2-Amino-5,5-dimethylthiazol-4(5<i>H</i>)-one

Josey, Daniel; Shank, Nathaniel; Padgett, Clifford W.

doi:10.1107/s2414314619006138

Cited by 2 publications

(3 citation statements)

References 6 publications

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“…Furthermore, the S39À C36, S39À N40, S39À O49, and S39À O50 lengths belonging to the benzenesulfonamide ring were determined by XRD at 1.76, 1.60, 1.39, and 1.41 Å [70] whereas they were predicted by DFT at 1.79, 1.71, 1.45, and 1.46 Å. Related to the thiazole ring, C42À N40, C42À N48, C42À S43, and S43À C45 lengths were calculated as 1.40, 1.30, 1.76, and 1.74 Å and recorded [71] as 1.31, 1.33, 1.75, and 1.83 Å. As expected aromatic ring systems, the bond angles C1À C2À C3, C3À C4À C8, C4À C5À C6, and C4À C5À C16 of the pyrene ring were estimated at 120.8°, 120.2°, 119.2°, and 118.8°whereas they were reported [69] at 120.5°, 119.8°, 119.6°, and 118.5°, respectively.…”

Section: Molecular Structure and Physicochemical Propertiesmentioning

confidence: 84%

“…[70] Related to the sulfonamide functional, the O49À S39À O50 and N40À S39À C36 bond angles were calculated as 123.3°with a deviation of 5.1°and 106.3°with a deviation of 2.9°, namely, which they were recorded as 118.2°and 109.2°. [70] The N40À C42À S43, N40À C42À N48, and S43À C42À N48 angles belonging to the thiazole ring were reported as 120.7°, 121.8°, and 117.4°, [71] which were calculated as 122.9°, 121.5°, and 115.3°. From Table 2, the dihedral angles C1À C2À C3À C4, C3À C4À C8À C9, and C10À C9À C11À C12 of the pyrene ring of the compound were determined as À 0.0°, À 0.7°, and 179.5°, respectively.…”

Section: Molecular Structure and Physicochemical Propertiesmentioning

confidence: 99%

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New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

Erdoğan

Serdaroğlu

2021

ChemistrySelect

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A novel pyrene-sulfathiazole-based potential drug candidate 3 was designed, successfully synthesized by a condensation reaction of pyrenecarboxaldehyde (1) with sulfathiazole (2) in good yield, and fully characterized by NMR, IR, UV-Vis, and HRMS spectroscopic techniques. The TD-DFT/B3LYP calculations displayed that the recorded peaks at 396, 377, 280, and 236 nm were due to the mainly n-π* and partially π-π* transitions that occurred on pyrene, azomethine, and sulfathiazole moieties. The NBO results disclosed that the electron delocalizations happened onto sulfathiazole, aromatic rings (pyrene and Ph-), and azomethine groups had the main responsibility of the lowering stabilization energy of compound 3. The NMR shifts were calculated by using the GIAO approaches in the DMSO phase and compared with the relevant data recorded. The thermodynamic and quantum chemical quantities were used for elucidating the physicochemical properties and reactivity behavior, in THF, DMSO, and water simulation environments. Accordingly, the calculated DM (D) and α (au) order of compound 3 were calculated in the order of vacuum < THF < DMSO < water, which indicated that the stability and thus reactivity of the compound strongly depended on the solvent environment. The FMO studies implied that the electron-donating possibility of compound 3 was dominant to the electron-accepting potency. In this work, the SMD version of IEFPCM was used in solvent media simulations.

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Section: Molecular Structure and Physicochemical Propertiesmentioning

confidence: 84%

Section: Molecular Structure and Physicochemical Propertiesmentioning

confidence: 99%

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

Erdoğan

Serdaroğlu

2021

ChemistrySelect

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“…Considering that tautomers may occur (Attanasi et al, 2008;Josey et al, 2019), we calculated the pKa's for all ionizable groups in both tautomers. The percent of compound ionized was calculated from the Henderson-Hasselbalch equation assuming each tautomer is pure.…”

Section: Modulation Of Single Channel Conductance Levelsmentioning

confidence: 99%

The Negative Allosteric Modulator EU1794-4 Reduces Single-Channel Conductance and Ca²⁺ Permeability of GluN1/GluN2A N-Methyl-d-Aspartate Receptors

et al. 2021

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NMDA receptors are ligand-gated ion channels that mediate a slow, Ca 2+-permeable component of excitatory synaptic currents. These receptors are involved in several important brain functions, including learning and memory, and have also been implicated in neuropathological conditions and acute CNS injury, which has driven therapeutic interest in their modulation. The EU1794 series of positive and negative allosteric modulators of NMDA receptors has structural determinants of action near the pre-M1 helix that is involved in channel gating. Here we describe the effects of the negative allosteric modulator EU1794-4 on GluN1/GluN2A channels studied in excised outside-out patches. Co-application of EU1794-4 with a maximally effective concentration of glutamate and glycine increases the fraction of time the channel is open by nearly 1.5-fold, yet reduces single channel conductance by increasing access of the channel to several subconductance levels, which has the net overall effect of reducing the macroscopic current. The lack of voltagedependence of negative modulation suggests this is unrelated to a channel block mechanism. As seen with other NMDA receptor modulators that reduce channel conductance, EU1794-4 also reduces the Ca 2+ permeability relative to monovalent cations of GluN1/GluN2A receptors. We conclude that EU1794-4 is a prototype for a new class of NMDA receptor negative allosteric modulators that reduce both the overall current that flows following receptor activation and the flux of Ca 2+ ion relative to monovalent cations. Significance Statement NMDA receptors are implicated in many neurological conditions but are challenging to target given their ubiquitous expression. Several newly identified properties of the negative allosteric modulator EU1794-4, including reducing Ca 2+ flux through NMDA receptors and attenuating channel conductance, explain why this modulator reduces but does not eliminate This article has not been copyedited and formatted. The final version may differ from this version.

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2-Amino-5,5-dimethylthiazol-4(5H)-one

Cited by 2 publications

References 6 publications

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

The Negative Allosteric Modulator EU1794-4 Reduces Single-Channel Conductance and Ca²⁺ Permeability of GluN1/GluN2A N-Methyl-d-Aspartate Receptors

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2-Amino-5,5-dimethylthiazol-4(5H)-one

Cited by 2 publications

References 6 publications

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

New Hybrid (E)‐4‐((pyren‐1‐ylmethylene)amino)‐N‐(thiazol‐2‐yl)benzenesulfonamide as a Potential Drug Candidate: Spectroscopy, TD‐DFT, NBO, FMO, and MEP Studies**

The Negative Allosteric Modulator EU1794-4 Reduces Single-Channel Conductance and Ca2+ Permeability of GluN1/GluN2A N-Methyl-d-Aspartate Receptors

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The Negative Allosteric Modulator EU1794-4 Reduces Single-Channel Conductance and Ca²⁺ Permeability of GluN1/GluN2A N-Methyl-d-Aspartate Receptors