5579-66-8Relevant academic research and scientific papers
PROTAC compound for targeted degradation of IDO1, and preparation method and application thereof
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Paragraph 0024-0026; 0036-0037, (2020/06/17)
The invention provides a PROTAC compound represented by formula I and used for targeted degradation of IDO1, and a pharmaceutically acceptable salt, a hydrate or a solvate thereof. In the formula I, Xrepresents -CH2 or -C = O, Y represents -CH2 or -C= O, and n is a natural number from 2 to 9. The PROTAC compound for targeted degradation of the IDO1 has efficient activity of targeted degradation of the IDO1 protein.
Highly efficient synthesis of monodisperse poly(ethylene glycols) and derivatives through macrocyclization of oligo(ethylene glycols)
Zhang, Hua,Li, Xuefei,Shi, Qiuyan,Li, Yu,Xia, Guiquan,Chen, Long,Yang, Zhigang,Jiang, Zhong-Xing
, p. 3763 - 3767 (2015/03/18)
A macrocyclic sulfate (MCS)-based approach to monodisperse poly(ethylene glycols) (M-PEGs) and their monofunctionalized derivatives has been developed. Macrocyclization of oligo(ethylene glycols) (OEGs) provides MCS (up to a 62-membered macrocycle) as versatile precursors for a range of monofunctionalized M-PEGs. Through iterative nucleophilic ring-opening reactions of MCS without performing group protection and activation, a series of M-PEGs, including the unprecedented 64-mer (2850Da), can be readily prepared. Synthetic simplicity coupled with versatility of this new strategy may pave the way for broader applications of M-PEGs. Macrocycles make synthesis easier: Convenient macrocyclization of the OEGs provides versatile macrocyclic sulfates. These compounds are cornerstones for both monofunctionalization of OEGs and highly efficient synthesis of monodisperse PEGs and derivatives, including an unprecedented 64-mer.
A cost-effective, column-free route to ethylene glycol oligomers EG 6, EG10, and EG12
Gothard, Chris M.,Grzybowski, Bartosz A.
experimental part, p. 717 - 722 (2012/04/04)
Although monodisperse ethylene glycol (EG) oligomers are important in a wide range of applications (ranging from drug therapeutics to materials science and engineering), their cost - especially for longer EG oligomers is often prohibitive. For example, decaethylene, EG10, and dodecaethylene, EG12, glycols cost hundreds of dollars per gram, and are only available from most vendors, including Sigma-Aldrich, in the polydispersed form. This high-cost is, in large part, due to laborious nature of synthesis and, above all, purification steps involved. Therefore, the motivation of our work was to design a cost-effective route to the EG oligomers that would altogether avoid the column-chromatography purification. This was achieved by a simple synthetic strategy, which combines bidirectional growth of the EG chains with the protection scheme using easy-to-remove trityl groups. Georg Thieme Verlag Stuttgart · New York.
Convenient multigram synthesis of monodisperse oligo(ethylene glycols): Effective reaction monitoring by infrared spectroscopy using an attenuated total reflection fibre optic probe
Lumpi, Daniel,Braunshier, Christian,Hametner, Christian,Horkel, Ernst,Zachhuber, Bernhard,Lendl, Bernhard,Fr?hlich, Johannes
supporting information; experimental part, p. 6469 - 6471 (2011/02/23)
A convenient approach for the synthesis of monodisperse oligo(ethylene glycols) up to 12 units is described. A novel cleavage protocol replacing laborious hydrogenolysis is introduced to achieve a fast, inexpensive and widely applicable procedure. In addition to the synthetic part, Fourier transform infrared (FTIR) spectroscopy using a fibre optic attenuated total reflection (ATR) sensor was applied to monitor the formation of sensitive key intermediates, resulting in optimized reaction times. By applying this in-line technique, the possibility of real-time analysis under inert conditions was impressively demonstrated.
Synthesis of oligo(ethylene glycol) toward 44-mer
Ahmed, Saleh A.,Tanaka, Mutsuo
, p. 9884 - 9886 (2007/10/03)
A synthetic method for oligo(ethylene glycol) toward 44-mer (FW = 1956.35) is described. Reiteration of Williamson's ether synthesis and hydrogenation to remove protecting benzyl group affords desired oligo(ethylene glycol) toward 44-mer in moderate yields. The advantages in this method are use of commercially easily available materials as starting materials and procedures avoiding difficulty in purification of the products as much as possible.
An expedient synthesis of monodispersed oligo(ethylene glycols)
Burkett, Brendan A.,Chan, Tak Hang
, p. 1007 - 1010 (2007/10/03)
A convenient approach to the synthesis of oligo(ethylene glycols) under phase transfer conditions is described. Oligo(ethylene glycols) (x = 7-12) are obtained in excellent yields and high purity via modular, bi-directional elongation of readily available ethylene glycol bis-tosylates.
An ion conductor that recognizes osmotically-stressed phospholipid bilayers
Bandyopadhyay, Prasun,Bandyopadhyay, Punam,Regen, Steven L.
, p. 11254 - 11255 (2007/10/03)
A synthetic ion conductor (1), derived from cholic acid and spermine, has been found capable of recognizing osmotic stress in liposomes made from 1,2-dipalmitoleoyl-sn-glycero-3-phosphocholine [(C16:1)PC]. Thus, when large unilamellar vesicles of (C16:1)PC are placed under hypotonic conditions, the Na+/Li+ transport activity of 1 increases by as much as 1 order of magnitude, relative to isotonic conditions Copyright
TEMPLATE EFFECTS. 7. LARGE UNSUBSTITUTED CROWN ETHERS FROM POLYETHYLENE GLYCOLS: FORMATION, ANALYSIS, AND PURIFICATION
Vitali, Chiara Antonini,Masci, Bernardo
, p. 2201 - 2212 (2007/10/02)
Through the reaction of polyethylene glycols with tosyl chloride and heterogeneous KOH in dioxane not only coronands from crown-4 to crown-8 can be obtained but also larger homologues.A systematic investigation has shown that: i) crown-9 and crown-10 can be formed from nona- and deca-ethylene glycol, respectively, and isolated in pure form; ii) the whole series of polyethylene glycols from tri- to deca-ethylene glycol yields not only the corresponding crown ethers but also higher cyclooligomers that can be analyzed up to about crown-20 by glc: in particular crown-12 and crown-16 were obtained from tetraethylene glycol and purified by column chromatography on cellulose; iii) the reaction, as applied to commercial mixtures of polyethylene glycols (from PEG 200 to PEG 1000), gives fairly high yields of crown ethers also in the region of large ring sizes.The contribution of the template effect of K(+) ion and the cyclooligomerization reactions for the various ring sizes are discussed.
Intramolecular End-to-End Reactions of Photoactive Terminal Groups Linked by Poly(oxyethylene) Chains
Ashikaga, Kazuo,Ito, Shinzaburo,Yamamoto, Masahide,Nishijima, Yasunori
, p. 2443 - 2450 (2007/10/02)
The triplet-sensitized photochemical reaction using a series of poly(oxyethylene) chains with a pair of photoactive terminal groups, dibenzazepine (DBA) chromophores (DBA-COCH2CH2(OCH2CH2)nOCH2CH2CO-DBA, n=0-10) was examined.The photoirradiation of bichromophoric compounds caused either intra- or intermolecular reactions.These reactions were kinetically analyzed by two different methods: the measurement of deactivation processes of the reaction intermediates (excited triplet state of DBA) by nanosecond laser photolysis and the quantitative analysis of the reaction products by GPC.The intramolecular deactivation rate constant, kintra, showed a remarkable chain-length dependence; the maximum kintra value appeared at n=5 and it was found to be 5.9X104 s-1.On the other hand, the intramolecular cyclization rate also depends on the chain length; the maximum quantum yield, φintrad, was given at n=7 (φintrad=0.51).The chain length for the maximum cyclization yield shifted slightly to the longer region than that for the maximum kintra value due to the restriction of the terminal structure (anti-configuration).The results obtained for this reaction system are compared with those obtained for the previously reported polymethylene system and the effect of chain flexibility on the intramolecular ring-closure reaction is discussed.
