101046-14-4Relevant articles and documents
An ESIPT-based two-photon fluorescent probe detection of hydrogen peroxide in live cells and tissues
Zhou, Liyi,Peng, Yongbo,Wang, Qianqian,Lin, Qinlu
, p. 264 - 268 (2017)
A variety of diseases associated with human aging, which have a strong oxidative stress, but connecting age-related diseases and oxidative stress of the basic molecular mechanisms still insufficiently understood. Oxidative stress origins from the unregulated production of reactive oxygen species (ROS), and oxidative damaging to tissues and organs from subsequent oxidation-reduction chemistry by cellular mismanagement. In particular, H2O2 is a major by-product of ROS in live organisms and a common marker for oxidative stress, and its dynamic equilibrium can have various physiological and pathological consequences. H2O2 is a small molecule, but it is an essential oxygen metabolite in living systems and acts as an important compound in cellular signal transduction by reversible oxidation of proteins. To quantitatively detect of H2O2 in biosystems, herein, we adopted a 2-(2′-hydroxyphenyl)-4(3H)-quinazolinone (HPQ), a small organic fluorophore known for its luminescence mechanism through excited-state intramolecular proton transfer (ESIPT). HPQ was employed as a precursor to develop a turn-on probe (HPQ-H) for bioimaging applications. After cleavaging the boronic ester moiety by H2O2, HPQ-H releases a HPQ fluorophore which shows a 45-fold fluorescence intensity enhancement with high sensitivity and selectivity over other reactive oxygen species (ROS), and a high resolution imaging and large tissue-imaging depth (70–170?μm) in living cells and tissues images under two-photon excitation (720?nm).
Identification of Potent Ebola Virus Entry Inhibitors with Suitable Properties for in Vivo Studies
Liu, Hu,Tian, Ye,Lee, Kyungae,Krishnan, Pranav,Wang, May Kwang-Mei,Whelan, Sean,Mevers, Emily,Soloveva, Veronica,Dedic, Benjamin,Liu, Xinyong,Cunningham, James M.
supporting information, p. 6293 - 6307 (2018/06/27)
Previous studies identified an adamantane dipeptide piperazine 3.47 that inhibits Ebola virus (EBOV) infection by targeting the essential receptor Niemann-Pick C1 (NPC1). The physicochemical properties of 3.47 limit its potential for testing in vivo. Optimization by improving potency, reducing hydrophobicity, and replacing labile moieties identified 3.47 derivatives with improved in vitro ADME properties that are also highly active against EBOV infection, including when tested in the presence of 50% normal human serum (NHS). In addition, 3A4 was identified as the major cytochrome P450 isoform that metabolizes these compounds, and accordingly, mouse microsome stability was significantly improved when tested in the presence of the CYP3A4 inhibitor ritonavir that is approved for clinical use as a booster of anti-HIV drugs. Oral administration of the EBOV inhibitors with ritonavir resulted in a pharmacokinetic profile that supports a b.i.d. dosing regimen for efficacy studies in mice.
2-aryl-3-methyl benzofuran-benzimidazole salt compound and preparation method thereof
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Paragraph 0012, (2017/08/29)
The invention discloses a series of 2-aryl-3-methyl benzofuran-benzimidazole salt compound with a structure general formula (such as formula I or II) and a preparation method thereof. The preparation method comprises the following steps: taking salicylic aldehyde as a raw material and synthesizing benzylide salicylic aldehyde with 4-substituted benzyl bromide in anhydrous DMF; then synthesizing 2-aryl-3-methyl benzofuran in phosphorus oxychloride and the anhydrous DMF; successively synthesizing 2-aryl-3-methanol benzofuran with sodium borohydride in methanol; finally firstly synthesizing methanesulfonate with methanesulfonyl chloride in dichloromethane, then synthesizing 2-aryl-3-methyl benzofuran-benzimidazole with benzimidazole or 5,6-dimethyl benzimidazole in methylbenzene and on the basis, synthesizing the 2-aryl-3-methyl benzofuran-benzimidazole salt compound with brominated alkanes in methylbenzene. The compound shows better antitumor cytotoxic activity.
Synthesis and biological evaluation of rhodanine derivatives as PRL-3 inhibitors
Ahn, Jin Hee,Kim, Seung Jun,Park, Woul Seong,Cho, Sung Yun,Ha, Jae Du,Kim, Sung Soo,Kang, Seung Kyu,Jeong, Dae Gwin,Jung, Suk-Kyeong,Lee, Sang-Hyeup,Kim, Hwan Mook,Park, Song Kyu,Lee, Ki Ho,Lee, Chang Woo,Ryu, Seong Eon,Choi, Joong-Kwon
, p. 2996 - 2999 (2008/09/20)
A series of rhodanine derivatives was synthesized and evaluated for their ability to inhibit PRL-3. Benzylidene rhodanine derivative showed good biological activity, while compound 5e was the most active in this series exhibiting an IC50 value of 0.9 μM in vitro and showed a reduced invasion in cell-based assay.
Synthesis of spiro-fused (C5)-isoxazolino-(C4)-pyrazolones (1-Oxa-2,7,8-triazaspiro[4,4]-2,8-dien-6-ones) via 1,3-dipolar cycloaddition and cycloelimination
Sammelson, Robert E.,Gurusinghe, Chamindra D.,Kurth, Jeffrey M.,Olmstead, Marilyn M.,Kurth, Mark J.
, p. 876 - 882 (2007/10/03)
An efficient and selective method for the synthesis of spiro-fused (C5)-isoxazolino-(C4)-pyrazolones (C) is reported. The process consists of utilizing the Baylis - Hillman reaction - or a quicker, stepwise MAC procedure - to give I followed by 1,3-dipolar cycloaddition and Swern oxidation to give β-ketoesters H, which were condensed with hydrazine derivatives to provide hydrazones that underwent cycloelimination. These novel spiro-fused (C5)-isoxazolino-(C4)-pyrazolones were confirmed by spectroscopic analysis as well as single-crystal X-ray of 5. We also concluded that all condensations/cycloeliminations, except with hydrazine itself, were more effective with catalysts or higher reaction temperatures. For example, TiCl4 was an efficient catalyst for hydrazone formation and cycloelimination with methylhydrazine, while phenyl-, benzyl-, and (4-methoxyphenyl)hydrazine reacted effectively without catalyst in refiuxing xylene.
Synthesis of heterocycles with MF/Al2O3 base-systems: 2-arylbenzofuranes and 2,3-diarylisoquinolin-1(2H)-ones
Hellwinkel,Goke
, p. 1135 - 1141 (2007/10/02)
2-Benzyloxybenzaldehydes, -acetophenones and -benzophenones substituted in the benzyl part with electron-withdrawing groups, cyclize easily to 2-arylbenzofuranes by using a standardized KF- or CsF-Al2O3 base system. An efficient one-pot synthesis for 2,3-diarylisoquinolin-1(2H)-ones is possible by reacting a variety of arene carbaldehyde anils with phthalides under the same reaction conditions.
Development and Application of Organic Reagents for Analysis. VI. Synthesis and Fluorescence Spectral Properties of 2-(4-Substituted phenyl)benzofurans
Akiyama, Shuzo,Akimoto, Hiroyuki,Nakatsuji, Shin'ichi,Nakashima, Kenichiro
, p. 2192 - 2196 (2007/10/02)
A synthesis of fifteen kinds of 2-(4-substituted phenyl)benzofurans (4n) was carried out and their fluorescence spectral properties were investigated concerning their applicability as organic reagents for analyses.
