7032-24-8Relevant articles and documents
Synthesis and smooth muscle calcium channel antagonist effects of alkyl 1,4-dihydro-2,6-dimethyl-4-(pyridinyl)-5-[2-(4,5-dihydro-4,4-dimethylo xazolin-2-yl)]-3-pyridinecarboxylates
Anana, Raymond D.,Knaus, Edward E.
, p. 408 - 412 (1996)
A group of racemic alkyl 1,4-dihydro-2,6-dimethyl-4-(3- or 4-pyridinyl)-5-[2-(4,5-dihydro-4,4-dimethyloxazolin-2-yl)]-3-pyridinec arboxylates 11a-e were prepared by using the Hantzsch reaction involving condensation of the Knoevenagel adducts 9a-e with 1-[2-(4,5-dihydro-4,4-dimethyloxazolin-2-yl)]-1-propen-2-amine (10). In contrast, the 4-(2-pyridinyl) analogue 11f was prepared by thionyl chloride mediated cyclization of the 5-{N-(1,1-dimethyl-2-hydroxyethyl)aminocarbonyl} moiety of 16 to the 5-[2-(4,5-dihydro-4,4-dimethyloxazolin-2-yl)] ring system (11f). In vitro calcium channel antagonist activity was determined by using the guinea pig ileum longitudinal smooth muscle (GPILSM) assay. Compared to the reference drug nifedipine (IC50=1.43 x 10-8 M), the title compounds 11 exhibited weak calcium channel antagonist activity (10-5 to 10-6 M range). A comparison of compounds 11 having a C-4 3-pyridinyl substituent showed that with respect to the alkyl ester R2-substituent, the relative potency order was i-Bu (11c)≤i-Pr (11e)>Me (11a). The point of attachment of the C-4 pyridinyl substituent in the isopropyl ester isomeric series of compounds was a determinant of activity where the potency profile was 4-py (11d)≤3-py (11e)>2-py (11f). Although less effective, the 4,5-dihydro-4,4-dimethyloxazolin-2-yl moiety acts as a bioisostere of the alkyl ester substituent present in classical 1,4-dihydropyridine calcium channel antagonists. The 4,5-dihydro-4,4-dimethyl-oxazolin-2-yl ring system is not an effective bioisostere of the 3-nitro group present in 1,4-dihydropyridine calcium channel agonists since isopropyl 1,4-dihydro-2,6-dimethyl-4-(2-pyridinyl)-5-[2-(4,5-dihydro-4,4-dimethy loxazolin-2-yl)]-3-pyridinecarboxylate (11f) produced a modest 10% increase in the in vitro contractile force of guinea pig left atrium at a concentration of 1.64 x 10-7 M, relative to the reference 3-nitro analogue 1 (EC50=9.6 x 10-6 M).
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Baehr,Doege
, p. 119,133 (1957)
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SERS/TERS Characterization of New Potential Therapeutics: The Influence of Positional Isomerism, Interface Type, Oxidation State of Copper, and Incubation Time on Adsorption on the Surface of Copper(I) and (II) Oxide Nanoparticles
Olszewski, Tomasz K.,Proniewicz, Edyta
supporting information, p. 4387 - 4400 (2022/03/16)
The aim of this study was to investigate how the oxidation state of copper (Cu(I) vs Cu(II)), the nature of the interface (solid/aqueous vs solid/air), positional isomerism, and incubation time affect the functionalization of the surface of copper oxide nanostructures by [(butylamino)(pyridine)methyl]phenylphosphinic acid (PyPA). For this purpose, 2-, 3-, and 4-isomers of PyPA and the nanostructures were synthesized. The nanostructure were characterized by UV-visible spectroscopy (UV-vis), scanning electron microscopy (SEM), Raman spectroscopy (RS), and X-ray diffraction (XRD) analysis, which proved the formation of spherical Cu2O nanoparticles (Cu2ONPs; 1500-600 nm) and leaf-like CuO nanostructures (CuONSs; 80-180/400-700 nm, width/length). PyPA isomers were deposited on the surface of NSs, and adsorption was investigated by surface-enhanced Raman scattering (SERS) and tip-enhanced Raman scattering (TERS). The changes of adsorption on the surface of copper oxide NSs caused by the above-mentioned factors were described and the enhancement factor on this substrate was calculated.
Dynamic Covalent Switches and Communicating Networks for Tunable Multicolor Luminescent Systems and Vapor-Responsive Materials
Zou, Hanxun,Hai, Yu,Ye, Hebo,You, Lei
, p. 16344 - 16353 (2019/10/16)
Molecular switches are an intensive area of research, and in particular, the control of multistate switching is challenging. Herein we introduce a general and versatile strategy of dynamic covalent switches and communicating networks, wherein distinct states of reversible covalent systems can induce addressable fluorescence switching. The regulation of intramolecular ring/chain equilibrium, intermolecular dynamic covalent reactions (DCRs) with amines, and both permitted the activation of optical switches. The variation in electron-withdrawing competition between the fluorophore and 2-formylbenzenesulfonyl unit afforded diverse signaling patterns. The combination of switches in situ further enabled the creation of communicating networks for multistate color switching, including white emission, through the delicate control of DCRs in complex mixtures. Finally, reversible and recyclable multiresponsive luminescent materials were achieved with molecular networks on the solid support, allowing visualization of different types of vapors and quantification of primary amine vapors with high sensitivity and wide detection range. The results reported herein should be appealing for future studies of dynamic assemblies, molecular sensing, intelligent materials, and biological labeling.
