298-94-8 6-O-phenylcarbamoylfumagillol 
• 129299-05-4 6-O-phenoxycarbonylfumagillol 
• 129299-03-2 6-O-(p-toluenesulfonyl)fumagillol 
• 129298-96-0 6-O-(3-trifluoromethylphenylcarbamoyl)fumagillol 
• 129299-13-4 6-O-benzoylcarbamoylfumagillol 
• 23110-15-8 fumagillin 
• 251111-15-6 CDK-731 

Relevant academic research and scientific papers

PRODRUG COMPOSITIONS, PRODRUG NANOPARTICLES, AND METHODS OF USE THEREOF

The present invention encompasses prodrug compositions, nanoparticles comprising one or more prodrugs, and methods of use thereof.

FUMAGILLOL DERIVATIVES

Disclosed are compounds of Formula (1), stereoisomers thereof and pharmaceutically acceptable salts of the compounds and stereoisomers, wherein R1 and R2 are defined in the specification. This disclosure also relates to materials and

Remodeling of fumagillol: Discovery of an oxygen-directed oxidative mannich reaction

An efficient, two-step construction of highly complex alkaloid-like compounds from the natural product fumagillol is described. This approach, which mimics a biosynthetic cyclase/oxidase sequence, allows for rapid and efficient structure elaboration of th

Synthesis and antiproliferative activity of ligerin and new fumagillin analogs against osteosarcoma

Ligerin (1) is a natural chlorinated merosesquiterpenoid related to fumagillin (2) exhibiting a selective antiproliferative activity against osteosarcoma cell lines and an in vivo antitumor activity in a murine model. Semisynthesis of ligerin analogs was performed in order to study the effects of the C3-spiroepoxide substitution by a halogenated moiety together with the modulation of the C6 chain. Results showed that all derivatives exhibited an in vitro antiproliferative activity against osteosarcoma cell lines and that chlorohydrin compounds were equally or more active than their spiroepoxy analogs. Among semisynthetic analogs, the parent compound 1 was the best candidate for further studies since it exhibited higher or equivalent activity compared to TNP470 (3) against SaOS2 and MG63 human osteosarcoma cells with a four times weaker toxicity against HFF2 human fibroblasts. Quantitative videomicroscopy analysis was conducted and allowed a better understanding of the mechanism of its antiproliferative activity.

Ligerin, an antiproliferative chlorinated sesquiterpenoid from a marine-derived penicillium strain

A new chlorinated sesquiterpenoid analogue of fumagillin, ligerin (1), was isolated from a marine-derived strain of Penicillium, belonging to the subgenus Penicillium, along with the known compounds penicillic acid (2), orcinol, and orsellinic acid. Chemical structures were established by an interpretation of spectroscopic data including IR, UV, and HRESIMS, together with analyses of 1D and 2D NMR spectra and X-ray analysis for the determination of the absolute configuration. Ligerin (1) displayed strong inhibitory activity against an osteosarcoma cell line. This is the first report of the isolation of a fumagillin analogue from a marine-derived Penicillium strain.

OXASPIRO [2.5] OCTANE DERIVATIVES AND ANALOGS

The invention provides oxaspiro[2.5]octane derivatives and analogs, methods for preparation thereof, intermediates thereto, pharmaceutical compositions, and uses thereof in the treatment of various disorders and conditions, such as overweight and obesity.

Antiparasitic activities of novel, orally available fumagillin analogs

Fumagillin, an irreversible inhibitor of MetAP2, has been shown to potently inhibit growth of malaria parasites in vitro. Here, we demonstrate activity of fumagillin analogs with an improved pharmacokinetic profile against malaria parasites, trypanosomes,

Carbamate analogues of fumagillin as potent, targeted inhibitors of methionine aminopeptidase-2

Inhibition of methionine aminopeptidase-2 (MetAP2) represents a novel approach to antiangiogenic therapy. We describe the synthesis and activity of fumagillin analogues that address the pharmacokinetic and safety liabilities of earlier candidates in this

Effective procedure for the oxidative cleavage of olefins by OsO4-NaIO4

Oxidative cleavage of olefins by OsO4-NaIO4 sometimes suffers from low yields due to the formation of side products. It is reported that the addition of pyrimidine can suppress the side reactions and dramatically improve the yield of

Concise enantio- and diastereoselective total syntheses of fumagillol, RK-805, FR65814, ovalicin, and 5-demethylovalicin

(Chemical Equation Presented) L-Proline-mediated α-aminoxylation is a key step in the enantio- and diastereoselective total syntheses of fumagillin, ovalicin, and related compounds (see scheme). These compounds contain a cyclohexane ring, two epoxides, an