391611-36-2

Usage

Uses

Used in Pharmaceutical Industry:
SPLICEOSTATIN A is used as an anti-cancer agent for its ability to selectively target and inhibit the growth of cancer cells. It achieves this by disrupting the pre-mRNA splicing process, which is essential for gene expression in these cells.
Used in Anti-Inflammatory Treatments:
In the field of inflammatory disease treatment, SPLICEOSTATIN A is used for its demonstrated anti-inflammatory properties. This makes it a potential candidate for the development of new therapies aimed at reducing inflammation and managing inflammatory conditions.
Used in Drug Development Research:
SPLICEOSTATIN A is utilized in research settings as a tool to explore the mechanisms of pre-mRNA splicing and its role in both cancer and inflammatory processes. Its potential applications in drug development are being investigated to create novel treatments for a range of diseases where splicing regulation may be a therapeutic target.

Upstream product

• 67-56-1 methanol 
• 146478-72-0 FR 901464 
• 112980-49-1 (Z)-(S)-4-(tert-butyldimethylsilanyloxy)pent-2-enoic acid methyl ester 
• 73591-64-7 methyl 1,3-dideoxy-α-D-arabino-heptulopyranoside 
• 878673-32-6 (S,Z)-4-((tert-butyldimethylsilyl)oxy)pent-2-enoic acid 
• 882028-31-1 (S,Z)-5-(((2R,3R,5S,6S)-2,5-dimethyl-6-((E)-3-methylpenta-2,4-dien-1-yl)tetrahydro-2H-pyran-3-yl)amino)-5-oxopent-3-en-2-yl acetate 
• 133906-32-8 (-)-(S)-4-hydroxypent-2-ynoic acid 
• 310397-95-6 (S)-4-acetoxypent-2-ynoic acid 
• 310397-89-8 (Z)-(4S)-4-acetoxypent-2-enoic acid 
• 878673-42-8 Acetic acid (Z)-(S)-3-((2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-4-(tert-butyl-dimethyl-silanyloxy)-7-methoxy-7-methyl-1,6-dioxa-spiro[2.5]oct-5-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-ylcarbamoyl)-1-methyl-allyl ester 
• 391611-35-1 Acetic acid (Z)-(S)-3-{(2R,3R,5S,6S)-6-[(2E,4E)-5-((2R,3S,6S)-3-hydroxy-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl)-3-methyl-penta-2,4-dienyl]-2,5-dimethyl-tetrahydro-pyran-3-ylcarbamoyl}-1-methyl-allyl ester 

Downstream Products

• 849367-75-5 Acetic acid (Z)-(S)-3-{(2R,3R,5S,6S)-6-[(2E,4E)-5-((3R,4R,5R,7S)-7-methoxy-7-methyl-4-triethylsilanyloxy-1,6-dioxa-spiro[2.5]oct-5-yl)-3-methyl-penta-2,4-dienyl]-2,5-dimethyl-tetrahydro-pyran-3-ylcarbamoyl}-1-methyl-allyl ester 
• 849367-76-6 (Z)-(S)-4-Hydroxy-pent-2-enoic acid {(2R,3R,5S,6S)-6-[(2E,4E)-5-((3R,4R,5R,7S)-7-methoxy-7-methyl-4-triethylsilanyloxy-1,6-dioxa-spiro[2.5]oct-5-yl)-3-methyl-penta-2,4-dienyl]-2,5-dimethyl-tetrahydro-pyran-3-yl}-amide 
• 849367-78-8 7-(9H-fluoren-9-ylmethoxycarbonylamino)-heptanoic acid 3-{6-[5-(4-hydroxy-7-methoxy-7-methyl-1,6-dioxa-spiro[2.5]oct-5-yl)-3-methyl-penta-2,4-dienyl]-2,5-dimethyl-tetrahydro-pyran-3-ylcarbamoyl}-1-methyl-allyl ester 
• 849367-77-7 7-(9H-fluoren-9-ylmethoxycarbonylamino)-heptanoic acid 3-{6-[5-(7-methoxy-7-methyl-4-triethylsilanyloxy-1,6-dioxa-spiro[2.5]oct-5-yl)-3-methyl-penta-2,4-dienyl]-2,5-dimethyl-tetrahydro-pyran-3-ylcarbamoyl}-1-methyl-allyl ester 
• 849367-74-4 7-(9H-fluoren-9-ylmethoxycarbonylamino)-heptanoic acid 5-{5-[5-(4-acetoxy-pent-2-enoylamino)-3,6-dimethyl-tetrahydro-pyran-2-yl]-3-methyl-penta-1,3-dienyl}-7-methoxy-7-methyl-1,6-dioxa-spiro[2.5]oct-4-yl ester 
• 146478-72-0 FR 901464 

Relevant academic research and scientific papers

Structure-activity relationship for FR901464: A versatile method for the conversion and preparation of biologically active biotinylated probes

The structure-activity relationship for FR901464, a potent cell-cycle inhibitor, was examined by synthesizing its analogs. A versatile method for converting FR901464 was devised. This method made it possible to synthesize biologically active FR901464-biotin conjugates which could be used to isolate the binding proteins.

Enantioselective total syntheses of fr901464 and spliceostatin a and evaluation of splicing activity of key derivatives

FR901464 (1) and spliceostatin A (2) are potent inhibitors of spliceosomes. These compounds have shown remarkable anticancer activity against multiple human cancer cell lines. Herein, we describe efficient, enantioselective syntheses of FR901464, spliceostatin A, six corresponding diastereomers and an evaluation of their splicing activity. Syntheses of spliceostatin A and FR901464 were carried out in the longest linear sequence of 9 and 10 steps, respectively. To construct the highly functionalized tetrahydropyran A-ring, we utilized CBS reduction, Achmatowicz rearrangement, Michael addition, and reductive amination as key steps. The remarkable diastereoselectivity of the Michael addition was specifically demonstrated with different substrates under various reaction conditions. The side chain B was prepared from an optically active alcohol, followed by acetylation and hydrogenation over Lindlars catalyst. The other densely functionalized tetrahydropyran C-ring was derived from readily available (R)-isopropylidene glyceraldehyde through a route featuring 1,2-addition, cyclic ketalization, and regioselective epoxidation. These fragments were coupled together at a late stage through amidation and cross-metathesis in a convergent manner. Six key diastereomers were then synthesized to probe the importance of specific stereochemical features of FR901464 and spliceostatin A, with respect to their in vitro splicing activity.

Enantioselective syntheses of FR901464 and spliceostatin A: Potent inhibitors of spliceosome

Enantioselective syntheses of FR901464 and spliceostatin A, potent spliceosome inhibitors, are described. The synthesis of FR901464 has been accomplished in a convergent manner in 10 linear steps (20 total steps). The A-tetrahydropyran ring was constructed from (R)-isopropylidene glyceraldehyde. The functionalized tetrahydropyran B-ring was synthesized utilizing a Corey-Bakshi-Shibata reduction, an Achmatowicz reaction, and a stereoselective Michael addition as the key steps. Coupling of A- and B-ring fragments was accomplished via cross-metathesis.

Total synthesis of FR901464: Second generation

FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral pool, l-threonine, ethyl (S)-lactate and 2-deoxy-d-glucose as starting materials.

Synthesis of affinity nanoparticles coupled to FR901464 derivatives

The synthesis of two latex nano-particles coupled to FR901464 derivatives is described. Two FR901464 derivatives attached with an amino-alkyl group at a different position were prepared from natural occurring FR 901464. Biological activities of the two ligands were significantly different. The acylation of two amino ligands with the activated esters on latex particles smoothly proceeded to provide the corresponding latex nano-particles coupled to FR 901464 at a different position.

A synthesis of FR901464

FR901464, a potent cell cycle inhibitor, was synthesized in a convergent manner using natural chiral pool, L-threonine, ethyl (S)-lactate and 2-deoxy-D-glucose as starting materials.