95332-26-6Relevant articles and documents
N-CONTAINING CHROMEN-4-ONE DERIVATIVES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION
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Page/Page column 51, (2020/07/07)
The present invention provides the compounds having the general formula: (I) wherein R1 to R8, and X are as described herein, compositions including the compounds and methods of using the compounds.
Total Synthesis of Caesalpinnone A
Liu, Zhigang,Meng, Yifei,Yuan, Pengrui,Wang, Zhengshen,Gao, Jin-Ming,Zheng, Huaiji
supporting information, p. 520 - 522 (2020/01/21)
Total synthesis of caesalpinnone A was achieved in 12 steps starting from resorcinol. Key features of the synthesis include BINOL-phosphoric acid catalyzed [4 + 2] cycloaddition, trans-selective nucleophilic substitution, deallylation/oxa-Michael addition cascade, and late-stage photo-Fries rearrangement.
STABLE COMPOSITIONS OF PEGYLATED CARFILZOMIB COMPOUNDS
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Paragraph 0235; 0236, (2019/05/24)
The present invention provides stable pharmaceutical compositions of pegylated carfilzomib compounds, methods for preparing the compositions, and uses of the compositions for treating cancer, including hematologic malignancies such as multiple myeloma. Th
A chiral pool approach for asymmetric syntheses of both antipodes of equol and sativan
Yalamanchili, Chinni,Chittiboyina, Amar G.,Chandra Kumar Rotte, Sateesh,Katzenellenbogen, John A.,Helferich, William G.,Khan, Ikhlas A.
, p. 2020 - 2029 (2018/03/21)
For the first time, both antipodes of the isoflavans, equol and sativan were synthesized in >98% ee with good overall yields starting from readily available starting materials. The chiral isoflavan, (?)-equol is produced from soy isoflavones, formonentin and daidzein by the action of intestinal bacteria in certain groups of population and other chiral isoflavans are reported from various phytochemical sources. To produce these chiral isoflavans in gram quantities, Evans’ enantioselective aldol condensation was used as a chiral-inducing step to introduce the required chirality at the C-3 position. Addition of chiral boron-enolate to substituted benzaldehyde resulted in functionalized syn-aldol products with >90% yield and excellent diastereoselectivity. Functional group transformations followed by intramolecular Mitsunobu reaction and deprotection steps resulted the target compounds, S-(?)-equol and S-(+)-sativan, with high degree of enantiopurity. By simply switching the chiral auxiliary to (S)-4-benzyloxazolidin-2-one and following the same synthetic sequence the antipodes, R-(+)-equol and R-(?)-sativan were achieved. Both enantiomers are of interest from a clinical and pharmacological perspective and are currently being developed as nutraceutical and pharmacological agents. This flexible synthetic process lends itself quite readily to the enantioselective syntheses of other biologically active C-3 chiral isoflavans.
PEGYLATED CARFILZOMIB COMPOUNDS
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Page/Page column 53, (2017/12/29)
The present invention provides polymeric pegylated carfilzomib compounds, and pharmaceutically acceptable salts thereof, of Formula I wherein R1, R2, linker, PEG, n and o are as defined herein. The invention also provides methods of
Glycosylation near infrared dye as well as preparation method and application thereof
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Paragraph 0043; 0044; 0045; 0046; 0047, (2016/10/10)
The invention discloses glycosylation near infrared dye as well as a preparation method and application thereof, in particular relates to dye shown as a general formula I. The dye is finally obtained by respective synthesis of three fragments and substitution and condensation reaction. The dye has the functions of ultraviolet absorption and near-infrared emission, is easy for detection and has a derivatization site which can be used for connecting molecules with different target abilities. In addition, the dye is also provided with a fluorescent switch which can be used for connecting anoxia, pH, enzyme and redox sensitive groups, so that the effect of selectively fluorescing is realized; the dye is applied to visualized target administration (see the description).
NIR fluorescent DCPO glucose analogues and their application in cancer cell imaging
Chen, Shiguang,Fang, Yanfen,Zhu, Qiwen,Zhang, Wanli,Zhang, Xiongwen,Lu, Wei
, p. 81894 - 81901 (2016/09/09)
Given the increased glucose uptake in cancer cells than normal cells, near-infrared (NIR) fluorescent glucose analogues have been previously synthesized and applied in cancer cell imaging. However, most NIR dyes usually have one or more charge in their structures, which may cause low cell membrane permeability and hamper their application in cell imaging. Here we report the synthesis and characterization of a series of DCPO-conjugated glucose analogues (N0-N4), which have no charge in their structures and have different lengths of the spacer arm. Experiments in different cancer cell lines showed the uptake of N0-N4 was dependent on the protein levels of GLUT-1. The distance between the dyes and glucose was adjusted by the length of PEG. Of these five glucose analogues, the length of the linker in N2 which contains a diethylene glycol was the most appropriate spacer arm, a longer or shorter linker exhibited reduced cellular uptake efficiency. Moreover, the uptake of DCPO-conjugated glucose analogues could be inhibited by phloretin, a GLUT-1 inhibitor or competitively inhibited by unlabeled d-glucose. Therefore, our study has reported a novel type of NIR-conjugated glucose analogues, whose cell permeability ensured the potential application for cancer cell bioimaging in the NIR region. We also demonstrated, for the first time, that the length of the linker between the dyes and glucose was also an important factor that will affect the delivery efficiency of the glucose analogues to cells.
Tandem Claisen Rearrangement/6-endo Cyclization Approach to Allylated and Prenylated Chromones
Schmidt, Bernd,Riemer, Martin,Schilde, Uwe
supporting information, p. 7602 - 7611 (2016/01/25)
Allyl, dimethylallyl and prenyl ethers derived from o-acylphenols reacted upon microwave irradiation to form C-allylated or -prenylated chromone derivatives, depending on the substitution pattern of the arene and the allyl substituent. The reaction proceeds through a tandem Claisen rearrangement and 6-endo-trig or 6-endo-dig cyclization sequence. For prenyl ethers, the tandem sequence can be extended by a Cope rearrangement to furnish 6-prenylchromones. The method is potentially useful for the synthesis of natural products and drugs.
Design, synthesis and docking study of 5-(substituted benzylidene) thiazolidine-2,4-dione derivatives as inhibitors of protein tyrosine phosphatase 1B
Wang, Zengtao,Liu, Zhiguo,Lee, Woojung,Kim, Su-Nam,Yoon, Goo,Cheon, Seung Hoon
supporting information, p. 3337 - 3340 (2014/07/22)
A series of novel 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives was designed, and synthesized based on our previous studies. Also their activities were evaluated as competitive inhibitors of protein tyrosine phosphatase 1B (PTP1B). Compounds 6d-6g, 7b, 7c, 7e, 7j, 7k, 7m, 14b and 14e-14f showed potent inhibitory effects against PTP1B, and compound 7e, the most potent among the series, had an IC50 of 4.6 μM. Also a Surflex-Dock docking model of 7e was studied. Compound 7e showed a negative binding energy of -7.35 kcal/mol and a high affinity to PTP1B residues (Gly220, Ala217, Arg221, Asp181, Ser216, Cys215, Phe182, Gln262 and Ile219) in the active sites, indicating that it may stabilize the open form and generate tighter binding to the catalytic sites of PTP1B.
Design and synthesis of 3,3′-biscoumarin-based c-Met inhibitors
Xu, Jimin,Ai, Jing,Liu, Sheng,Peng, Xia,Yu, Linqian,Geng, Meiyu,Nan, Fajun
, p. 3721 - 3734 (2014/06/09)
A library of biscoumarin-based c-Met inhibitors was synthesized, based on optimization of 3,3′-biscoumarin hit 3, which was identified as a non-ATP competitive inhibitor of c-Met from a diverse library of coumarin derivatives. Among these compounds, 38 and 40 not only showed potent enzyme activities with IC50 values of 107 nM and 30 nM, respectively, but also inhibited c-Met phosphorylation in BaF3/TPR-Met and EBC-1 cells. This journal is the Partner Organisations 2014.
