350791-64-9

Usage

Uses

Used in Pharmaceutical Industry:
Apratoxin A is used as a pharmaceutical compound for its potential therapeutic properties. Its unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Cancer Research:
In cancer research, Apratoxin A is used as a tool to study the mechanisms of cell growth and proliferation. Its ability to target specific cellular pathways may provide insights into the development of novel cancer treatments.
Used in Drug Delivery Systems:
Similar to gallotannin, Apratoxin A can also be employed in drug delivery systems to improve its bioavailability and therapeutic outcomes. By incorporating Apratoxin A into various organic and metallic nanoparticles, researchers can enhance its delivery to target cells and tissues, potentially increasing its efficacy in treating specific conditions.
Used in Chemical Synthesis:
Due to its unique cyclodepsipeptide skeleton and functional groups, Apratoxin A can be used as a starting material or intermediate in the synthesis of other bioactive compounds. This application can lead to the development of new drugs with improved properties and applications.

InChI:InChI=1/C45H69N5O8S/c1-13-27(3)38-43(55)50-20-14-15-35(50)44(56)58-37(45(7,8)9)22-26(2)21-36(51)29(5)40-46-32(25-59-40)23-28(4)39(52)47-34(24-31-16-18-33(57-12)19-17-31)42(54)48(10)30(6)41(53)49(38)11/h16-19,23,26-27,29-30,32,34-38,51H,13-15,20-22,24-25H2,1-12H3,(H,47,52)/b28-23+/t26-,27-,29-,30-,32-,34-,35-,36-,37-,38-/m0/s1

Upstream product

• 582321-82-2 C₆₅H₁₀₄N₄O₁₄SSi 
• 582321-66-2 C₅₇H₉₅N₇O₁₂SSi 
• 582321-84-4 C₅₇H₉₅N₇O₁₂SSi 
• 582321-83-3 C₅₇H₉₆N₄O₁₃SSi 
• 582321-86-6 C₅₂H₈₇N₅O₉SSi 
• 582321-87-7 pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-3-methyl-5-triethylsilanyloxy-heptyl ester 
• 582321-79-7 (2S,3S)-2-[((S)-2-{[(S)-2-[(E)-(R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-pent-2-enoylamino]-3-(4-methoxy-phenyl)-propionyl]-methyl-amino}-propionyl)-methyl-amino]-3-methyl-pentanoic acid methyl ester 
• 582321-81-1 (2S,3S)-2-[((S)-2-{[(S)-2-[(E)-(R)-5-Acetylsulfanyl-4-(4-methoxy-benzyloxy)-2-methyl-pent-2-enoylamino]-3-(4-methoxy-phenyl)-propionyl]-methyl-amino}-propionyl)-methyl-amino]-3-methyl-pentanoic acid methyl ester 
• 582321-67-3 (2S,3S)-2-[((S)-2-{[(S)-2-[(E)-(R)-5-Mercapto-4-(4-methoxy-benzyloxy)-2-methyl-pent-2-enoylamino]-3-(4-methoxy-phenyl)-propionyl]-methyl-amino}-propionyl)-methyl-amino]-3-methyl-pentanoic acid methyl ester 
• 582321-74-2 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-((1S,3S,5S,6S,8R)-8-benzoyloxy-1-tert-butyl-5-hydroxy-3,6-dimethyl-7-oxo-nonyl) ester 1-tert-butyl ester 
• 582321-71-9 pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[1-tert-butyl-5-(tert-butyl-dimethyl-silanyloxy)-3-methyl-pentyl] ester 
• 582321-78-6 (2E,4R)-2-methyl-4-(p-methoxybenzyl)oxy-5-(t-butyldimethylsilyl)oxypent-2-enoic acid 
• 582321-90-2 methyl (2E,4R)-2-methyl-4-(p-methoxybenzyl)oxy-5-(t-butyldimethylsilyl)oxypent-2-enoate 
• 582321-73-1 pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(1-tert-butyl-3-methyl-5-oxo-pentyl) ester 

Relevant academic research and scientific papers

Total synthesis of apratoxin A and B using Matteson's homologation approach

Apratoxin A and B, two members of an interesting class of marine cyclodepsipeptides are synthesized in a straightforward mannerviaMatteson homologation. Starting from a chiral boronic ester, the polyketide fragment of the apratoxins was obtainedviafive su

Total synthesis of (-)-apratoxin A, 34-epimer, and its oxazoline analogue

A concise and convergent total synthesis of the highly cytotoxic marine natural product apratoxin A is accomplished by an 18-step linear sequence. The high sensitivity of the thiazoline, bearing an adjacent β-hydroxyl group at the C35-position, results in

Total synthesis of the cyclodepsipeptide apratoxin A and its analogues and assessment of their biological activities

A novel total synthesis of apratoxin A is described, with key steps including the assembly of its ketide segment through a D-proline-catalyzed direct aldol reaction and Oppolzer's anti aldol reaction and the preparation of its thiazoline unit in a biomimetic synthesis. An oxazoline analogue of apratoxin A has also been elaborated by a similar approach. This compound has a potency against HeLa cell proliferation only slightly lower than that of apratoxin A, whilst a C(40)-demethylated oxazoline analogue of apratoxin A displays a much lower cytotoxicity and the C(37)-epimer and C(37) demethylation prod uct of this new analogue are inactive. These results suggest that the two methyl groups at C(37) and C(40) and the stereochemistry at C(37) are essential for the potent cellular activity of the oxazoline analogue of apratoxin A. Further biological analysis revealed that both synthetic apratoxin A and its oxazoline analogue inhibited cell proliferation by causing cell cycle arrest in the G1 phase.

Total synthesis of apratoxin A

We have achieved a total synthesis of apratoxin A in which thiazoline formation was accomplished from the moCys containing amide 4 using PPh 3(O)/Tf2O. Deprotection of the Troc and allyl ester in 17, coupling with tripeptide 3, and d

Total synthesis of apratoxin A

Apratoxin A, a cyclodepsipeptide isolated from cyanobacterial Lyngbya spp, has been synthesized. The total synthesis features stereocontrolled access to the novel polyketide and the late-stage installation of the sensitive 2,4-disubstituted thiazoline moi