4152-79-8Relevant articles and documents
Synthesis and in vitro antitumour activity of 4(R)-methyl-3-O-phosphonomethyl-α-L-threose nucleosides
Liu, Feng-Wu,Ji, Shujie,Gao, Yingying,Meng, Yao,Xu, Wenke,Wang, Haixia,Yang, Jing,Huang, Hao,Herdewijn, Piet,Wang, Cong
, (2021/05/19)
A series of novel α-L-threose nucleoside phosphonate analogs, 4(R)-methyl-3-O-phosphonomethyl-α-L-threose nucleosides, were synthesized in multistep sequences starting from D-xylose. The synthetic sequence consisted of the following key stages: (i) the multistep synthesis of 1,2-O-isopropylidenyl-4(R)-methyl-3-O-phosphonomethyl-L-threose, (ii) the transformation of 1,2-O-isopropylidenyl sugar into suitable 1,2-di-O-acyl L-threose precursor, and (iii) the construction of target α-L-threose nucleoside phosphonate analogs by Vorbrüggen glycosidation reaction, deprotection of acyl group, and hydrolysis of diethyl group on phosphonate. The target nucleoside phosphonates were evaluated for their antitumour activities in cell culture-based assays. Compound 8g, 2-fluroadenosine phosphonate, showed remarkable activity against human breast cancer cell lines (MCF-7 and MDA-MB-231) with IC50 values of 0.476 and 0.391 μM, corresponding to 41- and 47-fold higher potency than the reference compound 5-FU, respectively. Subsequent investigations found that the compound 8g can inhibit the proliferation of breast cancer cells and cell cloning. The mechanistic studies indicated that compound 8g could cause DNA damage to breast cancer cells through the ATM-Chk1/Chk2-cdc25c pathway, leading to blockage of the G2/M phase cycle of breast cancer cells, which ultimately led to apoptosis. Moreover, 8g could inhibit the PI3K/AKT signaling pathway and induce apoptosis. These results indicate that compound 8g holds promising potential as an antitumour agent.
Antitumor (4' R)-methyl - α-L . (by machine translation)
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Paragraph 0050; 0053, (2020/06/09)
The invention discloses novel α-L - fucosa nucleoside phosphonate analogs, and particularly relates to (4 ′). R- Methyl -3 ' - methyl phosphonic acid - α-L . It has the structure shown in Formula 1. Wherein R ' represents H, Na, K or NH. 4 Ions; B stands for uracil, thymine, 5 - chlorouracil, 5 - fluorouracil, 5 -bromouracil, 5 -fluorouracil, cytosine, 5 - fluorocytosine, adenine, 2 - fluoroadenine, 2 - chloroadenine, 2 - aminoadenine and guanine. The compound has anti-tumor activity and good development prospect. (by machine translation)
Generation of a low-valent titanium species from titanatrane and its catalytic reactions: Radical ring opening of oxetanes
Takekoshi, Naoto,Miyashita, Kenji,Shoji, Noriaki,Okamoto, Sentaro
supporting information, p. 2151 - 2157 (2013/10/01)
Treatment of a titanatrane complex with trimethylsilyl chloride and magnesium powder in tetrahydrofuran generated a low-valent titanium species. This species catalyzed the radical ring opening of epoxides and oxetanes to produce the corresponding less substituted alcohols. The reagent also catalyzed the deallylation and depropargylation of allylic and propargylic ethers, respectively, to provide the parent alcohols.