Synthesis, photochemical E (trans)→Z (cis) isomerization and antimicrobial activity of 2-chloro-5-methylpyridine-3-olefin derivatives

Gangadasu, B.; Reddy, Maruthi Janaki Ram; Ravinder, M.; Kumar, Sanjeev; Raju, B. China; Kumar, K. Pranay; Murthy, U. S. N.; Rao, V. Jayathirtha

doi:10.1016/j.ejmech.2009.07.002

Cited by 14 publications

(2 citation statements)

References 18 publications

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“…As pointed out by fluorescence studies, these isomerizations involved a polar singlet excited state or transfer of charge. As shown in Figure 6 , 2-chloro-5-methylpyridine-3-olefin derivatives ( 8a – e ) and their E→Z ( 9a – e ) isomeric compounds were monitored, and they showed moderate anti-microbial activity [ 69 ].…”

Section: Applications Of Heterocyclic Compoundsmentioning

confidence: 99%

Fluorescent and Phosphorescent Nitrogen-Containing Heterocycles and Crown Ethers: Biological and Pharmaceutical Applications

Ullah

Khan

et al. 2022

Molecules

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Fluorescent molecules absorb photons of specific wavelengths and emit a longer wavelength photon within nanoseconds. Recently, fluorescent materials have been widely used in the life and material sciences. Fluorescently labelled heterocyclic compounds are useful in bioanalytical applications, including in vivo imaging, high throughput screening, diagnostics, and light-emitting diodes. These compounds have various therapeutic properties, including antifungal, antitumor, antimalarial, anti-inflammatory, and analgesic activities. Different neutral fluorescent markers containing nitrogen heterocycles (quinolones, azafluoranthenes, pyrazoloquinolines, etc.) have several electrochemical, biological, and nonlinear optic applications. Photodynamic therapy (PDT), which destroys tumors and keeps normal tissues safe, works in the presence of molecular oxygen with light and a photosensitizing drugs (dye) to obtain a therapeutic effect. These compounds can potentially be effective templates for producing devices used in biological research. Blending crown compounds with fluorescent residues to create sensors has been frequently investigated. Florescent heterocyclic compounds (crown ether) increase metal solubility in non-aqueous fluids, broadening the application window. Fluorescent supramolecular polymers have widespread use in fluorescent materials, fluorescence probing, data storage, bio-imaging, drug administration, reproduction, biocatalysis, and cancer treatment. The employment of fluorophores, including organic chromophores and crown ethers, which have high selectivity, sensitivity, and stability constants, opens up new avenues for research. Fluorescent organic compounds are gaining importance in the biological world daily because of their diverse functionality with remarkable structural features and positive properties in the fields of medicine, photochemistry, and spectroscopy.

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Section: Applications Of Heterocyclic Compoundsmentioning

confidence: 99%

Fluorescent and Phosphorescent Nitrogen-Containing Heterocycles and Crown Ethers: Biological and Pharmaceutical Applications

Ullah

Khan

et al. 2022

Molecules

View full text Add to dashboard Cite

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“…cis-trans Photoisomerization of organic compounds such as olefins plays an important role in chemistry and biochemistry. [1][2][3][4][5] This phenomenon is utilized for photochromism and a large number of photochromic molecules based on the cis-trans isomerization of olefins and azo compounds have been designed and studied. [6][7][8][9][10][11][12][13][14][15] It has been shown that the CQN double bond in a Schiff base exhibits cis-trans isomerization.…”

Section: Introductionmentioning

confidence: 99%

Photochromism of (E)-4-phenyl-1-(pyridine-2-ylmethylene)semicarbazide

et al. 2012

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New and Facile Approach for the Synthesis of (E)‐α,β‐Unsaturated Esters and Ketones

Raju

Suman

2010

Chemistry A European J

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Preparation of (E)-a,b-unsaturated esters and ketones is an important task in organic synthesis.[1] Such esters and ketones are excellent building blocks for the synthesis of a plethora of synthetic and natural products.[2] The most versatile and widely used methods are the Wittig reaction [3] with aldehydes by using alkoxycarbonylmethylene(triphenyl)phosphoranes and the Horner-Wadsworth-Emmons [4] procedure using trialkyl phosphonoacetates with stronger bases. These methods generate stoichiometric amounts of byproducts, namely triphenylphosphine oxide and phosphate salts. Decarboxylative Knoevenagel-type reactions employing malonic acid half esters [5] and the olefination of aldehydes with ethyl diazoacetate [6] (EDA) are alternative methods reported for the synthesis of (E)-a,b-unsaturated esters. The synthesis of (E)-a,b-unsaturated ketones involves the reaction of aromatic aldehydes with aromatic ketones, alkynes and the Grignard reaction of unsaturated aromatic nitriles.[7] The Knoevenagel condensation is an important reaction for the synthesis of a,b-unsaturated compounds; aromatic aldehydes afforded (E)-a,b-unsaturated esters and salicylaldehydes afforded 3-substituted coumarins [8] with b-ketoesters in the presence of base. Generally, the condensation of carbonyl compounds with active methylene substrates containing trifluoroacetoacetate substituents seldom gives the condensation product; however, it has been reported that the reaction of benzaldehyde with ethyl-4,4,4-trifluoroacetoacetate in the presence of piperidine in toluene under reflux conditions afforded ethyl (E)-3-phenyl-2-(2,2,2-trifluoroacetyl)-2-propenoate in low yields. [9] As part of our ongoing efforts in developing approaches for the synthesis of various heterocyclic compounds with potential biological applications, [10] we recently reported the synthesis of methyl (E)-3-(2-chloro-5-methyl-3-pyridyl)-2-propenoate [11] by adopting Horner-Wadsworth-Emmons (HWE) reaction conditions and synthesized new Knoevenagel products. Herein, we report a new, general, and practical method for the synthesis of (E)-a,b-unsaturated esters and ketones by Aldol-adduct elimination under basic conditions. Treatment of 2-chloro-5-methylnicotinaldehyde (1 q) with ethyl-4,4,4-trifluoroacetoacetate (2 a) in CH 2 Cl 2 in the presence of piperidine at room temperature for 4-6 h gave the geometrically selective E product 3 qa instead of the condensation product (Scheme 1).The result surprised and encouraged us to search for the best reaction conditions. The optimization of the reaction conditions was first examined with the use of mostly basic catalysts, namely 1,4-diazabicycloA C H T U N G T R E N N U N G [2.2.2]octane (DABCO), 4-dimethylaminopyridine (DMAP), imidazole, triethylamine, NaOMe, pyridine, and picoline, and we found that the reaction did not take place under these basic conditions. However, when we studied the use of piperidine with various solvents we found that CH 2 Cl 2 was the solvent of choice in terms of yield, reaction time, and selectivity ...

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Synthesis, photochemical E (trans)→Z (cis) isomerization and antimicrobial activity of 2-chloro-5-methylpyridine-3-olefin derivatives

Cited by 14 publications

References 18 publications

Fluorescent and Phosphorescent Nitrogen-Containing Heterocycles and Crown Ethers: Biological and Pharmaceutical Applications

Fluorescent and Phosphorescent Nitrogen-Containing Heterocycles and Crown Ethers: Biological and Pharmaceutical Applications

Photochromism of (E)-4-phenyl-1-(pyridine-2-ylmethylene)semicarbazide

New and Facile Approach for the Synthesis of (E)‐α,β‐Unsaturated Esters and Ketones

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