676324-80-4

Upstream product

• 624-64-6 trans-2-Butene 
• 676324-77-9 (3R,5S)-5-(4-methoxybenzyloxy)-3,6,6-trimethylheptanal 
• 99745-86-5 (S,S)-diisopropyl tartrate (E)-crotylboronate 
• 2746-25-0 p-Methoxybenzyl bromide 
• 67760-86-5 (3S)-2,2-dimethyl-5-hexen-3-ol 
• 531559-40-7 (4R,6S)-6-tert-butyl-4-methyltetrahydro-2H-pyran-2-one 
• 612492-41-8 (S)-tert-butyl (1-tert-butylbut-3-enyloxy)dimethylsilane 
• 612492-55-4 (S)-5,5-dimethyl-4-(tert-butyldimethylsilyloxy)hexan-2-one 
• 630-19-3 pivalaldehyde 
• 676324-75-7 (4S)-3-[(3R,5S)-5-(4-methoxybenzyloxy)-3,6,6-trimethylheptanoyl]-4-phenyloxazolidin-2-one 
• 676324-74-6 (4S)-3-[(5S)-5-(4-methoxybenzyloxy)-6,6-dimethylhept-2-enoyl]-4-phenyloxazolidin-2-one 
• 676324-78-0 (3R,5S)-5-(4-methoxybenzyloxy)-3,6,6-trimethylheptanoic acid N-methoxy-N-methylamide 
• 676324-76-8 (3S,5S)-5-(4-methoxybenzyloxy)-3,6,6-trimethylheptan-1-ol 
• 676324-73-5 (3S)-3-(para-methoxybenzyloxy)-4,4-dimethylpentanal 

Downstream Products

• 676324-81-5 (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyl-4-(tert-butyldimethylsilanyloxy)dec-1-ene 
• 676324-84-8 (2S,3S,5R,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,5,8,8-tetramethyl-nonanal 
• 1177263-65-8 (3R,4S,6S,8S)-8-(4-methoxybenzyloxy)-3,6,9,9-tetramethyldec-1-en-4-yl 2,2,2-trichloroethyl carbonate 
• 1334149-95-9 apratoxin S₅ 
• 1334149-94-8 apratoxin S₄ 
• 1334149-96-0 apratoxin S₆ 
• 1333536-76-7 C₆₂H₈₅N₅O₁₁S 
• 1333536-77-8 C₆₀H₇₉N₅O₁₁S 
• 1333536-78-9 C₆₂H₈₃N₅O₁₁S 
• 1333536-80-3 C₆₂H₈₅N₅O₁₁S 
• 1242905-85-6 apratoxin F 

Relevant academic research and scientific papers

MACROCYCLIC THERAPEUTIC AGENTS, METHODS OF MANUFACTURE, AND METHODS OF TREATMENT

The instant invention describes macrocyclic compounds having therapeutic activity, and the mechanism and methods of treating disorders such as autoimmune diseases, inflammation, and cancer, tumors and cell proliferation related disorders.

Improved total synthesis and biological evaluation of potent apratoxin S4 based anticancer agents with differential stability and further enhanced activity

Apratoxins are cytotoxic natural products originally isolated from marine cyanobacteria that act by preventing cotranslational translocation early in the secretory pathway to downregulate receptor levels and inhibit growth factor secretion, leading to pot

Systematic chemical mutagenesis identifies a potent novel apratoxin A/E hybrid with improved in vivo antitumor activity

Apratoxins are cytotoxic marine natural products that prevent cotranslational translocation early in the secretory pathway. We showed that apratoxins downregulate receptors and growth factor ligands, giving a one"two punch to cancer cells, particularly those that rely on autocrine loops. Through total synthesis, we tested the effects of amino acid substitutions, including alanine scanning, on the downregulation of receptor tyrosine kinases and vascular endothelial growth factor A (VEGF-A) and probed the stereospecificity of target engagement by epimerization of selected chiral centers. Differential effects on two types of secretory molecules suggest that the apratoxins' substrate selectivity with respect to inhibition of secretion may be tuned through structural modifications to provide tailored therapy. Our structure"activity relationship studies and medicinal chemistry efforts led to a potent inhibitor with in vivo efficacy in a colorectal tumor xenograft model without irreversible toxicity exerted by apratoxin A, demonstrating that this novel mechanism of action has therapeutic potential.

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

Synthesis of the polyketide segment of apratoxin A

Apratoxin A 1 is a potent cytotoxic agent extracted from a marine cyanobacterium. We report the results of our synthetic approaches to the polyketide segment 3-OTBS-7-OPMB-2,5,8,8-tetramethylnonanoic acid 4, and the scope and limitations of these approach