16695-31-1Relevant academic research and scientific papers
A (Z, Z, E) - 7, 11, 13 - sixteen carbon three activated olefinic ketones synthesis method (by machine translation)
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Page/Page column 2; 3; 8; 11, (2018/07/15)
The invention relates to an improved synthetic method of (Z,Z,E)-7,11,13-hexadecatrienal, wherein the (Z,Z,E)-7,11,13-hexadecatrienal is an important component in a sex pheromone compound of phyllocnistis citrella. The improved synthetic method is carried out with 6-bromo-1-hexanol as an initial raw material and through a coupled reaction, a Wittig reaction and other reactions to synthesize the (Z,Z,E)-7,11,13-hexadecatrienal. The improved synthetic method is advantaged in that the raw material is low in cost and easy to get, and the reactions are safe and convenient in operations and is short in step periods. The improved synthetic method is high in product yield, is free of environmental pollution and can achieve better economic benefit.
Discovery of a Fluorinated Enigmol Analog with Enhanced in Vivo Pharmacokinetic and Anti-Tumor Properties
Miller, Eric J.,Mays, Suzanne G.,Baillie, Mark T.,Howard, Randy B.,Culver, Deborah G.,Saindane, Manohar,Pruett, Sarah T.,Holt, Jason J.,Menaldino, David S.,Evers, Taylor J.,Reddy, G. Prabhakar,Arrendale, Richard F.,Natchus, Michael G.,Petros, John A.,Liotta, Dennis C.
supporting information, p. 537 - 542 (2016/06/01)
The orally bioavailable 1-deoxy-sphingosine analog, Enigmol, has demonstrated anticancer activity in numerous in vivo settings. However, as no Enigmol analog with enhanced potency in vitro has been identified, a new strategy to improve efficacy in vivo by increasing tumor uptake was adopted. Herein, synthesis and biological evaluation of two novel fluorinated Enigmol analogs, CF3-Enigmol and CF2-Enigmol, are reported. Each analog was equipotent to Enigmol in vitro, but achieved higher plasma and tissue levels than Enigmol in vivo. Although plasma and tissue exposures were anticipated to trend with fluorine content, CF2-Enigmol absorbed into tissue at strikingly higher concentrations than CF3-Enigmol. Using mouse xenograft models of prostate cancer, we also show that CF3-Enigmol underperformed Enigmol-mediated inhibition of tumor growth and elicited systemic toxicity. By contrast, CF2-Enigmol was not systemically toxic and demonstrated significantly enhanced antitumor activity as compared to Enigmol.
Long-chain triazolyl acids as inhibitors of osteoclastogenesis
Marshall, Andrew J.,Lin, Jian-Ming,Grey, Andrew,Reid, Ian R.,Cornish, Jillian,Denny, William A.
, p. 4112 - 4119 (2013/07/27)
Saturated fatty acids (e.g., palmitic acid) are known to moderately inhibit the development of osteoclasts in vitro. In pursuit of more effective inhibitors of osteoclastogenesis we explored two new classes of palmitic acid analogues containing either an ether or triazolyl group at various positions along the chain. The compounds were evaluated for their ability to inhibit the formation of osteoclasts in primary mouse bone marrow cultures. The oxyacids were generally prepared by condensation of the appropriate alkyl halides and diols, followed by Jones oxidation. The triazolyl acids were prepared by copper-catalysed click chemistry between alkyl azides and acetylenic acids, or with the appropriately-protected azides and alkynes, followed by deprotection and oxidation. The oxyacids were little more effective than palmitic acid, but the triazolyl analogues were much more effective osteoclastogenesis inhibitors, especially when the triazole was distant from the acid unit.
Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I
Makabe, Hidefumi,Kimura, Yuka,Higuchi, Masaharu,Konno, Hiroyuki,Murai, Masatoshi,Miyoshi, Hideto
, p. 3119 - 3130 (2007/10/03)
A convergent stereoselective synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin and squamostolide was accomplished via a Pd-catalyzed cross-coupling reaction. The inhibitory activity of these compounds was examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed a remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin. Our results indicate that to maintain potent inhibitory effect, the hydroxylated lactone cannot substitute for the hydroxylated mono- or bis-THF rings with a long alkyl chain that can be seen in ordinary acetogenins.
Concise synthesis of (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, components of the essential oil of marine green alga Ulva pertusa
Akakabe, Yoshihiko,Washizu, Kensuke,Matsui, Kenji,Kajiwara, Tadahiko
, p. 1348 - 1352 (2008/02/01)
The long-chain aldehydes, (8Z,11Z,14Z)-8,11,14-heptadecatrienal, (7Z,10Z,13Z)-7,10,13-hexadecatrienal, and (8Z,11Z)-8,11-heptadecadienal, were concisely synthesized by using Grignard coupling, catalytic hydrogenation with the Lindlar catalyst, and oxidation with Dess-Martin periodinane as the key steps. Particularly, (8Z,11Z,14Z)-8,11,14-heptadecatrienal and (7Z,10Z, 13Z)-7,10,13-hexadecatrienal both possessed a seaweed-like odor.
Total synthesis and assignment of the double-bond position and absolute configuration of (-)-pyrinodemin A
Morimoto, Yoshiki,Kitao, Satoru,Okita, Tatsuya,Shoji, Takamasa
, p. 2611 - 2614 (2007/10/03)
(Matrix presented) The first asymmetric total synthesis of a structurally novel cis-cyclopent[c]isoxazolidine alkaloid, (-)-pyrinodemin A (3), which exhibits potent cytotoxicity, has been accomplished through a highly diastereoselective intramolecular nitrone - olefin cycloaddition reaction as the key step. Thus, it has been found that the hitherto unknown absolute configuration of pyrinodemin A is as indicated in the structural formula 3.
Electrotelluration: A new approach to tri- and tetrasubstituted alkenes
Marino, Joseph P.,Nguyen, Hanh Nho
, p. 6291 - 6296 (2007/10/03)
A novel electrotelluration process is described in which a Michael addition of an alkyl or aryl tellurolate anion occurs onto an activated alkyne with subsequent trapping of a vinyl anion with electrophiles (aldehydes and ketones) other than a proton. This process provides an efficient regio-and stereospecific route to tri- and tetrasubstituted alkenes. Methodologically significant examples of this chemistry were studied in which aryl and alkyl tellurolate anions were added to ω-keto alkynyl esters in a Michael reaction, and the incipient vinyl anions were trapped intramolecularly by the internal aldehydes. The reactive centers were tethered by different lengths of alkyl chains to form highly functionalized five-, six-, seven-, and eight-membered rings in modest to good yields.
New and simple syntheses of the attractants of the female melon fly, dacus cucurbitee
Yen, Yao-Pin,Chen, Pao-Hsing
, p. 87 - 90 (2007/10/03)
The attractant of the female melon fly, (E)-6-nonenyl acetate, and the two analogs, (E)-7-dodecenyl acetate and (E)-7-decenyl acetate were synthesized via hydrozirconation to control the regioselective coupling reactions and resulted in good yields.
Short and stereoselective syntheses of pheromone components of Aproaerema modicella
Yadav,Chandrasekhar,Kache
, p. 4035 - 4043 (2007/10/03)
Efficient syntheses of pheromone components of Aproaerema modicella starting from a common intermediate 7-octyn-1-ol is described.
Synthesis of (R,S)-10-methyloctadecanoic acid (tuberculostearic acid) and key chiral 2-methyl branched intermediates
Wallace, Paul A.,Minnikin, David E.,McCrudden, Katharine,Pizzarello, Andrea
, p. 145 - 162 (2007/10/02)
Tuberculostearic acid (R)-10-methyloctadecanoic acid, is a characteristic component of pathogenic mycobacteria and related organisms.Sensitive detection of this acid infected material allows rapid detection of mycobacterial disease.A novel, convergent synthesis of tuberculostearic acid and key chiral intermediates is described in this communication, to provide a reference compound.Racemic and (R)- and (S)-1-iodo-2-methyldecanes were synthesised from 1-octanal and 1-carboethoxyethylidenetriphenylphosphorane as initial starting materials. 1-Hydroxyoct-7-yne was made from 1,6-hexanediol by two alternative methods and coupled with the above racemic iodide.Hydrogenation and oxidation of the resulting (R,S)-10-methyloctadec-7-yn-1-ol gave racemic tuberculostearic acid. Keywords: Mycobacterium tuberculosis; Tuberculostearic acid; Acetylene coupling; (R,S)-10-methyloctadecanoic acid; Chiral 2-methyl branched fatty acids
