1426953-21-0

Basic information

• Product Name: [(3R,5S,7R,8R)-7-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-di-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetic acid
• Synonyms: [(3R,5S,7R,8R)-7-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-di-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetic acid
• CAS NO: 1426953-21-0
• Molecular Weight: 535.635
• Mol File: 1426953-21-0.mol
• Article Data: 0

Chemical Properties

• CAS DataBase Reference: [(3R,5S,7R,8R)-7-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-di-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: [(3R,5S,7R,8R)-7-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-di-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetic acid(1426953-21-0)
• EPA Substance Registry System: [(3R,5S,7R,8R)-7-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-di-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetic acid(1426953-21-0)

Safety Data

• Hazardous Substances Data: 1426953-21-0(Hazardous Substances Data)

Usage

Description

[(3R,5S,7R,8R)-7-(1E,3E)-5-[(2S,3S,5R,6R)-5-[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino-3,6-di-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetic acid is a complex organic compound with a unique molecular structure. It is characterized by its stereochemistry, which includes four chiral centers with specific configurations (3R, 5S, 7R, 8R). The molecule also contains multiple functional groups, such as acetyloxy, pent-2-enoyl, and 1,3-dien-1-yl, which contribute to its potential biological activities.

Uses

1. Used in Pharmaceutical Industry:
[(3R,5S,7R,8R)-7-(1E,3E)-5-[(2S,3S,5R,6R)-5-[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino-3,6-di-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetic acid is used as a lead compound for drug discovery and development. Its unique molecular structure and stereochemistry make it a promising candidate for the development of new therapeutic agents.
2. Used in Anticancer Applications:
[(3R,5S,7R,8R)-7-(1E,3E)-5-[(2S,3S,5R,6R)-5-[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino-3,6-di-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetic acid may be employed as an anticancer agent, particularly against various types of human cancer cell lines. Its cytotoxicity, which ranges from low nanomolar to subnanomolar levels, suggests that it could potentially inhibit tumor growth and progression.
3. Used in Drug Delivery Systems:
To enhance the bioavailability and therapeutic outcomes of [(3R,5S,7R,8R)-7-(1E,3E)-5-[(2S,3S,5R,6R)-5-[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino-3,6-di-methyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetic acid, novel drug delivery systems can be developed. These systems may involve the use of organic and metallic nanoparticles as carriers, aiming to improve the compound's delivery and efficacy against cancer cells.
4. Used in Research and Development:
The compound's unique structure and potential biological activities make it a valuable tool for research and development in the field of medicinal chemistry. It can be used to study the mechanisms of action, target identification, and optimization of drug candidates for various therapeutic applications.

Mechanism of action

The mechanism of action (MOA) of thailanstatin A is the inhibition of spliceosome assembly. Thailanstatin A binds firmly to the SF3b subunit of the U2 snRNA sub-complex, a crucial component of the spliceosome. Since the spliceosomes of cancer cells are more active and exhibits higher mutation rates than those of normal cells, this sub-cellular component is by far the most well-established anti-tumor target in novel drug discoveries.

Synthesis

Thailanstatin A (1): To a stirred solution of epoxide 6 (4.0 mg, 0.012 mmol, 1.0 equiv) and boronate 5 (5.8 mg, 13 μmol, 1.1 equiv) in rigorously degassed (freeze-pump-thaw technique3) 3:1:1 1,4-dioxane/MeCN/H2O (0.64 mL,) at 25°C. was added tripotassium phosphate monohydrate (2.8 mg, 0.012 mmol, 1.0 equiv) followed by Pd(dppf)Cl2.CH2Cl2 (0.1 mg, 0.125 μmol, 0.025 equiv). After 10 min, the reaction mixture was neutralized with phosphate buffer (NaH2PO4, 1.0 M, 2.5 mL), filtered through a layer of Celite, and rinsed thoroughly with ethyl acetate (20 mL). Then the organic layer was dried with anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was purified by reversed-phase HPLC (C18, φ19150 mm, Atlantis, 40→50% aqueous MeCN containing 0.03% TFA) to afford thailanstatin A (1) (ca. 3.0 mg, 6.0 μmol, 52%) as a white foam.

Downstream Products

• 1609106-72-0 (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-7-{2-[(trans-4-aminocyclohexyl)amino]-2-oxoethyl}-4-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl acetate 
• 1609106-00-4 pentafluorophenyl [(3R,5S,7R,8R)-7-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-dimethyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetate 
• 1609107-19-8 (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-7-{2-[(4-{[({4-[(N-{6-[(bromoacetyl)amino]hexanoyl}glycyl)amino]benzyl}oxy)carbonyl]amino}benzyl)amino]-2-oxoethyl}-4-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl acetate 
• 1609107-56-3 (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-4-hydroxy-7-{2-[(trans-4-hydroxycyclohexyl)amino]-2-oxoethyl}-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl acetate 
• 1609106-08-2 (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-7-{2-[(4-aminobenzyl)amino]-2-oxoethyl}-4-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl acetate 
• 1609108-85-1 (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-7-{2-[(4-carbamoylbenzyl)amino]-2-oxoethyl}-4-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl acetate 
• 1609108-98-6 (1S,5R)-5-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-dimethyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-1,5-anhydro-3-C-(chloromethyl)-2-deoxy-1-[2-oxo-2-(pentafluorophenoxy)ethyl]-D-erythro-pentitol 
• 1609106-19-5 4-{4-[(1E)-1-(2-{[(3R,5S,7R,8R)-7-{(1E,3E)-5-[(2S,3S,5R,6R)-5-{[(2Z,4S)-4-(acetyloxy)pent-2-enoyl]amino}-3,6-dimethyltetrahydro-2H-pyran-2-yl]-3-methylpenta-1,3-dien-1-yl}-8-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]acetyl}hydrazinylidene)ethyl]phenoxy}butanoic acid 
• 1609106-20-8 (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,4R,5R,7S)-7-(2-{(2E)-2-[1-(4-{4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutoxy}phenyl)ethylidene]hydrazinyl}-2-oxoethyl)-4-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl acetate 
• 1609108-86-2 (2S,3Z)-5-{[(2R,3R,5S,6S)-6-{(2E,4E)-5-[(3R,5R,7S)-7-{2-[(4-carbamoylphenyl)amino]-2-oxoethyl}-4-hydroxy-1,6-dioxaspiro[2.5]oct-5-yl]-3-methylpenta-2,4-dien-1-yl}-2,5-dimethyltetrahydro-2H-pyran-3-yl]amino}-5-oxopent-3-en-2-yl acetate