50816-20-1Relevant academic research and scientific papers
A NEW APPROACH TO CONJUGATED DIENES SYNTHESIS OF THE PHEROMONES OF LOBESIA BOTRANA AND BOMBYX MORI
Alexakis, A.,Jachiet, D.
, p. 381 - 390 (1989)
Cis or trans epoxysilanes are regio and stereoselectively opened by Z-alkenyl cuprates, in the presence of BF3*OEt2, affording erythro or threo β-hydroxy silanes respectively.These are, in turn, transformed into E-Z conjugated dienes of high stereoisomeric purity by acidic or basic elimination.The method serves to synthetize the pheromones of Lobesia botrana and Bombyx mori.
A 13-oxo-9,10-epoxytridecenoate phospholipid analogue of the genotoxic 4,5-epoxy-2E-decenal: Detection in vivo, chemical synthesis, and adduction with DNA
Mesaros, Clementina,Gugiu, Bogdan G.,Zhou, Rong,Lee, Seon Hwa,Choi, Jaewoo,Laird, James,Blair, Ian A.,Salomon, Robert G.
, p. 516 - 527 (2010)
Often guided by analogy with nonphospholipid products from oxidative cleavage of polyunsaturated fatty acids, we previously identified a variety of biologically active oxidatively truncated phospholipids. Previously, 4,5-epoxy-2(E)-decenal (4,5-EDE) was found to be produced by oxidative cleavage of 13-(S)-hydroperoxy-9,11-(Z,E)-octadeca-dienoic acid (13-HPODE). 4,5-EDE reacts with deoxy-adenosine (dAdo) and deoxy-guanosine (dGuo) to form mutagenic etheno derivatives. We hypothesized that a functionally similar and potentially mutagenic compound, that is, 13-oxo-9,10-epoxytridecenoic acid (OETA), would be generated from 9-HPODE through an analogous fragmentation. We expected that an ester of 2-lysophosphatidylcoline (PC), OETA-PC, would be produced by oxidative cleavage of 9-HPODEPC in biological membranes. An efficient, unambiguous total synthesis of trans-OETA-PC was first executed to provide a standard that could facilitate the identification of this phospholipid epoxyalkenal that was shown to be produced during oxidation of the linoleic acid ester of 2-lysoPC. Finally, trans-OETA-PC was detected in a lipid extract from rat retina. The identity of the naturally occurring oxidatively truncated phospholipid was further confirmed by derivatization with methoxylamine that produced characteristic mono and bis adducts. The average amount of trans-OETA-PC in rat retina, 0.33 pmol, is relatively low as compared to other oxidatively truncated PCs, for example, the 4-hydroxy-7-oxohept-5-enoic acid PC ester (2.5 pmol) or the 4-keto-7-oxohept-5- enoic acid PC ester (1.7 pmol), derived from the docosahexaenoic acid ester of 2-lysoPC. This, most likely, is because docosahexaenoate PCs are particularly abundant in the retina as compared to the linoleate PC ester precursor of OETA-PC. As predicted by analogy with 4,5-EDE, OETA-PC reacts with dAdo and dGuo, as well as with DNA, to form mutagenic etheno adducts.
Antibacterial Activity of Hexadecynoic Acid Isomers toward Clinical Isolates of Multidrug-Resistant Staphylococcus aureus
Carballeira, Néstor M.,Chorna, Nataliya,Díaz, Damarith,Medina, Solymar,Mooney, Joseph,Morales-Guzmán, Christian,Ocasio-Malavé, Carlimar,Pereles-De-León, Tomás,Rivera-Román, Ashley,Sanabria-Ríos, David J.
, (2020/02/04)
In the present study, the structural characteristics that impart antibacterial activity to C16 alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C-3, C-6, C-8, C-9, C-10, and C-12 were carried out in four steps and with an overall yield of 34–78%. In addition, HDA analogs containing a sulfur atom at either C-4 or C-5 were also prepared in 69–77% overall yields, respectively. Results from this study revealed that the triple bond at C-2 is pivotal for the antibacterial activity displayed by 2-HDA, while the farther the position of the triple bond from the carbonyl group, the lower its bactericidal activity against gram-positive bacteria, including clinical isolates of methicillin-resistant Staphylococcus aureus (CIMRSA) strains. The potential of 2-HDA as an antibacterial agent was also assessed in five CIMRSA strains that were resistant to Ciprofloxacin (Cipro) demonstrating that 2-HDA was the most effective treatment in inhibiting their growth when compared with either Cipro alone or equimolar combinations of Cipro and 2-HDA. Moreover, it was proved that the inhibition of S. aureus DNA gyrase can be linked to the antibacterial activity displayed by 2-HDA. Finally, it was determined that the ability of HDA analogs to form micelles can be linked to their decreased activity against gram-positive bacteria, since critical micellar concentrations (CMC) between 50 and 300 μg/mL were obtained.
Practical Synthesis and Field Application of the Synthetic Sex Pheromone of Rice Stem Borer, Chilo suppressalis (Lepidoptera: Pyralidae)
Chien, Wei-Jynn,Gupta, Sachin,Liu, Bin,Lou, Da Wei,Shen, Yu-Jhe,Syu, Kun-Jie,Tseng, Jui-Chang,Zhang, Yuan-Xin
, (2020/03/11)
Rice stem borer, Chilo suppressalis, is a common and major serious pest of rice, maize, and wheat crops across Asia, Europe, and Oceania countries. Its sex pheromone consists of three analogously compounds, i.e., (Z)-hexadec-11-enal (1), (Z)-octadec-13-enal (2), and (Z)-hexadec-9-enal (3), as long-chain aliphatic internal cis-alkenyl aldehydes. In order to perform an economic and widespread pest control management of rice stem borer, a versatile and efficient synthetic strategy is required. A versatile and efficient synthesis using a common synthetic route for cis-alkenals with high overall yields is described. Commercially available inexpensive aliphatic diols were chosen as starting materials. Two key steps were employed to synthesize the long-chain aliphatic internal cis-alkenes in excellent yields, including the alkylation of terminal alkynes without the utilization of a highly polar aprotic cosolvent and the versatile cis-selective semihydrogenation for the reduction of internal alkynes with excellent stereoselectivity. The results of field tests showed that the synthetic sex pheromone blend was highly effective for the capture of rice stem borer.
Identification and synthesis of the male produced volatiles of the carrion beetle, Oxelytrum erythrurum (Coleoptera: Silphidae)
Fockink, Douglas H.,Martins, Camila B.C.,Zarbin, Paulo H.G.
, p. 5353 - 5356 (2015/09/01)
Necrophagous beetles belonging to the family Silphidae are recognized as potentially useful in forensic investigations (to estimate post mortem interval). Gas chromatography analyses of extracts of aerations of adult Oxelytrum erythrurum revealed the presence of two male-specific compounds. These compounds were identified as (Z)-1,10-nonadecadiene (major) and 1-nonadecene (minor) using microderivatizations of the natural male extract, such as hydrogenation, partial reduction and methylthiolation, mass spectrum comparisons, and co-injections with authentic standards. Both compounds might be components of a pheromone responsible for sexual communication in this species.
Synthesis of corn rootworm pheromones from commercial diols
Nguyen, Thanh-Danh,Nguyen, Cong-Hao,Im, Chan,Dang, Chi-Hien
, p. 380 - 384 (2015/02/19)
A mixture of stereoisomers of the corn rootworm pheromones was synthesised via the Grignard coupling of protected bromohydrins with alkylcuprate as a key step. The synthesis of 8-methyldec-2- yl propanoate (I), the northern corn rootworm Diabrotica longicornis Say pheromone, was achieved from pentane-1,5-diol in four steps with an overall yield of 35.1 % and 10-methyltridecan-2-one (II), the southern corn rootworm Diabrotica undecimpunctata howardi Barber pheromone, was synthesised from octane-1,8-diol as commercially available starting material in five steps with an overall yield of 28.7 %.
The (5Z)-5-Pentacosenoic and 5-Pentacosynoic Acids Inhibit the HIV-1 Reverse Transcriptase
Moreira, Lizabeth Giménez,Orellano, Elsie A.,Rosado, Karolyna,Guido, Rafael V. C.,Andricopulo, Adriano D.,Soto, Gabriela Ortiz,Rodríguez, José W.,Sanabria-Ríos, David J.,Carballeira, Néstor M.
, p. 1043 - 1050 (2015/10/05)
The natural fatty acids (5Z)-5-pentacosenoic and (9Z)-9-pentacosenoic acids were synthesized for the first time in eight steps starting from either 4-bromo-1-butanol or 8-bromo-1-butanol and in 20-58 % overall yields, while the novel fatty acids 5-pentacosynoic and 9-pentacosynoic acids were also synthesized in six steps and in 34-43 % overall yields. The ?5 acids displayed the best IC50's (24-38 μM) against the HIV-1 reverse transcriptase (RT) enzyme, comparable to nervonic acid (IC50 = 12 μM). The ?9 acids were not as effective towards HIV-RT with the (9Z)-9-pentacosenoic acid displaying an IC50 = 54 μM and the 9-pentacosynoic acid not inhibiting the enzyme at all. Fatty acid chain length and position of the unsaturation was important for the observed inhibition. None of the synthesized fatty acids were toxic (IC50 > 500 μM) towards peripheral blood mononuclear cells. Molecular modeling studies indicated the structural determinants underlying the biological activity of the most potent compounds. These results provide new insights into the structural requirements that must be present in fatty acids so as to enhance their inhibitory potential towards HIV-RT.
Highly efficient preparation of selectively isotope cluster-labeled long chain fatty acids via two consecutive Csp3-Csp3 cross-coupling reactions
Lethu, Sebastien,Matsuoka, Shigeru,Murata, Michio
supporting information, p. 844 - 847 (2014/03/21)
An efficient synthesis involving two copper-catalyzed alkyl-alkyl coupling reactions has been designed to easily access doubly isotope-labeled fatty acids. Such NMR- and IR-active compounds were obtained in excellent overall yields and will be further used for determining the conformation of an alkyl chain of lipidic biomolecules upon interaction with proteins.
First total synthesis of acetylenic alcohol 15-methyltricosa-2,4-diyne-1, 6-diol (strongylodiol-G) derived from marine sponge
Gupta, Neeraj,Shallu,Kad, Goverdhan Lal,Singh, Jasvinder
, p. 424 - 430 (2014/04/17)
The first total and efficient synthesis of a naturally occurring acetylenic alcohol 15-methyltricosa-2,4-diyne-1,6-diol (strongylodiol-G) derived from marine sponge involving nine steps has been described. 1-Bromo-9- methyloctadecane (5) and hex-6-tetrahydropyranyloxyhex-2,4-diyn-1-al (9) which were initially synthesised separately starting from 1,8-octanediol (1) and propargyl alcohol (6), respectively, have been used as the final intermediates to obtain the title compound. The key steps in the synthesis involved ionic liquid-mediated bromination of 1,8-octanediol (1), tetrahydropyranylation of 8-bromooctan-1-ol (2) using acidic ionic liquid [bmim]HSO4 and monotetrahydropyranylation of hex-2,4-yn-1,6-diol (7) using ultrasonic energy.
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.
