33639-45-1Relevant academic research and scientific papers
Facilitating Myers-Saito cyclization through acid-triggered tautomerization for the development of maleimide-based antitumor agents
Lu, Haotian,Ma, Hailong,Li, Baojun,Zhang, Mengsi,Chen, Huimin,Wang, Yue,Li, Xinxin,Ding, Yun,Hu, Aiguo
, p. 1971 - 1979 (2020)
Enyne-allene compounds undergo Myers-Saito cyclization at physiological temperature to generate diradical intermediates that are capable of inducing DNA damage and cell death. The high reactivity of enyne-allene however limits their promising prospect as anticancer agents due to the spontaneous cyclization during storage and delivery. Regulating the cyclization process by taking advantage of the characteristics of a tumor cellular microenvironment, such as employing a low pH value to activate the cyclization process, is thus of essential importance. In this work, a novel enediyne (EDY) system with locked carbonyl groups was specifically designed and synthesized. Unlocking the protected carbonyl groups in the presence of acid would facilitate the rearrangement of propargyl moieties into an allene group, enabling the formation of an enyne-allene structure and occurrence of Myers-Saito cyclization. The pH-dependent diradical generation and DNA-cleavage ability of the designed EDY system were confirmed by electron paramagnetic resonance analysis and DNA gel electrophoresis. A promising cytotoxicity against HeLa cells with half inhibition concentrations (IC50) as low as 1.40 μM was obtained, which was comparable to those of many commercially applied anticancer drugs. Further in vitro experiments revealed that this EDY system induced intracellular DNA damage and subsequently resulted in S-phase arrest and cytotoxicity through programmed apoptosis.
Synthesis and Functional Assessment of a Novel Fatty Acid Probe, ω-Ethynyl Eicosapentaenoic Acid Analog, to Analyze the in Vivo Behavior of Eicosapentaenoic Acid
Tokunaga, Tomohisa,Watanabe, Bunta,Sato, Sho,Kawamoto, Jun,Kurihara, Tatsuo
, p. 2077 - 2085 (2017/08/21)
Eicosapentaenoic acid (EPA) is an ω-3 polyunsaturated fatty acid that plays various beneficial roles in organisms from bacteria to humans. Although its beneficial physiological functions are well-recognized, a molecular probe that enables the monitoring o
Benzannulation via the reaction of ynamides and vinylketenes. Application to the synthesis of highly substituted indoles
Lam, Tin Yiu,Wang, Yu-Pu,Danheiser, Rick L.
, p. 9396 - 9414 (2013/10/08)
A two-stage "tandem strategy" for the synthesis of indoles with a high level of substitution on the six-membered ring is described. Benzannulation based on the reaction of cyclobutenones with ynamides proceeds via a cascade of four pericyclic reactions to produce multiply substituted aniline derivatives in which the position ortho to the nitrogen can bear a wide range of functionalized substituents. In the second stage of the tandem strategy, highly substituted indoles are generated via acid-, base-, and palladium-catalyzed cyclization and annulation processes.
A unified synthetic approach to polyketides having both skeletal and stereochemical diversity
Shang, Shiying,Iwadare, Hayato,Macks, Daniel E.,Ambrosini, Lisa M.,Tan, Derek S.
, p. 1895 - 1898 (2008/02/12)
An efficient systematic approach to the diversity-oriented synthesis of polyketides has been developed to provide both skeletal and stereochemical diversity. Each synthetic intermediate is also a desired polyketide fragment and no protecting group manipul
Asymmetric synthesis of carbohydrates: Synthesis of 2-deoxy-D- and 2-deoxy-L-xylofuranosides from a simple achiral precursor
Jung, Michael E.,Gardiner, John M.
, p. 6755 - 6758 (2007/10/02)
The acetylenic alcohol, 3, readily prepared in two steps from propargyl bromide, 1, is converted to methyl 2-deoxy-D-xylofuranoside, 13, and to the unnatural L-enantiomer, 12, in 5 steps and 50% overall yield, utilizing asymmetric dihydroxylation (AD) of alkene 7 for introduction of chirality. A similar strategy from the isomeric Z-allylic alcohol, 4, afforded the 2-deoxy-L-ribofuranoside, but in modest enantiomeric excess.
Reaction of Trialkyl Orthoformates with the Aluminium Derivatives of Some α-Unsaturated Bromides. Preparation of β-Unsaturated Acetals
Picotin, Gerard,Miginiac, Philippe
, p. 1725 - 1730 (2007/10/02)
Die Aluminium-Derivate 2, 4, und 7 α-ungesaettigter Bromide, dargestellt in Ether, sind sehr reaktionsfaehig gegenueber Trialkylorthoformaten.Mit Hilfe dieser Reaktion, durchgefuehrt bei -80 deg C, koennen auf einfache Weise β-ungesaettigte Acetale 3, 5, bzw. 8 dargestellt werden.
DERIVATIVES OF BIACETYLENE. XLV. REACTION OF BIACETYLENE AND 1-METHOXY-1-BUTEN-3-YNE WITH DIETHYLENE GLYCOL
Vavilova, A. N.,Trofimov, B. A.,Volkov, A. N.
, p. 228 - 230 (2007/10/02)
The nucleophilic addition of diethylene glycol to biacetylene and methoxybutenyne and the electrophilic reaction of methoxybutenyne with diethylene glycol were investigated.In the presence of alkali two molecules of diethylene glycol add to biacetylene and methoxybutenyne.In the presence of mercury sulfate and water the reaction leads to the formation of a linear β-keto acetal.
CHEMISTRY OF ENOLIC ETHERS. LI. SYNTHESIS AND INVESTIGATION OF THE STEREOCHEMISTRY OF THE ACETALS OF β,γ-UNSATURATED δ-HYDROXYALDEHYDES BY NMR SPECTROSCOPY
Raifel'd, Yu. E.,Kusikova, I. P.,Zil'berg, L. L.,Arshava, B. M.,Limanova, O. V.,Makin, S. M.
, p. 1425 - 1429 (2007/10/02)
A new accessible method is proposed for the synthesis of the acetals of ethynylacetaldehyde by the addition of bromine to the acetals of vinylacetaldehyde and subsequent dehydrobromination of the obtained 1,1-dialkoxy-3,4-dibromobutanes with sodium amide.The Iotich condensation of the ethynylacetaldehyde acetals with paraform and acetaldehyde was investigated.A stereoselective synthesis of the individual cis and trans isomers of β,γ-unsaturated δ-hydroxyaldehydes was realized from the obtained acetylenic alcohols.
Action d'organometalliques sur les dialkylphenylorthoformiates. Preparation facile d'acetals
Barbot, Francis,Poncini, Laurence,Randrianoelina, Benjamin,Miginiac, Philippe
, p. 4016 - 4035 (2007/10/02)
The reaction of dialkylphenylorthoformiates with organometallic compounds proceeds with a good yield, at room temperature, giving the corresponding dialkylacetals ; it allows an easy preparation of acetals which are otherwise difficult to prepare.
