1711-10-0Relevant articles and documents
Thiophene Modulated BODIPY Dye as a Light Harvester
Li, Xiaochuan,Liao, Meifei,Sun, Jia,Heo, Gisu,Son, Young-A
, p. 127 - 136 (2019)
A new BODIPY dye with terthiophene branched is configured by Sonogashira coupling and fully characterized by NMR and MS. In general organic solvents, it emits typical green fluorescence ranging in 513-518 nm, like most BODIPY analogues. The terthiophene substitution is greatly improved and the emission peak does not sensitive to the polarity environment. More importantly, the terthiophene plays the role of antenna, harvesting the 340 nm’s excitation energy and transferring the energy to BODIPY efficiently. Even though the molar extinction coefficient in 340 nm is lower than that of maximum absorption, it can enlarge the pseudo Stoke’s shift to ～170 nm, well separating the excitation and emission. In film, the emission shifted to 562 nm due to the polymer chain dissipation part of the energy. It shifted further to 585 nm in solid. The branched terthiophene configures a twisted molecular conformation, which avoids the dye regular packing. Highly emission, excellent solubility and stability constitute the general character of the thiophene attached BIDIPY dye.
A BODIPY-based highly emissive dye with thiophene-based branch harvesting the light
Li, Xiaochuan,Han, Yujie,Kim, Myeong Jin,Son, Young-A
, p. 157 - 164 (2018)
A novel BODIPY-based dye with highly emissive character was configured by Sonogashira coupling and routinely characterized by NMR and MS technology. The emission of dye was investigated in solution/film/solid and shows intensive emission. In solution, the emission peak appeared around 510?nm with little influence by the polar environment. The terthiophene plays an effective antenna effect, harvesting the light and transferring the energy to BODIPY. The pseudo Stoke's shift enlarged to ～170?nm in solution. In film, the emission peak shifted to 563?nm in polycarbonate matrix. And it shifted further to 585?nm in solid due to the highly twisted structure, which avoided closely regular-tight packing. The dye rendered an intense fluorescence, good optothermal stability, and high fluorescence quantum yield (0.55). The solid emission showed highly red emission with Commission Internationale de L'Eclairage (CIE) coordinates of (X = 0.69, Y = 0.31). Thus, the synthesized dye is idea candidate for emitting materials.
Fluorogenic Trp(redBODIPY) cyclopeptide targeting keratin 1 for imaging of aggressive carcinomas
Subiros-Funosas, Ramon,Ho, Vivian Cheuk Lam,Barth, Nicole D.,Mendive-Tapia, Lorena,Pappalardo, Morena,Barril, Xavier,Ma, Ruoyu,Zhang, Cheng-Bin,Qian, Bin-Zhi,Sintes, Miquel,Ghashghaei, Ouldouz,Lavilla, Rodolfo,Vendrell, Marc
, p. 1368 - 1374 (2020)
Keratin 1 (KRT1) is overexpressed in squamous carcinomas and associated with aggressive pathologies in breast cancer. Herein we report the design and preparation of the first Trp-based red fluorogenic amino acid, which is synthetically accessible in a few steps and displays excellent photophysical properties, and its application in a minimally-disruptive labelling strategy to prepare a new fluorogenic cyclopeptide for imaging of KRT1+ cells in whole intact tumour tissues.
Synthesis and radioiodination of some 9-aminoacridine derivatives
Ghirmai, Senait,Mume, Eskender,Henssen, Cecile,Ghaneolhusseini, Hadi,Lundqvist, Hans,Tolmachev, Vladimir,Sjoeberg, Stefan,Orlova, Anna
, p. 3719 - 3725 (2004)
Derivatives of 9-aminoacridine, namely N-[ω-(acridin-9-yl-amino) alkyl]-3-(trimethylstannyl)benzamides (1), where the alkyl group is propyl (1a) and octyl (1b), and 2-(acridin-9-ylamino)-3-(4-hydroxyphenyl)propionic acid (2), have been synthesized with the aim to use them as precursors in the syntheses of radiolabeled DNA intercalators for biological experiments. It was observed that compounds 1a and 1b can exist in two isomeric forms at room temperature. Radioiodination of the two benzamides 1a and 1b was carried out with the Auger-emitting nuclide 125I by exchange of the trimethylstannyl group. The optimal conditions for radioiodination of the octyl derivative 1b were established and the labeling yield was found to be as high as 92%, according to TLC analysis in model experiments. Purification of the radioiodinated products gave radiochemical yields of 56% for the propyl and 74% for the octyl compound. The amino acid 2 was directly labeled with 125I at the ortho position to the hydroxyl group by taking advantage of the activated ring. The experiment afforded a very high labeling yield (92%). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Lead derivatization of ethyl 6-bromo-2-((dimethylamino)methyl)-5-hydroxy-1-phenyl-1H-indole-3-carboxylate and 5-bromo-2-(thiophene-2-carboxamido) benzoic acid as FabG inhibitors targeting ESKAPE pathogens
Varakala, Saiprasad Dasugari,Reshma, Rudraraju Srilakshmi,Schnell, Robert,Dharmarajan, Sriram
, (2021/11/26)
Our previous studies on FabG have identified two compounds 5-bromo-2-(thiophene-2-carboxamido) benzoic acid (A) and ethyl 6-bromo-2-((dimethylamino)methyl)-5-hydroxy-1-phenyl-1H-indole-3-carboxylate(B) as best hits with allosteric mode of inhibition. FabG is an integral part of bacterial fatty acid biosynthetic system FAS II shown to be an essential gene in most ESKAPE Pathogens. The current work is focussed on lead expansion of these two hit molecules which ended up with forty-three analogues (twenty-nine analogues from lead compound A and fourteen compounds from lead compound B). The enzyme inhibition studies revealed that compound 15 (effective against EcFabG, AbFabG, StFabG, MtFabG1) and 19 (inhibiting EcFabG and StFabG) had potency of broad-spectrum inhibition on FabG panel.
Nickel-mediated C(sp2)-H amidation in synthesis of secondary sulfonamides via sulfonyl azides as amino source
Xu, Peng,Ding, Peng-Fei,Zhang, Mei-Qi,Xia, Yu-Shi,Xie, Ting
supporting information, (2021/02/16)
In this paper, Ni(II)- Catalyzed ortho-amidation of C(sp2)-H bond with sulfonyl azides directed by (quinolin-8-yl) amine (AQ-amine) is described. The method provides a straightforward method for the synthesis of sulfonamides from available sulfonyl azides via the transition-metal-catalyzed C(sp2)-N bond forming reaction. The amidation reactions exhibit high functional group compatibility, which might proceed a Ni(III)/Ni(I) catalytic cycle. We also applied sulfonamide compound in OLEDs, which exhibits the certain application potential in OLEDs field.
Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides
Chen, Xi,Ding, Ya-Nan,Gou, Xue-Ya,Liang, Yong-Min,Luan, Yu-Yong,Niu, Zhi-Jie,Shi, Wei-Yu,Zhang, Zhe,Zheng, Nian
supporting information, p. 8945 - 8948 (2021/09/10)
C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.
Synthesis of N-trifluoromethyl amides from carboxylic acids
Flavell, Robert R.,Liu, Jianbo,Parker, Matthew F. L.,Toste, F. Dean,Wang, Sinan,Wilson, David M.
supporting information, p. 2245 - 2255 (2021/08/12)
Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.
Synthesis of new alkenyl iodobenzoate derivatives via Kharasch-Sosnovsky reaction using tert-butyl iodo benzoperoxoate and copper (I) iodide
Samadi, Saadi,Ashouri, Akram,Majidian, Shiva,I Rashid, Hersh
, (2020/11/05)
Abstract: The synthesis of new alkenyl iodobenzoate derivatives as allylic esters was investigated via the reaction of tert-butyl iodobenzoperoxoate with alkenes in the presence of copper salts. The best result was obtained using tert-butyl-iodobenzoperoxoate in the presence of copper (I) iodide (5?mol%) in refluxing acetonitrile with good yield (92%) in 32?h. The structure of peresters and alkenyl iodobenzoate derivatives were characterized on the basis of their FT-IR, 1HNMR, 13CNMR, and Mass spectra. Graphic abstract: The preparation of new iodo-allylic esters from alkenes in the presence of copper salts in good to excellent yields is reported in this article.[Figure not available: see fulltext.]
Chemical Proteomics and Phenotypic Profiling Identifies the Aryl Hydrocarbon Receptor as a Molecular Target of the Utrophin Modulator Ezutromid
Wilkinson, Isabel V. L.,Perkins, Kelly J.,Dugdale, Hannah,Moir, Lee,Vuorinen, Aini,Chatzopoulou, Maria,Squire, Sarah E.,Monecke, Sebastian,Lomow, Alexander,Geese, Marcus,Charles, Philip D.,Burch, Peter,Tinsley, Jonathan M.,Wynne, Graham M.,Davies, Stephen G.,Wilson, Francis X.,Rastinejad, Fraydoon,Mohammed, Shabaz,Davies, Kay E.,Russell, Angela J.
supporting information, p. 2420 - 2428 (2020/01/24)
Duchenne muscular dystrophy (DMD) is a fatal muscle-wasting disease arising from mutations in the dystrophin gene. Upregulation of utrophin to compensate for the missing dystrophin offers a potential therapy independent of patient genotype. The first-in-class utrophin modulator ezutromid/SMT C1100 was developed from a phenotypic screen through to a Phase 2 clinical trial. Promising efficacy and evidence of target engagement was observed in DMD patients after 24 weeks of treatment, however trial endpoints were not met after 48 weeks. The objective of this study was to understand the mechanism of action of ezutromid which could explain the lack of sustained efficacy and help development of new generations of utrophin modulators. Using chemical proteomics and phenotypic profiling we show that the aryl hydrocarbon receptor (AhR) is a target of ezutromid. Several lines of evidence demonstrate that ezutromid binds AhR with an apparent KD of 50 nm and behaves as an AhR antagonist. Furthermore, other reported AhR antagonists also upregulate utrophin, showing that this pathway, which is currently being explored in other clinical applications including oncology and rheumatoid arthritis, could also be exploited in future DMD therapies.
