112-13-0Relevant articles and documents
Unexpected stereoselective exchange of straight-chain fatty acyl-CoA α-protons by human α-methylacyl-CoA racemase 1A (P504S)
Sattar, Fouzia A.,Darley, Daniel J.,Politano, Francesco,Woodman, Timothy J.,Threadgill, Michael D.,Lloyd, Matthew D.
, p. 3348 - 3350 (2010)
α-Methylacyl-CoA racemase (AMACR; P504S) catalysed exchange of straight-chain fatty acyl-CoA α-protons. One α-proton was removed in each catalytic cycle, with the pro-S proton preferred. This reaction was most efficient for straight-chain substrates with longer side-chains. 2-Methyldecanoyl-CoA underwent α-proton exchange 3× more efficiently (as judged by Kcat/Km) than decanoyl-CoA.
"Meta elimination," a diagnostic fragmentation in mass spectrometry
Attygalle, Athula B.,Nishshanka, Upul,Weisbecker, Carl S.
, p. 1515 - 1525 (2011)
The diagnostic value of the "ortho effect" for unknown identification by mass spectrometry is well known. Here, we report the existence of a novel "meta effect," which adds to the repertoire of useful mass spectrometric fragmentation mechanisms. For example, the meta-specific elimination pathway described in this report enables unequivocal identification of meta isomers from ortho and para isomers of carboxyanilides. The reaction follows a specific path to eliminate a molecule of meta-benzyne, from the anion produced after the initial decarboxylation of the precursor. Consequently, in the CID spectra of carboxyanilides, a peak for the (R-CO-NH)- anion is observed only for the meta isomers. For example, the peaks observed at m/z 58, 86, 120, 128, and 170 from acetamido-, butamido-, benzamido, heptamido-, and decanamido-benzoates, respectively, were specific only to the spectra of meta isomers.
Synthesis, characterization, and properties of copolyanhydrides based on 2-octylsuccinic acid and sebacic acid
Hamdan, Yousef M.,Fu, Shitao,Jiang, Xiangmei,Cheng, Yinhua,Huang, Kaixun,Yu, Kaichao
, p. 762 - 767 (2008)
2-Octylsuccinic acid and its copolyanhydrides with sebacic acid have been synthesized by melt polycondensation, and were characterized by Fourier transform infrared spectroscopy, 1H NMR, gel permeation chromatography, differential scanning calorimetry, and thermal gravimetric analysis. In vitro studies showed that all copolymers are degradable in phosphate buffer at 37°C. The release profiles of the hydrophilic model drug ciprofloxacin hydrochloride follow first-order release kinetics. CSIRO 2008.
Ferroelectric liquid crystals induced by atropisomeric dopants: Dependence of the polarization power on the core structure of the smectic C host
Vizitiu, Despina,Lazar, Carmen,Halden, Brian J.,Lemieux, Robert P.
, p. 8229 - 8236 (1999)
A series of 11 chiral dopants with an atropisomeric core derived from 4,4′-dihydroxy-2,2′,6,6′-tetramethyl-3,3′- dinitrobiphenyl were synthesized in optically pure form. These compounds were doped into five different smectic C (SC) liquid crystal hosts to induce a ferroelectric SC* liquid crystal phase, and the reduced polarization Po was measured as a function of the dopant mole fraction xd over the range 0.005 d ≤ 0.05. The polarization power δp was found to strongly depend on the core structure of the SC host. For example, the dopant (+)-2,2′,6,6′-tetramethyl-3,3′-dinitro-4,4′-bis[(4- octyloxybenzoyl)oxy]biphenyl gave δp values of 2 in a phenyl benzoate SC host and 1738 nC/cm2 in a phenylpyrimidine SC host; the latter is one of the highest polarization power values reported thus far in the literature. In the phenylpyrimidine SC host, the polarization power was found to depend on the length of the dopant side chains and on the position of the atropisomeric core with respect to those of the surrounding SC host molecules, on the time average. The polarization power followed a trend opposite to that followed by the SC* helical pitch. Analysis of these results suggests that chirality transfer from the atropisomeric core of the dopant to those of the Sc host molecules plays a key role in amplifying the polarization induced in the phenylpyrimidine host. It is likely that such intercore chirality transfer results in an asymmetric distortion of the SC* lattice, which in turn, further increases the conformational asymmetry of the chiral dopant by virtue of increased diastereomeric bias between the SC* lattice and the chiral conformations of the dopant.
The effect of vicinal di-halo substituents on the organogelling properties of aromatic supramolecular gelators and their application as soft templates
Busch, Verónica M.,Di Chenna, Pablo H.,Di Salvo, Florencia,Giovanetti, Lisandro,Japas, M. Laura,MacCormack, Andrea S.
, p. 8198 - 8208 (2020)
A pronounced effect of vicinal dihalogen substituents on the gelling properties of aromatic low molecular weight organogelators is reported. A new family of N,N′-(4,5-dihalogen-1,2-phenylene)dialkylamides with fluorine, chlorine, bromine and iodine was designed and synthesized. A systematic investigation of their organogelling ability, thermic stability, mechanical properties and self-assembled structure was performed to elucidate the effect that the vicinal di-halo substituents have on the organogels. It was found that the presence of two halogen atoms (X) has a determinant effect as the brominated compounds are generally the most efficient organogelators. In hydrocarbons, the gelling ability increased from fluorine to iodine following the halogen bond donor ability trend. SAXS results were in agreement with a fibrillar self-assembly where the halogens are located at the surface of the fibers. Multiple cooperative interactions are involved in the self-assembly of the gels: π-π stacking, hydrogen bonds and X?X contacts. Thus, this work provides a new strategy for the design of new gelators or to improve the efficiency of known organogelators by introducing two vicinal halogen substituents into the aromatic rings. An ethanolic gel was also successfully used as a template to prepare silica and titania nanotubes. Hence, such organogels are promising materials for future research and development.
Synthesis and transdermal permeation-enhancing activity of carbonate and carbamate analogs of Transkarbam 12
Holas, Tomas,Vavrova, Katerina,Sima, Martin,Klimentova, Jana,Hrabalek, Alexandr
, p. 7671 - 7680 (2006)
Transkarbam 12 (5-(dodecyloxycarbonyl)pentylammonium-5-(dodecyloxycarbonyl)pentylcarbamate, T12) is a highly effective skin permeation enhancer. In this study, ester groups in the molecule of T12 were replaced by carbonate and carbamate ones, respectively. The in vitro permeation-enhancing activities were evaluated using porcine skin and compared with those of T12 and previously prepared series of amide, ketone, and alkyl analogs. According to the activities and behavior of the compounds in donor samples, ester group is essential for the activity of T12; its replacement not only decreases the enhancing potency, but is likely to change the mechanism of action.
Selective reduction of barbituric acids using SmI2/H 2O: Synthesis, reactivity, and structural analysis of tetrahedral adducts
Szostak, Michal,Sautier, Brice,Spain, Malcolm,Behlendorf, Maike,Procter, David J.
, p. 12559 - 12563 (2013)
Making a mark: Since the 1864 landmark discovery by Adolf von Baeyer, barbituric acids have played a prominent role in organic synthesis. Herein, the first chemoselective monoreduction of barbituric acids to the corresponding hemiaminals is described. The method delivers mono- and bicyclic hemiaminal products by a general single-electron-transfer polarity reversal mechanism. Re-use of this article is permitted in accordance with the Terms and Conditions set out at http://angewandte.org/open.
Differential scanning calorimetric and powder X-ray diffraction studies on a homologous series of N-acyl-L-alanine esters with matched chains (n = 9-18)
Sivaramakrishna,Swamy, Musti J.
, p. 1627 - 1635 (2015)
A homologous series of two chain derivatives of L-alanine, namely N-acyl L-alanine alkyl esters (NAAEs), bearing matched, saturated, acyl and alkyl chains (n= 9-18) have been synthesized. The thermotropic phase transitions and supramolecular structure of NAAEs were investigated by differential scanning calorimetry (DSC) and powder X-ray diffraction (PXRD). Results obtained from DSC studies indicate that the transition temperatures (T t), enthalpies (ΔH t) and entropies (ΔS t) exhibit odd-even alternation with compounds bearing odd acyl and alkyl chains showing higher values of T t, ΔH t and ΔS t as compared to NAAEs with even acyl and alkyl chains. However, the transition enthalpies and entropies of the odd- and even chain length series independently exhibit a linear dependence on the chain length. The d-spacings obtained from PXRD increase linearly with chain length with an increment of 1.76 ?/CH 2, suggesting that NAAEs adopt either a tilted bilayer structure or a bent structure. The present results provide a thermodynamic and structural basis for investigating the interaction of NAAEs with other membrane lipids, which in turn can shed light in understanding how they can enhance the transdermal permeability of stratum corneum.
L-ascorbyl 6-palmitate as lead compound targeting SphK1: an in silico and in vitro investigation
Chen, HaiJiao,Liu, Bo,Sun, Peng,Yang, Xinmei,Yao, Qingqiang,Zhi, Ying
, p. 781 - 787 (2021)
Sphingosine kinases (SphKs) are a class of lipid kinases, that have received extensive attention as important rate-limiting enzyme in tumor. Inhibition of the activity of SphK1 can lead to an anticancer effect. Herein, we describe the discovery process and biological characteristics of a new SphK1 inhibitor, ascorbyl palmitate, discovered through computer-aided drug design. Biochemical experiments show that ascorbyl palmitate has a strong inhibitory effect on SphK1, with an IC50 value of 6.4 μM. The MTT experiment showed that ascorbyl palmitate had anti-cancer effects toward the U87, A549, 22RV1, and A375 cell lines. Among them, ascorbyl palmitate has prominent inhibitory activity against the 22RV1 cell line, with an IC50 value of 41.57 μM. To explore the structure–activity relationship, four ascorbyl palmitate derivatives were synthesized and tested for kinase activity. The outstanding effect of ascorbyl palmitate toward SphK1 and its known non-toxicity suggest that ascorbyl palmitate may be a lead compound for the development of effective SphK1 anti-cancer inhibitors.
Benzimidazole tethered thioureas as a new entry to elastase inhibition and free radical scavenging: Synthesis, molecular docking, and enzyme inhibitory kinetics
Abbas, Qamar,Ashraf, Saba,Channar, Pervaiz Ali,Hassan, Abbas,Hassan, Mubashar,Rafique, Hummera,Raza, Hussain,Rind, Mahboob Ali,Saeed, Aamer,Seo, Sung-Yum,Ujan, Rabail,Ul-Hamid, Anwar
, (2021)
The porcine pancreatic elastase inhibition and free-radical scavenging play a crucial role in age progression. All the series of 10 newly synthesized benzimidazole thioureas (4a-j) were assessed for elastase inhibition and radical scavenging activity to identify the suitable anti-aging ingredient for cosmetics products. The compounds 4e, 4f, 4g, and 4h showed inhibition better than the standard, while compound 4f showed the most significant elastase inhibition with the IC50 value of 1.318 ± 0.025 μM compared with oleanic acid IC50 13.451 ± 0.014 used ±1.989 and 41.563 ± 0.824, respectively, as standard. Molecular docking studies were performed and the compound 4f showed binding energy of 7.2 kcal/mol. Kinetics studies revealed inhibition of the pancreatic elastase in a competitive manner. The relative binding energy and structure activity relationship (SAR) identified compound 4f as an effective inhibitor of porcine pancreatic elastase. Compounds 4e and 4i showed remarkable free-radical scavenging activity with SC50 values of 26.421.
