- t-BUTYL LITHIOACETATE ON ORTHO-HYDROXYPHENONES PROVIDING 2-METHYLCHROMONES. AN EASY ACCESS TO KHELLIN
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Reaction of t-butyl lithioacetate with several kinds of poly-substituted ortho-hydroxyphenones including khellinone and subsequent acid hydrolysis of the resulting hemiacetals provide the corresponding 2-methylchromone derivatives in excellent overall yields.
- Nagasawa, Kazuo,Kanbara, Hajime,Matsushita, Kazuya,Ito, Keiichi
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- A “turn-on” fluorescent probe with high selectivity and large stokes shift for the detection of hydrogen peroxide and its bioimaging applications
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Hydrogen peroxide (H2O2) plays pivotal roles in various biological functions and pharmacological activities. High selectivity and sensitivity remain challenges for fluorescent probes to detection of H2O2 with a large stokes shift. Herein, a new “turn-on” fluorescent probe (DCM-C) was designed based on the mechanism of intramolecular charge transfer (ICT). In PBS buffer (10 mM, pH 7.4, with 20% DMSO, v/v), DCM-C exhibited high selectivity and sensitivity for H2O2 over other interfering analytes with a large stokes shift (187 nm), and the detection limit was as low as 35.5 nM. In addition, the probe was effective for detecting exogenous and endogenous H2O2 in living cells, and identifying stained in cytoplasm. Moreover, the probe has been used successfully for determining H2O2 in zebrafish by fluorescence imaging.
- Gao, Mengjiao,Hua, Yun,Kang, Yanfei,Li, Jin,Shang, Yajing
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supporting information
(2021/09/11)
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- Access to Chiral Chromenones through Organocatalyzed Mannich/Annulation Sequence
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Herein we report an efficient and practical method to access chiral chromenones bearing one α-amino stereogenic center in the β position of the carbonyl group. The quinine-derived squaramide could efficiently promote Mannich/cycloketalization/dehydration tandem reactions between 1-(2-hydroxyaryl)-1,3-diketones and functionalized imines generated in situ, providing a wide range of chiral chromenones with propargylamine or α-amino ester moieties with good results (54 examples, up to 98% ee).
- Duan, Jingxiang,Xiong, Zongli,Zhou, Yuqiao,Yao, Weijun,Li, Xiaoyi,Zhang, Min,Wang, Zhen
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supporting information
p. 8007 - 8012
(2021/10/20)
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- A matrix targeted fluorescent probe to monitor mitochondrial dynamics
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Mitochondria are an indispensable organelle for energy production and regulation of cellular metabolism. The structural and functional alterations to mitochondria instigate pathological conditions of cancer, and aging-associated and neurodegenerative disorders. The normal functioning of mitochondria is maintained by quality control mechanisms involving dynamic fission, fusion, biogenesis and mitophagy. Under conditions of mitophagy and neurodegenerative diseases, mitochondria are exposed to different acidic environments and high levels of reactive oxygen species (ROS). Therefore stable molecular tools and methods are required to monitor the pathways linked to mitochondrial dysfunction and disease conditions. Herein, we report a far-red fluorescent probe (Mito-TG) with excellent biocompatibility, biostability, photostability, chemical stability and turn on emission for selective targeting of the mitochondrial matrix in different live cells. The probe was successfully employed for monitoring dynamic processes of mitophagy and amyloid beta (Aβ) induced mitochondrial structural changes.
- Ramesh, Madhu,Rajasekhar, Kolla,Gupta, Kavya,Babagond, Vardhaman,Saini, Deepak Kumar,Govindaraju, Thimmaiah
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supporting information
p. 801 - 808
(2021/02/09)
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- Design, synthesis, and evaluation of near-infrared fluorescent molecules based on 4h-1-benzopyran core
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A series of novel fluorescent 4H-1-benzopyrans was designed and developed as near-infrared fluorescent molecules with a compact donor–acceptor-donor architecture. Spectral intensity of the fluorescent molecules M-1, M-2, M-3 varied significantly with the increasing polarities of solvents, where M-3 showed high viscosity sensitivity in glycerol-ethanol system with a 3-fold increase in emission intensity. Increasing concentrations of compound M-3 to 5% BSA in PBS elicited a 4-fold increase in fluorescence intensity, exhibiting a superior environmental sensitivity. Furthermore, the in vitro cellular uptake behavior and CLSM assay of cancer cell lines demonstrated that M-3 could easily enter the cell nucleus and bind to proteins with low toxicity. Therefore, the synthesized near-infrared fluorescent molecules could provide a new direction for the development of optical imaging probes and potential further drugs.
- Li, Chuchu,Lu, Wei,Ma, Mingliang,Tanzeng, Yawen,Wang, Shuting,Zhang, Yuexing,Zhu, Shulei
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- Near-infrared compound with aggregation-induced emission property as well as preparation method and application thereof
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The invention discloses a near-infrared compound with an aggregation-induced emission property as well as a preparation method and application of the near-infrared compound. The near-infrared compoundhas high-brightness far-infrared and near-infrared fluorescence emission characteristics, has aggregation-induced emission and crystallization-induced emission characteristics in a near-infrared region, and has the characteristic of aggregation-induced nonlinear optical effect. The nanocrystal can be used for biological imaging and can be prepared into nanocrystals for living body deep high-resolution multi-photon fluorescence and third harmonic imaging. The material synthesized by the method shows the properties of aggregation-induced emission and crystallization-induced emission, while thetraditional fluorescent dye has the phenomenon of aggregation-induced fluorescence quenching under the condition of high concentration, so that the defects of the traditional fluorescent dye are effectively overcome.
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Paragraph 0021
(2021/02/10)
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- Near-infrared hydrazine fluorescence sensor as well as preparation method and application thereof
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The invention discloses a near-infrared hydrazine fluorescence sensor as well as a preparation method and application thereof. According to the method, a target product (E) 4-(2-(4-(dicyanomethylene) chroman-2-yl) vinyl) phenyl 4-bromobutyric acid is synthesized. An ultraviolet-visible spectrophotometer and a fluorescence spectrophotometer are adopted to determine the intensity change of a characteristic peak of a probe in a water phase, so as to determine the existence of hydrazine. The invention provides application of the hydrazine fluorescence sensor in hydrazine detection, and the hydrazine fluorescence sensor can be used for high-selectivity and high-sensitivity detection of hydrazine in a water phase. It is found that thehydrazine fluorescence sensor has a good hydrazine detection effect. Compared with the prior art, the hydrazine fluorescence sensor has the advantages of easily available raw materials, simple synthesis steps, convenient post-treatment, easy realization of large-scale production, and great application prospect in hydrazine detection.
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Paragraph 0042; 0049; 0052; 0053
(2021/04/21)
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- Rational Design of a Highly Selective Near-Infrared Two-Photon Fluorogenic Probe for Imaging Orthotopic Hepatocellular Carcinoma Chemotherapy
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Selective fluorescence imaging of biomarkers in vivo and in situ for evaluating orthotopic hepatocellular carcinoma (HCC) chemotherapy remains a great challenge due to current imaging agents suffering from the potential interferences of other hydrolases. Herein, we observed that carbamate unit showed a high selectivity toward the HCC-related biomarker carboxylesterase (CE) for evaluation of treatment. A near-infrared two-photon fluorescent probe was developed to not only specially image CE activity in vivo and in situ but also target orthotopic liver tumor after systemic administration. The in vivo signals of the probe correlate well with tumor apoptosis, making it possible to evaluate the status of treatment. The probe enables the imaging of CE activity in situ with a high-resolution three-dimensional view for the first time. This study may promote advances in optical imaging approaches for precise imaging-guided diagnosis of HCC in situ and its evaluation of treatment.
- Han, Jingjing,Kim, Heejeong,Kwon, Nahyun,Li, Haidong,Qi, Sujie,Wang, Rui,Wu, Xiaofeng,Yoon, Juyoung,Yu, Fabiao
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supporting information
p. 15418 - 15425
(2021/06/18)
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- Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization
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Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.
- Son, Seung Hwan,Cho, Yang Yil,Yoo, Hyung-Seok,Lee, Soo Jin,Kim, Young Min,Jang, Hyu Jeong,Kim, Dong Hwan,Shin, Jeong-Won,Kim, Nam-Jung
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p. 14000 - 14006
(2021/04/22)
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- A novel one-pot synthesis of flavones
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In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.
- Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi
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p. 11655 - 11662
(2021/03/31)
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- Unusual titanium-induced McMurry coupling of 4-oxo-4H-chromene-2-carbaldehydes enroute to bis-chromones
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Ti/Zn-mediated McMurry coupling of a series of 4-oxo-4H-chromene-2-carbaldehydes afforded unusual chemoselective CH2-CH2tethered bis-chromones. Studying the reaction parameters and reagents further confirmed that the formation of unexpected coupled products is selective to 4-oxo-4H-chromene-2-carbaldehydes. This methodology demonstrated a simple and efficient route for the synthesis of bis-chromones.
- Yerrabelly, Jayaprakash Rao,Bathini, Pavan Kumar,Yerrabelly, Hemasri,Vadapalli, Kishore
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p. 4705 - 4709
(2021/03/22)
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- A sensitive fluorescent probe for β-galactosidase activity detection and application in ovarian tumor imaging
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The development of non-invasive and sensitive optical probes for in vivo bioimaging of cancer-related enzymes is desirable for early diagnosis and effective cancer therapy. β-galactosidase (β-gal) is regarded as a key ovarian cancer biomarker, owing to its overexpression in primary ovarian cancer. Herein, we designed a sensitive near-infrared (NIR) probe (DCMCA-βgal) for the detection and real-time imaging of β-gal activity in ovarian tumors, thereby achieving the visualization of ovarian tumors by β-gal activity detection. DCMCA-β-gal could be triggered by β-gal, resulting in the release of a NIR chromophore, DCM-NH2; the linear range of fluorescent response to β-gal concentration was 0-1.2 U with a low detection limit of 1.26 × 10-3 U mL-1. We used DCMCA-β-gal to detect and visualize β-gal activity in SKOV3 human ovarian cancer cells, as well as for real-time imaging of β-gal activity in ovarian cancer mouse models. DCMCA-β-gal possessed high sensitivity, "turn-on"NIR emission, a large spectral shift, and high photostability in a dynamic living system and thus could serve as a highly sensitive sensor for real-time tracking of β-gal activity in vivo and ovarian tumor imaging.
- Fan, Fang,Zhang, Li,Zhou, Xinguang,Mu, Fangya,Shi, Guoyue
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supporting information
p. 170 - 175
(2021/01/12)
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- Molecular Chemiluminescent Probes with a Very Long Near-Infrared Emission Wavelength for in Vivo Imaging
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Chemiluminescence imaging is imperative for diagnostics and imaging due to its intrinsically high sensitivity. To improve in vivo detection of biomarkers, chemiluminophores that simultaneously possess near-infrared (NIR) emission and modular structures amenable to construction of activatable probes are highly desired; however, these are rare. Herein, we report two chemiluminophores with record long NIR emission (>750 nm) via integration of dicyanomethylene-4H-benzothiopyran or dicyanomethylene-4H-benzoselenopyran with dioxetane unit. Caging of the chemiluminophores with different cleavable moieties produces NIR chemiluminescence probes (NCPs) that only produce signals upon reaction with reactive oxygen species or enzymes, for example, β-galactosidase, with a tissue-penetration depth of up to 2 cm. Thus, this study provides NIR chemiluminescence molecular scaffolds applicable for in vivo turn-on imaging of versatile biomarkers in deep tissues.
- Huang, Jingsheng,Jiang, Yuyan,Li, Jingchao,Huang, Jiaguo,Pu, Kanyi
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supporting information
p. 3999 - 4003
(2020/12/22)
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- Preparation method and application of novel photosensitizer
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The invention relates to a preparation method and application of a novel photosensitizer. The photosensitizer is synthesized for the first time. A general formula compound represented by an intermediate formula (I) is used as a mother core, and is subjected to a Knoevenagel reaction with 4-hydroxybenzaldehyde, 3,5-dibromo-4-hydroxybenzaldehyde and 3,5-diiodo-4-hydroxybenzaldehyde to obtain the general formula photosensitizer represented by a formula (II). The method creatively reserves functional groups (R1, R2) on the intermediate formula (I) and the photosensitizer formula (II), and synthesizes the intermediate and the photosensitizer with S and Se as central atoms (Q) for the first time. The novel photosensitizer provided by the invention solves the technical problems that an existing photosensitizer has a narrow absorption range, a poor therapeutic effect in the visible light range, excessive power of a used light source, and inability to introduce functional groups.
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Paragraph 0022; 0029-0030
(2020/02/14)
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- Molecular Aggregation of Naphthalene Diimide(NDI) Derivatives in Electron Transport Layers of Inverted Perovskite Solar Cells and Their Influence on the Device Performance
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One of key factors to design applicable electron transport layers (ETLs) for perovskite solar cells is the morphology of ETLs since a good morphology would help to facilitate the carrier transport at two interfaces (perovskiteETL and ETLcathode). However, one drawback of most organic ETL small molecules is the internal undesired accumulation, which would cause the formation of inappropriate morphology and rough ETL surface. Here, by elaborately designing the side chains of NDI derivatives, the molecular interaction could be modified to achieve the aggregation in different degrees, which would eventually affect the accumulation of molecules and surface qualities of ETLs. By speculating from the comparison between the absorption spectra of solutions and films, the sequence of extent of molecule interaction and aggregation was built among three NDI derivatives, which is further confirmed by direct evidence of atomic force microscopy (AFM) images. Then, carrier exaction abilities are simply studied by steady-state photoluminescence spectroscopy. The carrier transport process is also discussed based on cyclic voltammetry, time-resolved photoluminescence spectroscopy and mobility. NDIF1 are proven to have the appropriate internal aggregation to smooth the contact with cathode and low series resistance, and a device performance of 15.6 % is achieved. With the ability of preventing the thermal diffusion of Ag towards the perovskite surface due to the strong interaction between molecules, NDIF2 at high concentration shows the highest fill factor (80 %).
- Liu, Wenbo,Shaikh, Dada B.,Rao, Pedada Srinivasa,Bhosale, Rajesh S.,Said, Ahmed Ali,Mak, Adrian M.,Wang, Zongrui,Zhao, Mu,Gao, Weibo,Chen, Bingbing,Lam, Yeng Ming,Fan, Weijun,Bhosale, Sidhanath V.,Bhosale, Sheshanath V.,Zhang, Qichun
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supporting information
p. 112 - 121
(2019/12/03)
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- Visualization of carboxylesterase 2 with a near-infrared two-photon fluorescent probe and potential evaluation of its anticancer drug effects in an orthotopic colon carcinoma mice model
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We establish a near-infrared two-photon fluorescent probe for the detection of CE2 with high selectivity and sensitivity. This probe exhibits low cytotoxicity and superior tissue penetration ability for evaluating the real-time activity of CE2 in living cells, in cancer tissues, and in a colon carcinoma mice model.
- Li, Mingshun,Luo, Xianzhu,Wang, Yan,Yu, Fabiao,Yu, Feifei,Zhao, Linlu
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supporting information
p. 4412 - 4415
(2020/05/05)
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- An Activatable AIEgen Probe for High-Fidelity Monitoring of Overexpressed Tumor Enzyme Activity and Its Application to Surgical Tumor Excision
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Monitoring fluctuations in enzyme overexpression facilitates early tumor detection and excision. An AIEgen probe (DQM-ALP) for the imaging of alkaline phosphatase (ALP) activity was synthesized. The probe consists of a quinoline-malononitrile (QM) core decorated with hydrophilic phosphate groups as ALP-recognition units. The rapid liberation of DQM-OH aggregates in the presence of ALP resulted in aggregation-induced fluorescence. The up-regulation of ALP expression in tumor cells was imaged using DQM-ALP. The probe permeated into 3D cervical and liver tumor spheroids for imaging spatially heterogeneous ALP activity with high spatial resolution on a two-photon microscopy platform, providing the fluorescence-guided recognition of sub-millimeter tumorigenesis. DQM-ALP enabled differentiation between tumor and normal tissue ex vivo and in vivo, suggesting that the probe may serve as a powerful tool to assist surgeons during tumor resection.
- Baek, Gain,Chung, Jeewon,Fan, Jiangli,Ge, Haoying,Hillman, Prima Fitria,Kim, Dayeh,Lee, Eun Young,Li, Haidong,Li, Yueqing,Nam, Sang-Jip,Peng, Xiaojun,Wang, Jingyun,Wu, Xiaofeng,Xu, Feng,Yao, Qichao,Yoon, Juyoung
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supporting information
p. 10186 - 10195
(2020/03/23)
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- Targeted and fluorescence tracing stimulation-responsive multifunctional nano-vesicle drug-loading system
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The invention relates to a targeted and fluorescence tracing stimulation-responsive multifunctional nano-vesicle drug-loading system. Sugar functionalized column [5] arene with targeted selectivity isused as a host molecule, a trimethylamine derivative of disulfide bond bridged dicyanomethylene 4H pyran with GSH response fluorescence tracing is used as a guest molecule, a GSH responsive column [5] arene amphiphilic molecule with targeted and fluorescence tracing is prepared through host-guest interaction, nano-vesicles are formed in a solution through hydrophilic-hydrophobic interaction, andan anticancer drug is encapsulated in a vesicle cavity. Mannose is specifically bound with a mannose receptor overexpressed on the surface of a breast cancer cell, so that targeted selective entry into the cancer cell is realized; meanwhile, a disulfide bond is quickly broken under the action of GSH with relatively high concentration in the cancer cell, so that the vesicles are promoted to break to quickly release the anticancer drug; and in addition, the dicyanomethylene 4H pyran is used as a fluorescent chromogenic group to realize fluorescence tracing. The system can be applied to transportation and tracing of the anticancer drug.
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Paragraph 0067-0070
(2020/10/12)
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- Hydrogen peroxide activated aspirin visual prodrug, preparation method and application thereof
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The invention discloses a hydrogen peroxide activated aspirin visual prodrug, a preparation method and application thereof. Salicylic acid is used as a new response group of hydrogen peroxide (H2O2),aspirin is integrated into a pyranonitrile (DCM) dye structure, and a new hydrogen peroxide responsive aspirin prodrug (DA) is synthesized. The prodrug molecule is activated by H2O2, releases an active drug aspirin, and has high-selectivity cell imaging on endogenous and exogenous H2O2. The prodrug DA not only can be used as an effective tool to track pathological reaction related to H2O2 in a living body system, but also a disconnected aspirin part has a potential prospect of being applied as a therapeutic drug to related disease treatment after reaction.
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Paragraph 0023; 0025; 0026; 0028; 0029
(2020/10/04)
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- An efficient TBHP/TBAI-mediated protocol for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation
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Abstract: A transition metal-free and efficient TBHP/TBAI-mediated protocol has been developed for the synthesis of 4H-chromen-4-ones from chroman-4-ones via oxidative C–C bond formation. It proceeds in the presence of a catalytic amount of tetrabutylammonium iodide and oxidant tert-butyl hydroperoxide (TBHP, 5–6 M in decane) to afford the corresponding products in good to excellent yields. Furthermore, it has been observed that an increase in the concentration of TBHP to 30 mol % drastically increases the yield of 4H-chromen-4-ones, any further increase will lead to a decrease in percent yield. The mechanism of this reaction involves the generation of tertiary butoxide radical initially which by oxidative single-electron transformation is converted to iodochroman-4-one. Later the hydrogen iodide is removed from iodochroman-4-one to give the desired product, i.e. 4H-chromen-4-ones. Moreover, this is a rare example of the n-Bu4NI/TBHP-mediated C–C bond through dehydrogenative reaction. Graphic abstract: [Figure not available: see fulltext.]
- Agisho, Habtamu Abebe,Hairat, Suboot,Zaki, Mehvash
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p. 599 - 603
(2020/05/04)
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- Fluorescent probe for differentially detecting GSH and H2Sn (n >1) through two channels
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The invention discloses a fluorescent probe for differentially detecting GSH and H2Sn (n > 1) through two channels, and belongs to the technical field of chemical analysis and detection. The probe hasa molecular structural formula shown in the description. The probe emits green fluorescence after reacting with GSH and emits red fluorescence after reacting with H2Sn. The probe not only can realizesimultaneous distinguishing detection of GSH and H2Sn (n > 1), but also has the characteristics of good selectivity, high sensitivity, relatively wide pH working range and the like. Meanwhile, in thedetection process, the probe can emit red fluorescence, and large Stokes shift is shown. The excellent properties show that the fluorescent probe has important application value in the fields of environment, biology and the like.
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Paragraph 0006; 0038
(2020/12/15)
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- New chromophores based on 2-(4-vinylchromen-2-ylidene)malononitrile and 2-(2-vinylchromen-4-ylidene)malononitrile
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New derivatives of 2-(4-vinylchromen-2-ylidene)malononitrile and 2-(2-vinylchromen-4-ylidene)malononitrile were synthesized using the Knoevenagel reaction of 2-(4-methyl-chromen-2-ylidene)malononitrile and 2-(2-methylchromen-4-ylidene)malononitrile, respectively, with the participation of [1-(2-n-butoxyethyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinolin-6-yl)]-carbaldehyde. First hyperpolarizability (β) was calculated for the obtained compounds using the M05-2X functional and 6-31+G (d) basis. Optical properties and solvatochromism in solvents of different polarity (toluene, 1,4-dioxane, chlorobenzene, dichloromethane, DMF, and ethanol) were also investigated.
- Levchenko,Chudov,Demin, D. Yu.,Adamov,Zinoviev,Lyssenko,Shokurov,Shmelin,Grebennikov
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p. 1883 - 1888
(2019/10/22)
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- MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)
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The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.
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Page/Page column 66
(2020/01/08)
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- A Dicyanomethylene-4H-Pyran Based NIR Ratiometric Fluorescent Probe for Diazane and its Bioimaging
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A near-infrared ICT-based fluorescent probe LX was successfully obtained. LX which detection limit is low as 22.2?nm shows excellent selectivity and high sensitivity to diazane. LX can selectively detected diazane from other species over a wide pH (3–10) range. A obvious color change of solution from yellow to orange can be found, allowing the naked eye to detect. The sensing mechanism was reasonably detected by ESI-MS and DFT calculations. In addition, LX succeed in the visualization of diazane in living cells and the detection of diazane in water samples.
- Li, Gongchun,Liu, Yongxiang,Yang, Xiaopeng,Ye, Yong
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p. 195 - 201
(2018/12/11)
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- A detection Cys benzo pyrane nitrile class of fluorescent probe molecule preparation process (by machine translation)
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The invention discloses a method for selectively detecting Cys benzo pyrane nitrile class of fluorescent probe molecule preparation process, its preparation process characteristic as follows: under nitrogen conditions, accurate weighing compound I (48 mg, 0 . 14 mmol) is dissolved in the water removal of dichloromethane (10 ml) in, fetch trifluoromethanesulfonic acid methyl ester (92 mg, 0 . 56 mmol) in the mixed solution, stirring at room temperature of not less than 12 hours. After the reaction is filtered and precipitated, absolute ethanol and ethyl ether washing, to get the crude product red powder, column chromatography separation and purification, eluent: dichloromethane/methanol=20/1, orange red powder obtained DCM - q (36 mg, 50%). Said product of this invention DCM - q relatively easy to obtain, the probe molecule mainly used for selectively detecting biological thiol of cysteine (Cys). (by machine translation)
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Paragraph 0017; 0019
(2019/01/20)
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- 2-Styrylchromone derivatives as potent and selective monoamine oxidase B inhibitors
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A series of eighteen 2-styrylchromone derivatives (see Chart 1) were synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activities. Many of the derivatives inhibited MAO-B comparable to pargyline (a positive control), and most of them inhibited MAO-B selectively. Of the eighteen derivatives, compound 9 having methoxy group at R1 and chlorine at R4 showed both the best MAO-B inhibitory activity (IC50 = 17 ± 2.4 nM) and the best MAO-B selectivity (IC50 for MAO-A/IC50 for MAO-B = 1500). The mode of inhibition of compound 9 against MAO-B was competitive and reversible. Quantitative structure–activity relationship (QSAR) analyses of the 2-styrylchromone derivatives were conducted using their pIC50 values with the use of Molecular Operating Environment (MOE) and Dragon, demonstrating that the descriptors of MAO-B inhibitory activity and MAO-B selectivity were 1734 and 121, respectively, that showed significant correlations (P 50 value indexes for MAO-B exhibited a determination coefficient (R2) of 0.873 as well as a Leave-One-Out cross-validated determination coefficient (Q2) of 0.675. These data suggested that the 2-styrylchromone structure might be a useful scaffold for the design and development of novel MAO-B inhibitors.
- Takao, Koichi,Endo, Saki,Nagai, Junko,Kamauchi, Hitoshi,Takemura, Yuri,Uesawa, Yoshihiro,Sugita, Yoshiaki
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- Temperature-Controlled Stereodivergent Synthesis of 2,2′-Biflavanones Promoted by Samarium Diiodide
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In this work, the first example of a radical stereodivergent reaction directed towards the stereoselective synthesis of both (R*,R*)- and (R*,S*)-2,2′-biflavanones promoted by samarium diiodide is reported. Control experiments showed that the selectivity of this reaction was exclusively controlled by the temperature. It was possible to generate a variety of 2,2′-biflavanones bearing different substitution patterns at the aromatic ring in good-to-quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of selectivity. A mechanism that explains both the generation of the corresponding 2,2′-biflavanones and the selectivity is also discussed. The structure and stereochemistry determination of each isomer was unequivocally elucidated by single-crystal X-ray diffraction experiments.
- Soto, Martín,Soengas, Raquel G.,Silva, Artur M. S.,Gotor-Fernández, Vicente,Rodríguez-Solla, Humberto
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supporting information
p. 13104 - 13108
(2019/10/21)
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- On-Water Cp?Ir(III)-catalyzed C-H functionalization for the synthesis of chromones through annulation of salicylaldehydes with diazo-ketones
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A high-valent Ir(III)-catalyzed C-H bond functionalization is carried out for the first time on water for the synthesis of a biologically relevant chromone moiety. The C-H activation and annulation of salicylaldehydes with diazo-compounds provided the desired chromones. The synthesis of C3-substitution-free chromones has also been demonstrated by a one-pot decarboxylation by employing tert-butyl diazoester. C3 and C5 C-H activations of the product chromone are also carried out under different conditions for further diversification.
- Debbarma, Suvankar,Sk, Md Raja,Modak, Biswabrata,Maji, Modhu Sudan
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- On-Water Cp?Ir(III)-Catalyzed C-H Functionalization for the Synthesis of Chromones through Annulation of Salicylaldehydes with Diazo-Ketones
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A high-valent Ir(III)-catalyzed C-H bond functionalization is carried out for the first time on water for the synthesis of a biologically relevant chromone moiety. The C-H activation and annulation of salicylaldehydes with diazo-compounds provided the desired chromones. The synthesis of C3-substitution-free chromones has also been demonstrated by a one-pot decarboxylation by employing tert-butyl diazoester. C3 and C5 C-H activations of the product chromone are also carried out under different conditions for further diversification.
- Debbarma, Suvankar,Sk, Md Raja,Modak, Biswabrata,Maji, Modhu Sudan
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p. 6207 - 6216
(2019/05/24)
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- An I6P7 peptide modified fluorescent probe for bio-imaging
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The I6P7 peptide was proved to specifically bind to the interleukin-6 receptor, which can be exploited as an effective tumor-targeting moiety. Herein, a novel tumor-targeting fluorescent probe (DMP) conjugated with the I6P7 peptide was designed and synthesized. This probe was validated to possess valuable photophysical properties. The biocompatibility was evaluated by investigating its cytotoxicity on HUVEC and U87 cells, respectively. The tumor cell affinity has been confirmed by bio-imaging of this probe on different human cancer cells (U87, A549 and MCF-7 cells) and normal cells (HUVEC cell). The probe demonstrates low cytotoxicity, high tumor cell affinity and favorable mitochondria-targeting capability. Overall, these results revealed that DMP can serve as an important fluorescent probe for tumor-targeted bio-imaging.
- Yao, Yuxin,Gui, Lijuan,Gao, Beike,Yuan, Zhenwei,Chen, Yisha,Wei, Chen,He, Qing,Wang, Fei,Xu, Mingjun,Chen, Haiyan
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supporting information
p. 1785 - 1790
(2019/01/28)
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- A medicinal composition for combining thioxanthone paclitaxel and STAT3 inhibitor
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A medicinal composition for combining thioxanthone paclitaxel and STAT3 inhibitor, comprising an active ingredient and a pharmaceutically acceptable adjuvant, characterized in that the active ingredient is composed of paclitaxel and a STAT3 inhibitor represented by formula (I) (shown in the description), and the mass ratio of the paclitaxel to the STAT3 inhibitor represented by formula (I) in theactive ingredient is (0.18 to 0.32): 1. The compound has an effect on MDA having persistently activated STAT3 activity-MB-468 cell, DU-145 cells had good inhibitory effect.
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Paragraph 0043; 0047; 0048; 0049
(2019/01/23)
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- A paclitaxel and carbazole class STAT inhibitors methanesulfonate crystalline form P combination pharmaceutical composition (by machine translation)
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Books invention provides a paclitaxel and carbazole class STAT inhibitors methanesulfonate crystalline form P combination pharmaceutical composition, comprising an active ingredient and a pharmaceutically acceptable auxiliary material, wherein the active ingredient by the taxol of formula (I) indicated by the STAT3 inhibitor P a crystalline form, the active ingredient of taxol in the formula (I) indicated by the STAT3 inhibitors crystal mass ratio of P (0.09 - 0.21): 1. The P crystalline form has good physical and chemical stability, solubility and bioavailability, particle size is suitable in size, and the distribution of the particle size distribution curve of a regular [...], suitable for formulation development. (by machine translation)
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Paragraph 0042; 0046-0048
(2019/02/13)
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- Medicinal composition for combination of paclitaxel and fluorene STAT3 inhibitor
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The invention belongs to the field of pharmaceutical chemistry, and relates to a medicinal composition for combination of paclitaxel and fluorene STAT3 inhibitors. The medicinal composition comprisesan active ingredient consisting of paclitaxel and a STAT3 inhibitor represented by formula (I), and a pharmaceutically acceptable adjuvant, wherein the mass ratio of the paclitaxel to the STAT3 inhibitor represented by formula (I) in the active ingredient is (0.27 to 0.39): 1. The compound has an effect on having persistently activated STAT3 activity MDA-MB-468 cell, DU-145 cells had good inhibitory effect.
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Paragraph 0045; 0049-0051
(2019/02/04)
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- A carbazole class STAT inhibitors maleic acid salt crystal form II combination pharmaceutical composition and its preparation method
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The invention belongs to the field of medicinal chemistry, and in particular relates to with tumor compound of 4 - (9 - ethyl - 9 H - carbazole - 4 - yl) - 6 - (4 - aminophenyl alkene propionyl) - N - (2 - methyl - 4 H - chromene - 4 - keto) - 1, 3, 5 - triazine - 2 - amine maleic acid salt of a new crystalline form, its preparation method, comprising the composition of said form, said form and said form or comprise the composition of use in the preparation of the medicament, the crystalline form II has good physical and chemical stability, solubility and bioavailability, is suitable for formulation development.
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Paragraph 0039; 0043-0045
(2019/02/13)
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- STAT3 inhibitors and application thereof
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The invention belongs to the field of medical chemistry, relates to STAT3 inhibitors and an application thereof and particularly relates to compounds for inhibiting the signal transduction and transcription activator-3, a pharmaceutical composition containing the compound and a use of the compounds or the pharmaceutical composition as cancer treatment drugs. The compounds can well inhibit MDA-MB-468 cells and DU-145 cells with sustained STAT3 activity.
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Paragraph 0037; 0041-0044
(2019/01/20)
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- Preparation method of STAT3 inhibitor
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The invention belongs to the field of medical chemistry, relates to a class-I STAT3 inhibitor and an application thereof, and particularly relates to a method for preparing compounds having signal transduction and transcriptional activator 3 inhibitory effects. The compounds can well inhibit MDA-MB-468 cells and DU-145 cells with continuous STAT3 activity.
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Paragraph 0047; 0051-0054
(2019/01/23)
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- A fluorene STAT3 inhibitor and its preparation method
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The invention belongs to the field of medicinal chemistry, relates to a compound of formula (I) of fluorene STAT3 inhibitor and its application, in particular to a kind of with signal conduction with a transcription activating factor - 3 inhibiting effect of a compound, pharmaceutical composition containing the compound, and the compound or pharmaceutical composition as the use of the cancer therapy, the compounds with sustained activation of STAT3 activity of MDA - MB - 468 cell, DU - 145 cell good inhibition effect.
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Paragraph 0044; 0048-0051
(2019/02/13)
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- Combined pharmaceutical composition of paclitaxel and dibenz [b, d] thiophene STAT inhibitor tartrate
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The invention provides a combined pharmaceutical composition of paclitaxel and dibenz [b, d] thiophene STAT inhibitor tartrate, comprising active ingredients and pharmaceutically acceptable excipients. The active ingredient consists of paclitaxel and dibenz [b, d] thiophene STAT inhibitor tartrate represented by formula (I), and the mass ratio of paclitaxel to dibenz [b, d] thiophene STAT inhibitor tartrate represented by formula (I) in the active ingredient is (0.09 to 0.21): 1. A tartrate salt in that composition has good water solubility, high bioavailability and good stability.
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Paragraph 0027; 0031-0033
(2019/01/24)
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- A medicinal composition for combine paclitaxel and fluorenone STAT3 inhibitor
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Disclosed is a medicinal composition for combine paclitaxel and fluorenone STAT3 inhibitor comprising an active ingredient and a pharmaceutically acceptable adjuvant, characterized in that the activeingredient is composed of paclitaxel and a STAT3 inhibitor represented by formula (I), and the mass ratio of the paclitaxel to the STAT3 inhibitor represented by formula (I) in the active ingredient is (0.21 to 0.32): 1. The compound has an effect on MDA having persistently activated STAT3 activity-MB-468 cell, DU-145 cells had good inhibitory effect.
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Paragraph 0042; 0046-0049
(2019/01/24)
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- A paclitaxel and carbazole class STAT3 inhibitor crystalline form A combination pharmaceutical composition
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The present invention provides a kind of paclitaxel and carbazole class STAT3 inhibitor crystalline form A combination pharmaceutical composition, comprising an active ingredient and a pharmaceutically acceptable auxiliary material, characterized in that the by the taxol the active ingredient of the formula (I) indicated by the STAT3 inhibitors A a crystalline form, the active ingredient of taxol in the formula (I) indicated by the STAT3 inhibitors the mass ratio of the crystalline form A (0.09 - 0.21): 1. The A crystalline form has good physical and chemical stability, solubility and bioavailability, suitable for formulation development.
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Paragraph 0029; 0040; 0044-0046
(2019/02/13)
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- Indoles STAT3 (Signal Transducer and Activator of Transcription-3) inhibitor and preparation method thereof
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The invention belongs to the field of medical chemistry, and relates to an STAT3 (Signal Transducer and Activator of Transcription-3) inhibitor represented by the formula (I) and a preparation methodand application thereof, in particular to a compound having a STAT3 inhibition effect, a pharmaceutical composition containing the compound, and use of the compound or pharmaceutical composition as atherapeutic drug for cancers. The compound has a good inhibition effect on MDA-MB-468 cells and DU-145 cells which have sustainably activated STAT3 activity.
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Paragraph 0038; 0042-0045
(2019/02/27)
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- Mesylate of STAT3 inhibitor as well as preparation method and application thereof
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The invention belongs to the field of medicinal chemistry and relates to mesylate of a STAT3 inhibitor as well as a preparation method and application thereof. Particularly, the invention relates to mesylate of 4-(9-ethyl-9H-carbazole-4-yl)-6-(4-allylaminophenyl)-N-(2-methyl-4H-chromene-4-one)-1,3,5-triazine-2-amine as well as a preparation method and application thereof. The structure of the mesylate of 4-(9-ethyl-9H-carbazole-4-yl)-6-(4-allylaminophenyl)-N-(2-methyl-4H-chromene-4-one)-1,3,5-triazine-2-amine is as shown in the description. The mesylate is excellent in water solubility, high in bioavailability and excellent in stability.
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Paragraph 0027; 0031-0034
(2019/02/27)
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- Dibenzo [b, d] thiophene STAT3 inhibitors of M crystal form and its preparation method
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The invention belongs to the field of medicinal chemistry, with tumor specific relates to the effect of a compound 4 - (dibenzo [b, d] thiophene - 4 - yl) - 6 - (4 - aminophenyl alkene propionyl) - N - (2 - methyl - 4 H - chromene - 4 - keto) - 1, 3, 5 - triazine - 2 - deferoxamine mesylate salt of a new crystalline form, its preparation method, comprising the composition of said form, said form and said form or comprise the composition of use in the preparation of the medicament, the A crystalline form has good physical and chemical stability, solubility and bioavailability, is suitable for formulation development.
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Paragraph 0042; 0046-0049
(2019/02/13)
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- Carbazole STAT3 inhibitor crystal form I and preparation method thereof
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The invention belongs to the field of medical chemistry and particularly relates to a novel crystal form of a compound 4-(9-ethyl-9H-carbazole-4)-6-(4-acrylyl aminophenyl)-N-(2-methyl-4H-chromene-4-ketone)-1,3,5-triazine-2-amine maleate with an anti-tumor effect, a preparation method of the novel crystal form, a composition comprising the crystal form, and an application of the crystal form or thecomposition comprising the crystal form in medicine preparation. The crystal form I has good physical and chemical stability, solubility and bioavailability and is suitable for preparation development.
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Paragraph 0032; 0043; 0047-0050
(2019/02/27)
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- Crystal form A of fluorenone STAT3 inhibitor and preparation method
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The invention belongs to the field of medical chemistry, relates to a fluorenone STAT3 inhibitor represented by a formula (I) and an application thereof and particularly relates to a compound with a signal transduction effect and an inhibition effect on a transcriptional activation factor-3, a pharmaceutical composition containing the compound and use of the compound or the pharmaceutical composition as a cancer treatment drug. The compound has good inhibition effect to MDA-MB-468 cells and DU-145 cells which have continuously-activated STAT3 activity.
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Paragraph 0049; 0053-0056
(2019/03/06)
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- Carbazole class STAT3 inhibitor crystalline form A and its preparation method (by machine translation)
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The invention belongs to the field of medicinal chemistry, and in particular relates to with tumor compound of 4 - (9 - ethyl - 9 H - carbazole - 4 - yl) - 6 - (4 - aminophenyl alkene propionyl) - N - (2 - methyl - 4 H - chromene - 4 - keto) - 1, 3, 5 - triazine - 2 - deferoxamine mesylate salt of a new crystalline form, its preparation method, comprising the composition of said form, said form and said form or comprise the composition of use in the preparation of the medicament, the A crystalline form has good physical and chemical stability, solubility and bioavailability, is suitable for formulation development. (by machine translation)
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Paragraph 0031; 0042; 0046-0048
(2019/02/27)
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- Maleate of STAT3 inhibitor as well as preparation method and application thereof
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The invention belongs to the field of medicinal chemistry and relates to maleate of a STAT3 inhibitor as well as a preparation method and application thereof. Particularly, the invention relates to maleate of 4-(9-ethyl-9H-carbazole-4-yl)-6-(4-allylaminophenyl)-N-(2-methyl-4H-chromene-4-one)-1,3,5-triazine-2-amine as well as a preparation method and application thereof. The structure of the maleate of 4-(9-ethyl-9H-carbazole-4-yl)-6-(4-allylaminophenyl)-N-(2-methyl-4H-chromene-4-one)-1,3,5-triazine-2-amine is as shown in the description. The maleate is excellent in water solubility, high in bioavailability and excellent in stability.
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Paragraph 0027; 0031-0034
(2019/02/27)
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- Crystal form P of carbazole STAT3 inhibitor and preparation method of crystal form P
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The invention belongs to the field of medical chemistry and particularly relates to a novel crystal form of a compound 4-(9-ethyl-9H-carbazole-4-yl)-6-(4-allylaminophenyl)-N-(2-methyl-4H-chromen-4-one)-1,3,5-triazin-2-amine methanesulfonate with an anti-tumor effect, a preparation method of the crystal form, a composition containing the crystal form and use of the crystal form or the composition containing the crystal form in the drug preparation. The crystal form P has good physical-chemical stability, solubility and bioavailability and is proper in particle size, D50 is 35-40 microns, particle distribution curves are distributed in a normal single-peak manner, and the crystal form is suitable for preparation development.
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Paragraph 0044; 0048-0051
(2019/03/06)
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- Paclitaxel and dibenzo[b,d]thiophene STAT (Signal Transducer and Activator of Transcription) inhibitor mesylate A crystal form combined pharmaceutical composition
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The invention provides a paclitaxel and dibenzo[b,d]thiophene STAT (Signal Transducer and Activator of Transcription) inhibitor mesylate A crystal form combined pharmaceutical composition, comprisingan active ingredient and a pharmaceutically acceptable excipient, and characterized in that: the active ingredient is composed of paclitaxel and dibenzo[B,D]thiophene STAT inhibitor mesylate A represented by the formula (I); a mass ratio of the paclitaxel to the dibenzo[B,D]thiophene STAT inhibitor mesylate A in the active ingredient is (0.09-0.21):1. The A crystal form has good physical and chemical stability, solubility and bioavailability, and is suitable for development of preparations.
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Paragraph 0041; 0045-0047
(2019/02/27)
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- Crystal form II of carbazole STAT3 inhibitor and preparation method of crystal form II
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The invention belongs to the field of medical chemistry and particularly relates to a novel crystal form of a compound 4-(9-ethyl-9H-carbazole-4-yl)-6-(4-allylaminophenyl)-N-(2-methyl-4H-chromen-4-one)-1,3,5-triazin-2-amine maleate with an anti-tumor effect, a preparation method of the crystal form, a composition containing the crystal form and use of the crystal form or the composition containingthe crystal form in the drug preparation. The crystal form II has good physical-chemical stability, solubility and bioavailability and is suitable for preparation development.
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Paragraph 0040; 0044-0047
(2019/03/06)
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- Tartrate of dibenzo[b,d]thiophene STAT3 (Signal Transducer and Activator of Transcription-3) inhibitor and preparation method and application of tartrate
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The invention belongs to the field of pharmaceutical chemistry, and relates to tartrate of a dibenzo[b,d]thiophene STAT3 (Signal Transducer and Activator of Transcription-3) inhibitor and a preparation method and application of the tartrate, particularly, the invention relates to the tartrate of 4-(dibenzo[b,d]thiophene-4-yl)-6-(4-allyl acylamino phenyl)-N-(2-methyl-4H-chromene-4-keto)-1,3,5-triazine-2-amine and the preparation method and the application of the tartrate, the structure of the tartrate of 4-(dibenzo[b,d]thiophene-4-yl)-6-(4-allyl acylamino phenyl)-N-(2-methyl-4H-chromene-4-keto)-1,3,5-triazine-2-amine is shown in the description, and the tartrate is good in water solubility, high in bioavailability and good in stability.
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Paragraph 0028; 0032; 0033; 0034; 0035
(2019/02/27)
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