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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Shalihi, Devy Janisca ; Murniati, Neni ; Rahman, Wiguna ; Hutabarat, Prima Wahyu Kusuma ; Lailaty, Intani Quarta ;
Abstract: Rhododendron multicolor Miq. exhibits distinctive morphoanatomical characteristics and various bioactive compounds with medicinal and horticultural potential. Numerous studies indicated Rhododendron species are widely utilized as medicinal and ornamental plants, owing to their diverse phytochemical profiles and distinctive morphoanatomical characteristics. However, comprehensive studies of the morphoanatomy and leaves metabolite profile of R. multicolor are still limited globally, as well as its minimal utilization by local communities, highlighting a significant knowledge gap. Therefore, this study aimed to analyze the morphology, paradermal anatomy, and metabolite profile of young leaves and mature leaves of R. multicolor. Morphoanatomy characteristics were analyzed descriptively, anatomical features were analyzed using specific formulas, and metabolite profiling was analyzed using qualitative phytochemicals and gas chromatography-mass spectrometry (GC-MS). The result shows that R. multicolor is a shrubby plant characterized by funnel-shaped flowers in a vibrant red hue, along with narrowly elliptic, scaly leaves. The scales are stellate lobed irregularly with lower density than stomata; the epidermis is polygonal to irregular that has a higher density compared to stomata. The results of the qualitative phytochemical test of Rhododendron multicolor are that it contains phenols, flavonoids, Mayer alkaloids, Bouchardat alkaloids, Dragendorf alkaloids, tannins, and saponins. Based on GC-MS analysis of young leaves and mature leaves of R. multicolor, a total of 31 metabolite compounds from 21 compound groups were identified, with the major compound being squalene from the terpenoid group, which has the potential to be an antioxidant, anticancer, antibacterial, antifungal, antitumor, and cardioprotective.
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Keywords: Morphoanatomy ; metabolite compounds ; Rhododendron multicolor Miq ; Vireya ; Cibodas Botanic Garden
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Marie L. Mortensen ; Shubham Bisht ; Muhammad Abbas ; Hamid Firouzi ; Gregory T. McCandless ; Michael Shatruk , et al.
Abstract: Two fluoro-bridged lanthanide-containing metal–organic frameworks (MOFs) were synthesized using 2,2′-bipyridine-4,4′-dicarboxylic acid (BPDC), a fluorinated modulator, and a lanthanide nitrate. The syntheses of MOFs containing Gd3+ or Tb3+ and a closely related MOF structure containing Ho3+, Gd3+, or Tb3+ are presented. The presence of the fluorinated metal chains in these MOFs is shown through single crystal X-ray diffraction, energy dispersion X-ray spectroscopy, 19F nuclear magnetic resonance, and X-ray photoelectron spectroscopy. Magnetic measurements reveal weak antiferromagnetic exchange between the Ln3+ ions mediated by fluoride anions along the zigzag ladder chains present in the crystal structures of these MOFs.
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Photophysical Properties of Rare-Earth Cluster-Based Metal–Organic Frameworks
Ajoyan, Zvart ;
Abstract: The work described herein explores the field of metal–organic frameworks (MOFs) with a particular emphasis on rare-earth (RE) cluster-based MOFs. MOFs are materials that are of interest due to their permanent porosity, high surface areas, and tunable structures. This thesis focuses on three different MOFs: RE-UiO-66 (UiO = University of Oslo), RE-CU-10 and RE-CU-27 (CU = Concordia University). The synthesis, characterization, and photophysical properties of these MOFs are presented. Chapter 2 explores tuning of the RE-UiO-66 platform by synthesizing and characterizing mono-, bi- and tri-metal RE-UiO-66 analogues where RE = Tb(III), Gd(III), and Eu(III), ultimately leading to the formation of a white light emitting MOF. Furthermore, a study of the photophysical properties of this series of MOFs is conducted and as a proof of concept, Tb:Gd:Eu-UiO-66 is deposited on a UV light emitting diode (LED), leading to a white light emitting diode (WLED). Chapter 3 describes a facile route for modulating the photoluminescent and radioluminescent properties of Tb(III) cluster-based MOFs. By using Tb(III)-cluster nodes as Xray attenuators, and organic linkers with varying excited state energies as sensitizers, MOFs with metal-based, linker-based, and metal+linker-based photo- and radioluminescence are reported.
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CAS No. : | 385-00-2 |
Formula : | C7H4F2O2 |
M.W : | 158.10 |
SMILES Code : | O=C(O)C1=C(F)C=CC=C1F |
MDL No. : | MFCD00002411 |
InChI Key : | ONOTYLMNTZNAQZ-UHFFFAOYSA-N |
Pubchem ID : | 9796 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium hydroxide In ethanol; water at 20℃; for 0.166667 h; | Sodium 2,6-difluorobenzoate; To a solution of 2,6-difluorobenzoic acid (1.0Og1 6.3mmol) in EtOH and water (5:1 , 6OmL) was added 1 N aqueous sodium hydroxide solution (6.33mL, 6.3mmol). The reaction mixture was stirred for 10 minutes at room temperature and then solvents were removed in vacuo to yield sodium 2,6-difluorobenzoate (1.22g, 6.3mmol, quantitative) as an off white solid. 1H NMR (DMSO) δ 6.89 (2H, m), 7.15 (1 H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sulfuric acid; for 6h;Reflux; | General procedure: A catalytic amount of concentrated H2SO4 wasadded to a solution of carboxylic acids 16(a-j) (1.0 mmol)in 50 mL of methanol, and the mixture was refluxed for 6 h. It was allowed to cool. The saturated solution ofNaHCO3 was added to the reaction mixture, and it wasextracted with EtOAc (2 X 50 mL). The combined organiclayer was dried Na2SO4 and concentrated to obtain puremethyl esters 17(a-j). |
75.9% | With toluene-4-sulfonic acid;Inert atmosphere; Reflux; | To a suspension of 2,6-difluorobenzoic acid (50 g, 316 mmol) in MeOH (800 mL) was added TsOH ( 6 g, 10%), the mixture was heated to reflux overnight. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with saturated NaHCO3 and brinesuccessively. The organic layer was separated, dried over Na2SO and concentrated under reduced pressure to give methyl 2,6-difluorobenzoate. 41 g (75.9% yield) 1 H NMR (400 MHz, CDCI3) delta ppm 7.37-7.46 (m, 1 H), 6.91 - 6.98 (m, 2H), 3.95 (s, 3H). |
73% | Step 2: methyl 2,6-difluorobenzoateTo a solution of 2,6-difluorobenzoic acid (100 g, 0.63 mol) in sulfurous dichloride (150 mL) and the resulting reaction mixture was heated to refluxing for 2 hrs. Sulfurous dichloride was removed in vacuo, the residue in pyridine (100 ml) was added MeOH (100 mL) slowly and stirred at room temperature for 2 hrs. The solvent was removed in vacuo, the residue was dissolved in EtOAc (200 mL) and washed with aqueous NaOH (IN), HC1 (IN) and brine. The solution was dried over Na2S04, filtered and concentrated to afford the desired product (78.8 g, 73%).1H NMR (CDCI3): ? 7.46-7.38 (1H, m), 6.98-9.93 (2H, m), 3.95 (3H, d, J = 2.0 Hz). |
73% | 2,6-difluorobenzoic acid (10 (^, 0.63111001) was dissolved in thionyl chloride (1501 ^), and the resulting mixture was heated under reflux for 2 hours. The excess sodium sulfoxide was distilled off and the resulting residue (100 mL) was added dropwise and the methanol was slowly added dropwise (100 mL). The reaction was stirred at room temperature for 2 hours and the solvent was removed in vacuo to remove the solvent. The resulting oil was dissolved in 200 mL of ethyl acetate and treated with IN sodium hydroxide solution, IN hydrochloric acid , Water and saturated salt water. After evaporation of the solvent in vacuo, the title compound (78.8 g, 73%) was obtained as an oil. | |
71% | With sulfuric acid; at 20℃;Reflux; | To a solution of 2,6-difluorobenzoic acid (30.0 g, 190.0 mmol) in MeOH (100 mL) was added concentrated sulfuric acid (5 mL) dropwise at room temperature. The reaction mixture was heated under reflux overnight. The solvent was removed in vacuo. The residue was dissolved in EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give 1 (23.2 g, 71%) as a yellow oil. 1H NMR (CDCl3): delta 7.45-7.39 (m, 1H), 6.98-6.93 (m, 2H), 3.96 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With hydroxylamine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; water; at 20℃; for 2h; | 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.43 ml, 2.90 mmol, 5.0 eq) wasadded to a solution of <strong>[13671-00-6]methyl 2,6-difluorobenzoate</strong> (100 mg, 0.58 mmol, 1.0 eq) in methanol (0.35 mL). The resulting solutionwas stirred at room temperature and hydroxylamine in aqueous solution 50% (0.36ml, 5.81 mmol, 10.0 eq) was added. After 2h the reaction was stopped and themixture is adjusted to pH 6 with acetic acid. The aqueous layer was extractedthree times with ethyl acetate. The combined organic layer was dried with MgSO4,concentrated and purified by preparative HPLC to afford 2,6-difluoro-N-hydroxy-benzamide (54 mg, 0.31 mmol, 54 %) as a white solid: MS ES+ m/z 174.1 (M+H)+; 1HNMR (400 MHz, DMSO-d6) delta 11.18 (s, 1H), 9.41 (s, 1H), 7.54 (m, 1H), 7.22 - 7.14 (m, 2H); 13CNMR (101 MHz, DMSO-d6) delta 159.3 (dd, J = 249.9, J = 8.4 Hz), 156.6, 132.2 (t, J = 10.3 Hz), 113.3 (t, J = 23.3 Hz), 112.1 (dd, J = 19.7, J = 5.4 Hz) ; 19FNMR (377 MHz, DMSO-d6) delta -113.6 (t, J = 7.0 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | Weigh 18mg 2,6-difluorobenzoic acid, 42mg HATU, 15mg HOAT in a 25ml round bottom flask, add 0.8ml DCM, 0.2ml DMF and 33mul DIEA as solvent, stir the reaction at room temperature for about 10 minutes, in the reaction system 37mg of A1 intermediate was added, the reaction was stirred at room temperature for about 1 hour, 100ml of saturated aqueous sodium bicarbonate solution was added, followed by extraction with 15ml of DCM 3 times. The resulting organic phase was dried under reduced pressure with DCM:MeOH=70:1 ( The volume ratio) was applied to a silica gel column to obtain 26 mg of the compound represented by Formula III-1 in a yield of 51%. |
Tags: 2,6-Difluorobenzoic acid | Fluorinated Building Blocks | Carboxylic Acids | Aryls | Insecticide | Organic Building Blocks | Pesticide Composition | Other Inhibitors/Agonists | 385-00-2
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