3430-17-9Relevant academic research and scientific papers
1,3-Disubstituted urea derivatives: Synthesis, antimicrobial activity evaluation and in silico studies
Gündüz, Miyase G?zde,U?ur, Sümeyye Buran,Güney, Funda,?zkul, Ceren,Krishna, Vagolu Siva,Kaya, Serdal,Sriram, Dharmarajan,Do?an, ?engül Dilem
, (2020)
The development of new antimicrobial compounds is in high demand to overcome the emerging drug resistance against infectious microbial pathogens. In the present study, we carried out the extensive antimicrobial screening of disubstituted urea derivatives. In addition to the classical synthesis of urea compounds by the reaction of amines and isocyanates, we also applied a new route including bromination, oxidation and azidination reactions, respectively, to convert 2-amino-3-methylpyridine to 1,3-disubstituted urea derivatives using various amines. The evaluation of antimicrobial activities against various bacterial strains, Candida albicans as well as Mycobacterium tuberculosis resulted in the discovery of new active molecules. Among them, two compounds, which have the lowest MIC values on Pseudomonas aeruginosa, were further evaluated for their inhibition capacities of biofilm formation. In order to evaluate their potential mechanism of biofilm inhibition, these two compounds were docked into the active site of LasR, which is the transcriptional regulator of bacterial signaling mechanism known as quorum sensing. Finally, the theoretical parameters of the bioactive molecules were calculated to establish their drug-likeness properties.
Preparation and characterization of methyl substituted 2,2′-dipyridyl diselenides and -ditellurides: X-ray structure of 6,6′-dimethyl-2,2′-dipyridyl diselenide
Bhasin,Venugopalan,Singh
, p. 2579 - 2587 (2002)
A convenient method for the preparation of various methyl substituted 2,2′-dipyridyl diselenides and -ditellurides by the aerial oxidation of lithium 2-pyridylselenolate/tellurolate, prepared from the lithium-halogen exchange between n-butyllithium and 2-bromo methyl substituted pyridines is reported. All the compounds prepared are new and have been characterized by elemental analysis, IR, 1H, 13C, 11Se NMR, and mass spectral studies. Crystal structure of 6,6′-dimethyl-2,2′-dipyridyl diselenide has been determined.
Synthesis of new 4-aza-indoles via acyl azides
Do?an, Sengul Dilem,Demirpolat, Eren,Yerer Aycan, Mükerrem Betül,Balci, Metin
, p. 252 - 258 (2015)
We hereby report the preparation of new azaindole derivatives starting from 2-(2-ethoxy-2-oxoethyl)nicotinic acid. Conversion of a half ester into acyl azide followed by Curtius rearrangement gave the corresponding isocyanate. Trapping of the isocyanate with different nucleophiles produced urea and urethane derivatives. Intramolecular cyclization reactions gave the target compounds.
Photophysical behavior of a novel 4-aza-indole derivative in different solvents: reverse solvatochromism
Bozkurt, Ebru,Dogan, Sengul Dilem
, p. 863 - 872 (2019)
The photophysical properties of a new 4-aza-indole derivative [ethyl 1-((2-(2-ethoxy-2-oxoethyl)pyridin-3-yl)carbamoyl)-2-hydroxy-1H-pyrrolo-[3,2-b]pyridine-3-carboxylate, 12] were determined in different solvents. Compound 12 exhibited an absorbance peak at 340–360?nm with high fluorescence intensity in the wavelength range from 405 to 417?nm in all solvents except N,N-dimethylformamide (DMF). Compound 12 exhibited reverse solvatochromism behavior depending on the solvent polarity. Furthermore, compound 12 showed very high quantum yield in all solvents independent of their polarity. The results suggest that this novel dye could be used for many applications, e.g., as a labeling agent and in bio- or analytical sensors and/or optoelectronic devices.
NEW COMPOUND
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Paragraph 0316; 0322, (2019/11/26)
PROBLEM TO BE SOLVED: To provide a new compound that does not have structural similarity to ceramide and has excellent CERT inhibitory activity. SOLUTION: The present invention provides a new compound of structural formula (I). A bond group -X- is cis-cyclopropyl-, R1, R2, R3, R4, and R5 independently represent a hydrogen atom, a halogen atom, a linear or branched C1-C8 alkyl group that may have a halogen atom, or OR6. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT
Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions
Zhang, Xitao,Feng, Xiujuan,Zhang, Haixia,Yamamoto, Yoshinori,Bao, Ming
supporting information, p. 5565 - 5570 (2019/10/22)
A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.
Generation and reactions of pyridyllithiums via Br/li exchange reactions using continuous flow microreactor systems
Nagaki, Aiichiro,Yamada, Daisuke,Yamada, Shigeyuki,Doi, Masatomo,Ichinari, Daisuke,Tomida, Yutaka,Takabayashi, Naofumi,Yoshida, Jun-Ichi
, p. 199 - 207 (2013/03/28)
A continuous flow microreactor method for generating and carrying out reactions on pyridyllithiums has been developed based on Br/Li exchange reactions of bromopyridines and dibromopyridines. The reactions can be carried out without using cryogenic conditions by virtue of short residence times and efficient heat transfer, while very low temperatures such as-78 or-110°C are required for conventional batch macro methods. Moreover, sequential introduction of two different electrophiles has been successfully achieved using dibromopyridines in an integrated flow microreactor system composed of four micromixers and four microtube reactors.
Flow microreactor synthesis of disubstituted pyridines from dibromopyridines via Br/Li exchange without using cryogenic conditions
Nagaki, Aiichiro,Yamada, Shigeyuki,Doi, Masatomo,Tomida, Yutaka,Takabayashi, Naofumi,Yoshida, Jun-Ichi
supporting information; experimental part, p. 1110 - 1113 (2011/06/26)
A flow microreactor method for the synthesis of disubstituted pyridines by generation of pyridyllithiums followed by reactions with electrophiles has been developed. By using a short residence time and efficient temperature control, the cryogenic conditions required for conventional batch macro processes can be avoided. Sequential introduction of two different electrophiles into dibromopyridines has been achieved using an integrated flow microreactor system composed of four micromixers and four microtube reactors, to obtain disubstituted pyridine compounds.
The expedient access to bromo-pyridine carbaldehyde scaffolds using gem-dibromomethyl intermediates
Mandal, Ashis Baran,Augustine, John Kallikat,Quattropani, Anna,Bombrun, Agnes
, p. 6033 - 6036 (2007/10/03)
A simple, efficient, and general two-step synthesis to bromo-pyridine carbaldehyde scaffolds is described. This direct route involves sequential reactions employing the dibromination of bromo-picolines followed by hydrolysis using an aqueous solution of calcium carbonate. Bromo-pyridine carbaldehyde scaffolds 1-7 were obtained in good overall yield. Bromo-dibromomethyl-pyridine intermediates have been isolated and characterized.
Base and cation effects on the suzuki cross-coupling of bulky arylboronic acid with halopyridines: Synthesis of pyridylphenols
Zhang, Huichang,Kwong, Fuk Yee,Tian, Yuan,Chan, Kin Shing
, p. 6886 - 6890 (2007/10/03)
Strong base and large size cation have been shown to accelerate the rate and the yield of Suzuki coupling of a sterically bulky boronic acid with halopyridines in DME for the synthesis of pyridylphenols.
