Synthesis of modified pyridine and bipyridine substituted coumarins as potent antimicrobial agents

Lad, Hemali B.; Giri, Rakesh R.; Chovatiya, Yogita L.; Brahmbhatt, D. I.

doi:10.2298/jsc140804004l

Cited by 9 publications

(5 citation statements)

References 20 publications

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“…The spectrum is characterized by bands at 3009 and 1195, which are due to the stretching frequency and deformation of aromatic (C–H); 1130, which is due to the stretching vibration of aromatic (C–N); and 867, 819, and 670 cm −1 , which are due to the ring bending of p ‐disubstituted and monosubstituted benzene ring, respectively. Furthermore, the IR spectrum of the ligand shows weak to strong bands at 3042; 1619 + 1494; 620, 573 and 488 and 470 cm −1 assigned to υ (C–H); [ υ (C = C) + υ (C = N)] of the pyridine ring; (CH) in‐plane and out‐of‐plane pyridine ring bending, respectively. The asymmetric and symmetric stretching and deformation vibrations of methylene group appear as a medium and weak bands at 2956, 2887, and 1442 cm −1 , respectively …”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, the IR spectrum of the ligand shows weak to strong bands at 3042; 1619 + 1494; 620, 573 and 488 and 470 cm −1 assigned to υ (C–H); [ υ (C = C) + υ (C = N)] of the pyridine ring; (CH) in‐plane and out‐of‐plane pyridine ring bending, respectively. The asymmetric and symmetric stretching and deformation vibrations of methylene group appear as a medium and weak bands at 2956, 2887, and 1442 cm −1 , respectively …”

Section: Resultsmentioning

confidence: 99%

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Coordination Behavior of N‐Donor Schiff Base Derived from 2‐Benzoylpyridine Toward Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Pd(II), and Cr(III) Metal Ions: Synthesis, Spectroscopic and Thermal Studies, and Biological Activity

Emam

Abouel‐Enein

El-Seady

2017

J Chinese Chemical Soc

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A new Schiff base was prepared from the reaction of 4,4 0 -methylenedianiline with 2benzoylpyridine in 1:2 molar ratio, as well as its different metal chelates. The structures of the ligand and its metal complexes were studied by elemental analyses, spectroscopic methods (infrared [IR], ultraviolet-visible [UV-vis], 1 H nuclear magnetic resonance [NMR], electron spin resonance [ESR]), magnetic moment measurements, and thermal studies. The ligand acts as tetradentate moiety in all complexes. Octahedral geometry was suggested for Mn(II), Cu(II), Cr(III), and Zn(II) chloride complexes and pentacoordinated structure and square planar geometry for Co(II), Ni(II), Cu(NO 3 ) 2 , CuBr 2 , and Pd(II) complexes. ESR spectra of copper(II) complexes (4)-(6) at room temperature display rhombic symmetry for complex (4) and axial type symmetry for complexes (5) and (6), indicating d x 2y 2 1 ground state for Cu(II) complexes. The derivative thermogravimetric (DTG) curves of the ligand and its metal complexes were analyzed by using the rate equation to calculate the thermodynamic and kinetic parameters, which indicated strong binding of the ligand with the metal ion in some complexes. Also, some of these compounds were screened to establish their potential as anticancer agents against the human hepatic cell line Hep-G 2 . The obtained IC 50 value of the copper(II) bromide complex (4.34 μg/mL) is the highest among the compounds studied. Biological studiesA preliminary investigation of antitumor activity of ligand L and some of its metal complexes (4-7, 9) was carried out against human hepatic cell line Hep-G 2 at the Regional Center for Mycology and Biotechnology, Al-262 www.jccs.wiley-vch.de JOURNAL OF THE CHINESE CHEMICAL SOCIETYPhysiochemical studies of transition metal complexes of 2-benzoylpyridine Schiff base Scheme 6. TG weight losses of Cr(III) complex (8). Scheme 5. TG weight losses of Mn(II) complex (1). JOURNAL OF THE CHINESE CHEMICAL SOCIETYPhysiochemical studies of transition metal complexes of 2-benzoylpyridine Schiff base Scheme 7. TG weight losses of Cu(II) bromide complex (5).

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Coordination Behavior of N‐Donor Schiff Base Derived from 2‐Benzoylpyridine Toward Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Pd(II), and Cr(III) Metal Ions: Synthesis, Spectroscopic and Thermal Studies, and Biological Activity

Emam

Abouel‐Enein

El-Seady

2017

J Chinese Chemical Soc

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“…In this work, a total of 48 leads were obtained from recent literatures. [26][27] The inhibitory activities of the leads were measured using the same experimental procedures and a wide range of inhibitory activities were covered. In order to get the minimum energy geometry of the leads and the standard antibiotics, they were optimized using the Density Functional Theorem (6-311G * basis set) technique embedded in Spartan'14 software (www.…”

Section: Lead Identification and Optimizationmentioning

confidence: 99%

Virtual screening of novel pyridine derivatives as effective inhibitors of DNA gyrase (GyrA) of salmonella typhi

Philip¹,

Uzairu²,

Shallangwa³

2023

10.5267/j.ccl

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In a bid to discovering novel antibiotics to combat growing trend of multi-drug resistance strains of Salmonella typhi, 48 new pyridine derivatives with significant inhibitory activities against the aforementioned bacterium were subjected to molecular docking against DNA gyrase protease of the bacterium, drug likeness evaluation and pharmacokinetics profiling. All the 48 leads displayed better binding affinity values when compared with Amoxicillin, Ciprofloxacin, Ceftriaxone, Ampicillin, and chloramphenicol, the standard antibiotics used herein for quality assurance. Furthermore, the majority of the compounds were, however, screened out due to their poor pharmacokinetics profiles and drug-likeness. Only five compounds emerged as the most promising leads and they include C4 with binding affinity of -8.0 kcal/mol, C8 (-8.6 kcal/mol), C9 (-8.1 kcal/mol), C26 (-8.3 kcal/mol), and C27 (-8.0 kcal/mol). These compounds not only displayed better binding affinity when compared with the reference antibiotics but also exhibit different modes of interactions with the target protease of the bacterium making them more potent and drug like. Toxicity evaluation of the leads also revealed that the compounds are neither tumorigenic nor mutagenic. In view of the excellent binding affinity, high pharmacokinetics profile and positive drug-likeness of the novel ligands, we recommend these promising compounds for in vitro and in vivo studies in order to discover novel antibiotics that could curb the dangerous trend of multiple drug resistance by Salmonella typhi.

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“…Earlier, we have reported the synthesis of bipyridyl‐substituted coumarins and pyrido‐fused coumarins . Therefore, in continuation of our effort to synthesize new heterocycles and study their biological responses, herein, we report the synthesis of 2‐aryl‐4‐(pyridin‐4‐yl)‐5 H ‐chromeno[4,3‐ b ]pyridin‐5‐one ( 3a – l ) (bipyrido‐fused coumarins) and their antimicrobial activity.…”

Section: Introductionmentioning

confidence: 99%

A Convenient Synthesis of Bipyrido‐Fused Coumarins and Their Biological Evaluation

Giri¹,

Brahmbhatt

2019

Journal of Heterocyclic Chem

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A convenient and efficient strategy has been devised for the synthesis of bipyrido‐fused coumarins employing Kröhnke's pyridine synthesis approach. In the present work, 4‐hydroxycoumarins 1a–d were reacted with appropriate chalcones 2a–c to afford desired bipyridyl‐fused coumarins 3a–l. The structures of all the newly synthesized compounds 3a–l were ascertained by IR, 1H NMR, 13C NMR, mass spectral data, and elemental analyses. The compounds were further evaluated for their antimicrobial response against representative panel of pathogens, and the results thus obtained were compared with those of standard drugs. Few of the derivatives 3c, 3f, and 3i exhibited promising potency.

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Synthesis of modified pyridine and bipyridine substituted coumarins as potent antimicrobial agents

Cited by 9 publications

References 20 publications

Coordination Behavior of N‐Donor Schiff Base Derived from 2‐Benzoylpyridine Toward Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Pd(II), and Cr(III) Metal Ions: Synthesis, Spectroscopic and Thermal Studies, and Biological Activity

Coordination Behavior of N‐Donor Schiff Base Derived from 2‐Benzoylpyridine Toward Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Pd(II), and Cr(III) Metal Ions: Synthesis, Spectroscopic and Thermal Studies, and Biological Activity

Virtual screening of novel pyridine derivatives as effective inhibitors of DNA gyrase (GyrA) of salmonella typhi

A Convenient Synthesis of Bipyrido‐Fused Coumarins and Their Biological Evaluation

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