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Search for "progesterone" in Full Text gives 9 result(s) in Beilstein Journal of Organic Chemistry.
Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold
Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262
- , the tetrahydropyridazines, six-atom nitrogenous heterocycles, are found in various bioactive molecules such as influenza virus neuraminidase inhibitors, GABA type A receptor modulators, and regulators of progesterone receptor or cannabinoid CB1 receptor antagonists (Figure 1) [6][7][8][9]. This
Natural resorcylic lactones derived from alternariol
Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187
- negative effect on progesterone synthesis in porcine granulosa cells [100], and to be an androgen antagonist with an EC50 value of 269 μM [101]. Phase I [102][103] and phase II [104][105][106] metabolization of AOH has been thoroughly investigated and it turned out that AOH is not metabolized by human
- : 87.2 μg/mL) [115]. It furthermore had a negative effect on progesterone synthesis in porcine granulosa cells [100] and selectively inhibited human monoamine oxidase-A (MAO-A) with an IC50 value of 1.71 μM (but did not inhibit MAO-B) and was thus considered for the treatment of depression, Parkinson’s
Syntheses and medicinal chemistry of spiro heterocyclic steroids
Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152
- and trifluoroacetamido groups in almost all cases. Spirooxazolines 60 were evaluated as progesterone receptor (PR) antagonist agents, comparing their activity to the abortifacient mifepristone, which has undesired glucocorticoid antagonist activity. The compounds exhibited high PR antagonist activity
- compound underwent further transformation through reaction with p-fluorobenzaldehyde in dry ethanol, yielding the corresponding 4-fluoroarylidene derivative 92 in an overall yield of 27%. The described reaction sequence was successfully replicated using testosterone and progesterone to produce a N-aryl-1,3
Entry to new spiroheterocycles via tandem Rh(II)-catalyzed O–H insertion/base-promoted cyclization involving diazoarylidene succinimides
Beilstein J. Org. Chem. 2024, 20, 561–569, doi:10.3762/bjoc.20.48
- ], drospirenone (exhibits high affinity to progesterone receptors and is used as a birth control medication) [26][27], griseofulvin (an antifungal agent used to treat fungal infections of the fingernails and toes) [28], as well as oliceridine (a selective G protein-biased μ-opioid receptor agonist used for
Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements
Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184
- ingredients (APIs) is necessary to render them bioavailable. This study addresses the poor solubility of two potent steroid hormones, 17β-estradiol (BES) and progesterone (PRO), via their complexation with two water-soluble native cyclodextrins (CDs) namely β-CD and γ-CD. The hydrated inclusion complexes β
- : cyclodextrin; complexation; 17β-estradiol; progesterone; solubility; X-ray diffraction; Introduction The insolubility of active pharmaceutical ingredients (APIs) and other bioactive compounds in aqueous media and the associated challenges for effective drug delivery are well known to have beleaguered the
- (BES) and progesterone (PRO), the steroid hormone associated with female fertility and pregnancy. Both compounds have very low aqueous solubility values (3.6 × 10−3 mg·cm−3 at 27 °C, and 8.81 × 10−3 mg·cm−3 at 25 °C, respectively) [6][7][8]. This drawback hinders their use as medications in hormone
Hydrazides in the reaction with hydroxypyrrolines: less nucleophilicity – more diversity
Beilstein J. Org. Chem. 2021, 17, 319–324, doi:10.3762/bjoc.17.29
- fragments of influenza neuraminidase inhibitors [1], nonsteroidal progesterone receptor regulators [2][3], anti-inflammatory [4], antihypertensive and spasmolytic [5][6][7] agents (Figure 1). It is due to their prospects in drug design that a search for effective synthetic protocols to construct partially
Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis
Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183
- rotation of the σ-bond between the carbonyl group and the α-position allows the fluorination of the β- or γ-position. A good practical example of such a competitive fluorination is progesterone, which was fluorinated at both the C12 (see 45) and the C16 (see 46) position in a 1.0:3.1 ratio (Scheme 22
- , Scheme 24), demonstrating the power of this method for LSF, especially given the biological activity and prevalence of steroids, such as cholesterol, progesterone and testosterone. Interestingly, under their conditions, 2-heptanone, 2-decanone and 2-dodecanone as the substrates gave in each case a
Selective allylic hydroxylation of acyclic terpenoids by CYP154E1 from Thermobifida fusca YX
Beilstein J. Org. Chem. 2014, 10, 1347–1353, doi:10.3762/bjoc.10.137
- have been made in this field. By using an iterative mutagenesis approach “combinatorial active-site saturation test (CAST)” Reetz and colleagues constructed several variants of CYP102A1 which demonstrate high regio- and stereoselectivity for testosterone and progesterone oxidation [42]. The parent F87A
N-Heterocyclic carbene–palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides
Beilstein J. Org. Chem. 2013, 9, 303–312, doi:10.3762/bjoc.9.35
- important research area in organic synthesis as such motives are known to be present in several bioactive molecules, such as Atorvastatin, which is used for lowering blood cholesterol, Fendosal, which is an anti-inflammatory agent, or Tanaproget, which is a progesterone-receptor agonist (Figure 1). The
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