137076-22-3Relevant articles and documents
A new approach to 4-aryl-1,3-butanediols by cobalt-catalyzed sequential radical cyclization-arylation reaction of silicon-tethered 6-iodo-1-hexene derivatives
Someya, Hidenori,Kondoh, Azusa,Sato, Akinori,Ohmiya, Hirohisa,Yorimitsu, Hideki,Oshima, Koichiro
, p. 3061 - 3064 (2006)
Treatment of 6-iodo-4-oxa-3-sila-1-hexene derivatives with arylmagnesium bromide in the presence of a catalytic amount of a cobalt-diamine complex in THF afforded the corresponding benzyl-substituted oxasilacyclopentanes in good yield. The products were converted to 4-aryl-1,3-diols after Tamao-Fleming oxidation. Georg Thieme Verlag Stuttgart.
An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764
Yamanaka, Toshio,Ohkubo, Mitsuru,Takahashi, Fumie,Kato, Masayuki
, p. 2843 - 2845 (2004)
An efficient synthesis of the orally-active GpIIb/IIIa antagonist FR184764 was achieved. The key intermediate, an optically active ethynyl β-amino ester, was synthesized efficiently by utilizing a lipase catalyzed kinetic resolution step.
Synthesis and antiplasmodial activity of streptocyanine/peroxide and streptocyanine/4-aminoquinoline hybrid dyes
Maether, Marie-Pierre,Bernat, Virginie,Maturano, Marie,Andre-Barres, Christiane,Ladeira, Sonia,Valentin, Alexis,Vial, Henri,Payrastre, Corinne
, p. 7400 - 7410 (2011)
Two series of streptocyanine dyes incorporating cyclic peroxide or 4-aminoquinoline moieties are prepared and X-ray diffraction structures for three compounds are determined. All hybrid dyes show good antiplasmodial activity (0.06 to 0.66 μM) and are not
Novel spiroindoline HDAC inhibitors: Synthesis, molecular modelling and biological studies
Brindisi, Margherita,Senger, Johanna,Cavella, Caterina,Grillo, Alessandro,Chemi, Giulia,Gemma, Sandra,Cucinella, Dora Mariagrazia,Lamponi, Stefania,Sarno, Federica,Iside, Concetta,Nebbioso, Angela,Novellino, Ettore,Shaik, Tajith Baba,Romier, Christophe,Herp, Daniel,Jung, Manfred,Butini, Stefania,Campiani, Giuseppe,Altucci, Lucia,Brogi, Simone
, p. 127 - 138 (2018)
This paper describes the rational development of a series of novel spiroindoline derivatives endowed with selective inhibitory activity on the HDAC6 isoform. A convenient multicomponent one-pot protocol was applied for the assembly of the desired N1-substituted spiroindoline core which allowed a straightforward analoging. Computational studies and in vitro determination of inhibitory potency for the developed compounds against HDAC6 and HDAC1 isoforms were flanked by cell-based studies on histone H3 and α-tubulin acetylation. The effects on cancer cell cycle and apoptosis of the best performing derivatives were assessed on cancer cell lines highlighting a promising antitumor potential. In view of cell-based data and calculated drug-like properties, the selective HDAC6 inhibitor 5b, with a spiroindoline-based hydroxamate bearing a tert-butyl carbamate functionality, was selected to be further investigated for its potential in inhibiting tumor cells migration. It was able to potently inhibit cell migration in SH-SY5Y neuroblastoma cells and did not display toxicity in NIH3T3 mouse fibroblasts. Taken together, these data foster further investigation and optimization for this class of compounds as novel anticancer agents.
Piperidine-based glycodendrons as protein N-glycan prosthetics
Hudak, Jason E.,Belardi, Brian,Appel, Mason J.,Solania, Angelo,Robinson, Peter V.,Bertozzi, Carolyn R.
, p. 4791 - 4800 (2016)
The generation of homogeneously glycosylated proteins is essential for defining glycoform-specific activity and improving protein-based therapeutics. We present a novel glycodendron prosthetic which can be site-selectively appended to recombinant proteins to create ‘N-glycosylated’ glycoprotein mimics. Using computational modeling, we designed the dendrimer scaffold and protein attachment point to resemble the native N-glycan architecture. Three piperidine–melamine glycodendrimers were synthesized via a chemoenzymatic route and attached to human growth hormone and the Fcregion of human IgG. These products represent a new class of engineered biosimilars bearing novel glycodendrimer structures.
A CLASS OF BIFUNCTIONAL CHIMERIC HETEROCYCLIC COMPOUNDS FOR TARGETED DEGRADATION OF ANDROGEN RECEPTORS AND USE THEREOF
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, (2022/03/07)
The present invention relates to a class of bifunctional chimeric heterocyclic compounds for targeted degradation of androgen receptors and use thereof, and specifically provides a compound of formula (I), or an isotopic compound thereof, or an optical isomer thereof, or a tautomer thereof, or a pharmacologically acceptable salt thereof, or a prodrug thereof, or a solvate thereof, wherein ARB is an androgen receptor recognition/binding part, L is a link part, and U is a ubiquitin protease recognition/binding part; and the three parts are connected by means of chemical bonds. The compound can perform the targeted degradation on androgen receptors in prostate cancer cells, and suppress the proliferation of the prostate cancer cells, and also show good metabolic stability and pharmacokinetic properties. The compound has good application prospect in the preparation of targeted chimeras for protein degradation of androgen receptors and in the preparation of drugs for treating the related diseases regulated by the androgen receptors.
C-H Alkylation of Aldehydes by Merging TBADT Hydrogen Atom Transfer with Nickel Catalysis
Murugesan, Vetrivelan,Ganguly, Anirban,Karthika, Ardra,Rasappan, Ramesh
, p. 5389 - 5393 (2021/07/21)
Catalyst controlled site-selective C-H functionalization is a challenging but powerful tool in organic synthesis. Polarity-matched and sterically controlled hydrogen atom transfer (HAT) provides an excellent opportunity for site-selective functionalization. As such, the dual Ni/photoredox system was successfully employed to generate acyl radicals from aldehydes via selective formyl C-H activation and subsequently cross-coupled to generate ketones, a ubiquitous structural motif present in the vast majority of natural and bioactive molecules. However, only a handful of examples that are constrained to the use of aryl halides are developed. Given the wide availability of amines, we developed a cross-coupling reaction via C-N bond cleavage using the economic nickel and TBADT catalyst for the first time. A range of alkyl and aryl aldehydes were cross-coupled with benzylic and allylic pyridinium salts to afford ketones with a broad spectrum of functional group tolerance. High regioselectivity toward formyl C-H bonds even in the presence of α-methylene carbonyl or α-amino/oxy methylene was obtained.
BIFUNCTIONAL MOLECULES CONTAINING AN E3 UBIQUITINE LIGASE BINDING MOIETY LINKED TO A BCL6 TARGETING MOIETY
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Paragraph 00475; 00476, (2021/04/23)
Bifunctional compounds, which find utility as modulators of B-cell lymphoma 6 protein (BCL6; target protein), are described herein. In particular, the bifunctional compounds of the present disclosure contain on one end a Von Hippel-Lindau, cereblon, Inhibitors of Apotosis Proteins or mouse double-minute homolog 2 ligand that binds to the respective E3 ubiquitin ligase and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The bifunctional compounds of the present disclosure exhibit a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.
Expansion of substrate scope for nitroxyl radical/copper-catalyzed aerobic oxidation of primary alcohols: A guideline for catalyst selection
Iwabuchi, Yoshiharu,Nagasawa, Shota,Sasaki, Ryota,Sasano, Yusuke,Yamaichi, Aoto
, p. 488 - 497 (2021/05/27)
Four distinctive sets of optimum nitroxyl radical/copper salt/additive catalyst combinations have been identified for accommodating the aerobic oxidation of various types of primary alcohols to their corresponding aldehydes. Interestingly, less nucleophilic catalysts exhibited higher catalytic activities for the oxidation of particular primary allylic and propargylic alcohols to give α,β-unsaturated aldehydes that function as competent Michael acceptors. The optimum conditions identified herein were successful in the oxidation of various types of primary alcohols, including unprotected amino alcohols and divalent-sulfur-containing alcohols in good-to-high yields. Moreover, N-protected alaninol, an inefficient substrate in the nitroxyl radical/ copper-catalyzed aerobic oxidation, was oxidized in good yield. On the basis of the optimization results, a guideline for catalyst selection has been established.
1,3-Alkyl Transposition in Allylic Alcohols Enabled by Proton-Coupled Electron Transfer
Knowles, Robert R.,Seidler, Gesa,Zhao, Kuo
supporting information, p. 20190 - 20195 (2021/08/13)
A method is described for the isomerization of acyclic allylic alcohols into β-functionalized ketones via 1,3-alkyl transposition. This reaction proceeds via light-driven proton-coupled electron transfer (PCET) activation of the O?H bond in the allylic al
