Solid-state investigation of polymorphism and tautomerism of phenylthiazole-thione: A combined crystallographic, calorimetric, and theoretical survey

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Résumé

In the context of solid-state polymorphism, a detailed crystallographic and theoretical investigation has been carried out on a dimorphic phenylthiazole-derived compound (4-phenylthiazole-2-thiol, labeled here as compound 1), considered here as a potential lead compound, for which we discovered original polymorphic behavior. A detailed crystallographic study and calorimetric investigation permit us to assess the monotropic relationship between polymorphic forms, and ab initio quantum methods, combined with Monte Carlo polymorphic prediction, allow rationalization of the thiol-thione tautomeric preferential character of the compound. The experimental and theoretical conclusions prove once more that in an early process of lead compound optimization, a combination of solid-state analysis and phase prediction with modeling methods can be a fast and efficient tool to select/disable a particular compound, in addition to well-known potential alert flags such as adsorption-distribution-metabolism-excretion/toxicology pharmacokinetic markers.

langueAnglais
Pages2461-2473
Nombre de pages13
journalCrystal Growth and Design
Volume15
Numéro5
Les DOIs
étatPublié - 6 mai 2015

Empreinte digitale

lead compounds
polymorphism
thiols
solid state
predictions
Lead compounds
Thiones
Polymorphism
Sulfhydryl Compounds
toxicology
excretion
metabolism
markers
optimization
adsorption
Pharmacokinetics
Metabolism
Adsorption

Citer ceci

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title = "Solid-state investigation of polymorphism and tautomerism of phenylthiazole-thione: A combined crystallographic, calorimetric, and theoretical survey",
abstract = "In the context of solid-state polymorphism, a detailed crystallographic and theoretical investigation has been carried out on a dimorphic phenylthiazole-derived compound (4-phenylthiazole-2-thiol, labeled here as compound 1), considered here as a potential lead compound, for which we discovered original polymorphic behavior. A detailed crystallographic study and calorimetric investigation permit us to assess the monotropic relationship between polymorphic forms, and ab initio quantum methods, combined with Monte Carlo polymorphic prediction, allow rationalization of the thiol-thione tautomeric preferential character of the compound. The experimental and theoretical conclusions prove once more that in an early process of lead compound optimization, a combination of solid-state analysis and phase prediction with modeling methods can be a fast and efficient tool to select/disable a particular compound, in addition to well-known potential alert flags such as adsorption-distribution-metabolism-excretion/toxicology pharmacokinetic markers.",
author = "Andrea Carletta and C\{'e}line Meinguet and Johan Wouters and Ana\{"e}lle Tilborg",
year = "2015",
month = "5",
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doi = "10.1021/acs.cgd.5b00237",
language = "English",
volume = "15",
pages = "2461--2473",
journal = "Crystal Growth and Design",
issn = "1528-7483",
publisher = "American Chemical Society",
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T1 - Solid-state investigation of polymorphism and tautomerism of phenylthiazole-thione: A combined crystallographic, calorimetric, and theoretical survey

AU - Carletta,Andrea

AU - Meinguet,Céline

AU - Wouters,Johan

AU - Tilborg,Anaëlle

PY - 2015/5/6

Y1 - 2015/5/6

N2 - In the context of solid-state polymorphism, a detailed crystallographic and theoretical investigation has been carried out on a dimorphic phenylthiazole-derived compound (4-phenylthiazole-2-thiol, labeled here as compound 1), considered here as a potential lead compound, for which we discovered original polymorphic behavior. A detailed crystallographic study and calorimetric investigation permit us to assess the monotropic relationship between polymorphic forms, and ab initio quantum methods, combined with Monte Carlo polymorphic prediction, allow rationalization of the thiol-thione tautomeric preferential character of the compound. The experimental and theoretical conclusions prove once more that in an early process of lead compound optimization, a combination of solid-state analysis and phase prediction with modeling methods can be a fast and efficient tool to select/disable a particular compound, in addition to well-known potential alert flags such as adsorption-distribution-metabolism-excretion/toxicology pharmacokinetic markers.

AB - In the context of solid-state polymorphism, a detailed crystallographic and theoretical investigation has been carried out on a dimorphic phenylthiazole-derived compound (4-phenylthiazole-2-thiol, labeled here as compound 1), considered here as a potential lead compound, for which we discovered original polymorphic behavior. A detailed crystallographic study and calorimetric investigation permit us to assess the monotropic relationship between polymorphic forms, and ab initio quantum methods, combined with Monte Carlo polymorphic prediction, allow rationalization of the thiol-thione tautomeric preferential character of the compound. The experimental and theoretical conclusions prove once more that in an early process of lead compound optimization, a combination of solid-state analysis and phase prediction with modeling methods can be a fast and efficient tool to select/disable a particular compound, in addition to well-known potential alert flags such as adsorption-distribution-metabolism-excretion/toxicology pharmacokinetic markers.

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U2 - 10.1021/acs.cgd.5b00237

DO - 10.1021/acs.cgd.5b00237

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