133499-60-2Relevant academic research and scientific papers
Total synthesis and cytotoxicity studies of a cyclic depsipeptide with proposed structure of palau'amide
Zou, Bin,Long, Kai,Ma, Dawei
, p. 4237 - 4240 (2005)
(Chemical Equation Presented) Total synthesis of a cyclic depsipeptide with proposed structure of palau'amide is achieved, which features a stereoselective elaboration of its 5,7-dihydroxy-2,6-dimethyldodec-2-en-11-ynoic acid unit. The synthetic compound
Solid-phase synthesis and configurational reassigment of callipeltin E. Implications for the structures of callipeltins A and B
Calimsiz, Selcuk,Ramos, Angel I. Morales,Lipton, Mark A.
, p. 6351 - 6356 (2007/10/03)
Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26% overall yields, respectively. The 1H NMR spectrum of synthetic 5 correlated closely with that of the natural product, whereas that of 1 did not, providing confirmation of the configurational reassignment of the N-terminal residue of callipeltin E as D-allothreonine. This result strongly implies that the corresponding residue in the closely related cyclic depsipeptides callipeltins A and B should also be considered a D-allothreonine residue.
Total synthesis of the cyclodepsipeptide apratoxin A and its analogues and assessment of their biological activities
Dawei, Ma,Zou, Bin,Cai, Guorong,Hu, Xiaoyi,Liu, Jun O.
, p. 7615 - 7626 (2007/10/03)
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.
Synthesis of an Oxazoline Analogue of Apratoxin A
Zou, Bin,Wei, Jingjun,Cai, Guorong,Ma, Dawei
, p. 3503 - 3506 (2007/10/03)
Equation presented. Michael addition of Me2Cu(CN)Li2 to α,β-unsaturated lactone 7 derived from β-hydroxyl ketone 5 provides lactone 8, which is converted to alcohol 11 using Oppolzer's methodology as the key step. Connection of 11 wi
Rational design and synthesis of unsaturated 2,5-dioxopiperazine derivatives as potential protein tyrosine kinase inhibitors
Li, Wen-Ren,Peng, Shao-Zheng
, p. 7373 - 7376 (2007/10/03)
The first general method for the synthesis of a library of trifunctionalized (Z)-3-alkylidene-2,5-piperazinediones as potential protein tyrosine kinase inhibitors from commercially available amino compounds, α- keto acids and aldehydes using a novel cyclization/cleavage strategy on solid support is described.
