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Query: UMLS:C0338671 (Steroids)
 9,479 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

Dibenzoylhydrazines are the nonsteroidal ecdysone agonists. Using comparative molecular field analysis, we previously found that the alkyl side chain of 20-hydroxyecdysone (20E) is three-dimensionally superposable with one of their two aryl moieties. To identify the aryl moiety that is better superposable on the alkyl chain, we synthesized compounds in which one of the two aryl groups of tebufenozide (N-t-butyl-N-3,5-dimethylbenzoyl-N'-4-ethylbenzoylhydrazine) is replaced by alkyl groups such as C4H9, C5H11, and C6H13. The molting hormonal activity of these compounds was measured using cultured integuments prepared from rice stem borers, Chilo suppressalis Walker, in terms of stimulation of incorporation of N-acetyl-[14C]glucosamine. N-t-Butyl-N-3,5-dimethylbenzoyl-N'-acylhydrazines with a hexanoyl or heptanoyl group were about 20-fold higher than that of 20E, whereas N-acyl-N-t-butyl-N'-4-ethylbenzoylhydrazines with a hexanoyl or heptanoyl group were much weaker than 20E. Their larvicidal activity was also measured against rice stem borers. The former series of compounds were much more active than the other series as well as 20E. Thus, the benzoyl moiety of dibenzoylhydrazines, which is bound to the secondary nitrogen atom (-NH-), is replaceable by aliphatic acyl groups without greatly affecting the biological activities.
Steroids 1997 Oct
PMID:Molting hormonal and larvicidal activities of aliphatic acyl analogs of dibenzoylhydrazine insecticides. 938 9

High doses of lipopolysaccharide (LPS) induce transient hyperglycemia, then chronic hypoglycemia and increased insulin resistance. In addition, appetite is reduced, while body temperature and concentrations of cortisol and tumor necrosis factor alpha (TNFalpha) are elevated. Furthermore, concentrations of GH and IGF-I are reduced in cattle. The objectives of this study were to determine whether a gonadal steroid implant (20 mg estrogen and 200 mg progesterone) given to endotoxemic steers would: (1) reduce hyperglycemia, reduce hypoglycemia, reduce insulin resistance, (2) reduce changes in concentrations of GH and IGF-I, (3) reduce inappetence and reduce concentrations of blood urea nitrogen (BUN) and non-esterified fatty acids (NEFA), and (4) reduce fever and concentrations of TNFalpha and cortisol. Holstein steers were assigned within a 2x2 factorial arrangement of treatments as follows (n=5 per group): C/C, no steroid and vehicle; S/C, steroid and vehicle; C/E, no steroid and LPS (1 microg/kg body weight (BW), i.v.); S/E, steroid and endotoxin. Steroid implants were given at 20 weeks of age (day 0) and serial blood samples (15 min) were collected on day 14 for 8 h, with vehicle or LPS injected after 2 h. Intravenous glucose tolerance tests (100 mg/kg BW) were carried out at 6 h and 24 h. Hyperglycemia was 67% lower (P<0.05) in S/E- compared with C/E-treated steers between 30 and 150 min after i.v. injection of LPS. Hypoglycemia developed after 4 h and insulin resistance was greater in S/E- compared with C/E-treated steers (P<0. 05) at 6 and 24 h. Concentrations of IGF-I were restored earlier in steroid-treated steers than in controls. Concentrations of GH were not affected by steroids, but increased 1 h after injection of LPS, then were reduced for 2 h. Appetite was greater (P<0.05) in S/E- (2.1% BW) compared with C/E-treated steers (1.1% BW) (pooled s.e.m.=0.3). Concentrations of NEFA increased after injecting LPS, but concentrations were lower (P<0.05) in S/E- compared with C/E-treated steers. LPS did not affect concentrations of BUN, but concentrations were lower in steroid-treated steers. Steroids did not affect body temperature or concentrations of TNFalpha and cortisol. In summary, gonadal steroids reduce hyperglycemia, reduce inappetence and tissue wasting, but increase insulin resistance. Furthermore, concentrations of IGF-I are restored earlier in steroid-treated than in non-steroid-treated steers injected with LPS. It is concluded that gonadal steroids reduce severity of some endocrine and metabolic parameters associated with endotoxemia. However, it is unlikely that gonadal steroids acted via anti-inflammatory and immunosuppressive actions of glucocorticoids or through reducing concentrations of cytokines.
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PMID:Estradiol/progesterone implants increase food intake, reduce hyperglycemia and increase insulin resistance in endotoxic steers. 983 64

A group of biologically active 4-azasteroids was studied by 13C-NMR spectroscopy in solution and in the solid phase. A full assignment of signals in the spectra of samples in chloroform was performed for thirteen 4-azasteroids using two-dimensional techniques. Substituent and steric effects of a nitrogen atom, and their influence on chemical shifts of the neighboring carbon atoms are discussed. CP MAS spectra were obtained for five 4-azasteroids including finasteride. The spectra confirmed polymorphism of the latter compound. In addition to the polymorphic forms that are already known, a new molecular complex of finasteride with dioxane is reported.
Steroids 2002 Jun
PMID:13C-NMR study of 4-azasteroids in solution and solid state. 1199 35

Copper is next to iron the most important element in the biological transport, storage and in redox reactions of dioxygen. A bioanalogous activation of dioxygen with copper complexes is used for catalytical epoxidation, allylic hydroxylation and oxidative coupling of aromatic substrates, for example. With stereochemical information in form of chiral ligands, enantioselective reactions may be possible. Another aspect of interest on copper catalyzed reactions with dioxygen is that the exact mechanism and biological function of some enzymes (especially catechol oxidase) is yet not fully clear. For studies mimicking the copper-containing catechol oxidase appropriate chiral steroid ligands with defined stereochemistry and conformation have been synthesized. The four diastereomeric 16,17-aminoalcohols of the 3-methoxy-estra-1,3,5(10)-triene series have been condensed with salicylic aldehyde and different beta-ketoenols to the chiral ligand types 1-5. These compounds with different steric and electronic properties and different arrangements of the neighboring hydroxy and nitrogen functions were reacted with copper(II) acetate to copper complexes. The structure of these complexes will be discussed. The bioanalogous oxidation of 3,5-di-tbutyl-catechol (dtbc) to the corresponding quinone was catalyzed by most of the complexes, indicating their ability to activate dioxygen. The trans configurations c and d showed an activity one magnitude higher than the cis configurations a and b. Comparing compounds with the same diastereomeric configuration, the main influence was that of the peripheral R(1-3) substituents at the beta-ketoenaminic group which are useful for the fine-tuning of the properties of the copper atoms like redox potential and Lewis acidity.
Steroids 2002 Sep
PMID:Synthesis, structure and catechol-oxidase activity of copper(II) complexes of 17-hydroxy-16-(N-3-oxo-prop-1-enyl)amino steroids. 1223 Nov 19

Azasteroids and derivatives thereof with antifungal potential are reviewed. Special emphasis is put on steroids with nitrogen as part of the steroidal framework, natural substances, and lines of development emerging from them.
Steroids 2003 Sep
PMID:Azasteroids as antifungals. 1295 63

A new synthetic procedure and a modification of the original method described in the literature for the synthesis of the steroidal B-D bilactam, 3 beta-hydroxy-7 alpha,17 alpha-diaza-B,D-dihomo-5-androsten-7,17-dione are reported. The key step in the modified method involved protection of the D-lactamic nitrogen atom of 3 beta-acetoxy-17 alpha-aza-D-homo-5-androsten-17-one using a reagent of specific electrophilicity (due to the stereoelectronic properties of the cyclic amide), as Beckmann rearrangement of the B-steroidal ring was hindered, possibly via long range effects, by the presence of the unprotected D-lactamic moiety. Using the 3 beta-acetoxy-5-androsten-17-one as starting material, a new synthetic procedure was developed through ketalization of the 17-ketone and allylic oxidation to the 7-ketone, which was subsequently followed by Beckmann rearrangement of the B- and D-steroid rings. Both approaches resulted in 45 and 67% yields of the desired B,D-bilactam, respectively, in contrast to the 15% yield, which has been reported in the literature.
Steroids 2003 Sep
PMID:Synthetic approaches for the synthesis of a cytostatic steroidal B-D bilactam. 1295 71

Neutral steroids are difficult to analyse using desorption ionisation methods coupled with mass spectrometry (MS). However, steroids with an unhindered ketone group can readily be derivatised with the Girard P (GP) reagent to give GP hydrazones. Steroid GP hydrazones contain a quaternary nitrogen atom and are readily desorbed in the matrix-assisted laser desorption/ionisation (MALDI) process, giving an improvement in sensitivity of two orders of magnitude. Steroids without a ketone group, but with a 3beta-hydroxy-Delta5 function, can be readily converted to 3-oxo-Delta4 steroids and subsequently derivatised to GP hydrazones for MALDI analysis. In addition to giving strong [M]+ ions upon MALDI, steroid GP hydrazones give informative post-source decay (PSD) spectra. By using the accurate mass of the precursor-ion measured by MALDI-MS, in combination with the structural information encoded in its PSD spectrum, steroid structures can readily be determined.
Steroids 2006 Jan
PMID:Analysis of derivatised steroids by matrix-assisted laser desorption/ionisation and post-source decay mass spectrometry. 1619 70

Manganese(III) acetate catalyzed allylic oxidation of alkenes to the corresponding enones was investigated, showing excellent regioselectivity and chemoselectivity (functional group compatibility). Delta(5)-Steroids were transformed into bioactive Delta(5)-en-7-ones under a nitrogen atmosphere, whereas simple alkenes were converted into the corresponding enones under an oxygen atmosphere in good yields.
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PMID:Mild manganese(III) acetate catalyzed allylic oxidation: application to simple and complex alkenes. 1680 74

Inhibition of cholesterol biosynthesis offers the opportunity for treatment of cardiovascular diseases. Numerous enzymes are involved in the post-squalene part of this biosynthesis, and selective inhibitors for almost all of the enzymes involved there have been described in literature. The only exception is the enzyme lathosterol oxidase (EC 1.14.21.6), for which up to now no selective inhibitor has been found. Up to date only triarimol has been reported as a weak inhibitor. In this paper we report on lathosterol side chain amides as a new class of selective lathosterol oxidase inhibitors. To study the influence of different sterol amides on inhibition of this enzyme, numerous compounds were prepared and the sterol patterns resulting from incubation of HL 60 cells with these enzyme inhibitors were monitored in a whole cell screening assay by means of GC/MS analysis. Small alkyl residues at the amide nitrogen (hydrogen and methyl) lead to an inhibition of the enzyme Delta24-reductase, the N-ethyl and N-propyl derivatives show a dual action, inhibiting both Delta24-reductase and lathosterol oxidase. Lathosterol-derived amides with larger substituents (butyl, isobutyl, tert-butyl, pentyl) at the amide nitrogen were found to be selective inhibitors of lathosterol oxidase. The corresponding 3beta-acetoxy derivatives showed comparable activities and can be considered as prodrugs, since they are transformed into the 3beta-hydroxy derivatives under the test conditions, as proven by HPLC analysis.
Steroids 2008 Mar
PMID:Lathosterol side chain amides: a new class of human lathosterol oxidase inhibitors. 1816 39

The aim of the present review is to summarize the current knowledge regarding pharmacological prevention and treatment of acute pancreatitis (AP) based on experimental animal models and clinical trials. Somatostatin (SS) and octreotide inhibit the exocrine production of pancreatic enzymes and may be useful as prophylaxis against post endoscopic retrograde cholangiopancreatography pancreatitis (PEP). The protease inhibitor gabexate mesilate (GM) is used routinely as treatment to AP in some countries, but randomized clinical trials and a meta-analysis do not support this practice. Nitroglycerin (NGL) is a nitrogen oxide (NO) donor, which relaxes the sphincter of Oddi. Studies show conflicting results when applied prior to ERCP and a large multicenter randomized study is warranted. Steroids administered as prophylaxis against PEP has been validated without effect in several randomized trials. The non-steroidal anti-inflammatory drugs (NSAID) indomethacin and diclofenac have in randomized studies showed potential as prophylaxis against PEP. Interleukin 10 (IL-10) is a cytokine with anti-inflammatory properties but two trials testing IL-10 as prophylaxis to PEP have returned conflicting results. Antibodies against tumor necrosis factor-alpha (TNF-alpha) have a potential as rescue therapy but no clinical trials are currently being conducted. The antibiotics beta-lactams and quinolones reduce mortality when necrosis is present in pancreas and may also reduce incidence of infected necrosis. Evidence based pharmacological treatment of AP is limited and studies on the effect of potent anti-inflammatory drugs are warranted.
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PMID:Pharmacological approach to acute pancreatitis. 1885


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