473-62-1Relevant academic research and scientific papers
Design and synthesis of pinane oxime derivatives as novel anti-influenza agents
Dong, Jianghong,Xiao, Mengjie,Ma, Qinge,Zhang, Guicheng,Zhao, Weijie,Kong, Mengjie,Zhang, Yue,Qiu, Luyun,Hu, Wenhui
, (2020)
Parasitic characteristics, mutations and resistance of influenza A virus make it difficult for current influenza antiviral drugs to maintain long-term effectiveness. Currently, to design non-adamantane compounds targeting the S31N mutant of M2 proton channel is a promising direction for the development of novel anti-influenza drugs. In our previous research, a pinanamine-based antiviral M090 was discovered to target hemagglutinin instead of M2, with its structure being highly similar to reported M2-S31N inhibitors. Herein, a series of pinane oxime derivatives were designed from scratch and evaluated for anti-influenza activity and their cytotoxicity in vitro. Utilizing a combination of structure-activity relationship analysis, electrophysiological assay and molecular docking, the most potent compound 11h, as a M2-S31N blocker, exhibited excellent activity with EC50 value at the low micromolar level against both H3N2 and H1N1. No significant toxicity of 11h was observed. In addition, compound 11h was located tightly in the pore of the drug-binding site with the thiophene moiety facing down toward the C-terminus, and did not adopt a similar position and orientation as the reference inhibitor.
Asymmetric Synthesis of Oxygenated Monoterpenoids of Importance for Bark Beetle Ecology
Ganji, Suresh,Svensson, Fredric G.,Unelius, C. Rikard
, p. 3332 - 3337 (2020/11/30)
Herein we report the asymmetric syntheses of a number of oxygenated terpenoids that are of importance in the chemical ecology of bark beetles. These are pinocamphones, isopinocamphones, pinocarvones, and 4-thujanols (= sabinene hydrates). The camphones were synthesized from isopinocampheol, the pinocarvones from β-pinene, and the thujanols from sabinene. The NMR spectroscopic data, specific rotations, and elution orders of their stereoisomers on a chiral GC-phase (β-cyclodextrin) are also reported. This enables facile synthesis of pure compounds for biological activity studies and identification of stereoisomers in mixed natural samples.
Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene
Kmieciak, Anna,Krzemiński, Marek P.
supporting information, p. 2493 - 2499 (2019/12/11)
New chiral regioisomeric γ-hydroxyphosphine ligands were synthesized from α-pinene. The key transformation was the thermal [2,3]-sigmatropic rearrangement of allyldiphenylphosphinites, obtained from (1R,2R,4S,5R)-3-methyleneneoisoverbanol and (1R,2R,3R,5R)-4-methyleneneoisopinocampheol, to allylphosphine oxides. Hydroxy groups were introduced stereoselectively through a hydroboration–oxidation reaction proceeding from the less hindered site providing a trans relationship between the hydroxy and the phosphine substituents.
Synthesis of bimetallic Zr(Ti)-naphthalendicarboxylate MOFs and their properties as Lewis acid catalysis
Rasero-Almansa, Antonia M.,Iglesias, Marta,Sánchez, Félix
, p. 106790 - 106797 (2016/11/23)
Bimetallic Zr(Ti)-NDC based metal-organic frameworks (MOFs) have been prepared by incorporation of titanium(iv) into zirconium(iv)-NDC-MOFs (UiO family). The resulting materials maintain thermal (up to 500 °C), chemical and structural stability with respect to parent Zr-MOFs as can be deduced from XRD, N2 adsorption, FTIR and thermal analysis. The materials have been studied in Lewis acid catalyzed reactions, such as, domino Meerwein-Ponndorf-Verley (MPV) reduction-etherification of p-methoxybenzaldehyde with butanol, isomerization of α-pinene oxide and cyclization of citronellal.
Identification of camphor derivatives as novel M2 ion channel inhibitors of influenza A virus
Zhao, Xin,Zhang, Zhen-Wei,Cui, Wei,Chen, Shengwei,Zhou, Yang,Dong, Jianghong,Jie, Yanling,Wan, Junting,Xu, Yong,Hu, Wenhui
supporting information, p. 727 - 731 (2015/04/27)
Amantadine derivatives have been the only drugs marketed as M2 inhibitors of influenza A for decades. The identification of pinanamine as a novel M2 inhibitor suggests that M2 ion channels can accommodate more types of hydrophobic scaffolds. Herein, we further investigated the M2 ion channels and identified camphor derivatives as new types of M2 inhibitors. Compound 18 was found to be more potent than amantadine against wild-type influenza virus. The molecular docking revealed that compound 18 occupies more space in the M2 ion channel than amantadine and thus exhibits enhanced activity. This journal is
Ring-opening of epoxides promoted by organomolybdenum complexes of the type [(η5-C5H4R)Mo(CO)2(η3-C3H5)] and [(η5-C5H5)Mo(CO)3(CH2R)]
Bruno, Sofia M.,Gomes, Ana C.,Abrantes, Marta,Valente, Anabela A.,Pillinger, Martyn,Gon?alves, Isabel S.
, p. 179 - 183 (2015/10/19)
The cyclopentadienyl molybdenum carbonyl complexes [(η5-C5H4R)Mo(CO)2(η3-C3H5)] and [(η5-C5H5)Mo(CO)3(CH2R)] (R = H, COOH) have been shown to promote acid-catalysed reactions in liquid phase, under moderate conditions. The catalytic alcoholysis of styrene oxide with ethanol at 35 °C gave 2-ethoxy-2-phenylethanol in 100% yield within 30 min for the dicarbonyl complexes and 3-6 h for the tricarbonyl complexes. Steady catalytic performances were observed in consecutive runs with the same catalytic solution, suggesting fairly good catalytic stability. In the second acid-catalysed reaction studied, the isomerization of α-pinene oxide at 55 °C gave campholenic aldehyde and trans-carveol in a total yield of up to 86% at 100% conversion. Chemoselectivity is shown to be solvent dependent.
Catalytic isomerisation of α-pinene oxide in the presence of ETS-10 supported ferrocenium ions
Bruno, Sofia M.,Gomes, Ana C.,Coelho, Ana C.,Brand?o, Paula,Valente, Anabela A.,Pillinger, Martyn,Gon?alves, Isabel S.
, p. 66 - 71 (2015/06/08)
Ferrocenium ions, [Fc]+, have been immobilised in the microporous titanosilicate ETS-10 by ion exchange of Na+/K+ ions under hydrothermal conditions. The resultant hybrid inorganic-organometallic (ETS-10/[Fc]+) material was characterised by elemental analysis, diffuse reflectance UV-Vis spectroscopy, FT-IR spectroscopy, powder X-ray diffraction, scanning electron microscopy, and thermogravimetric analysis. The ETS-10/[Fc]+ sample was tested as a catalyst for the isomerisation of α-pinene oxide (PinOx) at 35 C. With α, α, α-trifluorotoluene (TFT) as solvent, campholenic aldehyde (CPA) was the main product formed in 38% yield at 100% conversion and 30 min reaction. Other reaction products included trans-carveol, iso-pinocamphone and trans-pinocarveol. The same PinOx conversion and CPA yield could be reached within 1 min reaction time by increasing the reaction temperature (to 55 °C) and the Fe:PinOx molar ratio. Other solvents (hexane, CH3CN, toluene) led to poorer results than TFT. Characterisation of the used catalyst, together with an analysis of the catalytic activity of the liquid phase obtained after contact of ETS-10/[Fc]+ with TFT, indicated that the ETS-10/[Fc]+ sample was resistant toward leaching of iron-containing active species. When the recovered solid was reused in a second batch run, catalytic activity was lower than in the first run, while selectivity to CPA was higher.
Several monoterpenoid bromination products
Frolova,Bezuglaya,Alekseev,Slepukhin,Kuchin
, p. 449 - 454 (2014/08/18)
2α-Bromo,10β-pinanone-3 and 3α-bromo,10β-pinanone-4 were formed with 92-98% selectivity by bromination of isopinocamphone and cis-verbanone with Meldrum's acid dibromide. 3α-Bromo, 10β-pinanone-4 was prepared for the first time. Its structure was confirmed by an XSA. Bromination of menthone by Meldrum's acid dibromide formed mainly a mixture of diastereomeric 2-bromomenthones in a 2:1 ratio. Oxidative bromination of isopinocampheol by Ce(III)-LiBr-H2O2 caused rearrangement of the pinane structure into bornane and formed a mixture of 6-endo- and 6-exo-bromocamphor in a 5:1 ratio.
ANALGESIC COMPOUNDS, METHODS, AND FORMULATIONS
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Paragraph 0115-0116, (2013/09/12)
Provided are analgesic compounds, and salts thereof, of formula: (I) wherein A is: (A) Additionally, pharmaceutical formulations and methods of use employing the above compounds are provided.
ANALGESIC COMPOUNDS, METHODS, AND FORMULATIONS
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Page/Page column 76-77, (2012/08/08)
Provided are compounds, and salts thereof, of formula (I): wherein (A) is R1 is hydrogen, C1-C5 alkyl, C1-C5 alkoxy, C1-C5 haloalkyl, C1-C5 alkanol, -(C1-C5 alkyl)phenyl, or phenyl, or a group of the formula -C(O)-R12, where R12 may be C1-C5 alkyl, C1-C5 alkoxy, C1-C5 haloalkyl, C1-C5 alkanol, -(C1-C5 alkyl)phenyl, or phenyl; R2 and R3 are independently hydrogen, C1-C5 alkyl, C1-C5 alkoxy, halogen, C1-C5 haloalkyl, or C1-C5 haloalkoxy; R4 and R5 are independently hydrogen, C1-C5 alkyl, or -(C1-C5 alkyl)phenyl; R6 is hydrogen, hydroxy, or is absent; R7 is hydrogen; R8 and R9 are independently hydrogen or methyl; R10 is hydrogen; R11 is hydrogen or C1-C5 alkyl; or R7 and R10 combine to form -CH2- or -(CH2)2-; or R8 and R9 combine to form a cyclopropyl group with the carbon to which they are attached; or R10 and R11 combine to form -CH2- or -(CH2)3-. Additionally, pharmaceutical formulations and methods of use employing the above compounds are provided.
