Thermodynamics of Solubility Processes of Novel Drug-like Spiro-Derivatives in Model Biological Solutions

Blokhina, Svetlana V.; Ol’khovich, Marina V.; Sharapova, Angelica; Прошин, А. Н.; Perlovich, German L.

doi:10.1021/je300143a

Cited by 10 publications

(11 citation statements)

References 22 publications

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“…The higher the temperature, the more shift to the hexane phase is observed. It is interesting that the log D H/B value for isopropyl substituted thiazine of the same molecular structure 16 is higher than that of compound II.…”

Section: Resultsmentioning

confidence: 98%

New Bicyclic 1,3-Selenazine Derivatives: Distribution in Model Biological Media and Membrane Permeability

et al. 2015

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2-Amino-1,3-selenazine template derivatives in the form of hydrobromides were synthesized. Phenyl, paraisopropylphenyl, and para-fluorophenyl were used as substituents. The distribution coefficients of the compounds in two-component systems modeling biological membranes, pH 2.0 and 7.4 buffer solution−organic solvent, were determined by a shake-flask method within the temperature range of 293 K to 313 K. Influences of the molecular structure, pK a , and pH of the buffer solutions, temperature, and solvent chemical nature on the distribution processes were investigated. Distribution thermodynamic functions were calculated for the selenazines under 298 K. It was established that the selenazines studied are substances with high membrane permeability.

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Section: Resultsmentioning

confidence: 98%

New Bicyclic 1,3-Selenazine Derivatives: Distribution in Model Biological Media and Membrane Permeability

et al. 2015

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“…The molar solubilities of drugs were measured spectrophotometrically with an accuracy of (2 to 3) % using a protocol described earlier. 16 2.3. Differential Scanning Calorimetry.…”

Section: Methodsmentioning

confidence: 99%

“…Introduction of a Cl atom into the ortho position of the first phenyl ring of compound (16) (which leads to the formation of compound (31)) reduces solubility by 2.5 times. In its turn, the transfer of a Cl atom from the ortho (29) to the para (31) position of the first phenyl ring results in a 4-time solubility growth.…”

Section: Methodsmentioning

confidence: 99%

“…And replacing a Cl atom in the ortho position of the second phenyl ring of compound (23) with a methyl group (34) results in a 2-time solubility rise. It is interesting that the introduction of a methyl group into the ortho-position of either the first or the second phenyl ring of compound (16) (which results in the formation of compounds ( 28) and (36), respectively) leads to a 2-time solubility decrease. On the other hand, the solubility of compounds ( 28) and ( 36) is almost equal.…”

Section: Methodsmentioning

confidence: 99%

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Impact of Sulfonamide Structure on Solubility and Transfer Processes in Biologically Relevant Solvents

et al. 2014

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Solubility values of 39 sulfonamides in water, 1-octanol, and 1-hexane were determined by the isothermal saturation method. Thermophysical characteristics of fusion processes (melting points and fusion enthalpies) of the selected substances were measured by the DSC method. The impact of molecule structural modification on solubility processes in the solvents was analyzed. Transfer processes from water to 1-octanol, water to 1-hexane, and 1-hexane to 1-octanol were studied. Correlation equations connecting Gibbs energies of the solubility and the transfer processes with physicochemical descriptors and thermophysical characteristics were obtained.

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“…The present work is a continuation of our previous attempts to study the passive transport properties of 1,2,4-thiadiazoles [17][18][19][20][21][22][23] and the relationship between the biological activity and transport characteristics of drugs and drug-like compounds. 23,24 2. Materials and methods 2.1.…”

Section: Introductionmentioning

confidence: 99%

Towards the rational design of novel drugs based on solubility, partitioning/distribution, biomimetic permeability and biological activity exemplified by 1,2,4-thiadiazole derivatives

et al. 2017

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Novel 1,2,4-thiadiazole derivatives as potent neuroprotectors were synthesized and identified. Their ability to inhibit the glutamate stimulated Ca uptake was investigated. The solubility of thiadiazoles was measured in a buffer solution (pH 7.4) at 298 K. The distribution coefficients in 1-octanol/buffer (pH 7.4) and 1-hexane/buffer (pH 7.4) immiscible phases as model systems imitating the gastrointestinal tract epithelium and the blood-brain barrier were determined. Permeation experiments the new Permeapad™ barrier using Franz diffusion cells were conducted and the apparent permeability coefficients were obtained. The influence of the compound structure on the physicochemical properties determining the bioavailability of drug-like substances was revealed. Solubility-permeability interplay has been assessed to evaluate potential bioavailability of the compounds studied.

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Thermodynamics of Solubility Processes of Novel Drug-like Spiro-Derivatives in Model Biological Solutions

Cited by 10 publications

References 22 publications

New Bicyclic 1,3-Selenazine Derivatives: Distribution in Model Biological Media and Membrane Permeability

New Bicyclic 1,3-Selenazine Derivatives: Distribution in Model Biological Media and Membrane Permeability

Impact of Sulfonamide Structure on Solubility and Transfer Processes in Biologically Relevant Solvents

Towards the rational design of novel drugs based on solubility, partitioning/distribution, biomimetic permeability and biological activity exemplified by 1,2,4-thiadiazole derivatives

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