71655-17-9Relevant academic research and scientific papers
Conformationally Controlled Linear and Helical Hydrocarbons Bearing Extended Side Chains
Aggarwal, Varinder K.,Butts, Craig P.,Davy, Matthew,Dutton, Oliver J.,Guo, Lin,Kucukdisli, Murat,Myers, Eddie L.,Wagnières, Olivier
, p. 16682 - 16692 (2021/10/21)
Conformationally controlled flexible molecules are ideal for applications in medicine and materials, where shape matters but an ability to adapt to multiple and changing environments is often required. The conformation of flexible hydrocarbon chains bearing contiguous methyl substituents is controlled through the avoidance of syn-pentane interactions: alternating syn-anti isomers adopt a linear conformation while all-syn isomers adopt a helical conformation. From a simple diamond lattice analysis, larger substituents, which would be required for most potential applications, result in significant and unavoidable syn-pentane interactions, suggesting substantially reduced conformational control. Through a combination of computation, synthesis, and NMR analysis, we have identified a selection of substitution patterns that allow large groups to be incorporated on conformationally controlled linear and helical hydrocarbon chains. Surprisingly, when the methyl substituents of alternating syn-anti hydrocarbons are replaced with acetoxyethyl groups, the main chain of almost 95% of the population of molecules adopt a linear conformation. Here, the side chains adopt nonideal eclipsed conformations with the main chain, thus minimizing syn-pentane interactions. In the case of all-syn hydrocarbons, concurrent removal of some methyl groups on the main chain adjacent to the large substituents is required to maintain a high population of molecules adopting a helical conformation. This information can now be used to design flexible hydrocarbon chains displaying functional groups in a defined relative orientation for multivalent binding or cooperative reactivity, for example, in targeting the interfaces defined by disease-relevant protein-protein interactions.
STING AGONISTS AND USES THEREOF
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Paragraph 00687, (2020/07/14)
The present invention provides compounds, compositions thereof, and methods of using the same for the modulation of STING, and the treatment of STING-mediated disorders.
Grubbs Catalysts Immobilized on Merrifield Resin for Metathesis of Leaf Alcohols by using a Convenient Recycling Approach
Xia, Liang,Peng, Tao,Wang, Gang,Wen, Xiaoxue,Zhang, Shouguo,Wang, Lin
, p. 45 - 48 (2019/02/06)
Three new types of heterogeneous catalysts were prepared using a facile approach by the immobilization of Grubbs catalysts on PEGylated Merrifield resin. One of the immobilized catalysts was more efficient than the free catalyst for the metathesis of leaf alcohols in conversion and selectivity and was reused repeatedly (up to 5 cycles) with only a slight loss of activity (10.5 %). The long-chain PEGylated linker provided an appropriate distance between the resin and the catalytic center so that the ruthenium catalysts acted as the free catalyst.
Compounds and Their Use in Treating Cancer
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Paragraph 0710-0712, (2019/07/10)
The specification generally relates to compounds of Formula (I): and pharmaceutically acceptable salts and prodrugs thereof, where R1, R4, R5, R6, R7, Linker, X, Y, A, G, D and E have any of the meanings defined herein. This specification also relates to the use of such compounds and pharmaceutically acceptable salts and prodrugs thereof in methods of treatment of the human or animal body, for example in prevention or treatment of cancer. This specification also relates to processes and intermediate compounds involved in the preparation of such compounds and to pharmaceutical compositions containing them.
Synthesis of the C18–C26 tetrahydrofuran-containing fragment of amphidinolide C congeners via tandem asymmetric dihydroxylation and SN2 cyclization
Su, Ye-Xiang,Dai, Wei-Min
, p. 1546 - 1554 (2018/02/26)
The C18–C26 fragment of amphidinolide C congeners has been synthesized starting from methyl acetoacetate in 14 steps in >17.0% overall yield. The C20 stereogenic center was secured by asymmetric hydrogenation of a β-keto ester and the configuration at both C23 and C24 was introduced by asymmetric dihydroxylation (AD). The trans-2,5-disubstituted tetrahydrofuran ring was assembled via the tandem AD–SN2 sequence. The latter protocol could be employed for accessing the corresponding cis-2,5-disubstituted tetrahydrofuran rings from the same alkene substrates simply by choosing a suitable AD ligand. Moreover, functional group compatibility was observed for the Ru(II)-catalyzed hydrogenation of β-keto esters and the Pd(0)–Cu(I)-catalyzed Sonogashira cross-coupling reaction. These findings should be valuable for general synthetic design and application.
Singlet oxygen-mediated synthesis of bis -spiroketals found in azaspiracids
Triantafyllakis, Myron,Tofi, Maria,Montagnon, Tamsyn,Kouridaki, Antonia,Vassilikogiannakis, Georgios
supporting information, p. 3150 - 3153 (2014/06/23)
Conversion of a simple furan into the ABCD-ring skeleton of the azaspiracids via a singlet oxygen-initiated one-pot process has been accomplished.
Synthesis and biological evaluation of new cytotoxic indazolo[4,3-gh] isoquinolinone derivatives
Shahabi, Manochehr,Schirmer, Eva,Shanab, Karem,Leepasert, Theerachart,Ruzicka, Jana,Holzer, Wolfgang,Spreitzer, Helmut,Aicher, Babette,Schmidt, Peter,Blumenstein, Lars,Müller, Gilbert,Günther, Eckhard
, p. 1846 - 1852 (2013/04/10)
A series of indazolo[4,3-gh]isoquinolinones derivatives have been synthesized to decrease cardiotoxic side effects in comparison to Mitoxantrone. The antiproliferative effects of different side chains were investigated and tested on at least four different cell lines of cervix, ovarian, CNS, NSCLC (non-small-cell lung cancer) and colon carcinoma. In addition to antiproliferative activities, influence on cell cycle and intercalation behavior have been tested.
Synthesis of dipeptide isosteres by cross-metathesis
Enholm, J. Eric,Low, Tammy,Cooper, Daniel,Ghivirija, Ion
, p. 6920 - 6927 (2012/08/29)
This work describes the attachment of two amino acid derivatives by olefin cross-metathesis using Grubbs' second generation catalyst. They were connected at the carboxyl termini. In addition, a cyclic dilactam scaffold was used, which reacted with only a
Synthesis, redox properties, and conformational analysis of vicinal disulfide ring mimics
Ruggles, Erik L.,Deker, P. Bruce,Hondal, Robert J.
experimental part, p. 1257 - 1267 (2009/05/07)
A vicinal disulfide ring (VDR) results from disulfide-bond formation between two adjacent cysteine residues. This eight-membered ring is a rare motif in protein structures and is functionally important to those few proteins that posses it. This article focuses on the construction of strained and unstrained VDR mimics, discernment of the preferred conformation of these mimics, and the determination of their respective disulfide redox potentials.
MACROCYCLIC COMPOUNDS USEFUL AS INHIBITORS OF KINASES AND HSP90
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Page/Page column 146, (2010/11/30)
Disclosed are macrocyclic compounds of formulae I-V,which are analogs of the pochonin resorcylic acid lactones, and processes for the preparation of the compounds. The compounds disclosed are useful as inhibitors of kinases and Heat Shock Protein 90 (HSP 90). Also disclosed are pharmaceutical compositions comprising an effective kinase-inhibiting amount or an effective HSP90-inhibiting amount of the compounds and methods for the treatment of disorders that are mediated by kinases and HSP90.
