19254-84-3Relevant academic research and scientific papers
Synthesis, anionophoric activity and apoptosis-inducing bioactivity of benzimidazolyl-based transmembrane anion transporters
Yu, Xi-Hui,Peng, Chen-Chen,Sun, Xiao-Xiao,Chen, Wen-Hua
, p. 115 - 125 (2018)
In this paper we show that a series of 1,3-bis(benzimidazol-2-yl)benzene (m-Bimbe) derivatives exhibit excellent performance as transmembrane anion transporters with anticancer activity. The transport efficiency of m-Bimbe and its derivatives has been fir
Aromatic Linkers Unleash the Antiproliferative Potential of 3-Chloropiperidines Against Pancreatic Cancer Cells
Helbing, Tim,Carraro, Caterina,Francke, Alexander,Sosic, Alice,De Franco, Michele,Gandin, Valentina,G?ttlich, Richard,Gatto, Barbara
, p. 2040 - 2051 (2020/09/21)
In this study, we describe the synthesis and biological evaluation of a set of bis-3-chloropiperidines (B?CePs) containing rigid aromatic linker structures. A modification of the synthetic strategy also enabled the synthesis of a pilot tris-3-chloropiperidine (Tri-CeP) bearing three reactive meta-chloropiperidine moieties on the aromatic scaffold. A structure–reactivity relationship analysis of B?CePs suggests that the arrangement of the reactive units affects the DNA alkylating activity, while also revealing correlations between the electron density of the aromatic system and the reactivity with biologically relevant nucleophiles, both on isolated DNA and in cancer cells. Interestingly, all aromatic 3-chloropiperidines exhibited a marked cytotoxicity and tropism for 2D and 3D cultures of pancreatic cancer cells. Therefore, the new aromatic 3-chloropiperidines appear to be promising contenders for further development of mustard-based anticancer agents aimed at pancreatic cancers.
AMINOGUANIDINE HYDRAZONES AS RETROMER STABILIZERS USEFUL FOR TREATING NEUROLOGICAL DISEASES
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Page/Page column 20-21; 45-47; 51, (2020/10/20)
The present invention relates to novel aminoguanidine hydrazone-derivatives of Formula (I) which are effective as retromer stabilizers and useful as neuroprotecting drugs. The invention also relates to pharmaceutical compositions comprising the compounds and their use in therapy and diagnostic.
Substituents Have a Large Effect on Photochemical Generation of Benzyl Cations and DNA Cross-Linking
Fan, Heli,Sun, Huabing,Peng, Xiaohua
, p. 7671 - 7682 (2018/05/14)
Photoactivated DNA interstrand cross-linking agents have a wide range of biological applications. Recently, several aryl boronates have been reported to induce DNA interstrand cross-link (ICL) formation via carbocations upon photoirradiation. Herein, we synthesized a series of new bifunctional phenyl compounds to test the generality of such a mechanism, and to understand how the chemical structure influences carbocation formation and the DNA cross-linking process. These compounds efficiently form DNA ICLs via generated benzyl cations upon 350 nm irradiation. The DNA cross-linking efficiency and the pathway for carbocation generation depend on both the aromatic substituents and the leaving groups. Bromine as a leaving group facilitates the DNA cross-linking process in comparison with trimethyl ammonium salt. Both electron-donating and -withdrawing substituents induce bathochromic shifts, which favor photoinduced DNA ICL formation. For the bromides, the benzyl cation intermediates were generated through oxidation of the corresponding benzyl radicals. However, for the ammonia salts, the benzyl cations were formed through two pathways: either through oxidation of the benzyl radicals or by direct heterolysis of the C?N bond. Photoinduced C?N homolysis to form benzyl radicals occurred with compounds having donating substituents, whereas direct heterolysis of the C?N bond occurred with those bearing withdrawing substituents. The adducts formed between 1 a and four natural nucleosides were characterized, indicating that the alkylation sites for the photogenerated benzyl cations are dG, dA, and dC.
Synthesis and conformational analysis of 2,11-dioxa[3.3]metacyclophanes
Maeda, Hajime,Endo, Shinsuke,Ouchi, Takashi,Mizuno, Kazuhiko,Segi, Masahito
supporting information, p. 1357 - 1360 (2017/08/14)
Synthesis and conformational analysis of three members of the dioxa[3.3]metacyclophane family were carried out. Variable-temperature 1H NMR spectroscopy was employed to show that three substances exist as equilibrium mixtures of syn and anti conformers in ratios that depend on the nature of arene ring substituent, temperature, and solvent. The findings are explained in terms of thermodynamic parameters and dipole moments of the metacyclophanes.
Birch Reductive Alkylation of Methyl m-(Hydroxymethyl)benzoate Derivatives and the Behavior of o- and p-(Hydroxymethyl)benzoates under Reductive Alkylation Conditions
Fretz, Samuel J.,Hadad, Christopher M.,Hart, David J.,Vyas, Shubham,Yang, Dexi
, p. 83 - 92 (2013/03/29)
Birch reductive alkylation of methyl m-(hydroxymethyl)benzoate derivatives, using lithium in ammonia-tetrahydrofuran in the presence of tertbutyl alcohol, can be achieved without significant loss of benzylic oxygen substituents. Similar treatment of o- and p-(hydroxymethyl)benzoate derivatives results largely in loss of benzylic oxygen substituents. The results are rationalized by computations describing electron density patterns in the putative radical anion intermediate involved in these reactions.
Energy transfer labels with mechanically linked fluorophores
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, (2008/06/13)
Mechanically linked energy transfer labels comprising at least one donor fluorophore, at least one acceptor fluorophore, and at least one support member, wherein steric interactions between the donor fluorophore(s), the acceptor fluorophore(s), and/or the support member(s) induce non-covalent association between the fluorophores and the support member(s), thereby forming a three-dimensional macromolecular structure which mechanically links the donor fluorophore(s) and the acceptor fluorophore(s). Fluorescence resonance energy transfer (FRET) occurs from donor fluorophore to acceptor fluorophore through space. No direct connectivity with covalent bonds exists between the fluorophores. Instead, mechanical barriers hold the donor/acceptor fluorophores in place during the FRET process.
Quinones. XIII. Synthesis of 4,5,9,10-Tetrahydropyrene-2,7-dione and Attempted Preparation of Pyrene-2,7-dione
Boldt, Peter,Bruhnke, Detlev
, p. 110 - 114 (2007/10/02)
The title quinones 7 and 9 are of interest as electron acceptors for organic conductors.The synthesis of their conjugate hydroquinones 6 and 8 via the metacyclophane derivative 3 is described.The tetrahydropyrene-2,7-dione 7 - obtained by oxidation of 6 -
SUBSTITUTED MONOCYCLIC ARYL COMPOUNDS EXHIBITING SELECTIVE LEUKOTRIENE B4 ANTAGONIST ACTIVITY
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, (2008/06/13)
Monocyclic aryl compounds having selective LTB 4 antagonists properties and comprising an amido substituent, a substituent group having a terminal carboxylic acid or derivative thereof and a lipophilic substituent, therapeutic compositions and methods of treatment of disorders which result from LTB. sub.4 activity using the monocyclic aryl compounds are disclosed.
Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor
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, (2008/06/13)
A novel synthesis of compounds having the formula: STR1 wherein T is a stabilizing spiro-linked polycycloalkylidene group, R3 is a C1 -C20 alkyl, aralkyl or heteroatom containing group, Y is an aromatic fluorescent chromophore, and Z is a cleavable group which, when cleaved, induces decomposition of the dioxetane ring and emission of optically detectable light, is disclosed. A tertiary phosphorous acid alkyl ester of the formula: wherein R1 is a lower alkyl group, is reacted with an aryl dialkyl acetal produced by reacting a corresponding aryl aldehyde with an alcohol of the formula: wherein R3 is as defined above, to produce a 1-alkoxy-1-arylmethane phosphonate ester of the formula: STR2 reacting the phosphonate with base to produce a phosphonate-stabilized carbanion, reacting the carbanion with a ketone of the formula: wherein T is as defined above, to produce an enol ether of the formula: STR3 then oxygenating the double bond in the enol ether to give the corresponding 1,2-dioxetane compound.
