100751-65-3Relevant academic research and scientific papers
Synthesis of metallo-supramolecular polymers with a bis-ono-tridentate ligand by coordination programming
Kanao, Miki,Higuchi, Masayoshi
, p. 1075 - 1077 (2014)
A novel ONO-type bis-tridentate ligand L1 was synthesized by a diazocoupling reaction of 3,3'-dihydroxybenzidine with 6-octyl-2-naphthol in 58% yield. Azo-hydrazo tautomerization in L1 was indicated by the NMR and IR spectra. The 1:1 complexation of L1 and Mn(III) or Co(II) ions was confirmed by titration experiments at room temperature. Mn-, Co-, and Crbased metallo-supramolecular polymers were prepared via the 1:1 complexation of the ditopic ligand with the metal ions at 100 °C. The Mn- and Cr-based polymers exhibited reversible redox properties.
Novel enantiopure sigma receptor modulators: Quick (semi-)preparative chiral resolution via hplc and absolute configuration assignment
Rui, Marta,Marra, Annamaria,Pace, Vittorio,Juza, Markus,Rossi, Daniela,Collina, Simona
, (2016)
The identification of novel pan-sigma receptor (SR) modulators, potentially useful in cancer treatment, represents a new goal of our research. Here, we report on the preparation of novel chiral compounds characterized by a 3-C alkyl chain bridging an arom
Synthesis and biological evaluation of new aryl-alkyl(alkenyl)-4-benzylpiperidines, novel Sigma Receptor (SR) modulators, as potential anticancer-agents
Rui, Marta,Rossi, Daniela,Marra, Annamaria,Paolillo, Mayra,Schinelli, Sergio,Curti, Daniela,Tesei, Anna,Cortesi, Michela,Zamagni, Alice,Laurini, Erik,Pricl, Sabrina,Schepmann, Dirk,W?nsch, Bernhard,Urban, Ernst,Pace, Vittorio,Collina, Simona
, p. 649 - 665 (2016)
In the early 2000s, the Sigma Receptor (SR) family was identified as potential “druggable” target in cancer treatment. Indeed, high density of SRs was found in breast, lung, and prostate cancer cells, supporting the idea that SRs could play a role in tumor growth and progression. Moreover, a link between the degree of SR expression and tumor aggressiveness has been postulated, justified by the presence of SRs in high metastatic-potential cancer cells. As a consequence, considerable efforts have been devoted to the development of small molecules endowed with good affinity towards the two SR subtypes (S1R and S2R) with potential anticancer activity. Herein, we report the synthesis and biological profile of aryl-alkyl(alkenyl)-4-benzylpiperidine derivatives - as novel potential anticancer drugs targeting SR. Among them, 3 (RC-106) exhibited a preclinical profile of antitumor efficacy on a panel of cell lines representative of different cancer types (i.e. Paca3, MDA-MB 231) expressing both SRs, and emerged as a hit compound of a new class of SR modulators potentially useful for the treatment of cancer disease.
CELL SURFACE RECEPTOR BINDING COMPOUNDS AND CONJUGATES
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Paragraph 00885-00886, (2021/07/17)
The present disclosure provides a class of compounds including a ligand moiety that specifically binds to a cell surface receptor, such as a mannose-6-phosphate receptor (M6PR) or a cell surface asialoglycoprotein receptor (ASGPR). The cell surface M6PR or ASGPR binding compounds can trigger the receptor to internalize into the cell a bound compound. The ligand moieties of this disclosure can be linked to a variety of moieties of interest without impacting the specific binding to, and function of, the cell surface receptor, e.g., M6PR or ASGPR. Also provided are compounds that are conjugates of the ligand moieties linked to a biomolecule, such as an antibody, which conjugates can harness cellular pathways to remove specific proteins of interest from the cell surface or from the extracellular milieu. Also provided are methods of using the conjugates to target a polypeptide of interest for sequestration and/or lysosomal degradation.
The Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols
He, Zhen,Pulis, Alexander P.,Procter, David J.
supporting information, p. 7813 - 7817 (2019/05/15)
A benzothiophene S-oxide catalyst, generated in situ by sulfur oxidation with H2O2, mediates the oxidative coupling of 2-naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2-naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S-oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)-nigerone and (±)-isonigerone. Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal-free C?C bond formation.
Nickel-Catalyzed Amination of Silyloxyarenes through C–O Bond Activation
Wiensch, Eric M.,Montgomery, John
supporting information, p. 11045 - 11049 (2018/07/31)
Silyloxyarenes were utilized as electrophilic coupling partners with amines in the synthesis of aniline derivatives. A diverse range of amine substrates were used, including cyclic or acyclic secondary amines, secondary anilines, and sterically hindered primary anilines. Additionally, a range of sterically hindered and unhindered primary aliphatic amines were employed, which have previously been challenging with other classes of aryl ether electrophiles. Orthogonal couplings of silyloxyarenes with aryl methyl ethers are illustrated, where selectivity between the two C?O electrophiles is determined by ligand control, thereby allowing complementary and selective late-stage diversification of either electrophile. Finally, a sequential coupling displays the utility of this amination method along with the reversal in intrinsic reactivity between aryl methyl ethers and silyloxyarenes.
17,20-Lyase inhibitors. Part 4: Design, synthesis and structure-activity relationships of naphthylmethylimidazole derivatives as novel 17,20-lyase inhibitors
Kaku, Tomohiro,Matsunaga, Nobuyuki,Ojida, Akio,Tanaka, Toshimasa,Hara, Takahito,Yamaoka, Masuo,Kusaka, Masami,Tasaka, Akihiro
experimental part, p. 1751 - 1770 (2011/04/17)
A novel series of naphthylmethylimidazole derivatives and related compounds have been investigated as selective 17,20-lyase inhibitors. Optimization of the substituent at the 6-position on the naphthalene ring was performed to yield a methylcarbamoyl derivative, which exhibited potent inhibitory activity against human 17,20-lyase and promising selectivity (>200-fold) for 17,20-lyase over CYP3A4. Further modifications of the methylcarbamoyl derivative led to the discovery of the corresponding tricyclic compound, which showed highly potent activity against human 17,20-lyase (IC50 19 nM) and good selectivity (>1000-fold) for inhibition of 17,20-lyase over CYP3A4. Additional biological evaluation revealed that the tricyclic compound had potent in vivo efficacy in monkeys and favorable pharmacokinetic profiles when administered in rats. Asymmetric synthesis of the selective tricyclic inhibitor was also achieved using a chiral α-hydroxy ketone.
TRI-2-NAPHTHYLAMINES
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Page/Page column 13, (2011/04/25)
The invention relates to tri-2-naphthylamines that can be useful in a variety of optical devices as hole-transport materials. For example, the tri-2-naphthylamines can be useful as hole-transport materials in organic light emitting diodes.
BICYCLIC ARYL SPHINGOSINE 1-PHOSPHATE ANALOGS
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Page/Page column 82-83, (2011/02/24)
Compounds that have agonist activity at one or more of the SlP receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at SlP receptors.
Synthesis and biological evaluation of 11C-labeled β-galactosyl triazoles as potential PET tracers for in vivo LacZ reporter gene imaging
Celen, Sofie,Cleynhens, Jan,Deroose, Christophe,de Groot, Tjibbe,Ibrahimi, Abdelilah,Gijsbers, Rik,Debyser, Zeger,Mortelmans, Luc,Verbruggen, Alfons,Bormans, Guy
experimental part, p. 5117 - 5125 (2009/11/30)
In our aim to develop LacZ reporter probes with a good retention in LacZ expressing cells, we report the synthesis and preliminary evaluation of two carbon-11 labeled β-galactosyl triazoles 1-(β-d-galactopyranosyl)-4-(p-[11C]methoxyphenyl)-1,2,
