1476-64-8Relevant articles and documents
Synthesis of some analogues of blattellastanoside A, the steroidal aggregation pheromone of the German cockroach
Mori, Kenji,Nakayama, Toru,Sakuma, Masayuki
, p. 401 - 408 (1996)
Blattellastanoside A, the aggregation pheromone of the German cockroach, is a chlorinated steroid glucoside with the 5β-stigmastane skeleton. Its analogues were synthesized in order to clarify the structure-activity relationship. They are 1a with the 5β-cholestane skeleton, 1b with the 5β-androstane skeleton, 1c with a fluorine substituent instead of the chlorine and 1d with a β-D-galactopyranose instead of the β-D-glucopyranose of the original pheromone. Their bioassay shows that 1a and 1c are active, while 1b and 1d are totally devoid of pheromone activity. The aglycone of blattellastanosides A and B were active.
First synthesis of 7α- and 7β-amino-DHEA, dehydroepiandrosterone (DHEA) analogues and preliminary evaluation of their cytotoxicity on Leydig cells and TM4 Sertoli cells
Bazin, Marc-Antoine,Travert, Carine,Carreau, Serge,Rault, Sylvain,Kihel, La?la El
, p. 3152 - 3160 (2007)
Efficient syntheses of new DHEA analogues, and their apoptotic and necrotic effects on Leydig cells and TM4 Sertoli cells are described. The key step in the synthetic strategy of 7-amino-DHEA derivatives involves a bromination on C-7 position to give an epimeric mixture of bromides which were substituted by azides and reduced to give 7α- and 7β-amino-3β-hydroxyandrost-5-en-17-ones. No cytotoxic effect induced by apoptosis mechanism was observed on Leydig and TM4 Sertoli cells by treatment with these amino-DHEA analogues. A necrotic effect was induced only in TM4 Sertoli cells. The best activity was obtained with 7α,β-amino-androst-5-en-3β-ol and 7β-amino-3β-hydroxy-androst-5-en-17-one.
Positive Modulators of the N-Methyl- d -aspartate Receptor: Structure-Activity Relationship Study of Steroidal 3-Hemiesters
Krausova, Barbora,Slavikova, Barbora,Nekardova, Michaela,Hubalkova, Pavla,Vyklicky, Vojtech,Chodounska, Hana,Vyklicky, Ladislav,Kudova, Eva
, p. 4505 - 4516 (2018)
Here, we report the synthesis of pregn-5-ene and androst-5-ene dicarboxylic acid esters and explore the structure-activity relationship (SAR) for their modulation of N-methyl-d-aspartate receptors (NMDARs). All compounds were positive modulators of recombinant GluN1/GluN2B receptors (EC50 varying from 1.8 to 151.4 μM and Emax varying from 48% to 452%). Moreover, 10 compounds were found to be more potent GluN1/GluN2B receptor modulators than endogenous pregnenolone sulfate (EC50 = 21.7 μM). The SAR study revealed a relationship between the length of the residues at carbon C-3 of the steroid molecule and the positive modulatory effect at GluN1/GluN2B receptors for various D-ring modifications. A selected compound, 20-oxo-pregnenolone hemiadipate, potentiated native NMDARs to a similar extent as GluN1/GluN2A-D receptors and inhibited AMPARs and GABAAR responses. These results provide a unique opportunity for the development of new steroid based drugs with potential use in the treatment of neuropsychiatric disorders involving hypofunction of NMDARs.
A synthetic steroid 5α-Androst-3β,5,6-Triol blocks hypoxia/reoxygenation - Induced neuronal injuries via protection of mitochondrial function
Chen, Jiesi,Leng, Tiandong,Chen, Wenli,Yan, Min,Yin, Wei,Huang, Yijun,Lin, Suizhen,Duan, Dayue,Lin, Jun,Wu, Gongxiong,Zhang, Jingxia,Yan, Guangmei
, p. 996 - 1002 (2013)
Ischemic stroke is a leading cause of death worldwide, yet therapies are limited. During periods of ischemia following reperfusion in ischemic stroke, not only loss of energy supply, but a few other factors including mitochondrial dysfunction and oxidative stress also make vital contribution to neuronal injury. Here we synthesized a steroid compound 5α-androst-3β,5, 6β-triol by 3 steps starting from dehydroepiandrosterone and examined its effect on mitochondrial function and oxidative stress in primary cultured cortical neurons exposed to hypoxia followed by reoxygenation. 5α-Androst-3β,5,6β-triol dose-dependently protected cortical neurons from hypoxia/reoxygenation exposure. Rates of reduction in neuronal viability, loss of mitochondrial membrane potential, disruption of ATP production and oxidative stress were ameliorated in 5α-androst-3β,5, 6β-triol pretreated cultures. In summary, these results suggest that 5α-androst-3β,5,6β-triol is neuroprotective against hypoxia/reoxygenation induced neuronal injuries through mediation of mitochondrial function and oxidative stress.
Catalytic Ring-Opening of Cyclic Alcohols Enabled by PCET Activation of Strong O-H Bonds
Yayla, Hatice G.,Wang, Huaiju,Tarantino, Kyle T.,Orbe, Hudson S.,Knowles, Robert R.
, p. 10794 - 10797 (2016/09/09)
We report a new photocatalytic protocol for the redox-neutral isomerization of cyclic alcohols to linear ketones via C-C bond scission. Mechanistic studies demonstrate that key alkoxy radical intermediates in this reaction are generated via the direct homolytic activation of alcohol O-H bonds in an unusual intramolecular PCET process, wherein the electron travels to a proximal radical cation in concert with proton transfer to a weak Br?nsted base. Effective bond strength considerations are shown to accurately forecast the feasibility of alkoxy radical generation with a given oxidant/base pair.
