92189-38-3Relevant academic research and scientific papers
Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase
Silvestri, Romano,Artico, Marino,De Martino, Gabriella,Ragno, Rino,Massa, Silvio,Loddo, Roberta,Murgioni, Chiara,Giulia Loi, Anna,La Colla, Paolo,Pani, Alessandra
, p. 1567 - 1576 (2007/10/03)
A novel series of 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazole (DAMNI) analogues were synthesized and tested in cell-based assays and in enzyme assays against HIV-1 recombinant reverse transcriptase (RT). Preparation of the new derivatives was performed by reacting the appropriate benzhydrols or the correspondig bromides with 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole or the 3-hydroxypropyl homologue. Several compounds showed anti-HIV-1 activity in the submicromolar range. Structure-activity relationship studies suggested that meta substitution at one phenyl ring of the diarylmethane moiety strongly influences the antiviral activity. The 3,5-disubstitution at the same phenyl ring led to less potent derivatives. Molecular modeling and docking studies within the RT non-nucleoside binding site confirmed that DAMNIs, similar to other NNRTIs such as TNK-651 and delavirdine (BHAP U90152), assume a butterfly-like conformation that appears to be halfway between that of classical NNRTIs, such as nevirapine, HEPT, TBZ, TIBO, and DABOs, and the conformation of BHAPs. In particular, the diphenylmethane moiety mimics the wings whereas the 1-(2-methyl-5-nitroimidazolyl)ethane portion resembles the BHAP 5-methanesulfonamidoindole-2-carbonylpiperazine portion.
Tricyclic compounds, their production and use
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, (2008/06/13)
A compound of the formula: wherein R1 is H or a substituent; m is 1-3; Ar is an aromatic group which may be substituted; X is a bond or a divalent straight-chain group having 1-6 atoms which may be substituted; Y is —S—, —O—, or —N(R2— (R2 is H or a substituent group), Z is —N= or —C(R3)= (R3 is H or a hydrocarbon group), ring A is a benzene ring; ring B is a 5- to 7-membered ring which may be substituted, or a salt thereof is useful for eliciting a prostaglandin I2 receptor agonistic effect.
Benzylphosphonic acid inhibitors of human prostatic acid phosphatase
Schwender,Beers,Malloy,Cinicola,Wustrow,Demarest,Jordan
, p. 311 - 314 (2007/10/03)
A series of α-substituted benzylphosphonic acids is described as inhibitors of human prostatic acid phosphatase, an enzyme has been used as a model to study aryl phosphatases. The most potent inhibitors in this series are 2-trifluoromethylbenzhydrylphosphonic acid (9 μM), and α-(2-phenylethyl)benzylphosphonic acid (14 μM). The structure-activity studies suggest that bulk tolerance beyond the phosphate binding area limits the steric or hydrophobic contribution to inhibitor potency achieved through α-carbon substitution.
Phosphorus Lone Pairs Stabilization of Carbocations: the Synthesis and Dynamics of Unsymmetrical Methylene Phosphonium Ions
Heim, Udo,Pritzkow, Hans,Schoenberg, Hartmut,Gruetzmacher, Hansjoerg
, p. 673 - 674 (2007/10/02)
Halide abstractions from P-chlorinated phosphorus ylides 9a-c either by AlCl3 or SnCl2 yield unsymmetrical methylene phosphonium ions 10a-c in which energy barriers > 83 kJ mol-1 for the rotation around the P=C have been estimated by NMR techniques.The salts with AlCl4- counteranions are stable, but compounds with SnCl3- anions decompose stereoselectively to unsymmetrical methylene phosphanes, SnCl2, and t-BuCl.
