10160-28-8Relevant articles and documents
Streamlined One-Pot Synthesis of Nitro Fatty Acids
El Rady, Eman A.,Hassan, Mohamed,Krieg, Sara-Cathrin,Maier, Thorsten J.,Manolikakes, Georg,Ndefo Nde, Cedric,Raslan, Mohamed A.,Roos, Jessica,Sadek, Kamal U.
, p. 2239 - 2252 (2021/07/22)
A novel method for the synthesis of nitro fatty acids (NFAs), an intriguing class of endogenously occurring lipid mediators, is reported. This one-pot procedure enables the controlled and stereoselective construction of nitro fatty acids from a simple set of common building blocks in a highly facile manner. Thereby, this methodology offers a streamlined, highly modular access to naturally occurring nitro fatty acids as well as non-natural NFA derivatives.
Total Synthesis of the Endocannabinoid Uptake Inhibitor Guineensine and SAR Studies
Bartholom?us, Ruben,Nicolussi, Simon,Baumann, Alice,Rau, Mark,Sim?o, Ana Catarina,Gertsch, Jürg,Altmann, Karl-Heinz
supporting information, p. 1590 - 1596 (2019/08/30)
Guineensine ((2E,4E,12E)-13-(benzo[d][1,3]dioxol-5-yl)-N-isobutyltrideca-2,4,12-trienamide) is a plant-derived natural product that inhibits reuptake of the endocannabinoid anandamide with sub-micromolar potency. We have established a highly efficient tot
Enantioselective Rhodium-Catalyzed Dimerization of ω-Allenyl Carboxylic Acids: Straightforward Synthesis of C2-Symmetric Macrodiolides
Steib, Philip,Breit, Bernhard
, p. 6572 - 6576 (2018/05/08)
Herein, we report on the first enantioselective and atom-efficient catalytic one-step dimerization method to selectively transform ω-allenyl carboxylic acids into C2-symmetric 14- to 28-membered bismacrolactones (macrodiolides). This convenient asymmetric access serves as an attractive route towards multiple naturally occuring homodimeric macrocyclic scaffolds and demonstrates excellent efficiency to construct the complex, symmetric core structures. By utilizing a rhodium catalyst with a modified chiral cyclopentylidene-diop ligand, the desired diolides were obtained in good to high yields, high diastereoselectivity, and excellent enantioselectivity.
Dynamic Rotational Motions of Vaulted Chiral trans-Bis(salicylaldiminato)palladium(II) Complexes Bearing Rigid or Flexible Carbon Chain Linkers
Ikeshita, Masahiro,Naota, Takeshi
, p. 4689 - 4695 (2018/11/23)
Planar chiral, trans-bis(salicylaldiminato)palladium(II) complexes having a macrocyclic vaulting structure consisting of either a heptamethylene-butadiynylene-heptamethylene (1) or polymethylene (2) bridge were synthesized and subsequently characterized by NMR, IR, high-resolution mass spectrometry, and single crystal XRD. The dynamic rotational behaviors of these vaulted complexes resulting from a skipping-rope-like molecular motion were examined on the basis of kinetic studies of the racemization of the optically pure (100 % ee) complexes. The chiral inversion rate was found to be significantly affected by the conformational flexibility of the complexes, which in turn could be controlled by adjusting the linker length, the linker rigidity, and the ligation properties of the solvent.
20-HETE RECEPTOR (GPR75) ANTAGONISTS AND METHODS OF USE
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Paragraph 00129, (2017/09/27)
The present invention concerns compounds and their use to treat cardiovascular disease, renal disease, thrombic disease, stroke, metabolic syndrome, cell proliferation, and ischemic cardiovascular disorders. Compounds of the present invention display sign
Identification of Novel Triazole-Based Nicotinamide Phosphoribosyltransferase (NAMPT) Inhibitors Endowed with Antiproliferative and Antiinflammatory Activity
Travelli, Cristina,Aprile, Silvio,Rahimian, Reza,Grolla, Ambra A.,Rogati, Federica,Bertolotti, Mattia,Malagnino, Floriana,Di Paola, Rosanna,Impellizzeri, Daniela,Fusco, Roberta,Mercalli, Valentina,Massarotti, Alberto,Stortini, Giorgio,Terrazzino, Salvatore,Del Grosso, Erika,Fakhfouri, Gohar,Troiani, Maria Pia,Alisi, Maria Alessandra,Grosa, Giorgio,Sorba, Giovanni,Canonico, Pier Luigi,Orsomando, Giuseppe,Cuzzocrea, Salvatore,Genazzani, Armando A.,Galli, Ubaldina,Tron, Gian Cesare
, p. 1768 - 1792 (2017/03/17)
Nicotinamide phosphoribosyltransferase (NAMPT) is a key enzyme involved in the recycling of nicotinamide to maintain adequate NAD levels inside the cells. It has been postulated to be a pharmacological target, as it is overexpressed in cancer cells as well as in inflammatory diseases. We describe the synthesis and characterization of a novel class of one-digit nanomolar NAMPT inhibitors based on in vitro characterization. The most active compound tested, 30c, displayed activity in xenograft and allograft models, strengthening the potential of NAMPT inhibitors as antitumoral drugs. Furthermore, in the present contribution we describe the ability of 30c to significantly improve the outcome of colitis in mice. Given that this is the first report of an effect of NAMPT inhibitors in colitis, this result paves the way for novel applications for this class of compounds.
Catalysis of Michael Additions by Covalently Modified G-Quadruplex DNA
Dey, Surjendu,Rühl, Carmen L.,J?schke, Andres
, p. 12162 - 12170 (2017/09/14)
Enantioselective catalysis utilizing G-quadruplex DNA-based artificial metalloenzymes has emerged as a new approach in the field of aqueous-phase homogeneous catalysis. Recently, a catalytic asymmetric Michael addition employing a covalently modified G-quadruplex in combination with CuII ions has been reported. Here we assess, by systematic chemical variation and using various spectrometric techniques, a variety of parameters that govern rate acceleration and stereoselectivity of the reaction, such as the position of modification, the topology of the quadruplex, the nature of the ligand, the length of the linker between ligand and DNA, the chemical identity of monovalent ions and transition metal complexes. The DNA quadruplex modified at position 10 (dU10) with hexynyl-linked bpy ligand showed twice the initial reaction rate as compared with the DNA strand derivatized at position 12 (dU12). The strikingly different dependence of the stereoselectivity on the linker length, and their different spectroscopic properties indicate large differences in the architecture of the catalytic centers between the dU10-derivatized and the dU12-modified quadruplexes. Upon addition of CuII, both types of bpy-derivatized DNA strands form defined 1:1 Cu–DNA complexes stable enough for mass spectrometric analysis, while the underivatized strands exhibit weak and unspecific binding, correlated with much lower catalytic rate acceleration. Both dU10- and dU12-derivatized quadruplexes could be reused ten times without reduction of stereoselectivity.
NOVEL CYP-EICOSANOID DERIVATIVES
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Paragraph 0262-0263, (2017/01/31)
The present invention relates to compounds according to general formula (I) which are analogues of epoxymetabolites produced by cytochrome P450 (CYP) enzymes from omega-3 (n-3) polyunsaturated fatty acids (PUFAs). The present invention further relates to compositions containing one or more of these compounds and to the use of these compounds or compositions for C the treatment or prevention of conditions and diseases associated with inflammation, proliferation, hypertension, coagulation, immune function, pathologic angiogenesis, heart failure and cardiac arrhythmias.
Asymmetric synthesis of 12-hydroxyheptadecatrienoic acid and its 5,6-dihydro- and 14,15-dehydro-derivatives
Kobayashi, Yuichi,Morita, Masao,Ogawa, Narihito,Kondo, Daiki,Tojo, Toshifumi
supporting information, p. 10667 - 10673 (2016/11/30)
Natural 12-hydroxyheptadecatrienoic acid (12-HHT) with an S configuration was synthesised by a Suzuki-Miyaura coupling of C10-C17 iodo alcohol with C1-C9 vinylborane. The iodo alcohol was synthesised by utilising Sharpless asymmetric epoxidation of the corresponding trimethylsilyl alcohol. The method yielded more than 100 mg of 12-HHT. Similarly, syntheses of 5,6-dihydro- and 14,15-dehydro derivatives of 12-HHT, known as HHD and HHTE, respectively, were completed in a stereoselective manner.
The synthesis and biological evaluation of a kabiramide C fragment modified with a WH2 consensus actin-binding motif as a potential disruptor of the actin cytoskeleton
Tetlow, Daniel J.,Winder, Steve J.,A?ssa, Christophe
supporting information, p. 807 - 810 (2016/01/12)
The F-actin depolymerisation potency of a fragment of kabiramide C was increased when modified with a WH2 consensus actin-binding motif LKKV. Despite its low affinity for actin monomers, a shorter analogous fragment not bearing LKKV was identified as a potent inhibitor of actin polymerisation and a promoter of its depolymerisation, resulting in a loss of actin stress fibres in cells.
