365564-11-0Relevant articles and documents
Preparation of novel pyridine-fused tris-heterocycles; pyrido[4,3-e]pyrrolo-/pyrido[4,3-e]furano[2,3-c]pyridazines and pyrido[3,4-b]pyrrolo[3,2-d]pyrrole
Stockmann, Vegar,Eriksen, Kristine L.,Fiksdahl, Anne
, p. 11180 - 11184 (2008)
Three novel pyrido-fused tris-heterocycles have been prepared based on a Suzuki coupling and subsequent cyclisation approach. Pyrido[4,3-e]pyrrolo[2,3-c]pyridazine (3b, 77%) and pyrido[4,3-e]furano[2,3-c]pyridazine (5b, 76%) were obtained by intramolecular diazocoupling. Successful diazocoupling of furan (5b) is thus reported for the first time by NOBF4 generation of the diazonium intermediate. N-TIPS-pyrido[3,4-b]pyrrolo[3,2-d]pyrrole (TIPS-4b) was synthesised by thermal cyclisation of pyridyl nitrene in considerably higher yield (71%) than previously experienced from similar cyclisations, due to TIPS-activation.
Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity
Kaplan, Anna R.,Musaev, Djamaladdin G.,Wuest, William M.
, p. 544 - 551 (2021/03/03)
Pseudomonads employ several strategies to sequester iron vital for their survival including the use of siderophores such as pyoverdine and pyochelin. Similar in structure but significantly less studied are pyochelin biosynthetic byproducts, dihydroaeruginoic acid, aeruginoic acid, aeruginaldehyde (IQS), and aeruginol, along with two other structurally related molecules, aerugine and pyonitrins A-D, which have all been isolated from numerous Pseudomonad extracts. Because of the analogous substructure of these compounds to pyochelin, we hypothesized that they may play a role in iron homeostasis or have a biological effect on other bacterial species. Herein, we discuss the physiochemical evaluation of these molecules and disclose, for the first time, their ability to bind iron and promote growth in Pseudomonads.
Alkylammoniotrifluoroborate functionalized polystyrenes: Polymeric pre-catalysts for the metal-free borylation of heteroarenes
Bouchard, Nicolas,Fontaine, Frédéric-Georges
supporting information, p. 4846 - 4856 (2019/04/17)
Three polymeric versions of ansa-N,N-dialkylammoniumtrifluoroborate ambiphilic molecules based on the styrene motif (poly(1-NMe2H+-2-BF3--4-styrene) (P-Me), poly(1-NEt2H+-2-BF3--4-styrene) (P-Et) and poly(1-piperidinyl-H+-2-BF3--4-styrene) (P-Pip)) were synthesized, characterized and tested as heterogeneous pre-catalysts for the borylation of electron-rich heteroarenes. These heterogeneous versions of previously reported pre-catalysts show similar reactivity patterns and represent the first examples of solid-supported FLP metal-free catalysts for the C-H borylation of heteroarenes.
BENZOTHIAZOL COMPOUNDS AND METHODS USING THE SAME FOR TREATING NEURODEGENERATIVE DISORDERS
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Paragraph 0521; 0524; 0525, (2019/04/18)
The present disclosure provides a compound of general Formula (I) having c-abl kinase inhibitory activity or pharmaceutically acceptable salt thereof, a pharmaceutical composition comprising the compound, and a method useful to treat or prevent neurodegenerative diseases using the compound.
SUBSTITUTED [5,6]CYCLIC-4(3H)-PYRIMIDINONES AS ANTICANCER AGENTS
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Page/Page column 48; 49-50, (2018/12/13)
The present invention relates to novel substituted [5,6]cyclic-4(3H)-pyrimidinone compounds of formula (I) and their preparation methods. (I) In particular, the present invention relates to novel substituted [5,6]cyclic-4(3H)- pyrimidinone compounds useful as inhibitors of protein kinases, specifically CDC7 (cell division cycle 7) inhibitors.
NOVEL NICOTINAMIDE DERIVATIVES OR SALTS THEREOF
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Paragraph 0814; 0815, (2018/09/08)
An object of the present invention is to provide to a compound and a pharmaceutical composition, which have excellent Syk-inhibitory activity. Th e present invention provides a nicotinamide derivative represented by the follo wing formula (I) (wherein R 1 represents a halogen atom; R 2 represents a C 1-12 alkyl group, a C 2-12 alkenyl group, a C 2-12 alkynyl group, a C 3-8 cycloalkyl g roup, an aryl group, an ar-C 1-6 alkyl group or a heterocyclic group, each opti onally having at least one substituent; R 3 represents an aryl group or a hetero cyclic group each optionally having at least one substituent; and R 4 and R 5 e ach independently represent a hydrogen atom; and R 2 and R 4 may form a cyc lic amino group optionally having at least one substituent together with the ni trogen atom to which they bind) or a salt thereof, and a pharmaceutical comp osition for use in the treatment of a Syk-related disease which comprises the nicotinamide derivative or a salt thereof.
Catalytic Friedel–Crafts C?H Borylation of Electron-Rich Arenes: Dramatic Rate Acceleration by Added Alkenes
Yin, Qin,Klare, Hendrik F. T.,Oestreich, Martin
supporting information, p. 3712 - 3717 (2017/03/21)
In the electrophilic C?H borylation of electron-rich aromatic compounds with catecholborane, the catalytic generation of the boron electrophile is initiated by heterolysis of the B?H bond by various Lewis and Br?nsted acids, with a boronium ion formed exclusively. After ligand dissociation, the corresponding borenium ion undergoes regioselective electrophilic aromatic substitution on aniline derivatives as well as nitrogen-containing heterocycles. The catalysis is optimized using B(C6F5)3 as the initiator and proceeds without the addition of an external base or dihydrogen acceptor. Temperatures above 80 °C are generally required to secure efficient turnover in these Friedel–Crafts-type reactions. Mechanistic experiments reveal that regeneration of the boronium/borenium ion with dihydrogen release is rate-determining. This finding finally led to the discovery that, with added alkenes, catalytic C?H borylations can, for the first time, be carried out at room temperature.
Catalytic aromatic borylation via in situ-generated borenium species
Kitani, Fumiya,Takita, Ryo,Imahori, Tatsushi,Uchiyama, Masanobu
, p. 158 - 166 (2017/07/28)
We have developed a catalytic direct borylation of arenes via in situ-generated borenium species. The choice of appropriate Lewis base was crucial to achieve the catalytic system. Electron-rich arenes were borylated in a regioselective manner.
Metal-free catalytic C-H bond activation and borylation of heteroarenes
Légaré, Marc-André,Courtemanche, Marc-André,Rochette, étienne,Fontaine, Frédéric-Georges
, p. 513 - 516 (2015/09/08)
Transition metal complexes are efficient catalysts for the C-H bond functionalization of heteroarenes to generate useful products for the pharmaceutical and agricultural industries. However, the costly need to remove potentially toxic trace metals from the end products has prompted great interest in developing metal-free catalysts that can mimic metallic systems.We demonstrated that the borane (1-TMP-2-BH2-C6H4)2 (TMP, 2,2,6,6-tetramethylpiperidine) can activate the C-H bonds of heteroarenes and catalyze the borylation of furans, pyrroles, and electron-rich thiophenes. The selectivities complement those observed with most transition metal catalysts reported for this transformation.
A Palladium(II)-Catalyzed C-H Activation Cascade Sequence for Polyheterocycle Formation
Cooper, Stephen P.,Booker-Milburn, Kevin I.
supporting information, p. 6496 - 6500 (2015/06/02)
Polyheterocycles are found in many natural products and are useful moieties in functional materials and drug design. As part of a program towards the synthesis of Stemona alkaloids, a novel palladium(II)-catalyzed C-H activation strategy for the construction of such systems has been developed. Starting from simple 1,3-dienyl-substituted heterocycles, a large range of polycyclic systems containing pyrrole, indole, furan and thiophene moieties can be synthesized in a single step. Don't overdo it: A palladium(II)-catalyzed C-H activation cascade sequence for the synthesis of polyheterocycles is reported. Aromatization of the initially formed dihydro species occurred with a quinone oxidant. In some cases the use of one equivalent of the oxidant enabled isolation of the dihydro species as a single isomer (see scheme; X=NMe, O, S).
