Synthesis and comprehensive structural and physicochemical characterization of dutasteride hydrochloride hydrate solvates

Górecki, Marcin; Dziedzic, Alicja; Luboradzki, Roman; Ostaszewska, Anna; Frelek, Jadwiga; Szczepek, W. J.

doi:10.1016/j.steroids.2017.05.014

Cited by 4 publications

(3 citation statements)

References 8 publications

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“…This selection was inspired based on our previous study on steroid-based compounds. 26 − 29 All spectra were generated using the program SpecDis. 30 …”

Section: Methodsmentioning

confidence: 99%

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Steroidal Molecular Rotors with 1,4-Diethynylphenylene Rotators: Experimental and Theoretical Investigations Toward Seeking Efficient Properties

et al. 2020

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Properly designed molecular rotors with sizable stators and a fast-moving rotator could provide efficient building blocks for amphidynamic crystals. Herein, we report the synthesis of steroidal compounds 1 , 2 , and 3 and their deuterated analogues 1D , 2D , and 3D envisioned to work as molecular rotors. The obtained compounds were characterized by attenuated total reflection-infrared, Raman, and circular dichroism (CD) spectroscopy measurements. The interpretation of spectra was supported by theoretical calculations using density functional theory methods. The analysis of the most characteristic bands confirmed different molecular dynamics of the rotors investigated. Angle-dependent polarized Raman spectra showed the crystallinity of some samples. Electronic CD (ECD) spectra of compounds 1–3 and their relevant deuterated analogues 1D–3D are identical. The increase of the band intensity with lowering the temperature shows that the equilibrium is shifted to the thermodynamically most stable conformer. ECD spectra simulated at the TDFFT level of theory for compound 3 were compared with experimental results. It was proved that conformer 3a , with a torsion angle of +50°, exhibits the best agreement with the experimental results. Simulated vibrational CD and IR spectra for conformer 3a and its deuterated analogue 3Da also display good agreement with experimental results. In light of our comprehensive investigations, we evidenced that steroidal compounds 1 , 2 , and 3 can work as molecular rotors.

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“…This selection was inspired based on our previous study on steroid-based compounds. 26 − 29 All spectra were generated using the program SpecDis. 30 …”

Section: Methodsmentioning

confidence: 99%

“…Time-dependent-DFT calculations were run with functional CAM-B3LYP and def2-TZVP basis sets, including a PCM for CH 3 CN. This selection was inspired based on our previous study on steroid-based compounds. − All spectra were generated using the program SpecDis …”

Section: Methodsmentioning

confidence: 99%

Steroidal Molecular Rotors with 1,4-Diethynylphenylene Rotators: Experimental and Theoretical Investigations Toward Seeking Efficient Properties

et al. 2020

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“…In conclusion, we have developed a method for the Pdcatalyzed transfer hydrogenation of a variety of unsaturated C-C bonds mediated by B2(OH)4 using Pd(OAc)2 as a convenient precatalyst, 20,21…”

Section: H(d)mentioning

confidence: 99%

Pd-Catalyzed Transfer Hydrogenation of Alkenes Using Tetrahydroxydiboron as the Sole Hydrogen Donor

Stokes,

Yaghoubi,

Reyes

2024

SynOpen

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Tetrahydroxydiboron-mediated catalytic transfer hydrogenations have typically involved co-additives that, like tetrahydroxydiboron itself, are H atom donors. Herein we report an alkene transfer hydrogenation method with tetrahydroxydiboron as the sole source of H atoms. The reaction uses Pd(OAc)2 as a convenient putative colloid pre-catalyst, and cyclic monoethers are competent solvents. Highly efficient alkene deuteration is demonstrated using tetradeuteroxydiboron.

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Differentiation of solvatomorphs of active pharmaceutical ingredients (API) by solid-state vibrational circular dichroism (VCD)

Rode,

Wasilczenko,

Górecki

2024

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Synthesis and comprehensive structural and physicochemical characterization of dutasteride hydrochloride hydrate solvates

Cited by 4 publications

References 8 publications

Steroidal Molecular Rotors with 1,4-Diethynylphenylene Rotators: Experimental and Theoretical Investigations Toward Seeking Efficient Properties

Steroidal Molecular Rotors with 1,4-Diethynylphenylene Rotators: Experimental and Theoretical Investigations Toward Seeking Efficient Properties

Pd-Catalyzed Transfer Hydrogenation of Alkenes Using Tetrahydroxydiboron as the Sole Hydrogen Donor

Differentiation of solvatomorphs of active pharmaceutical ingredients (API) by solid-state vibrational circular dichroism (VCD)

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