Phase Transformations of a Conformational Solvatomorphic Steroid: [23(23<i>E</i>,25R]-23(28)-(3′-Acetoxybenzyliden)-5α-spirostan-3β-ol acetate

Ramos-Enrı́quez, Manuel A.; Colin‐Molina, Abraham; Flores‐Álamo, Marcos; Rodrı́guez-Molina, Braulio; Iglesias-Arteaga, Martı́n A.

doi:10.1021/acs.cgd.0c00808

Cited by 2 publications

(1 citation statement)

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“…Thus, correlation between the conformational state of the API molecule in the saturated solution and the molecular structure in the solid phase allows performing fast screening [ 14 ] and determining the probability of obtaining a certain solvate form, rather than the polymorphic form. Studies on this topic, however, are often based solely on X-ray structural analysis [ 15 , 16 ]. Therefore, it is necessary to develop approaches capable of preliminary estimating of the producing probability of a desired API form on early stages of the mechanochemical synthesis.…”

Section: Introductionmentioning

confidence: 99%

Conformational Screening of Arbidol Solvates: Investigation via 2D NOESY

et al. 2023

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Understanding of the nucleation process’s fundamental principles in saturated solutions is an urgent task. To do this task, it is necessary to control the formation of polymorphic forms of biologically active compounds. In certain cases, a compound can exist in a single polymorphic form, but have several solvates which can appear in different crystal forms, depending on the medium and conditions of formation, and show different pharmaceutical activity. In the present paper, we report on the analysis of Arbidol conformational preferences in two solvents of different polarities—deuterated chloroform and dimethyl sulfoxide—at 25 °C, using the 2D NOESY method. The Arbidol molecule has various solvate forms depending on the molecular conformation. The method based on the nuclear Overhauser effect spectroscopy was shown to be efficient in the analysis of complex heterocyclic compounds possessing conformation-dependent pseudo-polymorphism. It is one of the types of polymorphism observed in compounds forming crystal solvates. Combined use of NMR methods and X-ray data allowed determining of conformer populations of Arbidol in CDCl3 and DMSO-d6 which were found to be 8/92% and 37/63%, respectively. The preferred conformation in solution is the same that appears in stable crystal solvates of Arbidol.

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Section: Introductionmentioning

confidence: 99%

Conformational Screening of Arbidol Solvates: Investigation via 2D NOESY

et al. 2023

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Study on Triflumezopyrim Solid Forms: Crystal Structure Analysis and Suspension Concentrate Application Insights

Wang,

Li,

Zhu

et al. 2024

Crystal Growth & Design

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Polymorphism in solid molecules is increasingly recognized in the field of agriculture. Triflumezopyrim (TFM) is a pioneering mesoionic insecticide that has played a pivotal role in the control of resistant rice hoppers, yet studies of its polymorphs are scarce. This study systematically investigated the polymorphism of Triflumezopyrim, identifying four new polymorphs (Forms II−V), a hydrate (Form H), and an amorphous form. The crystal structures of Forms III, V, and H were identified by singlecrystal X-ray diffraction analysis for the first time. Solubility, dissolution, and stability tests were conducted. Thermal analysis, solvent-mediated transformation experiments, and lattice energy calculations clarified the transformation relationships among the different forms, identifying Form V as the most thermodynamically stable polymorph with the lowest solubility. Furthermore, Forms I, II, V, and H were formulated as suspension concentrates, and their formulation capabilities and bioactivity were tested. Moreover, the fluorescence change of different solid polymorphs was observed. The analysis of the weak interaction in the single-crystal structure revealed that the change in the π−π packing pattern was the possible reason for the observed fluorescence change. These findings significantly enrich our understanding of the solid-state properties of Triflumezopyrim and provide substantial guidance for future processing and formulation selection.

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Phase Transformations of a Conformational Solvatomorphic Steroid: [23(23E,25R]-23(28)-(3′-Acetoxybenzyliden)-5α-spirostan-3β-ol acetate

Cited by 2 publications

References 30 publications

Conformational Screening of Arbidol Solvates: Investigation via 2D NOESY

Conformational Screening of Arbidol Solvates: Investigation via 2D NOESY

Study on Triflumezopyrim Solid Forms: Crystal Structure Analysis and Suspension Concentrate Application Insights

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