- Annulation of Conjugated Azine-Imine with a Sulfoxonium Ylide in a Noncarbenoid Route to Synthesize Multisubstituted Imidazole-Fused Heterocycles
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A new [4+1]-annulation of in situ generated heterocyclic azine-aldimines with β-keto sulfoxonium ylides has been developed. The reaction constructs N-fused imidazole rings. In the reaction, the ylides play a dual-functional role of a nucleophilic 1,1-dipo
- Guchhait, Sankar K.,Saini, Meenu,Khivsara, Viren J.,Giri, Santosh K.
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p. 5380 - 5387
(2021/05/05)
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- Bioactivity of azomethines derived mechanochemically from 2-amino pyridine and studies on the effect of substituents on the reaction
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Azomethines with pyridine framework serve as excellent pharmacophore. A number of azomethine derivatives were synthesised from 2-aminopyridine and differently substituted aromatic aldehydes in excellent to almost quantitative yields through green, mechanochemical protocol. Influence of the substituents in the nuclei of aromatic aldehydes on the rate of the reaction was investigated. Presence of ortho hydroxy groups in the nucleus of aromatic aldehydes led to the completion of the reactions in almost no time with nearly quantitative yields. 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical was used to evaluate the in vitro antioxidant activity of the prepared azomethines and the results were compared with standard natural antioxidant L-ascorbic acid. Most of the derivatives showed fairly strong antioxidant property. Antibacterial activity of the prepared azomethines were examined against Bacillus subtilis (Gram-positive) and Escherichia coli (Gram-negative) strains by using agar well diffusion method. Some of the azomethines exhibited encouraging antibacterial activities.
- Sarma, Madhushree Das,Ghosh, Subhojit
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p. 1295 - 1303
(2020/12/04)
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- The discovery of new and more potent chloropyramine (C4) analogues for the potential treatment of invasive breast cancer
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Breast cancer is the second most common cancer worldwide, accounting for 25% of all female cancers. Although the survival rate has increased significantly in the past few decades, patients who develop secondary site metastasis as well as those diagnosed with triple negative breast cancer still represent a real unmet medical challenge. Previous studies have shown that chloropyramine (C4) inhibits FAK-VEGFR3 signalling. More recently, C4 is reported to have SASH1 inducing properties. However, C4 exerts its antitumour and antiangiogenic effects at high micromolar concentrations (>100?μm) that would not be compatible with further drug development against invasive breast cancer driven by FAK signalling. In this study, molecular modelling guided structural modifications have been introduced to the chloropyramine C4 scaffold to improve its activity in breast cancer cell lines. Seventeen compounds were designed and synthesized, and their antiproliferative activity was evaluated against three human breast cancer lines (MDA-MB-231, BT474 and T47D). Compound 5c was identified to display an average activity of IC50?=?23.5–31.3?μm, which represents a significant improvement of C4 activity in the same assay model. Molecular modelling and pharmacokinetic studies provided more promising insights into the mechanistic features of this new series.
- Kandil, Sahar,Prencipe, Filippo,Jones, Samuel,Hiscox, Stephen,Westwell, Andrew D.
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p. 314 - 321
(2017/12/29)
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- Access to Amide from Aldimine via Aerobic Oxidative Carbene Catalysis and LiCl as Cooperative Lewis Acid
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Herein, an efficient route to amides from aldimines via aza-Breslow intermediates through aerobic oxidative carbene catalysis with LiCl as a cooperative Lewis acid is described. Many of the obtained N-heteroarylamides feature biological activity. Ambient
- Wang, Guanjie,Fu, Zhenqian,Huang, Wei
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supporting information
p. 3362 - 3365
(2017/07/13)
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- Novel one-pot pseudo four component reaction: Expeditious synthesis of functionalized imidazo[1,2-a]pyridines
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A new and efficient one-pot synthesis of imidazo[1,2-a]pyridines has been described. In this approach the installation of C-3 imine substituent on the imidazopyridine framework was developed. Corresponding products were prepared in mild conditions by reac
- Sanaeishoar, Haleh,Nazarpour, Roya,Mohave, Fouad
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p. 68571 - 68578
(2015/09/01)
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- Copper(II)-Mediated Aerobic Synthesis of Imidazo[1,2-a]pyridines via Cascade Aminomethylation/Cycloisomerization of Alkynes
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A single copper(II)-catalyzed three-component cascade aminomethylation/cycloisomerization of propiolates to form imidazo[1,2-a]pyridines was explored. A straightforward method was developed for the practical synthesis of functionalized imidazo[1,2-a]pyridines from benzaldehydes, 2-aminopyridines, and propiolate derivatives catalyzed by Cu(OAc)2 hydrate in the presence of air. The protocol is marked by excellent yields, functional group tolerance, and, above all, adaptability to synthesize imidazo[1,2-a]pyridine-based drug molecules such as Alpidem.
- Rassokhina, Irina V.,Shirinian, Valerii Z.,Zavarzin, Igor V.,Gevorgyan, Vladimir,Volkova, Yulia A.
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p. 11212 - 11218
(2015/11/18)
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- Copper(I)-catalyzed [3+2] cycloaddition/ring-opening rearrangement/[4+2] cycloaddition/aromatization cascade: An unprecedented chemo- and stereoselective three component coupling of sulfonyl azide, alkyne and N-arylidenepyridin-2- amine to pyrido[1,2-a]pyrimidin-4-imine
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A novel synthetic protocol for the one-pot chemo- and stereoselective construction of diversely functionalized pyrido[1,2-a]pyrimidin-4-imines via copper(I)-catalyzed [3+2] cycloaddition/ring-opening rearrangement/[4+2] cycloaddition/aromatization cascade of sulfonyl azides, alkynes and N-arylidenepyridin-2-amines under mild reaction conditions is reported. In addition, the catalytic activity of copper(I)-modified zeolite, a recyclable, heterogeneous catalyst is also investigated, which gives improved yield compared to its homogeneous equivalents. Copyright
- Namitharan, Kayambu,Pitchumani, Kasi
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supporting information
p. 93 - 98
(2013/03/13)
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- Physico-chemical investigation of Th(IV) and UO2(VI) complexes of schiff bases
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Schiff bases were obtained using p-methoxy benzaldehyde and p-chloro benzaldehyde and 2-amino pyridine to prepare new complexes of thorium(IV) and dioxouranium(VI) metals by various anions. The synthesized ligands and complexes were analytically studied t
- Agnihotri, Sonal,Arora, Kishor
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p. 4323 - 4326
(2013/07/25)
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- A metal-free tandem demethylenation/C(sp2)-H cycloamination process of N -Benzyl-2-aminopyridines via C-C and C-N bond cleavage
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A mild, metal-free synthesis of pyrido[1,2-a]benzimidazoles starting with N-benzyl-2-aminopyridines, which employs PhI(OPiv)2 as a stoichiometric oxidant, has been developed. The process is initiated by an unusual PhI(OPiv)2-mediated ipso SEAr reaction, followed by solvent-assisted C-C and C-N bond cleavage.
- Liang, Dongdong,He, Yimiao,Liu, Lanying,Zhu, Qiang
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supporting information
p. 3476 - 3479
(2013/07/26)
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- A novel pathway to imidazo[1,2-a]pyridines. Access through imino pyridinium salts
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A new synthetic strategy for the preparation of imidazo[1,2-a]pyridines 10 is reported, which is based on the electrocyclization reaction of imino pyridinium salts 7 upon treatment with a strong base. The starting materials are easily prepared from 2-amin
- Neue, Benedikt,Froehlich, Roland,Wuerthwein, Emst-Ulrich
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experimental part
p. 295 - 304
(2012/07/14)
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- CuSO4-glucose for in situ generation of controlled Cu(I)-Cu(II) bicatalysts: Multicomponent reaction of heterocyclic azine and aldehyde with alkyne, and cycloisomerization toward synthesis of N-fused imidazoles
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The catalytic efficiency of mixed Cu(I)-Cu(II) system in situ generated by partial reduction of CuSO4 with glucose in ethanol (nonanhydrous) under open air has been explored. With this catalysis, the multicomponent cascade reaction of A3-coupling of heterocyclic amidine with aldehyde and alkyne, 5-exo-dig cycloisomerization, and prototropic shift has afforded an efficient and eco-friendly synthesis of therapeutically important versatile N-fused imidazoles. Diverse heterocyclic amidines, several of which are known to be poorly reactive, and aldehydes are compatible in this catalytic process.
- Guchhait, Sankar K.,Chandgude, Ajay L.,Priyadarshani, Garima
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experimental part
p. 4438 - 4444
(2012/07/03)
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- Ultrasonics promoted synthesis of thiazolidinones from 2-aminopyridine and 2-picolilamine
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The efficient multicomponent synthesis of thiazolidinones from the reaction of arenealdehydes, mercaptoacetic acid and 2-picolilamine or 2-aminopyridine under ultrasound irradiation are reported. The reaction with 2-aminopyridine needs a Lewis acid cataly
- Gouvêa, Daniela P.,Bare?o, Valéria D.O.,Bosenbecker, Juliano,Drawanz, Bruna B.,Neuenfeldt, Patrícia D.,Siqueira, Geonir M.,Cunico, Wilson
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experimental part
p. 1127 - 1131
(2012/08/08)
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- Simple and efficient one-pot synthesis of imidazo[1,2-a]pyridines catalyzed by magnetic nano-Fe3O4-KHSO4·SiO 2
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The present report highlights a magnetic nano-Fe3O 4-KHSO4·SiO2 catalyzed synthesis of imidazo[1,2-a]pyridines. The synthetic strategy adopted is expedient, versatile, and offers good to excellent yields from readily available starting materials.
- Guntreddi, Tirumaleswararao,Allam, Bharat Kumar,Singh, Krishna Nand
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p. 2635 - 2638,4
(2012/12/12)
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- Copper-catalyzed intramolecular dehydrogenative aminooxygenation: Direct access to formyl-substituted aromatic N-heterocycles
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A direct synthesis of carbaldehydes through intramolecular dehydrogenative aminooxygenation has been developed. The process uses a catalytic amount of copper(II) in DMF or DMA under oxygen and does not require additional oxidants (see scheme). Mechanistic studies suggest that the carbonyl oxygen atom of the aldehyde is derived from oxygen through a copper-mediated oxygen activation process via a peroxy-copper(III) intermediate. Copyright
- Wang, Honggen,Wang, Yong,Liang, Dongdong,Liu, Lanying,Zhang, Jiancun,Zhu, Qiang
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supporting information; experimental part
p. 5678 - 5681
(2011/08/02)
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- Theoretical vibrational mode analysis of schiff bases using semi empirical methods-II
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Two new Schiff bases viz., 2N-[(4-chlorobenzalidene)aminopyridine] and 2N-[(4-hydroxybenzalidene)aminopyridine] were synthesized using 4-chlorobenzaldehyde, 4-hydroxybenzaldehyde and 2-amino pyridine in separate procedures. Their IR spectra was obtained e
- Agnihotri, Sonal,Singh, Bhoop,Burman, Kiran,Arora, Kishor
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experimental part
p. 2089 - 2091
(2012/02/14)
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- Synthesis and microbiological evaluations of (N-heteroaryl)arylmethanamines and their Schiff bases
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The synthesis as well as the antimicrobial and antiviral activities of new (N-heteroaryl)arylmethanamines and their Schiff bases are reported. None of the tested compounds showed activity against Herpes simplex virus type 2 and against Gram positive and Gram negative bacteria. Weak or moderate activity on poliovirus Sabin type 1, on reverse transcriptase and against Cryptococcus neoformans was shown by some of the tested compounds. Viceversa several synthesized compounds exhibited a moderate or good activity against strains of Candida albicans, while only some of the tested compounds were found moderately active against strains of Candida sp. Instead numerous new compounds 3 or 4 were active as control against isolates of plant pathogenic fungi. The obtained results are discussed on the basis of structure-activity relationships.
- Fioravanti,Biava,Donnarumma,Porretta,Simonetti,Villa,Porta-Puglia,Deidda,Maullu,Pompei
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p. 643 - 652
(2007/10/03)
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- INVERSE ELECTRON DEMAND DIELS-ALDER REACTION OF 2-(ARYLMETHYLENEAMINE)-PYRIDINES WITH ENAMINES AND STYRENES. SYNTHESIS OF PYRAMIDINE DERIVATIVES
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The reaction of 2-(arylmethyleneamino)-pyridines bearing an electron withdrawing group on the arylmethylene moiety 1 a, b and 2 a, b as heterodienes, with enamines 3 a, b or styrenes 4 a, b as dienophiles, affords, the corresponding pyrimidines by means o
- Abdel-Rahman, Mahmoud A.
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p. 535 - 540
(2007/10/03)
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