One‐pot, four‐component synthesis of 1,3,4‐oxadiazole derivatives containing a ferrocene unit and their antimicrobial activity

Kazemizadeh, Ali Reza; Shajari, Nahid; Shapouri, Reza; Adibpour, Neda; Teimuri‐Mofrad, Reza; Dinmohammadi, Parisa

doi:10.1002/aoc.3410

Cited by 10 publications

(4 citation statements)

References 55 publications

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“…When these compounds were tested for their potential effect on the permeabilisation of the bacteria, we obtained no effect. Therefore, these Zn and Co anti-tumour compounds did not seem to damage the cell wall of Gram-positive or -negative bacteria, which is in opposition to other published studies that tested different compounds with effects on the bacterial membrane [11,16,23,24].…”

Section: Discussioncontrasting

confidence: 86%

A Tale of Two Ends: Repurposing Metallic Compounds from Anti-Tumour Agents to Effective Antibacterial Activity

et al. 2020

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The rise in antibiotic resistance coupled with the gap in the discovery of active molecules has driven the need for more effective antimicrobials while focusing the attention into the repurpose of already existing drugs. Here, we evaluated the potential antibacterial activity of one cobalt and two zinc metallic compounds previously reported as having anticancer properties. Compounds were tested against a range of Gram-positive and -negative bacteria. The determination of the minimum inhibitory and bactericidal concentrations (MIC/MBC) of the drugs were used to assess their potential antibacterial activity and their effect on bacterial growth. Motility assays were conducted by exposing the bacteria to sub-MIC of each of the compounds. The effect of sub-MIC of the compounds on the membrane permeability was measured by ethidium bromide (EtBr) accumulation assay. Cell viability assays were performed in human cells. Compound TS262 was the most active against the range of bacteria tested. No effect was observed on the motility or accumulation of EtBr for any of the bacteria tested. Cell viability assays demonstrated that the compounds showed a decrease in cell viability at the MIC. These results are promising, and further studies on these compounds can lead to the development of new effective antimicrobials.

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Section: Discussioncontrasting

confidence: 86%

A Tale of Two Ends: Repurposing Metallic Compounds from Anti-Tumour Agents to Effective Antibacterial Activity

et al. 2020

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“…Organic synthesis in aqueous media is very important because toxic and volatile organic solvents are not used. In line with our interest in the synthesis of heterocycles, we report a three‐component reaction of phthalhydrazide, dimedone, aromatic aldehydes, and ZrO(NO 3 ) 2 .2H 2 O as a novel catalyst at reflux conditions in water, leading to the synthesis of 1 H ‐indazolo [1, 2‐ b ] phthalazinetrione derivatives. The catalyst ZrO(NO 3 ) 2 .2H 2 O that we used to produce 1 H ‐indazolo[1,2‐ b ]phthalazine‐1,6,11(13 H )‐trione derivatives is important in many respects.…”

Section: Introductionmentioning

confidence: 83%

Green and efficient synthesis of 1H‐indazolo[1,2‐b] phthalazine‐1,6,11(13H)‐triones using ZrO(NO₃)₂.2H₂O as a novel catalyst and theoretical study of synthesized compounds

Biroon

Shajari

Yahyaei

2020

Journal of Heterocyclic Chem

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The one‐pot three‐component synthesis for the preparation of 1H‐indazolo[1,2‐b] phthalazine‐1,6,11(13H)‐triones through condensation of phthalimide, hydrazine monohydrate, dimedone, and aromatic aldehydes in the presence of a novel catalytic amount of ZrO(NO3)2.2H2O at reflux conditions in water has been reported. Quantum theoretical calculations for the three structures of compounds (5a, 5b, and 5c) were performed using the G3MP2, LC‐ωPBE, MP2, and B3LYP methods with the 6‐311 + G** basis set. After optimizing the structures, geometric parameters were obtained and experimental measurements were compared with the calculated data. The structures of the products were confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. IR spectra data and 1H NMR and 13C NMR chemical shifts computations of the 1H‐indazolo[1,2‐b]phthalazine‐1,6,11(13H)‐trione derivatives in the ground state were calculated. Frontier molecular orbitals, total density of states, thermodynamic parameters, and molecular electrostatic potentials of the title compounds were investigated by theoretical calculations. Molecular properties such as the ionization potential (I), electron affinity (A), chemical hardness (η), electronic chemical potential (μ), and electrophilicity (ω) were investigated for the structures. Consequently, there was an excellent agreement between experimental and theoretical results.

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“…Some of these organometallic compounds were tested against microorganisms Brucella abortus, Staphylococcus aureus, and Pseudomonas aeruginosa, showing moderate antimicrobial properties. 126,127 Recently, an interesting publication by Brunschweiger, Domling, and co-workers described the use of the Ramazani-4CRalong with other I-MCRs, such as the Ugi, Ugi-azide, and Groebke−Blackburn−Bienayméreactionfor the construction of DNA-encoded libraries of heterocycles compounds. 130 In this seminal report, Brunschweiger's group demonstrated the compatibility of isonitrile chemistry with the solid-phase derivatization of DNA oligonucleotides.…”

Section: Reactionsmentioning

confidence: 99%

“…The Ramazani-4CR has been widely employed to obtain compound libraries of medicinal interest, including oxadiazole-based cytotoxic agents and ferrocene derivatives. − As shown in Scheme B, two alternative strategies have been explored, which employ the ferrocene functionalized either as aldehyde 46 , or carboxylic acid 49 , to efficiently produce diverse ferrocenyl oxadiazoles without affecting the metal complex. Some of these organometallic compounds were tested against microorganisms Brucella abortus , Staphylococcus aureus , and Pseudomonas aeruginosa , showing moderate antimicrobial properties. , …”

Section: Oxadiazole Synthesis By Four-component Reactionsmentioning

confidence: 99%

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

et al. 2020

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N-Isocyaniminotriphenylphosphorane (NIITP) is a functionalized isonitrile that has been extensively applied in a variety of organic reactions during the last two decades. This Review summarizes the most important applications in organic synthesis of this versatile reactant, with the focus posed on mechanistic and methodological aspects allowing the generation of molecular diversity. NIITP combines the reactivity of isonitriles with that of phosphoranes to enable chemical transformations employed in the construction of compound libraries. Here, we cover from the initial applications of NIITP in the Nef isocyanide reaction to further derivations that render a variety of heterocyclic scaffolds. The presence of the isonitrile moiety in this singular compound makes possible the double addition of nucleophiles and electrophiles, which followed by inter(intra)molecular aza-Wittig type transformations enable several multicomponent and tandem processes. In particular, we stress the impact of NIITP in oxadiazole chemistry, from the early two-component transformations to recent examples of multicomponent reactions that take place in the presence of suitable electrophiles. In addition, we briefly describe the role of NIITP chemistry in generating skeletal and conformational diversity in cyclic peptides. The reaction of NIITP with alkynes is thoroughly revised, with particular emphasis on silver-catalyzed processes that have been developed in the last years. Biomedicinal applications of some reaction products are also mentioned along with a perspective of future applications of this reactant.

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One‐pot, four‐component synthesis of 1,3,4‐oxadiazole derivatives containing a ferrocene unit and their antimicrobial activity

Cited by 10 publications

References 55 publications

A Tale of Two Ends: Repurposing Metallic Compounds from Anti-Tumour Agents to Effective Antibacterial Activity

A Tale of Two Ends: Repurposing Metallic Compounds from Anti-Tumour Agents to Effective Antibacterial Activity

Green and efficient synthesis of 1H‐indazolo[1,2‐b] phthalazine‐1,6,11(13H)‐triones using ZrO(NO₃)₂.2H₂O as a novel catalyst and theoretical study of synthesized compounds

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

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One‐pot, four‐component synthesis of 1,3,4‐oxadiazole derivatives containing a ferrocene unit and their antimicrobial activity

Cited by 10 publications

References 55 publications

A Tale of Two Ends: Repurposing Metallic Compounds from Anti-Tumour Agents to Effective Antibacterial Activity

A Tale of Two Ends: Repurposing Metallic Compounds from Anti-Tumour Agents to Effective Antibacterial Activity

Green and efficient synthesis of 1H‐indazolo[1,2‐b] phthalazine‐1,6,11(13H)‐triones using ZrO(NO3)2.2H2O as a novel catalyst and theoretical study of synthesized compounds

One Reacts as Two: Applications of N-Isocyaniminotriphenylphosphorane in Diversity-Oriented Synthesis

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Green and efficient synthesis of 1H‐indazolo[1,2‐b] phthalazine‐1,6,11(13H)‐triones using ZrO(NO₃)₂.2H₂O as a novel catalyst and theoretical study of synthesized compounds