627-13-4Relevant academic research and scientific papers
NOVEL OXALYL PIPERAZINES ACTIVE AGAINST THE HEPATITIS B VIRUS (HBV)
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Page/Page column 123, (2020/11/12)
The present invention relates generally to novel antiviral agents. Specifically, the present invention relates to compounds which can inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV replication cycle, compositions comprising such compounds, methods for inhibiting HBV viral replication, methods for treating or preventing HBV infection, and processes and intermediates for making the compounds.
Practical catalytic nitration directly with commercial nitric acid for the preparation of aliphatic nitroesters
An, Jichao,He, Pan,Li, Wenhao,Liu, Peipei,Si, Mengyuan,Yang, Bo,Yang, Guanyu
supporting information, p. 6612 - 6616 (2020/09/21)
To pursue a sustainable and efficient approach for aliphatic nitroester preparation from alcohol, europium-triflate-catalyzed nitration, which directly uses commercial nitric acid, has been successfully developed. Gram scalability with operational ease showed its practicability.
Kinetics and Products of the Reactions of Ethyl and n-Propyl Nitrates with OH Radicals
Morin, Julien,Bedjanian, Yuri,Romanias, Manolis N.
, p. 822 - 829 (2016/11/02)
The kinetics of the reactions of ethyl (1) and n-propyl (2) nitrates with OH radicals has been studied using a low-pressure flow tube reactor combined with a quadrupole mass spectrometer. The rate constants of the title reactions were determined under pseudo–first-order conditions from kinetics of OH consumption in high excess of nitrates. The overall rate constants, k1 = 1.14 × 10?13 (T/298)2.45 exp(193/T) and k2 = 3.00 × 10?13 (T/298)2.50 exp(205/T) cm3 molecule?1 s?1 (with conservative 15% uncertainty), were determined at a total pressure of 1 Torr of helium over the temperature range (248–500) and (263–500) K, respectively. The yields of the carbonyl compounds, acetaldehyde and propanal, resulting from the abstraction by OH of an α-hydrogen atom in ethyl and n-propyl nitrates, followed by α-substituted alkyl radical decomposition, were determined at T = 300 K to be 0.77 ± 0.12 and 0.22 ± 0.04, respectively.
Novel analgesic/anti-inflammatory agents: 1,5-Diarylpyrrole nitrooxyalkyl ethers and related compounds as cyclooxygenase-2 inhibiting nitric oxide donors
Anzini, Maurizio,Di Capua, Angela,Valenti, Salvatore,Brogi, Simone,Rovini, Michele,Giuliani, Germano,Cappelli, Andrea,Vomero, Salvatore,Chiasserini, Luisa,Sega, Alessandro,Poce, Giovanna,Giorgi, Gianluca,Calderone, Vincenzo,Martelli, Alma,Testai, Lara,Sautebin, Lidia,Rossi, Antonietta,Pace, Simona,Ghelardini, Carla,Di Cesare Mannelli, Lorenzo,Benetti, Veronica,Giordani, Antonio,Anzellotti, Paola,Dovizio, Melania,Patrignani, Paola,Biava, Mariangela
supporting information, p. 3191 - 3206 (2013/06/05)
A series of 3-substituted 1,5-diarylpyrroles bearing a nitrooxyalkyl side chain linked to different spacers were designed. New classes of pyrrole-derived nitrooxyalkyl inverse esters, carbonates, and ethers (7-10) as COX-2 selective inhibitors and NO donors were synthesized and are herein reported. By taking into account the metabolic conversion of nitrooxyalkyl ethers (9, 10) into corresponding alcohols, derivatives 17 and 18 were also studied. Nitrooxy derivatives showed NO-dependent vasorelaxing properties, while most of the compounds proved to be very potent and selective COX-2 inhibitors in in vitro experimental models. Further in vivo studies on compounds 9a,c and 17a highlighted good anti-inflammatory and antinociceptive activities. Compound 9c was able to inhibit glycosaminoglycan (GAG) release induced by interleukin-1β (IL-1β), showing cartilage protective properties. Finally, molecular modeling and 1H- and 13C-NMR studies performed on compounds 6c,d, 9c, and 10b allowed the right conformation of nitrooxyalkyl ester and ether side chain of these molecules within the COX-2 active site to be assessed.
NO-donating tacrine hybrid compounds improve scopolamine-induced cognition impairment and show less hepatotoxicity
Fang, Lei,Appenroth, Dorothea,Decker, Michael,Kiehntopf, Michael,Lupp, Amelie,Peng, Sixun,Fleck, Christian,Zhang, Yihua,Lehmann, Jochen
supporting information; experimental part, p. 7666 - 7669 (2009/12/07)
A series of tacrine - NO donor hybrid compounds are synthesized and evaluated for cholinesterase inhibitory activity, cognition improving activity, and hepatotoxicity. The pharmacological results indicate that hybrid compounds 1, 2, and 3a potently inhibit cholinesterase in vitro and significantly improve the scopolamine-induced cognition impairment, whereas an analogue (3h) of 2 without the NO donor moiety does not. Compared to tacrine, 1 and 2 show much less hepatotoxicity. Molecular modeling studies suggest that 2 may interact with the catalytic and the peripheral anionic site of acetylcholinesterase.
Nitration of alcohols by nitryl fluoride
Fedorov,Eremenko
, p. 1022 - 1023 (2007/10/03)
A general method for the preparation of nitrates by treatment of alcohols with nitryl fluoride (FNO2) in MeCN in the presence of KF has been developed.
Separation of Diastereomeric and Enantiomeric Alkyl Nitrates - Systematic Approach to Chiral Discrimination on Cyclodextrin LIPODEX-D
Schneider, Manfred,Ballschmiter, Karlheinz
, p. 539 - 544 (2007/10/03)
High-resolution gas chromatographic separation of all diastereomeric monomethyl-substituted cyclohexyl nitrates is shown on a nonpolar methylpolysiloxane stationary phase, and the first application of this procedure to the environmental diastereomeric analysis of alkyl nitrates is presented.Two characteristic signals in the achiral analysis of atmospheric samples could be assigned to the smallest alkyl nitrate containing two asymmetric carbon atoms, 3-methyl-2-pentyl nitrate.Retention indices in the temperature-programmed separation based on the n-alkanes were determined.The homologous series of 1-alkyl nitrates were found to be useful as ECD-visible n-alkanes.Enantiomeric separation of alkyl nitrates was achieved on heptakis(3-O-acetyl,-2,6-di-O-pentyl)-β-cyclodextrin (LIPODEX-D).The influence of the nitrooxy group and the alkyl chain length on the chiral discrimination on LIPODEX-D is discussed for 25 chiral alkyl nitrates.The absolute configurations of some alkyl nitrates were assigned by asymmetric synthesis of enantiomerically pure references.The complexity of the alkyl nitrate mixtures present in air samoles does not allow a direct chiral separation as the alkyl nitrates partly coelute on the LIPODEX-D column.Column coupling of LIPODEX-D with a polar achiral stationary phase like polyalkylenglocol (PAG) was successfully applied to solve this problem, and the chiral alkyl nitrates present in a typical air sample were separated.A systematic nomenclature for alkyl nitrates is introduced to handle the steadily growing number of branched and long-chain nitrates detected in environmental analysis. - Keywords: analytical methods; alkyl nitrates; chiral resolution; cyclodextrins; gas chromatography
Formation of Organic Nitro-compounds in Flowing H2O2+NO2+N2+Organic Vapour Systems. Part 2.-H2O2+NO2+N2+Alkane System
Baulch, Donald L.,Campbell, Ian M.,Chappel, Jonathan M.
, p. 609 - 616 (2007/10/02)
The principal products from the surface-initiated reactions in flowing mixtures of H2O2, NO2,N2 and RH, where RH=ethane, propane, n-butane and n-pentane, have been identified as the nitroalkane, alkyl nitrite and alkyl nitrate.The product yields have been measured; in the case of propane the variation of the yields with total gas pressure has also been studied.Values have been obtained for the relative rates of primary and secondary H-atom abstraction from each alkane by OH and for the rate-constant ratios k3/k4 and k5/k6 at 298 K:.The trends in the product yields with the variation of pressure and change of R indicate that RO radicals are produced via reactions (4)-(6) rather than by a single-step reaction of R with NO2.
Formation of Organic Nitro-compounds in Flowing H2O2+NO2+N2+Organic Vapour Systems. Part 3.-Effects of O2 Addition on H2O2+NO2+N2+Alkane Systems
Baulch, Donald L.,Campbell, Ian M.,Chappel, Jonathan M.
, p. 617 - 628 (2007/10/02)
The effects of oxygen on the product distribution from the surface-initiated reactions in flowing mixtures of H2O2, NO2, N2 and RH, where RH=ethane, propane, n-butane and n-pentane, at 298 K have been studied.In the absence of O2, the principal products are the corresponding nitroalkane, alkyl nitrite and alkyl nitrate.In the presence of sufficiently large concentrations of O2, the predominant product is the alkyl nitrate and the only other products of significance, in some cases, are the corresponding carbonyl compounds.The variation of the product yields with / gives values for the rate-constant ratios k8/(k3+k4) for reaction at both primary and secondary radical sites:.Possible mechanisms by which the products are formed are discussed.
