629-89-0Relevant academic research and scientific papers
Total Synthesis of Natural Lembehyne C and Investigation of Its Cytotoxic Properties
Dzhemileva, Lilya U.,D'Yakonov, Vladimir A.,Makarov, Alexey A.,Makarova, Elina Kh.,Andreev, Evgeny N.,Dzhemilev, Usein M.
, p. 2399 - 2409 (2020)
The first Z-stereoselective method for the synthesis of the natural marine alkynol lembehyne C, containing a 1Z,5Z,9Z-triene moiety, in 41% yield was developed using the new Ti-catalyzed cross-coupling of oxygenated and aliphatic 1,2-dienes as the key step. It was found for the first time that lembehyne C exhibits moderate cytotoxicity against Jurkat, K562, U937, and HL60 cancer cells and also efficiently induces apoptosis in Jurkat cells, with the cell death mechanism being activated by the mitochondrial pathway. The lembehyne C inhibition of the cell cycle follows the mitotic catastrophe mechanism.
The influence of distal substitution on the base-induced isomerization of long-chain terminal alkynes
Mohammad, Innus,Mun, JiYoung,Onorato, Amber,Morton, Martha D.,Saleh, Abdullah I.,Smith, Michael B.
supporting information, p. 4162 - 4165 (2017/10/13)
When compared to a long-straight chain terminal alkyne, a long chain terminal alkyne with a distal isopropyl unit (isobranched) isomerizes about two times faster when treated with strong base under identical conditions, and appears to follow pseudo first order kinetics. In both cases, equilibration to a 95–97:5–3 mixture of terminal:internal alkyne accompanies isomerization. The difference in rate may be due to an unusual folding of both long-chain alkynes, bringing the distal substituent close to the carbon-carbon-triple bond moiety. The distal isopropyl moiety may provide unanticipated steric hindrance that disrupts such folding, making the propargylic proton more available for reaction with base.
Development of a benzophenone and alkyne functionalised trehalose probe to study trehalose dimycolate binding proteins
Khan, Ashna A.,Kamena, Faustin,Timmer, Mattie S.M.,Stocker, Bridget L.
supporting information, p. 881 - 885 (2013/02/26)
Trehalose dimycolates (TDMs) are the most abundant glycolipids found in the cell wall of Mycobacterium tuberculosis (M. tb). TDMs play an important role in the pathogenesis of M. tb yet the only known receptor for TDM is the macrophage inducible C-type lectin (mincle). To understand more about the interaction of TDMs with immune cells, affinity based proteome profiling (AfBPP) can be used to determine receptors that bind TDMs. To this end, we present the synthesis of the first AfBPP-TDM probe and report on its ability to activate macrophages. By doing so, we establish that the AfBPP-TDM probe appears to be a suitable substrate for future proteomic profiling experiments.
Formation of conjugated polynaphthalene via Bergman cyclization
Miao, Changcheng,Zhi, Jian,Sun, Shiyuan,Yang, Xi,Hu, Aiguo
, p. 2187 - 2193 (2011/04/15)
A series of enediyne containing chiral phthalimides were synthesized through Sonogashira coupling reactions. These enediynes were then subjected to thermal Bergman cyclization under vacuum. Polynaphthalenes with pendant chiral groups were obtained and characterized using GPC, IR spectroscopy, NMR spectroscopy, UV-Vis spectroscopy, and photoluminescence analysis. Under properly optimized conditions, the chirality of chiral directing group was maintained according to CD spectra of final products. After removal of chiral directing groups, weak CD signals representative of main chain chirality were visible. Further modification of the structure of the enediyne compounds will facilitate the synthesis of chiral polynaphthalene through this rather simple way. Extension of the Bergman cyclization to polymer chemistry is promising in the construction of novel polymers with rigid polyarene back-bones.
PMHS-mediated couplings of alkynes or benzothiazoles with various electrophiles: Application to the synthesis of (-)-akolactone A
Gallagher, William P.,Maleczka Jr., Robert E.
, p. 6775 - 6779 (2007/10/03)
Polymethylhydrosiloxane (PMHS) in combination with CsF facilitates the cross-coupling of alkynes or benzothiazoles with an array of vinyl, styryl, and aryl halides or nonaflates as well as acid chlorides. Experimental and spectroscopic evidence indicates that these reactions involve the in situ generation of a siloxyl intermediate. These cross-couplings proceed relatively quickly at room temperature and under amine-free conditions. To demonstrate the applicability of the method, a total synthesis of the cyctotoxic butanolide (-)-akolactone A was carried out.
Plant Growth Regulators: Syntheses of n-Triacontynol, n-Triacontenol and n-Triacontanol
Iyer, R. R.,Mamdapur, V. R.
, p. 1216 - 1219 (2007/10/02)
Convenient syntheses of n-triacontynols (VII), n-triacontenols (VIII and IX) and n-triacontanol (X) are described.The alkynes (III) are coupled with bromo THP-ethers (VI) to yield the disubstituted n-triacontynols (VII).These on selective partial hydrogenation afford the disubstituted n-triacontenols (VIII and IX).Alkynols (VII) on complete hydrogenation give the n-triacontanol (X).Biological studies reveal that the acetylenes (VII) and olefins (VIII and IX) are better plant growth regulators than the n-triacontanol (X).
