Synthesis and biological activity of novel substituted benzanilides as potassium channel activators. V

Biagi, Giuliana; Giorgi, Irene; Livi, Oreste; Nardi, Antônio Egídio; Calderone, Vincenzo; Martelli, Alma; Martinotti, Enrica; Salerni, Oreste LeRoy

doi:10.1016/j.ejmech.2004.02.006

Cited by 44 publications

(32 citation statements)

References 30 publications

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“…Earlier reports have identified a number of both synthetic and naturally occurring compounds that could activate BK currents, including NS1608 (25,40,42), NS004 (25,26,32,49), NS1619 (11,50,51), as well as a number of other less well-characterized compounds and their derivatives (3,7,8,23,38). However, to date, these synthetic BK channel openers have lacked selectivity, particularly on native tissue (35).…”

Section: Discussionmentioning

confidence: 96%

BK channel activation by NS11021 decreases excitability and contractility of urinary bladder smooth muscle

Layne

Nausch

Olesen

et al. 2010

American Journal of Physiology-Regulatory, Integrative and Comp

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Large-conductance Ca(2+)-activated potassium (BK) channels play an important role in regulating the function and activity of urinary bladder smooth muscle (UBSM), and the loss of BK channel function has been shown to increase UBSM excitability and contractility. However, it is not known whether activation of BK channels has the converse effect of reducing UBSM excitability and contractility. Here, we have sought to investigate this possibility by using the novel BK channel opener NS11021. NS11021 (3 microM) caused an approximately threefold increase in both single BK channel open probability (P(o)) and whole cell BK channel currents. The frequency of spontaneous action potentials in UBSM strips was reduced by NS11021 from a control value of 20.9 + or - 5.9 to 10.9 + or - 3.7 per minute. NS11021 also reduced the force of UBSM spontaneous phasic contractions by approximately 50%, and this force reduction was blocked by pretreatment with the BK channel blocker iberiotoxin. NS11021 (3 microM) had no effect on contractions evoked by nerve stimulation. These findings indicate that activating BK channels reduces the force of UBSM spontaneous phasic contractions, principally through decreasing the frequency of spontaneous action potentials.

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Section: Discussionmentioning

confidence: 96%

BK channel activation by NS11021 decreases excitability and contractility of urinary bladder smooth muscle

Layne

Nausch

Olesen

et al. 2010

American Journal of Physiology-Regulatory, Integrative and Comp

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“…Arslan et al [16] reported the molecular structure and vibrational spectra of 2-chloro-N-(diethylcarbamothioyl) benzamide by Hartree-Fock (HF) and density functional theory (DFT) methods. Biagi et al [17] reported the synthesis and biological activity of novel, substituted benzanilides as potassium channel activators. The spin-trapping behavior of carbamoyl substituted derivatives toward different oxygen-and carbon-centered radicals has been reported.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic investigations and computational study of 2‐[acetyl(4‐bromophenyl)carbamoyl]‐4‐chlorophenyl acetate

Panicker¹,

Varghese

Mariamma³

et al. 2009

J Raman Spectroscopy

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The Fourier transform Raman (FT-Raman) and Fourier transform infrared (FT-IR) spectra of 2-[acetyl(4-bromophenyl)carbamoyl]-4-chlorophenyl acetate were studied. The vibrational wavenumbers were examined theoretically using the Gaussian03 set of quantum chemistry codes, and the normal modes were assigned by potential energy distribution (PED) calculations. The simultaneous Raman and infrared (IR) activations of the C O stretching mode in the carbamoyl moiety show a charge transfer interaction through a π-conjugated path. From the optimized structure, it is clear that the hydrogen bonding decreases the double bond character of the C O bond and increases the double bond character of the C-N bonds. The first hyperpolarizability and predicted IR intensities are reported. The calculated first hyperpolarizability is comparable with the reported values of similar structures, which makes this compound an attractive object for future studies of nonlinear optics. Optimized geometrical parameters of the compound are in agreement with similar reported structures.

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“…The use of strong acids such as HCl facilitated cyclization rather than migration (entry 15), whereas the use of Lewis acids such as InCl 3 produced a low yield of 1. In attempts to improve the reaction profile by changing the solvent, we also examined cosolvent systems, and the combination of THF and H 2 O as cosolvents enormously improved the reaction temperature and reaction time (entries [9][10][11][12], that is, the reaction proceeded at room temperature in a reduced reaction time. From the various reaction conditions that were examined, the optimized reaction conditions were found to be 2-nitrophenyl benzoate (1 mmol, 1 equiv)/indium (5 equiv)/AcOH (10 equiv) in THF/H 2 O (3:3 v/v, mL) at room temperature (entry 10).…”

Section: Resultsmentioning

confidence: 99%

N‐(2‐hydroxyaryl)benzamide synthesis from 2‐nitroaryl benzoates via an indium‐mediated reduction‐migration reaction

Lee¹,

Kim²,

Jun³

et al. 2011

Heteroatom Chemistry

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A one‐pot reduction‐triggered N‐(2‐hydroxyaryl)benzamide synthesis from 2‐nitroaryl benzoate substrates was investigated. In the presence of indium/AcOH in THF/H2O, 2‐nitroaryl benzoates produced reasonable yields of the benzo group migrated N‐(2‐hydroxyaryl)benzamides at room temperature within 1 h. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:158–167, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20669

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Synthesis and biological activity of novel substituted benzanilides as potassium channel activators. V

Cited by 44 publications

References 30 publications

BK channel activation by NS11021 decreases excitability and contractility of urinary bladder smooth muscle

BK channel activation by NS11021 decreases excitability and contractility of urinary bladder smooth muscle

Spectroscopic investigations and computational study of 2‐[acetyl(4‐bromophenyl)carbamoyl]‐4‐chlorophenyl acetate

N‐(2‐hydroxyaryl)benzamide synthesis from 2‐nitroaryl benzoates via an indium‐mediated reduction‐migration reaction

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