42151-23-5Relevant articles and documents
Analysis of testosterone and dehydroepiandrosterone in saliva by gas chromatography-mass spectrometry
Gaskell,Pike,Griffiths
, p. 219 - 228 (1980)
Testosterone and 3β-hydroxyandrost-5-en-17-one (dehydroepiandrosterone) have been identified in human parotid fluid and saliva by gas chromatography-mass spectrometry/selected ion monitoring analyses of the t-butyldimethylsilyl ether and methyl oxime, t-butyldimethylsilyl ether derivatives. High specificity of analysis has been achieved by the use of high mass spectrometric resolution or by the monitoring of metastable peaks. Quantitative analyses indicate concentrations of both unconjugated testosterone and unconjugated dehydroepiandrosterone in the range 200-800 pmol/l in the saliva and parotid fluid of the normal males examined. These represent 1.5-7.5% of the concentrations of the steroids in blood plasma taken from the same subjects.
Novel steroidal vinyl fluorides as inhibitors of steroid C17(20) lyase
Burkhart, Joseph P,Weintraub, Philip M,Gates, Cynthia A,Resvick, Robert J,Vaz, Roy J,Friedrich, Dirk,Angelastro, Michael R,Bey, Philippe,Peet, Norton P
, p. 929 - 934 (2002)
20-Fluoro-17(20)-pregnenolone derivatives were designed as enol mimics of pregnenolone. All of the targeted, novel fluoroolefins were potent inhibitors of C17(20) lyase. Copyright
Inhibition of steroid C(17(20)) lyase with C-17-heteroaryl steroids
Burkhart, Joseph P.,Gates, Cynthia A.,Laughlin, Marie E.,Resvick, Robert J.,Peet, Norton P.
, p. 1411 - 1420 (1996)
Steroids bearing a heteroaromatic substituent at C-17 were designed as inhibitors of C(17(20)) lyase. The thiazoles, furans, and thiophenes appended to the steroid nucleus were positioned on the α-face and the β-face of the steroid, and conjugated with a 16,17-olefin, to test their ability to coordinate the heme iron of the P450 enzyme complex. The position of the heterocycle with respect to the steroid skeleton was determined to be important for optimum affinity and, in general, compounds with the heterocycle attached to a trigonal center at C-17, had the best affinity for C(17(20)) lyase. Simple molecular models were used to compare the three types of heterocyclic-substituted steroids.
Structure-activity relationship and mechanistic study on guggulsterone derivatives; Discovery of new anti-pancreatic cancer candidate
Kohyama, Aki,Kim, Min Jo,Yokoyama, Rei,Sun, Sijia,Omar, Ashraf M.,Phan, Nguyen Duy,Meselhy, Meselhy R.,Tsuge, Kiyoshi,Awale, Suresh,Matsuya, Yuji
supporting information, (2021/12/24)
Pancreatic cancer is one of the deadliest types of malignancies. A new intervention aiming to combat pancreatic cancer is targeting its extra-ordinary ability to tolerate nutrition starvation, a phenomenon known as “Austerity”. As a part of a research program aiming to develop a new-generation of anticancer agents, known as “anti-austerity agents”, guggulsterone derivatives (GSDs) were identified as unique anti-austerity agents in terms of potency and selectivity. These agents are able to exert preferential cytotoxic activity only under nutrient-deprived conditions with little or no toxicity under normal conditions. In the present study, a library of 14 GSDs was synthesized and screened against PANC-1 human pancreatic cells. Among tested compounds, GSD-11 showed the most potent activity with PC50 a value of 0.72 μM. It also inhibited pancreatic cancer cell migration and colony formation in a concentration-dependent manner. A mechanistic study revealed that this compound can inhibit the activation of the Akt/mTOR signaling pathway. Therefore, GSD-11 could be a promising lead compound for the anticancer drug discovery against pancreatic cancer.
Chemo- and Enantioselective Oxidative α-Azidation of Carbonyl Compounds
Hattori, Yuhei,Ishihara, Kazuaki,Sahara, Naoto,Tsukahara, Mayuko,Uyanik, Muhammet
supporting information, p. 17110 - 17117 (2020/08/10)
We report high-performance I+/H2O2 catalysis for the oxidative or decarboxylative oxidative α-azidation of carbonyl compounds by using sodium azide under biphasic neutral phase-transfer conditions. To induce higher reactivity especially for the α-azidation of 1,3-dicarbonyl compounds, we designed a structurally compact isoindoline-derived quaternary ammonium iodide catalyst bearing electron-withdrawing groups. The nonproductive decomposition pathways of I+/H2O2 catalysis could be suppressed by the use of a catalytic amount of a radical-trapping agent. This oxidative coupling tolerates a variety of functional groups and could be readily applied to the late-stage α-azidation of structurally diverse complex molecules. Moreover, we achieved the enantioselective α-azidation of 1,3-dicarbonyl compounds as the first successful example of enantioselective intermolecular oxidative coupling with a chiral hypoiodite catalyst.
ENZYME COMPOSITIONS, STEROID DERIVATIVES, ENZYME INHIBITORS, AND METHODS OF MAKING SAME FOR PHARMACEUTICAL APPLICATIONS
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Paragraph 0135, (2020/06/29)
The present disclosure provides for a synthetic strategy to incorporate a C12α-hydroxy group from the methylene (—CH2-) in a steroid backbone, combining synthetic chemistry and enzymology techniques to develop a selective inhibitor for cytochrome P450 8B1, and developing a selective P450 8B1 inhibitor, which can be used as a tool to study P450 8B1 and treat health issues.
