Synthesis, NoSpherA2 refinement, and noncovalent bonding of abiraterone bromide monohydrate

Korlyukov, Alexander A.; Buikin, Petr A.; Dorovatovskii, Pavel V.; Вологжанина, Анна В.

doi:10.1007/s11224-023-02210-3

Cited by 5 publications

(5 citation statements)

References 45 publications

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“…Unfortunately, the only iron(II) complex with AbirAc was obtained by reaction of FeBr3 with AbirAc in acidic media and had the composition (Abi-rAcH)[FeBr4] (11). With the absence of HBr, single crystals of (HAbirOH)Br • H2O and colloid Fe(OH)3 precipitated from the same FeBr3:AbirAc = 1:1 mixture, and the structure of this salt has been published elsewhere [37]. The recrystallization of AbirAc from 2M and concentrated 48% HBr affords only the starting AbirAc.…”

Section: Molecular and Crystal Structuresmentioning

confidence: 99%

“…Thus, attempts to find more soluble and less food-dependent forms of abiraterone are still ongoing. The search for novel solid forms of AbirAc with enhanced solubility included co-crystallization of AbirAc with some co-formers [ 34 , 35 ] and formation of (HAbirOH)Hal · H 2 O salts (Hal = Cl – [ 36 ]; Br – [ 37 ]). Based on numerous X-ray diffraction data of ligand (AbirOH): receptor (human cytochrome P450 17A1 or CYP17A1) complexes, the most specific feature of their binding is coordination between the iron atom of the heme fragment and the nitrogen atom N Py of the pyridine-3-yl ring of abiraterone [ 38 , 39 , 40 , 41 , 42 ].…”

Section: Introductionmentioning

confidence: 99%

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Abiraterone Acetate Complexes with Biometals: Synthesis, Characterization in Solid and Solution, and the Nature of Chemical Bonding

Buikin,

Vologzhanina,

Novikov

et al. 2023

Pharmaceutics

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Abiraterone acetate (AbirAc) is the most used steroidal therapeutic agent for treatment of prostate cancer. The mainly hydrophobic molecular surface of AbirAc results in its poor solubility and plays an important role for retention of abiraterone in the cavity of the receptor formed by peptide chains and heme fragments. In order to evaluate the hydrolytic stability of AbirAc, to modify its solubility by formation of new solid forms and to model bonding of this medication with the heme, a series of d-metal complexes with AbirAc was obtained. AbirAc remains stable in water, acetonitrile, tetrahydrofuran, and ethanol, and readily interacts with dications as a terminal ligand to create discrete complexes, including [FePC(AbirAc)2] and [ZnTPP(AbirAc)] (H2PC = phthalocyanine and H2TPP = 5,10,15,20-tetraphenylporphyrine) models for ligand–receptor bonding. In reactions with silver(I) nitrate, AbirAc acts as a bridge ligand. Energies of chemical bonding between AbirAc and these cations vary from 97 to 235 kJ mol−1 and exceed those between metal atoms and water molecules. This can be indicative of the ability of abiraterone to replace solvent molecules in the coordination sphere of biometals in living cells, although the model [ZnTPP] complex remains stable in CDCl3, CD2Cl2, and 1,1,2,2-tetrachloroethane-d2 solvents and decomposes in polar dimethylsulfoxide-d6 and methanol-d4 solvents, as follows from the 1H DOSY spectra. Dynamics of its behavior in 1,1,2,2-tetrachloroethane-d2 were studied by ROESY and NMR spectra.

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Section: Molecular and Crystal Structuresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Abiraterone Acetate Complexes with Biometals: Synthesis, Characterization in Solid and Solution, and the Nature of Chemical Bonding

Buikin,

Vologzhanina,

Novikov

et al. 2023

Pharmaceutics

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“…Within our study of the crystal and molecular structures of the solid forms of active pharmaceutical ingredients [7][8][9], the powder pattern of alectinib hydrochloride was measured using CuK α radiation. Room temperature was maintained to overcome the effects of thermal contraction and to avoid possible phase transitions.…”

Section: Introductionmentioning

confidence: 99%

9-Ethyl-6,6-dimethyl-8-[4-(morpholin-4-yl)piperidin-1-yl]-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile Hydrochloride

Buikin,

Vologzhanina,

Novikov

et al. 2024

Molbank

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Alectinib hydrochloride is an anticancer medication used for the first-line treatment of non-small cell lung cancer. Although it was approved for medical use ten years ago, and three polymorphs of this substance were proposed based on X-ray diffraction patterns, their crystal structures remained unknown to date. The main problem was the preparation of high quality single crystals due to the very low solubility of the salt. Herein, we report on the molecular and crystal structure of form I of alectinib hydrochloride as obtained using powder X-ray diffraction data from a laboratory source. Short Cl…N distances between the anion and the nitrogen atoms of the morpholine and benzo[b]carbazole rings indicate the positions of the H(N) atoms. As a result, the cation and anion form infinite Cl…H(N)-bonded chains.

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“…This information is required for phase identification and purity control. In our study of novel solid forms of known active pharmaceutical ingredients [7][8][9], the ability of sumatriptan succinate to form various solvates was examined. Recrystallization from ethanol afforded a hemisolvate, HSum + •HSucc − •0.5EtOH (1).…”

Section: Introductionmentioning

confidence: 99%

Sumatriptan Succinate Hemi(Ethanol Solvate)

Buikin,

Vologzhanina,

Korlyukov

2024

Molbank

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1-(3-(2-(Dimethylammonio)ethyl)-1H-indol-5-yl)-N-methylmethanesulfonamide succinate (sumatriptan succinate, HSum+·HSucc−) is a serotonin receptor agonist used to treat migraines. By the recrystallization of this substance from ethanol, its hemi(ethanol solvate), HSum+·HSucc−·0.5EtOH, was obtained. The solid was characterized by X-ray diffraction and FT-IR spectroscopy. In HSum+·HSucc−·0.5EtOH, solvent molecules link succinate anions into infinite O–H…O bonded chains, which are further connected by N–H…O interactions with cations into H-bonded layers.

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Synthesis, NoSpherA2 refinement, and noncovalent bonding of abiraterone bromide monohydrate

Cited by 5 publications

References 45 publications

Abiraterone Acetate Complexes with Biometals: Synthesis, Characterization in Solid and Solution, and the Nature of Chemical Bonding

Abiraterone Acetate Complexes with Biometals: Synthesis, Characterization in Solid and Solution, and the Nature of Chemical Bonding

9-Ethyl-6,6-dimethyl-8-[4-(morpholin-4-yl)piperidin-1-yl]-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile Hydrochloride

Sumatriptan Succinate Hemi(Ethanol Solvate)

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