Total assignment of1H and13C NMR spectra of pregnenolone and progesterone haptens using 2D NMR spectroscopy

Korde, Shilpa S.; Katoch, Rita; A, Udasi R; Trivedi, Gaurav

doi:10.1002/(sici)1097-458x(199908)37:8<594::aid-mrc484>3.0.co;2-j

Cited by 8 publications

(2 citation statements)

References 13 publications

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“…After a big effort, single crystals suitable for X-ray diffraction were acquired except Prog-RSV, whose stoichiometric ratio of Prog and RSV (2:1) can only be confirmed by 1 H NMR analysis (Figure S1). 67,68 Crystallographic data and H-bond parameters are summarized in Tables 1 and S1, respectively. All of these cocrystals could be prepared by slow evaporation in different solvents and verified by PXRD (Figure 1a,b).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Drug–Drug Cocrystals Provide Significant Improvements of Drug Properties in Treatment with Progesterone

Guo

Zhang

Zhu

et al. 2020

Crystal Growth & Design

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Progesterone (Prog), a natural steroid hormone, is widely used in birth control pills and menopausal hormone replacement therapies. Phloroglucinol (SPF) and resveratrol (RSV) are also two kinds of active products that can be used during pregnancy. Drug–drug cocrystals of Prog with SPF and RSV were designed and successfully synthesized for purpose of bringing improvements of drug properties, including solubility, hydroscopic stability, and color stability. The cocrystals and their hydrate structures were systematically characterized by X-ray diffraction, differential scanning calorimetry, and thermogravimetric analysis. In addition, powder dissolution experiments of Prog, Prog-SPF, and Prog-RSV were conducted in aqueous solutions with the presence of different surfactants, and the result revealed that the Prog-SPF cocrystal exhibits a superior solubility compared with Prog and Prog-RSV. Furthermore, the Prog-SPF cocrystal also enhances the hydroscopic stability and color stability of SPF. Those findings may provide a promising formulation to overcome some weaknesses of the parent drugs.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Drug–Drug Cocrystals Provide Significant Improvements of Drug Properties in Treatment with Progesterone

Guo

Zhang

Zhu

et al. 2020

Crystal Growth & Design

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“…The 13 C NMR signals for the CH 2 carbon units (C-6,7,11,12,15,16) are not so obviously confirmed due to close or overlapped resonances that are very sensitive by even small structural changes. On the basis of several published reference compounds, − we assigned 35.86, 29.77, 27.78, 27.73, 26.55, and 24.61 ppm to C-16, C-6, C-12, C-7, C-11, and C-15, respectively. On the basis of the same criteria, we assigned each of the corresponding C-13 NMR spectra for compounds 6 , 7 , 8 , 9 , 10 , 11 , 12 , and 1 , as summarized in Table .…”

Section: Resultsmentioning

confidence: 99%

An Improved Synthesis of Nomegestrol Acetate

Lű

Song

et al. 2014

Org. Process Res. Dev.

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Oral contraceptives (OCs) are synthetic steroids, or progestins, which are structurally related to testosterone or to progesterone. Many progestins have been synthesized and approved for OCs, hormonal replacement therapy (HRT), or the treatment of some gynecological disorders. Nomegestrol acetate (NOMAc) is a newly approved OC and has gained rapid acceptance in many countries for OC or HRT. The synthesis of NOMAc remains challenging and costly. We have developed a novel and improved procedure for the synthesis of NOMAc with a total of 11 steps and an overall good yield without the use of hazardous reagents.

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Inclusion complex characterization between progesterone and hydroxypropyl-β-cyclodextrin in aqueous solution by NMR study

Torri

Bertini

Giavana

et al. 2007

J Incl Phenom Macrocycl Chem

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Total assignment of1H and13C NMR spectra of pregnenolone and progesterone haptens using 2D NMR spectroscopy

Cited by 8 publications

References 13 publications

Drug–Drug Cocrystals Provide Significant Improvements of Drug Properties in Treatment with Progesterone

Drug–Drug Cocrystals Provide Significant Improvements of Drug Properties in Treatment with Progesterone

An Improved Synthesis of Nomegestrol Acetate

Inclusion complex characterization between progesterone and hydroxypropyl-β-cyclodextrin in aqueous solution by NMR study

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