69022-70-4Relevant articles and documents
Metal-ligand charge-transfer-promoted photoelectronic Bergman cyclization of copper metalloenediynes: Photochemical DNA cleavage via C-4′ H-atom abstraction
Benites, Pedro J.,Holmberg, Rebecca C.,Rawat, Diwan S.,Kraft, Brian J.,Klein, Lee J.,Peters, Dennis G.,Thorp, H. Holden,Zaleski, Jeffrey M.
, p. 6434 - 6446 (2003)
Metal-to-ligand charge-transfer (MLCT) photolyses (λ ≥ 395 nm) of copper complexes of cis-1,8-bis(pyridin-3-oxy)oct-4-ene-2,6-diyne (bpod, 1), [Cu(bpod)2]PF6 (2), and [Cu(bpod)2](NO3)2 (3) yield Bergman cyclization of the bound ligands. In contrast, the uncomplexed ligand 1 and Zn(bpod)2(CH3COO)2 compound (4) are photochemically inert under the same conditions. In the case of 4, sensitized photochemical generation of the lowest energy 3π-π* state, which is localized on the enediyne unit, leads to production of the trans-bpod ligand bound to the Zn(II) cation by photoisomerization. Electrochemical studies show that 1, both the uncomplexed and complexed, exhibits two irreversible waves between Ep values of -1.75 and -1.93 V (vs SCE), corresponding to reductions of the alkyne units. Irreversible, ligand-based one-electron oxidation waves are also observed at +1.94 and +2.15 V (vs SCE) for 1 and 3. Copper-centered oxidation of 2 and reduction of 3 occur at E1/2 = +0.15 and +0.38 V, respectively. Combined with the observed Cu(I)-to-pyridine(π*) MLCT and pyridine(π*)-to-Cu(II) ligand-to-metal charge transfer (LMCT) absorption centered near ～315 nm, the results suggest a mechanism for photo-Bergman cyclization that is derived from energy transfer to the enediyne unit upon charge-transfer excitation. The intermediates produced upon photolysis degrade both pUC19 bacterial plasmid DNA, as well as a 25-base-pair, double-stranded oligonucleotide. Detailed analyses of the cleavage reactions reveal 5′-phosphate and 3′-phosphoglycolate termini that are derived from H-atom abstraction from the 4′-position of the deoxyribose ring rather than redox-induced base oxidation.
A convenient method for the synthesis of 1,8-bis(pyridin-3-oxy)oct-4-ene-2,6-diyne
Rawat, Diwan S.,Zaleski, Jeffrey M.
, p. 1489 - 1494 (2002)
A convenient and rapid synthesis of the title compound is described. The key step in the procedure is the Stephens Castro coupling of 3-prop-2-ynyloxy-pyridine with cis-1,2- dichloroethylene and subsequent column purification in the final stage.
Preparation method and application of propyne aryl ether compound
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Paragraph 0085-0086, (2021/08/28)
The invention particularly relates to a method for preparing propyne aryl ether compounds from aryl phenol, halogenated propyne and derivatives of the halogenated propyne, and belongs to the technical field of preparation of the propyne aryl ether compoun
BTK Inhibitors and uses thereof
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Paragraph 0923-0928, (2020/05/02)
The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.
COMPOUNDS, DEVICES, AND USES THEREOF
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Paragraph 00544, (2018/04/21)
The present invention provides compounds, e.g., compounds of Formula (I) and pharmaceutically acceptable salts, solvates, hydrates, tautomers, stereoisomers, isotopically labeled derivatives, and compositions thereof. Also provided are implantable elements (e.g., devices and materials) comprising the same, as well as methods of use thereof, e.g., for treating or preventing a disease, disorder, or condition.
Benzenesulfonamides Incorporating Flexible Triazole Moieties Are Highly Effective Carbonic Anhydrase Inhibitors: Synthesis and Kinetic, Crystallographic, Computational, and Intraocular Pressure Lowering Investigations
Nocentini, Alessio,Ferraroni, Marta,Carta, Fabrizio,Ceruso, Mariangela,Gratteri, Paola,Lanzi, Cecilia,Masini, Emanuela,Supuran, Claudiu T.
, p. 10692 - 10704 (2016/12/16)
Herein we report the synthesis of two series of benzenesulfonamide containing compounds that incorporate the phenyl-1,2,3-triazole moieties. We explored the insertion of appropriate linkers, such as ether, thioether, and amino type, into the inner section
Synthesis and biological evaluation of 4-(1,2,3-triazol-1-yl)coumarin derivatives as potential antitumor agents
Zhang, Wenjuan,Li, Zhi,Zhou, Meng,Wu, Feng,Hou, Xueyan,Luo, Hao,Liu, Hao,Han, Xuan,Yan, Guoyi,Ding, Zhenyu,Li, Rui
supporting information, p. 799 - 807 (2014/02/14)
In this research, a series of 4-(1,2,3-triazol-1-yl)coumarin conjugates were synthesized and their anticancer activities were evaluated in vitro against three human cancer cell lines, including human breast carcinoma MCF-7 cell, colon carcinoma SW480 cell and lung carcinoma A549 cell. To increase the biological potency, structural optimization campaign was conducted focusing on the C-4 position of 1,2,3-triazole and the C-6, C-7 positions of coumarin. In addition, to further evaluate the role of 1,2,3-triazole and coumarin for antiproliferative activity, 9 compounds possessing 4-(piperazin-1-yl)coumarin framework and 3 derivatives baring quinoline core were also synthesized. By MTT assay in vitro, most of the compounds display attractive antitumor activities, especially 23. Further flow cytometry assays demonstrate that compound 23 exerts the antiproliferative role through arresting G2/M cell-cycle and inducing apoptosis.
1,4-Dihydroindeno[1,2-c]pyrazoles with acetylenic side chains as novel and potent multitargeted receptor tyrosine kinase inhibitors with low affinity for the hERG ion channel
Dinges, Jürgen,Albert, Daniel H.,Arnold, Lee D.,Ashworth, Kimba L.,Akritopoulou-Zanze, Irini,Bousquet, Peter F.,Bouska, Jennifer J.,Cunha, George A.,Davidsen, Steven K.,Diaz, Gilbert J.,Djuric, Stevan W.,Gasiecki, Alan F.,Gintant, Gary A.,Gracias, Vijaya J.,Harris, Christopher M.,Houseman, Kathryn A.,Hutchins, Charles W.,Johnson, Eric F.,Li, Hu,Marcotte, Patrick A.,Martin, Ruth L.,Michaelides, Michael R.,Nyein, Michelle,Sowin, Thomas J.,Su, Zhi,Tapang, Paul H.,Xia, Zhiren,Zhang, Henry Q.
, p. 2011 - 2029 (2008/02/04)
The synthesis of a novel series of 1,4-dihydroindeno[1,2-c]pyrazoles with acetylene-type side chains is described. Optimization of those compounds as KDR kinase inhibitors identified 8, which displayed an oral activity in an estradiol-induced murine uterine edema model (ED50 = 3 mg/kg) superior to Sutent (ED50 = 9 mg/kg) and showed potent antitumor efficacy in an MX-1 human breast carcinoma xenograft tumor growth model (tumor growth inhibition = 90% at 25 mg/kg·day po). The compound was docked into a homology model of the homo-tetrameric pore domain of the hERG potassium channel to identify strategies to improve its cardiac safety profile. Systematic interruption of key binding interactions between 8 and Phe656, Tyr652, and Ser624 yielded 90, which only showed an IC50 of 11.6 μM in the hERG patch clamp assay. The selectivity profile for 8 and 90 revealed that both compounds are multitargeted receptor tyrosine kinase inhibitors with low nanomolar potencies against the members of the VEGFR and PDGFR kinase subfamilies.
A new series of pyridinyl-alkynes as antagonists of the metabotropic glutamate receptor 5 (mGluR5)
Bach, Peter,Nilsson, Karolina,Wallberg, Andreas,Bauer, Udo,Hammerland, Lance G.,Peterson, Alecia,Svensson, Tor,Oesterlund, Krister,Karis, David,Boije, Maria,Wensbo, David
, p. 4792 - 4795 (2007/10/03)
Synthesis and some structure-activity relationships for a new series of propargyl ethers as mGluR5 antagonists are reported.
Iodopropargyl pyridyl and picolinyl ethers and thioethers as paint fungicides
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, (2008/06/13)
Novel iodopropargyl pyridyl and picolinyl ethers and thioethers are effective antifungal agents. They find special utility in paint for protecting finished paint films from fungal attack.
