710-27-0Relevant academic research and scientific papers
Inhibition of LDL oxidation and inflammasome assembly by nitroaliphatic derivatives. Potential use as anti-inflammatory and anti-atherogenic agents
Cataldo, Nicolás,Musetti, Bruno,Celano, Laura,Carabio, Claudio,Cassina, Adriana,Cerecetto, Hugo,González, Mercedes,Thomson, Leonor
, p. 178 - 186 (2018/10/15)
We have previously shown the antioxidant and anti-inflammatory properties of several para-substituted arylnitroalkenes. Since oxidative stress and inflammation are key processes that drive the initiation and progression of atherosclerosis, in the present work the antioxidant, anti-inflammatory and anti-atherogenic properties of an extended library of aryl-nitroaliphatic derivatives, including several newly designed nitroalkanes, was explored. The antioxidant capacity of the nitroaliphatic compounds, measured using the oxygen radical absorbance capacity assay (ORAC) showed that the p-methylthiophenyl-derivatives were about three times more effective than Trolox to prevent fluorescein oxidation, independently of the presence or the absence of the double bond next to the nitro group. The peroxyl radical scavenger capacity of the p-dimethylaminophenyl-derivatives was even higher, being the reduced form of these compounds even more active. In fact, while the antioxidant capacity of 1-dimethylamino-4-(2-nitro-1Z-ethenyl)benzene and 1-dimethylamino-4-(2-nitro-1Z-propenyl)benzene was 4.2 ± 0.1 and 5.4 ± 0.1 Trolox Eq/mol, respectively; ORAC values obtained with the ethyl and the propyl derivatives were 10 ± 1 and 13 ± 2 Trolox Eq/mol, respectively. The p-dimethylamino-derivatives, especially the nitroalkanes, were also able to prevent LDL oxidation mediated by peroxyl radicals. Oxygen consumption due to the oxidation of fatty acids was delayed in the presence of the dimethylamino substituted compounds, only the alkanes interrupted the chain of lipid oxidations decreasing the rate of oxygen consumption. Although the formation of foam cells in the presence of oxidized-LDL (oxLDL) remained unaffected, the molecules containing the dimethylamino moiety were able to decrease the expression of IL-1β in LPS/INF-γ challenged macrophages.
TiO2-SO42- Catalyzed Synthesis and Antimicrobial Activity/Molecular Docking Studies of β-Indolylnitroalkanes
Santhisudha, Sarva,Jayaprakash, Soora Harinath,Mohan, Gundluru,Kumar, Yellapu Nanda,Suganthi, Vaithiyanathan,Mohanasrinivasan, Vaithiyalingam,Reddy, Cirandur Suresh
, p. 290 - 297 (2016/05/19)
Michael addition of indole derivatives with various substituted nitrostyrenes to yield β- indolylnitroalkanes is accomplished effectively under solvent free conditions using TiO2-SO4 2- as efficient catalyst at 60 ° C. All the synthesized compounds were screened for their antibacterial activity through in silico and in vitro methods. The molecular docking studies against FabH enzyme, a potential drug target of bacterial fatty acid biosynthetic pathway indicated the scope of developing them a new class of antimicrobial agents. Among the title compounds, 5h exhibited the highest dock score and the highest antibacterial activity when compared with other compounds and the standard drug Ampicillin. In addition, the compounds 5d, 5e, 5g, 5h, 5i, 5j and 5l showed significant inhibitory activity at different dose concentrations under in vitro conditions against the specified bacterial strains thus qualifying for further clinical evaluation so that they can be used as effective anti-bacterial agents.
Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1- propenes as a new class of anticancer agents
McNamara, Yvonne M.,Cloonan, Suzanne M.,Knox, Andrew J.S.,Keating, John J.,Butler, Stephen G.,Peters, Günther H.,Meegan, Mary J.,Williams, D. Clive
scheme or table, p. 1328 - 1348 (2011/04/17)
Structural derivatives of 4-MTA, an illegal amphetamine analogue have been previously shown to have anticancer effects in vitro. In this study we report the synthesis of a series of novel 1,3-bis(aryl)-2-nitro-1-propene derivatives related in structure to 4-MTA. A number of these compounds containing a classic nitrostyrene structure are shown to have antiproliferative activities in vitro in a range of malignant cell lines, particularly against Burkitt's lymphoma derived cell lines, whilst having no effect on 'normal' peripheral blood mononuclear cells. Such effects appear to be independent of the serotonin transporter, a high affinity target for amphetamines and independent of protein tyrosine phosphatases and tubulin dynamics both of which have been previously associated with nitrostyrene-induced cell death. We demonstrate that a number of these compounds induce caspase activation, PARP cleavage, chromatin condensation and membrane blebbing in a Burkitt's lymphoma derived cell line, consistent with these compounds inducing apoptosis in vitro. Although no specific target has yet been identified for the action of these compounds, the cell death elicited is potent, selective and worthy of further investigation.
Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted α-alkylthioamphetamines
Cloonan, Suzanne M.,Keating, John J.,Corrigan, Desmond,O'Brien, John E.,Kavanagh, Pierce V.,Williams, D. Clive,Meegan, Mary J.
scheme or table, p. 4009 - 4031 (2010/08/06)
4-Methylthioamphetamine (4-MTA) is recognised as a 3,4-methylenedioxymethamphetamine (MDMA)-like drug of abuse. Such amphetamine-type drugs often contain byproducts of uncontrolled, illegal clandestine synthetic processes. We report the isolation and stru
6-SUBSTITUTED PHENOXYCHROMAN CARBOXYLIC ACID DERIVATIVES
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Page/Page column 153, (2010/01/30)
Compounds of Formula (I): in which A1, A2, W, L, G, R7a, R7b, R8, R9 and R10 have the meanings given in the specification, are DP2 receptor modulators useful in the treatment of immunologic diseases.
Kinetics of Reversible Thiolate Ion Addition to Substituted β-Nitrostyrenes in Water. Radicaloid Transition State or Principle of Nonperfect Synchronization?
Bernasconi, Claude F.,Schuck, David F.
, p. 2365 - 2373 (2007/10/02)
The kinetics of reversible nucleophilic thiolate ion (RS- with R = n-Bu, HOCH2CH2, MeO2CCH2CH2 and MeO2CCH2) addition to Z-substituted β-nitrostyrenes (Z = 4-Me2N, 4-MeO, 4-MeS, 4-Me, H, 3-Cl, 4-Cl, 3-CN, 4-CN, and 3-NO2), to form ArCH(RS)CH=NO2-, have been measured in water at 20 deg C.Rate constants in the forward (k1) and reverse direction (k-1) and equilibrium constants (K1) correlate reasonably well with Hammett ?-constants for the non-?-donor substituents but show deviations for the ?-donors 4-Me2N, 4-MeO, and 4-MeS.These deviations are negativefor K1 but positive for k1 and k-1; the positive deviations for the ?-donor substituents are also observed when plotting log k1 vs log K1 (Broensted plots).The negative deviations of K1 are a consequence of resonance stabilization of the olefin.The positive deviations are attributed to a transition-state stabilization stemming from a preorganization created by the ?-donor which leads to a better delocalization of the negative charge into the nitro group.An alternative interpretation of the rate acceleration in terms of a radicaloid transition state (Gross, Z.; Hoz, S.J.Am.Chem.Soc. 1988, 110, 7489) cannot be ruled out but is shown to be less attractive and unnecessary.Broensted parameters such as βnuc, βeq, βnnuc, and βnlg, and intrinsic rate constants (k0 = k1 = k-1 when K1 = 1) were determined from the dependence on the RS- basicity for β-nitrostyrene and 3-cyano-β-nitrostyrene. βeq is low (0.5), indicating that the carbon basicity of RS- is less sensitive to electronic effects in R than its proton basicity. βnuc (βnnuc) is very low, suggesting a transition state withvery little C-S bond formation.The low βnnuc (0.22) contrasts with a large αnnuc = d log k1/d log K1 = 0.74 (variation of Z), indicating a large transition-state imbalance (αnnuc - βnnuc), as previously observed in the reaction of RS- with α-nitrostilbenes.The intrinsic rate constant (log k0 = 3.5) is also similar to that for the reaction of RS- with α-nitrostilbenes and significantly higher than for the reaction of amines with β-nitrostyrenes.Most of these features can, at least in part, be attributed to the soft acid-soft base interactions of RS- with the nitroolefins.Rate constants for carbon protonation of several of the ArCH(RS)CH=NO2- adducts by acetic acid (kHAp were also determined.They display the unusual, but for nitronate ions typical, acceleration when Ar and/or R is made more electron withdrawing.
