88109-73-3Relevant articles and documents
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.
A versatile approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid
Ishmuratov,Kharisov,Yakovleva,Botsman,Galeeva,Ishmuratova,Tolstikov
, p. 1595 - 1597 (2007/10/03)
A general approach to the synthesis of 9(Z)-unsaturated acyclic insect pheromones from undec-10-enoic acid was developed. The method comprises the conversion of the acid into undec-10-enyl acetate, shortening of its carbon chain to afford dec-9-enyl acetate (via 11-acetoxyundecanoic acid), and a two-step transformation of the latter into the key intermediate, dec-9-yn-1-ol, by sequential bromination - dehydrobromination. The elimination of two HBr molecules from the dibromide is effectively performed using Bu1OK in the presence of dibenzo-18-crown-6 as the catalyst.
INSECT PHEROMONES AND THEIR ANALOGUES. XVI. PRACTICAL SYNTHESIS OF HEXADEC-9Z-ENAL - A COMPONENT OF THE SEX PHEROMONE OF THE COTTON BOLLWORM Heliothis armigera
Odinolov, V. N.,Dzhemilev, U. M.,Ishmuratov, G. Yu.,Botsman, L. P.,Vostrikova, O. S.,et al.
, p. 242 - 244 (2007/10/02)
A synthesis of hexadec-9Z-enal - a component of the sex pheromone of the cotton bollworm Heliothis armigera (Huebner) - based on cyclooctene (I) is proposed.Through a solution of 22 g of (I), 250 ml of cyclohexane, and 40 ml of MeOH is passed (at 5 deg C) 0.2 M O3/O2, the solution is decanted off, and the precipitated ozonide is dissolved in 200 ml of MeOH and is reduced with 19 g of NaBH4 (40 deg C) with the isolation, after the usual working up, of 23.4 g of octane-1,8-diol (II).From 0.5 mole of (II) and 0.6 mole of 45percent HBr 8-bromooctan-1-ol (III) is obtained and this is converted into 1-(2-(THPL)oxy)-8-bromooctane (IV).The condensation of (IV) with oct-1-yne (Ar, LiNH2, HMPTA, 10 deg C, 1 h, and then 55 deg C, 10 h) leads to 1-(2-THPL-oxy)hexadec-9-yne (V) the hydrolysis of which (MeOH, H2O, p-TsOH, 20 deg C for 20 h) yields hexadec-9-yn-ol (VI).The reduction of (VI) (Et2O, iso-BuMgBr, Cp2TiCl2, 0 deg C, 15 min, then 20 deg C, 1 h) yields hexadec-9Z-en-1-ol (VII).The oxidation of (VII) (PyHCrO3+ Cl-, CH2Cl2, 20 deg C, 2 h) gives hexadec-9Z-enal (VIII).Characteristics of the compounds (yield (percent), nD20(25): (II) - 80, mp 61-62 deg C; (III) - 75, 1.4807; (IV) - 99, -; (V) - 52, 1,4650; (VI) - 85, 1.4657; (VII) - 99, 1.4650; (VIII) - 98, 1.4600.Characteristics of the IR and PMR spectra of compounds (V-VII) are given.
