6311-35-9Relevant articles and documents
CANCER TREATMENTS TARGETING CANCER STEM CELLS
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Paragraph 0448; 0463; 0467-0470; 01101; 01104-01106, (2021/05/15)
Disclosed are compounds, methods, compositions, uses, and kits that allow for treating cancer. In some embodiments, the compounds are used to treat diseases or disorders. The compounds may treat cancer by targeting cancer stem cells. In some embodiments, the cancer is colorectal cancer, gastric cancer, gastrointestinal stromal tumor, ovarian cancer, lung cancer, breast cancer, pancreatic cancer, prostate cancer, testicular cancer, lymphoma, liver cancer, endometrial cancer, leukemia, or multiple myeloma. Disclosed are compounds, methods, compositions, uses, and kits that may be used in regenerative medicine. The compounds utilized in the disclosure are of Formula (0) and (I).
Dual Reactivity of 1,2,3,4-Tetrazole: Manganese-Catalyzed Click Reaction and Denitrogenative Annulation
Chattopadhyay, Buddhadeb,Das, Sandip Kumar,Khatua, Hillol,Roy, Satyajit
supporting information, p. 304 - 312 (2020/10/29)
A general catalytic method using a Mn-porphyrin-based catalytic system is reported that enables two different reactions (click reaction and denitrogenative annulation) and affords two different classes of nitrogen heterocycles, 1,5-disubstituted 1,2,3-triazoles (with a pyridyl motif) and 1,2,4-triazolo-pyridines. Mechanistic investigations suggest that although the click reaction likely proceeds through an ionic mechanism, which is different from the traditional click reaction, the denitrogenative annulation reaction likely proceeds via an electrophilic metallonitrene intermediate rather than a metalloradical intermediate. Collectively, this method is highly efficient and offers several advantages over other methods. For example, this method excludes a multi-step synthesis of the N-heterocyclic molecules described and produces only environmentally benign N2 gas a by-product.
Iron(II)-Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation
Roy, Satyajit,Khatua, Hillol,Das, Sandip Kumar,Chattopadhyay, Buddhadeb
supporting information, p. 11439 - 11443 (2019/07/17)
A unique concept for the intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by using a catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.
ARYL-BIPYRIDINE AMINE DERIVATIVES AS PHOSPHATIDYLINOSITOL PHOSPHATE KINASE INHIBITORS
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Paragraph 0475, (2019/07/13)
The invention relates to inhibitors of PI5P4K inhibitors useful in the treatment of cancers, neurodegenerative diseases, inflammatory disorders, and metabolic diseases, having the Formula (I): wherein A, X, Y, Z, Q, R1, R2, R3, R4, R5, and n are described herein.
A biocatalytic method for the chemoselective aerobic oxidation of aldehydes to carboxylic acids
Knaus, Tanja,Tseliou, Vasilis,Humphreys, Luke D.,Scrutton, Nigel S.,Mutti, Francesco G.
supporting information, p. 3931 - 3943 (2018/09/11)
Herein, we present a study on the oxidation of aldehydes to carboxylic acids using three recombinant aldehyde dehydrogenases (ALDHs). The ALDHs were used in purified form with a nicotinamide oxidase (NOx), which recycles the catalytic NAD+ at the expense of dioxygen (air at atmospheric pressure). The reaction was studied also with lyophilised whole cell as well as resting cell biocatalysts for more convenient practical application. The optimised biocatalytic oxidation runs in phosphate buffer at pH 8.5 and at 40 °C. From a set of sixty-one aliphatic, aryl-Aliphatic, benzylic, hetero-Aromatic and bicyclic aldehydes, fifty were converted with elevated yield (up to >99%). The exceptions were a few ortho-substituted benzaldehydes, bicyclic heteroaromatic aldehydes and 2-phenylpropanal. In all cases, the expected carboxylic acid was shown to be the only product (>99% chemoselectivity). Other oxidisable functionalities within the same molecule (e.g. hydroxyl, alkene, and heteroaromatic nitrogen or sulphur atoms) remained untouched. The reaction was scaled for the oxidation of 5-(hydroxymethyl)furfural (2 g), a bio-based starting material, to afford 5-(hydroxymethyl)furoic acid in 61% isolated yield. The new biocatalytic method avoids the use of toxic or unsafe oxidants, strong acids or bases, or undesired solvents. It shows applicability across a wide range of substrates, and retains perfect chemoselectivity. Alternative oxidisable groups were not converted, and other classical side-reactions (e.g. halogenation of unsaturated functionalities, Dakin-Type oxidation) did not occur. In comparison to other established enzymatic methods such as the use of oxidases (where the concomitant oxidation of alcohols and aldehydes is common), ALDHs offer greatly improved selectivity.
Protein-inorganic array construction: Design and synthesis of the building blocks
Bogdan, Niculina D.,Matache, Mihaela,Meier, Veronika M.,Dobrotae, Cristian,Dumitru, Ioana,Roiban, Gheorghe D.,Funeriu, Daniel P.
experimental part, p. 2170 - 2180 (2010/07/05)
Herein we describe the design and synthesis of the first series of di-functional ligands for the directed construction of inorganic-protein frameworks. The synthesized ligands are composed of a metal-ion binding moiety (terpyridine-based) conjugated to an epoxysuccinyl peptide, known to covalently bind active cysteine proteases through the active-site cysteine. We explore and optimize two different conjugation chemistries between the di-functionalized metal-ion ligand and the epoxysuccinyl-containing peptide moiety: peptide-bond formation (with limited success) and Cu'-catalysed click chemistry (with good results). Further, the complexation of the synthesized ligands with Fe" and NiII" ions is investigated: the di-functional ligands are confirmed to behave similarly to the parent terpyridine. As designed, the peptidic moiety does not interfere with the complexation reaction, in spite of the presence of two triazole rings that result from the click reaction. ES-MS together with NMR and UV/Vis stud-ies establish the structure, the stoichiometry of the complexation reactions, as well as the conditions under which chemically sensitive peptide-containing polypyridine ligands can undergo the self-assembly process. These results establish the versatility of our approach and open the way to the synthesis of di-functional ligands containing more elaborated polypyridine ligands as well as affinity labels for different enzyme families. As such, this paper is the first step towards the construction of robust supramolecular species that cover a size-regime and organization level previously unexplored.
Enhanced electron injection and efficiency in blended-layer organic light emitting diodes with aluminium cathodes: New 2,5-diaryl-1,3,4-oxadiazole- fluorene hybrids incorporating pyridine units
Oyston, Stephen,Wang, Changsheng,Perepichka, Igor F.,Batsanov, Andrei S.,Bryce, Martin R.,Ahn, Jin H.,Petty, Michael C.
, p. 5164 - 5173 (2007/10/03)
This work focuses on the first 2,5-diaryl-1,3,4-oxadiazole-fluorene hybrids which incorporate pyridine units within the π-electron system, viz. 2,7-bis{5-[2-(4-dodecyloxyphenyl)-1,3,4-oxadiazol-5-yl]-2-pyridyl}-9, 9-dihexylfluorene (6) and 2,7-bis{5-[2-(4-dodecyloxyphenyl)-1,3,4-oxadiazol-5- yl]-2-pyridyl}spirobifluorene (7). The thiophene analogue 2,7-bis{5-[5-(4-tert- butylphenyl)-1,3,4-oxadiazol-2-yl]-thien-2-yl}-9,9-dihexylfluorene 11 was also synthesised and its X-ray crystal structure was obtained. There is a progressive red shift in the UV-Vis absorption and photoluminescence spectra on replacing benzene (8) with pyridine (6) and thiophene (11) consistent with increased planarity of the π-system and reduced HOMO-LUMO gap along the series. Calculations at the DFT (density functional theory) level establish that inclusion of the pyridyl rings in 6 and 7 considerably enhances the electron affinity of the system, compared to phenyl analogues. Single-layer organic light-emitting diodes (OLEDs) have been fabricated by spin-coating blends of poly[2-(2-ethylhexyloxy)-5-methoxy-1,4-phenylenevinylene] (MEH-PPV) as the emissive material with added electron transport compounds 6 or 7 to enhance electron injection. The external quantum efficiencies of the devices were greatly enhanced compared to pure MEH-PPV reference devices. ITO/PEDOT : PSS/MEH-PPV : 7 (30 : 70% by weight)/Al devices exhibited an external quantum efficiency (EQE) of 0.5% and a luminous efficiency of 0.93 cd A-1 at 9.5 V and a luminance of 100 cd m-2. The modest increase in efficiency for the same device when Al was replaced by a Ca/Al cathode (EQE 0.6% and 1.2 cd A-1 at 10.5 V) suggests that the two methods of enhancing electron injection into the MEH-PPV emitter are mutually exclusive. Utilising blended layers is an attractive alternative to using Ca electrodes, which are highly reactive and are unstable in the atmosphere. The Royal Society of Chemistry 2005.
Inhibition of Src kinase activity by 7-[(2,4-dichloro-5-methoxyphenyl) amino]-2-heteroaryl-thieno[3,2-b]pyridine-6-carbonitriles
Boschelli, Diane H.,Wu, Biqi,Barrios Sosa, Ana Carolina,Chen, Joan J.,Golas, Jennifer M.,Boschelli, Frank
, p. 4681 - 4684 (2007/10/03)
7-[(2,4-Dichloro-5-methoxyphenyl)amino]thieno[3,2-b]pyridine-6- carbonitriles with various heteroaryl groups at C-2 are inhibitors of Src kinase activity. Of these new analogs, compounds substituted at C-2 by a 3,5-furan or a 2,5-pyridine had the best activity in the Src enzyme and cell assays.
2-IMINOPYRROLIDINE DERIVATES
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Page 143, (2008/06/13)
A 2-iminopyrrolidine derivative represented by the formula: {wherein ring B represents a benzene ring, pyridine ring, etc.; R101 - R103 represent hydrogen, halogen, C1-6 alkyl, etc.; R5 represents hydrogen, C1-6 alkyl, C1-6 alkoxy-C1-6 alkyl, etc.; R6 represents hydrogen, C1-6 alkyl, C1-6 alkyloxycarbonyl, etc.; Y1 represents a single bond, -CH2-, etc.; Y2 represents a single bond, -CO-, etc.; and Ar represents hydrogen, a group represented by the formula: [wherein R10-R14 represent hydrogen, C1-6 alkyl, hydroxyl, C1-6 alkoxy, etc.; and R11 and R12 or R12 and R13 may bond together to form a 5- to 8-membered heterocyclic ring], etc.}, or a salt thereof.
Synthesis of formylphenylpyridinecarboxylic acids using Suzuki-Miyaura coupling reactions
Meier, Peter,Legraverant, Stephanie,Mueller, Sascha,Schaub, Josette
, p. 551 - 554 (2007/10/03)
Formylphenylboronic acids were coupled with bromopyridylcarboxylic acids in the presence of a palladium catalyst. The yields of the different biaryls are strongly dependant on the substitution pattern of the two coupling partners. The electronic and steric effects of these are discussed.
