- Modular synthesis, spectroscopic characterization and in situ functionalization using "click" chemistry of azide terminated amide containing self-assembled monolayers
-
A general and modular synthetic route is developed for the synthesis of azidoalkylthiol molecules, which contain an amide functional group, from common and easily available precursors. SAMs (self-assembled monolayers) formed by these amide containing azidoalkylthiols are characterised by attenuated total reflectance FTIR spectroscopy, X-ray photoelectron spectroscopy, contact angle goniometry and surface enhanced Raman spectroscopy. Signature peaks are identified in the data which allows direct observation of all the functional groups on Au electrodes bearing these monolayers. The terminal azide group is functionalised with electroactive ferrocene group in situ, using "click" chemistry. An alkyne bearing heme derivative is covalently attached using the same technique resulting in O2 reducing electrodes.
- Bandyopadhyay, Sabyasachi,Mukherjee, Sohini,Dey, Abhishek
-
-
Read Online
- An Intramolecular Iodine-Catalyzed C(sp3)?H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans
-
The formation of ubiquitous occurring tetrahydrofuran patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C?H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts. An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecologically favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)?H bond under visible-light irradiation. The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.
- Br?se, Stefan,Koch, Vanessa
-
supporting information
p. 3478 - 3483
(2021/07/22)
-
- IRAK DEGRADERS AND USES THEREOF
-
The present invention provides compounds, compositions thereof, and methods of using the same.
- -
-
Paragraph 2529; 2531
(2019/07/10)
-
- Iron(II)-Catalyzed Site-Selective Functionalization of Unactivated C(sp3)?H Bonds Guided by Alkoxyl Radicals
-
An alkoxyl radical guided strategy for site-selective functionalization of unactivated methylene and methine C?H bonds enabled by an FeII-catalyzed redox process is described. The mild, expeditious, and modular protocol allows efficient remote aliphatic fluorination, chlorination, amination, and alkynylation of structurally and electronically varied primary, secondary, and tertiary hydroperoxides with excellent functional-group tolerance. The application for one-pot 1,4-hydroxyl functionalization of non-oxygenated alkane substrates initiated by aerobic C?H oxygenation is also demonstrated.
- Guan, Honghao,Sun, Shutao,Mao, Ying,Chen, Lei,Lu, Ran,Huang, Jiancheng,Liu, Lei
-
supporting information
p. 11413 - 11417
(2018/08/28)
-
- Hydroxypyridinone and 5-Aminolaevulinic Acid Conjugates for Photodynamic Therapy
-
Photodynamic therapy (PDT) is a promising treatment strategy for malignant and nonmalignant lesions. 5-Aminolaevulinic acid (ALA) is used as a precursor of the photosensitizer, protoporphyrin IX (PpIX), in dermatology and urology. However, the effectiveness of ALA-PDT is limited by the relatively poor bioavailability of ALA and rapid conversion of PpIX to haem. The main goal of this study was to prepare and investigate a library of single conjugates designed to coadminister the bioactive agents ALA and hydroxypyridinone (HPO) iron chelators. A significant increase in intracellular PpIX levels was observed in all cell lines tested when compared to the administration of ALA alone. The higher PpIX levels observed using the conjugates correlated well with the observed phototoxicity following exposure of cells to light. Passive diffusion appears to be the main mechanism for the majority of ALA-HPOs investigated. This study demonstrates that ALA-HPOs significantly enhance phototherapeutic metabolite formation and phototoxicity.
- Battah, Sinan,Hider, Robert C.,MacRobert, Alexander J.,Dobbin, Paul S.,Zhou, Tao
-
p. 3498 - 3510
(2017/05/05)
-
- Synthesis and biological evaluation of an 18fluorine-labeled COX inhibitor - [18F]fluorooctyl fenbufen amide - For imaging of brain tumors
-
Molecular imaging of brain tumors remains a great challenge, despite the advances made in imaging technology. An anti-inflammatory compound may be a useful tool for this purpose because there is evidence of inflammatory processes in brain tumor micro-envi
- Huang, Ying-Cheng,Chang, Yu-Chia,Yeh, Chun-Nan,Yu, Chung-Shan
-
-
- Synthesis, cytotoxicity and cellular uptake studies of N3 functionalized Re(CO)3 thymidine complexes
-
Nucleoside-derived drugs play an important role in the treatment of cancer. Here, we present the synthesis and characterization of an intriguing series of N3 conjugated Re(CO)3 thymidine complexes. The complexes were characterized by NMR spectr
- Bartholomae, Mark D.,Vortherms, Anthony R.,Hillier, Shawn,Joyal, John,Babich, John,Doyle, Robert P.,Zubieta, Jon
-
experimental part
p. 6216 - 6225
(2011/08/02)
-
- PYRIDINYL DERIVATIVES AS INHIBITORS OF ENZYME NICOTINAMIDE PHOSPHORIBOSYLTRANSFERASE
-
The present application discloses a compound of the formula (I) wherein Q is optionally substituted pyridyl; p is 0-6; Y is formulae (i), (ii) and (iii) where X is =O, =S and =N-CN, r is 1-12, R is -Z-A, Z is a single bond, -S(=O)2-, >P=O, >C=O, -C(=O)NH-, and -C(=S)NH-; and A is hydrogen, C1-12-alkyl, C3-12-cycloalkyl, - [CH2CH2O]1-10-(C1-6-alkyl), C1-12-alkenyl, aryl, heterocyclyl, and heteroaryl; B is a single bond, -NRN-, -S(=O)2- and -O-; wherein RN is selected from hydrogen, C1-12-alkyl, C3-12-cycloalkyl, -[CH2CH2O]1-10-(C1-6-alkyl), C1-12-alkenyl, aryl, heterocyclyl, and heteroaryl; s is 0-6; and Cy is aryl, cycloalkyl, heterocyclyl, and heteroaryl. The compounds are usefuld for use as a medicament for the treatment of a disease or a condition caused by an elevated level of nicotinamide phosphoribosyltransferase (NAMPRT).
- -
-
Page/Page column 31; 35
(2010/12/29)
-
- Synthesis, cytotoxicity, and insight into the mode of action of Re(CO) 3 thymidine complexes
-
Nucleoside analogues are extensively used in the treatment of cancer and viral diseases. The antiproliferative properties of organorhenium(I) complexes, however, have been scarcely explored to date. Herein we present the syntheses, characterization, and in vitro evaluation of ReI(CO)3 core complexes of thymidine and uridine. For the binding of the Re I(CO)3 core, a tridentate dipicolylamine metal chelate was introduced at positions C5′, C2′, N3, and C5 with spacers of various lengths. The corresponding organometallic thymidine complexes were fully characterized by IR and NMR spectroscopy and mass spectrometry. Their cytotoxicity was assessed against the A549 lung carcinoma cell line. Toxicity is dependent on the site and mode of conjugation as well as on the nature and the length of the tether. Moderate toxicity was observed for conjugates carrying the rhenium moiety at position C5′ or N3 (IC50=124-160 μm). No toxicity was observed for complexes modified at C2′ or C5. Complex 53, with a dodecylene spacer at C5′, exhibits remarkable toxicity and is more potent than cisplatin, with an IC50 value of 6.0 μm. To the best of our knowledge, this is the first report of the antiproliferative properties of [M(CO)3]+1-nucleoside conjugates. In competitive inhibition experiments with A549 cell lysates and purified recombinant human thymidine kinase 1 (hTK-1), enzyme inhibition was observed for complexes modified at either N3 or C5′, but our results suggest that the toxicity cannot be attributed solely to interaction with hTK-1.
- Bartholomae, Mark D.,Vortherms, Anthony R.,Hillier, Shawn,Ploier, Birgit,Joyal, John,Babich, John,Doyle, Robert P.,Zubieta, Jon
-
experimental part
p. 1513 - 1529
(2011/11/29)
-
- Anti-androgenic pyrrolidines with tumor-inhibiting action
-
This invention relates to anti-androgenic N-[ω-[3-[4-cyano-3-(trifluoromethyl)-phenyl]-5,5-dimethyl-4-oxo-2-thioxoimidazolidin-1-yl]alkyl]-substituted pyrrolidines of general formula I, with a strongly pronounced antiproliferative profile of action; process for the production of the compounds of general formula I, pharmaceutical preparations and the use for the production of pharmaceutical agents.
- -
-
Page/Page column 21-22
(2009/10/18)
-
- Synthesis and pharmacological testing of polyaminoquinolines as blockers of the apamin-sensitive Ca2+-activated K+ channel (SKCa)
-
The synthesis and pharmacological testing of a series of non-peptidic blockers of the SKCa (SK-3) channel is described. Target compounds were designed to mimic the spatial relationships of selected key residues in the energy-minimised structure of the octadecapeptide apamin, which are a highly potent blocker of this channel. Structures consist of a central unit, either a fumaric acid or an aromatic ring, to which are attached two alkylguanidine or two to four alkylaminoquinoline substituents. Potency was tested by the ability to inhibit the SKCa channel-mediated after-hyperpolarization (AHP) in cultured rat sympathetic neurones. It was found that bis-aminoquinoline derivatives are significantly more potent as channel blockers than are the corresponding guanidines. This adds to the earlier evidence that delocalisation of positive charge through the more extensive aminoquinolinium ring system is important for effective channel binding. It was also found that an increase in activity can be gained by the addition of a third aminoquinoline residue to give non-quaternized amines which have submicromolar potencies (IC50 = 0.13-0.36 μM). Extension to four aminoquinoline residues increased the potency to IC50 = 93 nM.
- Fletcher, David I.,Ganellin, C. Robin,Piergentili, Alessandro,Dunn, Philip M.,Jenkinson, Donald H.
-
p. 5457 - 5479
(2008/09/18)
-
- ANTITUMORAL ANTIADROGENIC PYRROLIDINES
-
The invention relates to substituted antiadrogenic pyrrolidines N-[ω-[3-[4-cyan-3-(trifluoromethyl)-phenyl]-5.5-dimethyl-4-oxo2-thioxoimidazoline-1-yle]alkyl] of formula (I) having a salient antiproliferative effect profile. Said invention also relates to a method for producing compounds of the formula (I), pharmaceutical preparations and to the use thereof for producing drugs.
- -
-
Page/Page column 29-30
(2008/06/13)
-
- A new affinity ligand for the isolation of a single 'feruloyl esterase' (FAE-III) from Aspergillus niger
-
8-Aminooctyl 5'-S-coniferyl-5'-deoxy-thio-α-L-arabinofuranoside has been synthesised and shown to be a selective affinity ligand for the feruloyl esterase III of Aspergillus niger. The hydrolyses of methyl 5-O-coumaroyl, feruloyl, or sinapoyl α-L-arabinofuranosides by this enzyme proceed at comparable rates. (C) 2000 Elsevier Science Ltd.
- Zhao, Yongxin,Sinnott, Michael L.
-
p. 917 - 924
(2007/10/03)
-
- Synthesis of 8-aminooctyl glycopyranosides and of their conjugates with poly(L-glutamic acid) having a 2-(4-hydroxyphenyl)ethylamino group for radiolabeling
-
8-Aminooctyl glycopyranosides of β-D-galactose, β-L-fucose, α- and β-D-xyloses, α- and β-D-mannoses, 2-acetamido-2-deoxy-β-D-mannose, and 2-acetamido-2-deoxy-α-L-fucose were synthesized under Koenigs-Knorr type glycosylation reaction conditions using the
- Sugawara, Tamio,Susaki, Hiroshi,Nogusa, Hideo,Gonsho, Akinori,Iwasawa, Hiroyuki,et al.
-
p. 163 - 184
(2007/10/02)
-