3381-54-2Relevant articles and documents
Effective gene-silencing of siRNAs that contain functionalized spacer linkages within the central region
Desaulniers, Jean-Paul,Hagen, Gordon,Anderson, Jocelyn,McKim, Chris,Roberts, Blake
, p. 3450 - 3454 (2017)
Short-interfering RNAs containing a variety of functional groups at the central region of the sense strand were synthesized and evaluated. The gene-silencing data suggest that these siRNAs are biocompatible and are very effective in cell-based assays.
Synthesis and acetylcholinesterase inhibitory activity of 2β,3α-disulfoxy-5α-cholestan-6-one
Richmond, Victoria,Santos, Gustavo A. Garrido,Murray, Ana P.,Maier, Marta S.
, p. 1160 - 1165 (2011)
Disodium 2β,3α-dihydroxy-5α-cholestan-6-one disulfate (8) has been synthesized using cholesterol (1) as starting material. Sulfation was performed using trimethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The acetylcholinesterase inhibitory activity of compound 8 was evaluated and compared to that of disodium 2β,3α-dihydroxy- 5α-cholestane disulfate (10) and diols 7 and 9. Compounds 8 and 10 were active with IC50 values of 14.59 and 59.65 μM, respectively. Diols 7 and 9 showed no inhibitory activity (IC50 > 500 μM).
A Simple Synthesis of Steroidal 3α,5-Cyclo-6-ones and their Efficient Transformation to Steroidal 2-En-6-ones
Aburatani, Masakazu,Takeuchi, Tadashi,Mori, Kenji
, p. 181 - 183 (1987)
Sterols 1 were converted to 3α-5-cyclo-6-ones 4 via their mesylates and subsequent oxidation.Refluxing 4 with sodium bromide/p-toluene sulfonic acid in dimethylformamide gave steroidal 2-en-6-ones 5, among which 5 is an important brassinolide intermediate.
Synthesis of a carborane-containing cholesterol derivative and evaluation as a potential dual agent for MRI/BNCT applications
Alberti, Diego,Toppino, Antonio,Geninatti Crich, Simonetta,Meraldi, Chiara,Prandi, Cristina,Protti, Nicoletta,Bortolussi, Silva,Altieri, Saverio,Aime, Silvio,Deagostino, Annamaria
, p. 2457 - 2467 (2014)
In this study the synthesis and characterization of a new dual, imaging and therapeutic, agent is proposed with the aim of improving the efficacy of Boron Neutron Capture Therapy (BNCT) in cancer treatment. The agent (Gd-B-AC01) consists of a carborane un
Synthesis and antitumor activity of novel steroidal imidazolium salt derivatives
Deng, Guogang,Zhou, Bei,Wang, Jing,Chen, Zhuo,Gong, Liang,Gong, Yaxiao,Wu, Dongmei,Li, Yan,Zhang, Hongbin,Yang, Xiaodong
, p. 232 - 252 (2019)
Sixty-one novel steroidal imidazolium salt derivatives were synthesized and evaluated in vitro against a panel of human tumor cell lines. The results showed that diosgenin?imidazolium salt derivatives displayed much higher cytotoxic activities than choles
Cyclic Diaryl λ3-Bromanes: A Rapid Access to Molecular Complexity via Cycloaddition Reactions
Lanzi, Matteo,Ali Abdine, Racha Abed,De Abreu, Maxime,Wencel-Delord, Joanna
supporting information, p. 9047 - 9052 (2021/12/06)
Biaryls have widespread applications in organic synthesis. However, sequentially polysubstituted biaryls are underdeveloped due to their challenging preparation. Herein, we report the synthesis of dissymetric 2,3,2′,3′,4-substituted biaryls via pericyclic reactions of cyclic diaryl λ3-bromanes. The functional groups tolerance and atom economy allow access to molecular complexity in a single reaction step. Continuous flow protocol has been designed for the scale-up of the reaction, while postfunctionalizations have been developed taking advantage of the residual Br-atom.
Apoptosis inducing properties of 3-biotinylate-6-benzimidazole B-nor-cholesterol analogues
Zhu, Zhiling,Liu, Zhiping,Cui, Jianguo,Huang, Yanmin,Chen, Hualong,Wu, Yulan,Huang, Xiaotong,Gan, Chunfang
, (2021/03/22)
In this work, a series of Biotin-substituted B-nor-cholesteryl benzimidazole compounds were synthesized. The antiproliferative activities of these compounds were evaluated in vitro using a series of human cancer cell lines, including HeLa (cervical cancer), SKOV3 (ovarian cancer), T-47D (thymus gland cancer), MCF-7 (human breast cancer) and HEK293T (normal renal epithelial) cells. These compounds displayed distinct antiproliferative activities against the currently tested cancer cells. The apoptotic properties induced by compound 6d were further investigated. Our results showed that compound 6d could induce the apoptosis of SKOV3 cells, blocking the cell growth in S-phase. Western blotting analyses revealed that compound 6d can induce cell apoptosis via the mitochondria-dependent pathway.
Synthesis and search for 3β,3′β-disteryl ethers after high-temperature treatment of sterol-rich samples
Bus, Katarzyna,Ofiara, Karol,Sitkowski, Jerzy,Szterk, Arkadiusz,Zmys?owski, Adam
, (2020/06/08)
It has been proven that at increased temperature, sterols can undergo various chemical reactions e.g., oxidation, dehydrogenation, dehydration and polymerisation. The objectives of this study are to prove the existence of dimers and to quantitatively analyse the dimers (3β,3′β-disteryl ethers). Sterol-rich samples were heated at 180 °C, 200 °C and 220 °C for 1 to 5 h. Quantitative analyses of the 3β,3′β-disteryl ethers were conducted using liquid extraction, solid-phase extraction and gas chromatography coupled with mass spectrometry. Additionally, for the analyses, suitable standards were synthetized from native sterols. To identify the mechanism of 3β,3′β-disteryl ether formation at high temperatures, an attempt was made to use the proposed synthesis method. Additionally, due to the association of sterols and sterol derivatives with atherosclerosis, preliminary studies with synthetized 3β,3′β-disteryl ethers on endothelial cells were conducted.
Steroid compound 3-site hydroxyl configuration inversion method
-
Paragraph 0086; 0087; 0088, (2018/12/14)
The invention discloses a steroid compound 3-site hydroxyl configuration inversion method. The method specifically comprises the following steps that (1) a steroid compound containing a 3-site hydroxyl reacts with an acyl chloride compound; (2) the product obtained in the step (1) and a substituting agent are subjected to SN2 nucleophilic substitution reaction under existing of a phase transfer catalyst; and (3) the product obtained in the step (2) is subjected to a hydrolysis reaction. Compared with a Mitsunobu method, the method does not need to use triphenylphosphine and azodiformate pricedhigher, and accordingly the production cost is greatly lowered; meanwhile, a p-nitrobenzoic acid derivative which seriously affects the water environment does not need to be used, and therefore the method is more environmentally friendly. The method adopts cesium acetate/18-crown ether-6 system to conduct 3-site hydroxyl configuration inversion, can remarkably reduce occurrence of side reactions,accordingly a higher reaction yield is obtained, and the method is finally applicable to industrialized production.
Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors
Wu, Xiangyu,Hao, Wei,Ye, Ke-Yin,Jiang, Binyang,Pombar, Gisselle,Song, Zhidong,Lin, Song
supporting information, p. 14836 - 14843 (2018/11/10)
Alkyl chlorides are common functional groups in synthetic organic chemistry. However, the engagement of unactivated alkyl chlorides, especially tertiary alkyl chlorides, in transition-metal-catalyzed C-C bond formation remains challenging. Herein, we describe the development of a TiIII-catalyzed radical addition of 2° and 3° alkyl chlorides to electron-deficient alkenes. Mechanistic data are consistent with inner-sphere activation of the C-Cl bond featuring TiIII-mediated Cl atom abstraction. Evidence suggests that the active TiIII catalyst is generated from the TiIV precursor in a Lewis-acid-assisted electron transfer process.
