- Synthesis and fluorescent study of 5-phenyl furocoumarin derivatives as vasodilatory agents
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Two series of 5-phenyl furocoumarin derivatives were designed and prepared based on our previous research. All new compounds were characterized by 1H NMR, 13C NMR and mass spectra. Furthermore, they were screened for their vasodilato
- Wang, Cheng,Wang, Tao,Huang, Limin,Lu, Wen,Zhang, Jie,He, Huaizhen
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- Synthesis and vasorelaxation evaluation of novel biphenyl-furocoumarin derivatives
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A series of novel biphenyl-furocoumarin derivatives were synthesized and evaluated for their vasorelaxant activities in vitro against rat mesenteric artery, basilar artery, and renal artery ring models pre-contracted by high KCl. The results showed that c
- Wang, Tao,Wang, Cheng,Zhou, Nan,Pan, Xiaoyan,He, Huaizhen
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- Synthesis and evaluation of linear furanocoumarins as potential anti-breast and anti-prostate cancer agents
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A series of 22 furanocoumarin derivatives were synthesized and evaluated for cytotoxicity against breast cancer (MCF-7 and MDA-MB-231) and prostate cancer (PC-3) cell lines along with normal cell line. Several analogs were synthesized by replacing prenyl moiety with alkyl, aromatic, and heteroaromatic functionality to study the structure-activity relationship. Compounds 20 and 22 with adamantoylamino, diprenylamino and substituted benzene sulfonamide substituents showed potent antiproliferative activity in MCF-7 cell line with IC50 values of 0.48 and 0.53 μM, respectively. Both the compounds showed higher IC50 value in MCF-10A cell lines indicating nontoxicity in normal cell lines.
- Chauthe, Siddheshwar K.,Mahajan, Shivani,Rachamalla, Mahesh,Tikoo, Kulbhushan,Singh, Inder P.
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- Fluorescent donor-acceptor psoralen cruciforms by consecutive suzuki-suzuki and sonogashira-sonogashira one-pot syntheses
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Two novel donor-acceptor cruciform topologies are efficiently synthesized by site-selective Suzuki-Suzuki and Sonogashira-Sonogashira multicomponent reactions starting from a bromo-triflato-functionalized psoralen scaffold. In addition to tunability of photophysical properties, such as absorption and emission, many derivatives possess partially high relative fluorescence quantum yields in solution and fluoresce strongly in the solid state. Additionally, the promising compounds show solvatochromism and acidochromic effects. In addition, 8-p-anisyl-5-p-cyanophenyl-substituted psoralen exhibits aggregation-induced emission properties. Experimentally (applying the Lippert-Mataga model) and computationally (TD-DFT calculations), the pronounced charge transfer character of the longest wavelength absorption band was confirmed.
- Geenen, Sarah R.,Schumann, Torben,Müller, Thomas J.J.
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- Generation of Dimethyl Sulfoxide Coordinated Thermally Stable Halogen Cation Pools for C?H Halogenation
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A method to generate halogen cation pools from the reaction of 1,2-dihaloethanes (hal=Br, I) and dimethyl sulfoxide (DMSO) for C?H halogenation of arenes and heteroarenes was reported. The initial reaction of DMSO and 1,2-dihaloethane generates the sulfur
- Dalai, Pallaba Ganjan,Palit, Kuntal,Panda, Niranjan
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supporting information
p. 1031 - 1038
(2022/02/02)
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- Efficient halogenation synthesis method of aryl halide
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The invention discloses an efficient halogenation synthesis method of aryl halide. The method comprises the following step: in the presence of a catalyst (sulfoxide or oxynitride), a halogenation reagent and a solvent, carrying out a halogenation reaction on an aromatic ring compound to obtain the aryl halide. According to the present invention, in the presence of a catalyst (sulfoxide or nitrogenoxide), a halogenation reagent and a solvent, the aromatic ring is subjected to an efficient halogenation reaction, such that the very useful aryl halide can be obtained with high activity and high selectivity; and by adopting the method disclosed by the invention, aryl halides can be efficiently synthesized, and the method has a wide application prospect in actual production.
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Paragraph 0287-0291
(2021/03/31)
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- Electronic Finetuning of 8-Methoxy Psoralens by Palladium-Catalyzed Coupling: Acidochromicity and Solvatochromicity
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Differently 5-substituted 8-methoxypsoralens can be synthesized by an efficient synthetic route with various cross-coupling methodologies, such as Suzuki, Sonogashira and Heck reaction. Compared to previously synthesized psoralens, thereby promising daylight absorbing compounds as potentially active agents against certain skin diseases can be readily accessed. Extensive investigations of all synthesized psoralen derivatives reveal fluorescence in the solid state as well as several distinctly emissive derivatives in solution. Donor-substituted psoralens exhibit remarkable photophysical properties, such as high fluorescence quantum yields and pronounced emission solvatochromicity and acidochromicity, which were scrutinized by Lippert–Mataga and Stern–Volmer plots. The results indicate that the compounds exceed the limit of visible light, a significant factor for potential applications as an active agent. In addition, (TD)DFT calculations were performed to elucidate the underlying electronic structure and to assign experimentally obtained data.
- Geenen, Sarah R.,Presser, Lysander,H?lzel, Torsten,Ganter, Christian,Müller, Thomas J. J.
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p. 8064 - 8075
(2020/06/02)
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- Aryl halide and synthesis method and application thereof
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The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.
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Paragraph 0106-0108
(2020/06/02)
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- Visible-light-promoted oxidative halogenation of (hetero)arenes
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Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.
- Jiang, Xuefeng,Li, Yiming,Lu, Lingling
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supporting information
p. 5989 - 5994
(2020/10/18)
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- A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source
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A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX 2 alone or with ZnX 2) promoted halogenation with N -halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X +) by the coordination of copper or zinc with the N -halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.
- Su, Jinling,Zhang, Yan,Chen, Mingren,Li, Weiming,Qin, Xuewei,Xie, Yanping,Qin, Lixiao,Huang, Shihua,Zhang, Min
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supporting information
p. 630 - 634
(2019/03/08)
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- Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization
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An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.
- Song, Song,Sun, Xiang,Li, Xinwei,Yuan, Yizhi,Jiao, Ning
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supporting information
p. 2886 - 2889
(2015/06/30)
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- Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives
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A series of 5- and 8-methoxypsoralen (MOP) analogs, suitable for structure-antioxidative/anti-inflammatory activity relationship studies, were synthesized using as key-reactions the selective monobromination of MOPs with N-bromosaccharin and either a Heck reaction or a Suzuki coupling or a Suzuki coupling followed by a Wittig reaction to install side-chains of the acrylate- or benzoate- or cinnamate-type, respectively. The 8-MOP analogs 19 and 24, incorporating at position 5 of the psoralen nucleus a butyl acrylate or a tert-butyl cinnamate moiety, were the most powerful inhibitors of soybean LOX and inhibited effectively lipid peroxidation. Analog 19 was a more potent anti-inflammatory agent than the reference compound indomethacin and of comparable cytocompatibility to 8-MOP whereas analog 24 was a weaker inhibitor of inflammation than indomethacin and significantly more cytotoxic than 8-MOP. The results of the biological tests are discussed in terms of structural characteristics.
- Bariamis, Stavros E.,Marin, Marilena,Athanassopoulos, Constantinos M.,Kontogiorgis, Christos,Tsimali, Zinovia,Papaioannou, Dionissios,Sindona, Giovanni,Romeo, Giovanni,Avgoustakis, Konstantinos,Hadjipavlou-Litina, Dimitra
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p. 155 - 169
(2013/04/10)
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- Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure-activity relationship study
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Psoralen (1a) was found to be a specific and potent antimicrobial lead against Helicobacter pylori (H. pylori) from a traditional Chinese medicine (TCM) in the bioassay directed isolation. A series of structurally diverse analogues of 1a were thus designed and synthesized to improve the antimicrobial potency, some of which showed more potent activities than the lead compound (1a) against H. pylori. Among them, compound 25a is 16-fold stronger (MIC = 0.39 μg/mL) than 1a (MIC = 6.25 μg/mL), and is even potent than the positive control metronidazole (MIC = 0.50 μg/mL). The in vitro antimicrobial activities against H. pylori of these structurally diverse analogues based on the scaffold of 1a have also led to an outline of structure-activity relationship.
- Zhang, Bang-Le,Fan, Cheng-Qi,Dong, Lei,Wang, Fang-Dao,Yue, Jian-Min
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experimental part
p. 5258 - 5264
(2011/01/04)
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- Psoralen sensitizers for viral inactivation
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The present invention relates to novel, halogenated psoralen compounds that are useful for inactivating vital contaminants in blood-derived products, particularly blood-derived products that contain platelets or red blood cells. The psoralen compounds of
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- Method of inactivation of viral and bacterial blood contaminants
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A compound is provided for inactivating viral, bacterial or other contamination in cells, body fluids or fractions thereof. The compound comprises a psoralen with a single substituent that is either a quaternary phosphonium or ammonium moiety, and at least one substituent that is a halogen. The compound selectively binds to the contaminant, and upon activation by irradiation, damages the contaminant.
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- SYNTHESIS OF FUROCOUMARIN DERIVATIVES LIKELY TO POSSESS ANTIMICROBIAL ACTIVITY
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The reaction of fuming nitric acid with bergapten (I) and xanthotoxin (II) afforded the corresponding nitro derivatives (IV and V respectively). With imperatorin (III) the reaction was found to be oxidation rather than nitration, and a nitrogen-free compound (VII) resulted. Molecular bromine reacted with bergapten (I) to afford three products (VIIIa - c) in a mixture, and with xanthotoxin (II) to produce the 5-bromo derivative (IX). Anomalously, molecular bromine reacted with imperatorin (III) to give the phenolic compound 5-bromo-9-hydroxy-furo(3,2-g)-coumarin (X). Structures of all products (VI - X) were confirmed by IR, 1H-NMR and mass spectral data.
- Kadry, H.,Osman, A. N.,Al-Azizi, M.,Ashour, M. S.
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p. 915 - 920
(2007/10/03)
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