Synthesis and Properties of Methyl-, Formyl- and Amino-Diazaphenanthrene

Chrzastek, Lidia; Mianowska, Barbara; Śliwa, Wanda

doi:10.1071/ch9942129

Cited by 31 publications

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“…The pharmaceutical importance of organic compounds containing azo group have been found to exhibit a wide range of biological activities like antibacterial, antitumor and as potent local anesthetics [4,5] . Aryl diazonium salts represent a well‐known and important group to synthesize heterocyclic compounds that possess many diverse biological activities such as bactericidal, pesticidal, anticonvulsant, anti‐inflammatory and antithyroid diseases and tuberculostatic treatment [6–8] . During the last two decades, considerable attention has been paid to the chemistry of the metal complexes of organic heterocyclic compounds containing nitrogen and other donors due to their stability and promising biological activities [9–15] …”

Section: Introductionmentioning

confidence: 99%

Biochemical Characterization and Antimicrobial Activity against Some Human or Phyto‐Pathogens of New Diazonium Heterocyclic Metal Complexes

El‐Attar

Elshafie

Sadeek

et al. 2022

Chemistry & Biodiversity

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String of vanadium (IV), zirconium (IV), palladium (II), platinum (IV) and uranium (VI) chelates of 2‐cyano‐2‐[(2‐nitrophenyl)hydrazono]thioacetamide (Cnphta) were prepared and characterized by physicochemical, spectroscopic and thermal analyses. The formulae of the isolated solid complexes were assigned as [VO(Cnphta)2(H2O)]SO4 ⋅ 5H2O (1), [ZrO(Cnphta)2(H2O)]Cl2 ⋅ 4H2O (2), [Pd(Cnphta)2]Cl2 (3), [Pt(Cnphta)2Cl2]Cl2 (4) and [UO2(Cnphta)2](NO3)2 ⋅ 5H2O (5). The infrared assignments clearly showed that Cnphta ligand coordinated as a bidentate feature through the hydrazono nitrogen and the thioacetamide nitrogen for V(IV), Zr(IV) and U(VI) but displayed different behavior for Pd(II) and Pt(IV). Results of the molar conductivities measurements showed that the metal complexes were electrolytes in contrast with Cnphta ligand. The interpretation, mathematical analysis and evaluation of kinetic parameters were also carried out. In addition, the studied ligand and its new chelates were tested for their antimicrobial activity against some human or phytopathogenic microorganisms. The new metal complexes explicated promising antibacterial activity against all tested bacteria especially Staphylococcus aureus and Bacillus subtilis. Regarding the antifungal activity, all metal complexes were able to inhibit the mycelium growth of both tested pathogenic fungi. In particular Zr(IV) and Pt(IV) complexes showed the highest significant fungicidal effect against A. fumigatus similar to positive control.

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Section: Introductionmentioning

confidence: 99%

Biochemical Characterization and Antimicrobial Activity against Some Human or Phyto‐Pathogens of New Diazonium Heterocyclic Metal Complexes

El‐Attar

Elshafie

Sadeek

et al. 2022

Chemistry & Biodiversity

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“…Moreover, through chemotherapy of solid-tumor-bearing mice, this compound II resulted as potent as amsacrine (m-AMSA) but less toxic towards the host. In 1994, Sliwa et al showed that benzo[ b ]1,5-naphthyridine III ( Figure 1 ) presented higher activity against Gram-positive than Gram-negative strains [ 9 ]. Years later, 5 H -benzo[ c ][1,5]naphthyridin-6-ones IV ( Figure 1 ) showed poly ADP ribose polymerase (PARP)-1 inhibition and protective effects in rat models of stroke and heart ischemia [ 10 ].…”

Section: Introductionmentioning

confidence: 99%

Fused 1,5-Naphthyridines: Synthetic Tools and Applications

et al. 2020

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Heterocyclic nitrogen compounds, including fused 1,5-naphthyridines, have versatile applications in the fields of synthetic organic chemistry and play an important role in the field of medicinal chemistry, as many of them have a wide range of biological activities. In this review, a wide range of synthetic protocols for the construction of this scaffold are presented. For example, Friedländer, Skraup, Semmlere-Wolff, and hetero-Diels-Alder, among others, are well known classical synthetic protocols used for the construction of the main 1,5-naphthyridine scaffold. These syntheses are classified according to the nature of the cycle fused to the 1,5-naphthyridine ring: carbocycles, nitrogen heterocycles, oxygen heterocycles, and sulphur heterocycles. In addition, taking into account the aforementioned versatility of these heterocycles, their reactivity is presented as well as their use as a ligand for metal complexes formation. Finally, those fused 1,5-naphthyridines that present biological activity and optical applications, among others, are indicated.

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“…However, their main application lies in the medicinal chemistry because some bioactive compounds are based on the benzo[ f ][1,7]naphthyridine core. As representative examples, benzo[ f ][1,7]naphthyridine-1-carbaldehyde ( 1 , Figure 1) exhibited good MIC values against some pathogenic microbes like Gram negative bacteria ( E. coli = 0.2 μg/mL; P. aeruginosa = 0.2 μg/mL; K. pneumoniae = 0.3 μg/mL), Gram positive bacteria ( L. monocytogenes = 0.05 μg/mL; S. aureus = 0.1 μg/mL; S. faecium = 0.2 μg/mL) and pathogenic fungus ( C. albicans = 0.05 μg/mL) [6]. In the same way, the 1,3-diaryl-benzo[ f ][1,7]naphthyridine 2 exhibited very interesting cytotoxicity GI 50 values against human cell lines (lung: NCIH23 = 1.72 μM, colon: HCT15 = 1.86 μM, gastric: NUGC-3 = 1.95 μM, renal: ACHN = 1.98 μM, prostate: PC-3 = 2.98 μM, and breast: MDA-MB-231 = 2.30 μM), as well as outstanding human topoisomerase II α inhibitory properties (91.3% at 100 μM) [7].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New 5-Aryl-benzo[f][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization

et al. 2018

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A series of eight new 5-aryl-benzo[f][1,7]naphthyridines were synthesized in 17 to 64% overall yields via an improved MW-assisted cascade-like one pot process (Ugi–three component reaction/intramolecular aza-Diels-Alder cycloaddition) coupled to an aromatization process from tri-functional dienophile-containing ester-anilines, substituted benzaldehydes and the chain-ring tautomerizable 2-isocyano-1-morpholino-3-phenylpropan-1-one as starting reagents, under mild conditions. The doubly activated dienophile and the aza-diene functionalities of the eight new Ugi-adducts were exploited to perform an in situ aza-Diels-Alder cycloaddition/aromatization (dehydration/oxidation) process, toward the complex polysubstituted 5-aryl-polyheterocycles, which could be taken as starting point for further SAR studies because the benzo[f][1,7]naphthyridine is the core of various bioactive products. It is relevant to emphasize that the synthesis or isolation of benzo[f][1,7]naphthyridines containing a substituted aromatic ring in the C-5 position, has not been published before.

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Synthesis and Properties of Methyl-, Formyl- and Amino-Diazaphenanthrene

Abstract: Methyl, formyl and amino derivatives of the isomeric benzo [c][1,5] naphthyridine and benzo [f][1,7] naphthyridine have been obtained, and their structures confirmed by 1H n.m.r. spectroscopy. Biological activity data (MIC) for some methyl and formyl derivatives are presented.

Cited by 31 publications

References 0 publications

Biochemical Characterization and Antimicrobial Activity against Some Human or Phyto‐Pathogens of New Diazonium Heterocyclic Metal Complexes

Biochemical Characterization and Antimicrobial Activity against Some Human or Phyto‐Pathogens of New Diazonium Heterocyclic Metal Complexes

Fused 1,5-Naphthyridines: Synthetic Tools and Applications

Synthesis of New 5-Aryl-benzo[f][1,7]naphthyridines via a Cascade Process (Ugi-3CR/Intramolecular Aza-Diels-Alder Cycloaddition)/Aromatization

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