ORCID Profile
0000-0003-2203-233X
Current Organisation
Monash University
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Publisher: Elsevier BV
Date: 12-2013
DOI: 10.1016/J.STEROIDS.2013.09.011
Abstract: This paper describes the regio- and stereoselective reduction of △⁴-3-keto moiety in certain steroids using Na₂S₂O₄/NaHCO₃ and CuCl/NaBH₄, respectively. Using either one of the two reduction agents in the reaction, the 17-substituents in the D ring were observed to have clearly influenced the stereoselective reduction of 4-ene in the A ring by the so-called conformational transmission effect. Na₂S₂O₄/NaHCO₃ regioselectively reduced CC at 4-position of 17-substituted-androst-4-en-3-one derivatives to 5α-H-3-one as the main isomer. And as an extended application, Epiandrosterone (11) was further synthesized from androst-4-en-3,17-dione (AD) via four steps. The total yield from this was about 45%. In the presence of CuCl/NaBH₄, △⁴-3-keto conjugated reduction of 17-spirocyclic ethylene ketal protected androst-4-en-3-one derivatives mainly produced 3α-hydroxy-5β-H isomers, at a yield around 81%. Considering the scaffold configuration of 3α-hydroxy-5β-H moiety coincided with that of bile acid analogs, this selective reduction could also be used as an alternative method for the synthetic study of bile acids using AD and its derivatives, which are from the microorganism degradation of natural sterols, as the potential materials. Meanwhile, configurations of the reductive compounds 5b, 6b, 9, 10 and 17e were identified by X-ray diffraction.
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2NJ01992B
Abstract: A rare instance in rhodium catalysis of an in situ formed rhodacycle that undergoes a formal 1,8-acyloxy migration-initiated reductive elimination.
Publisher: American Chemical Society (ACS)
Date: 10-11-2014
DOI: 10.1021/JM500613M
Abstract: Sixteen furoxan-based nitric oxide (NO) releasing coumarin derivatives (6a-c, 8a-g, 10a, 13a,b, 15, and 17a,b) were designed, synthesized, and evaluated against the A549, HeLa, A2780, A2780/CDDP, and HUVEC cell lines. Most derivatives displayed potent antiproliferation activities. Among them, 8b exhibited the strongest antiproliferation activity on the four sensitive cell lines mentioned above and three drug resistant tumor cell lines A2780/CDDP, MDA-MB-231/Gem, and SKOV3/CDDP with IC50 values from 14 to 53 nM and from 62 to 140 nM, respectively. Furthermore, 8b inhibited the growth of A2780 in vivo and displayed lower toxicity on nontumorigenesis T29, showing good selectivity against malignant cells in vitro. Preliminary pharmacological studies showed that 8b induces apoptosis, arrests the cell cycle at the G2/M phase in the A2780 cell line, and disrupts the phosphorylation of MEK1 and ERK1. Overall, the NO-releasing capacity and the inhibition of ERK/MAPK pathway signaling may explain the potent antineoplastic activity of these compounds.
Publisher: Elsevier BV
Date: 2019
DOI: 10.1016/J.BMCL.2018.11.023
Abstract: Twenty-five seco-4-methyl-DCK derivatives were designed, synthesized and evaluated for chemoreversal activity when combined with paclitaxel or vincristine in two drug-resistant cancer cell lines (A2780/T and KB-V) respectively. Most of the new compounds displayed moderate to significant MDR reversal activities in the P-gp overexpressing A2780/T and KB-V cells. Especially, compounds 7o and 7y showed the most potent chemosensitization activities with more than 496 and 735 reversal ratios at a concentration of 10 μM. Unexpectedly the newly synthesized compounds did not show chemosensitization activities observed in a non-P-gp overexpressing cisplatin resistant human ovarian cancer cell line (A2780/CDDP), implying that the MDR reversal effects might be associated with P-gp overexpression. Moreover, these compounds did not exhibit significant antiproliferative activities against nontumorigenic cell lines (HUVEC, HOSEC and T29) compared to the positive control verapamil at the tested concentration, which suggested better safety than verapamil. The pharmacological actions of the compounds will be studied further to explore their merit for development as novel candidates to overcome P-gp mediated MDR cancer.
Publisher: Elsevier BV
Date: 09-2021
Publisher: CSIRO Publishing
Date: 2020
DOI: 10.1071/CH20175
Abstract: A synthetic method to prepare 1H-indenes and partially hydrogenated methanonaphtho[1,2-c]furan-1,3(4H)-diones from gold(i)-catalysed 1,4-enyne acetate cycloisomerisation and oxidation or Diels–Alder reaction with maleic anhydride is described. The proposed mechanism involves Rautenstrauch rearrangement of the 1,4-enyne motif to give an insitu formed 1,3-cyclopentadiene intermediate. This is followed by 6-endo-dig cyclisation of the cyclic adduct and oxidation to give the aromatic carbocycle or Diels–Alder reaction with maleic anhydride to afford the bridged furan product.
Publisher: American Chemical Society (ACS)
Date: 26-03-2020
Publisher: American Chemical Society (ACS)
Date: 11-08-2022
Abstract: Nitric oxide (NO)-releasing nanoparticles are effective nanomedicines with erse therapeutic advantages compared with small molecule-based NO donors. Here, we report a new class of furoxan-based NO-releasing nanoparticles using a simple, creative yet facile coassembly approach. This is the first time we demonstrated that the coassembled NO-releasing nanoparticles with poly(ethylene glycol)
Publisher: American Chemical Society (ACS)
Date: 26-02-2018
DOI: 10.1021/ACS.ORGLETT.8B00267
Abstract: A synthetic method to prepare 1,2,3,5-tetrahydrobenzo[ g]quinolines efficiently that relies on gold(I)-catalyzed cycloisomerization of 5-(ethynylamino)pent-2-yn-1-yl esters at room temperature under atmospheric conditions is described. The proposed reaction mechanism presents a unique instance of an in situ formed allenic ester and gold keteniminium species to undergo a formal [4 + 2] cycloaddition pathway.
Publisher: American Chemical Society (ACS)
Date: 28-10-2016
DOI: 10.1021/ACS.ORGLETT.6B03049
Abstract: A synthetic method for the efficient assembly of bicyclo[2.2.1]hept-2-en-7-ones that relies on gold(I)-catalyzed Rautenstrauch rearrangement followed by Brønsted acid-mediated formal [3 + 2]-cycloaddition/deacetylation of 1,8-diynyl vinyl acetates at room temperature under atmospheric conditions is described.
Publisher: American Chemical Society (ACS)
Date: 03-2021
No related grants have been discovered for Xiaoyu Chen.