Design, Synthesis, and Cytotoxicity of 5-Fluoro-2-methyl-6-(4-aryl-piperazin-1-yl) Benzoxazoles

Al-Harthy, Thuraya; Zoghaib, Wajdi M.; Pflüger, Maren; Schöpel, Miriam; Önder, Kamil; Reitsammer, Maria; Hundsberger, Harald; Stoll, Raphael; Abdel‐Jalil, Raid J.

doi:10.3390/molecules21101290

Cited by 11 publications

(5 citation statements)

References 18 publications

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“…Punji , utilized an unsymmetrical pincer PCN/Pd complex (0.5% catalyst, Figure ) to catalyze the direct Csp 2 –H arylation of benzoxazole, − but CuI was necessary as a cocatalyst in this system and the substrates were limited to only aryl iodides. The versatile applications of 2-substituted benzoxazoles were taken into consideration, − but to date, the reported arylation systems of benzoxazoles, whichever Pd and Ni systems or Pd/Cu system, − had typical limitations, including the high loading of catalysts, activated substrates, and complicated catalyst systems.…”

Section: Introductionmentioning

confidence: 99%

Unsymmetrical Pincer N-Heterocyclic Carbene–Nitrogen–Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp²–H Arylation of Benzoxazoles

Wang

et al. 2018

Organometallics

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An unsymmetrical pincer N-heterocyclic carbene–nitrogen–phosphine (CNP) and its palladium complexes PdCl2(κ2-CP) (4) and [PdCl(κ3-CNP)]PF6 (5·PF 6 ) were synthesized. NMR spectra disclosed that the transformation of complex 4 structure occurred in the solution. Further NMR experimental and single crystal structure analysis of complex 4 provided unequivocal and structural evidence for the formation of complex [PdCl(κ3-CNP)]Cl (5·Cl) in the solution of complex 4. The catalytic performance of palladium complexes 4 and 5·PF 6 was investigated with the direct Csp2–H arylation of benzoxazoles with aryl bromides. Notably, aryl bromides could give up to 97% arylation products in the presence of 0.5% complex 4. For ortho-substituted substrates, the steric hindrance had a significant impact, but product yields could be improved remarkably by extending reaction time. This result implied the catalytic active species in this system was stable and kept in a long lifetime. The flexible backbone and unsymmetrical pincer structure with a flank N-heterocyclic carbine should be a feasible strategy to realize an efficient catalytic transformation. This simple catalyst system first realized the direct arylation of aryl bromides with a catalyst loading as low as 0.25% without excessive base and copper as assistant catalyst.

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Section: Introductionmentioning

confidence: 99%

Unsymmetrical Pincer N-Heterocyclic Carbene–Nitrogen–Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp²–H Arylation of Benzoxazoles

Wang

et al. 2018

Organometallics

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“…At low concentration, 10 μM, compounds (46)(47)(48)(49) were highly toxic to lung cancer cells, killing 30-40% of all cancer cells at this low concentration. Concentrations below 10 were not toxic for both [74].…”

Section: Benzoxazoles Containing Piperazinementioning

confidence: 85%

The Impact of Incorporation Piperazine on Biological Activities of Benzazoles

Al-Harthy,

Zoghaib,

Abdel-Jalil

2024

Heterocyclic Chemistry - New Perspectives [Working Title]

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Heterocycles are widely distributed compounds in natural products and are involved in many biological processes. Its uses have been extended to different fields, including industry, medicine, and agriculture sectors. Benzazole is one of the popular heterocycle scaffolds known as a privilege structure which is commonly found in many pharmaceutical agents. Another outstanding scaffold is piperazine that is known as a distinguishable motif in drug design with a wide range of biological activities. One of the fruitful approaches in the drug design is a hybridization of privilege structures in one skeleton which are believed to grant a characteristic feature with improved or more selective biological activities than the two scaffolds. The effect that piperazine imparted while introduced into a benzazole has drawn attention since first used in the nineteenth century. Numerous research has been performed discussing the synthesis and biological activities of benzazoles containing piperazine. In this chapter, we will highlight a general introduction about chemistry and structure of piperazine, and its importance in medicinal chemistry and benzazole as well. Next, several studies will be discussed that highlight the importance of incorporating piperazine in benzazole skeletons, benzimidazole, benzothiazole, and benzoxazole, and biological activity inherited from this combination.

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“…Whereas, the initial results obtained were too low owing to the low solubility of aryl-piperazine. 43 Murty et al, synthesized benzoxazole derivatives coupled with piperazine ring (2) and evaluated their cytotoxic potential towards five distinct human cancer cell lines of various origins viz. Hela (cervical), MCF-7 (Breast), A431 (skin), HepG2 (liver) and A549 (lung).…”

Section: Benzoxazolementioning

confidence: 99%

Heterocyclic Compounds and their Derivatives with Potential Anticancer Activity

Kaur,

Shakya,

Singh

et al. 2024

Ind. J. Pharm. Edu. Res

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Cancer is the second leading cause of the death worldwide. As per the reports published by WHO, the cases of cancer in the world will increase to 22 million by 2030. Many resources are investigated all around the world for developing preventive, diagnostic and therapeutic strategies for cancer. Malignant cells display metabolic changes because of genetic and epigenetic alterations as compared to normal cell. Heterocycles are the key structural feature of many anti-cancer drugs present in the market. Between 2010 to 2015, FDA approved anticancer drugs also contain heterocyclic rings in their structures. Their presence in anti-cancer drugs can be credited to their being extremely common in nature, with enormous cellular processes and mechanisms. This review throws light on several heterocyclic compounds containing nitrogen, sulphur and oxygen in their rings, possessing anticancer activity on different cell lines. A compiled data of heterocyclic rings will help in providing a new way towards future development of new compound for treatment of cancer.

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Design, Synthesis, and Cytotoxicity of 5-Fluoro-2-methyl-6-(4-aryl-piperazin-1-yl) Benzoxazoles

Cited by 11 publications

References 18 publications

Unsymmetrical Pincer N-Heterocyclic Carbene–Nitrogen–Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp²–H Arylation of Benzoxazoles

Unsymmetrical Pincer N-Heterocyclic Carbene–Nitrogen–Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp²–H Arylation of Benzoxazoles

The Impact of Incorporation Piperazine on Biological Activities of Benzazoles

Heterocyclic Compounds and their Derivatives with Potential Anticancer Activity

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Design, Synthesis, and Cytotoxicity of 5-Fluoro-2-methyl-6-(4-aryl-piperazin-1-yl) Benzoxazoles

Cited by 11 publications

References 18 publications

Unsymmetrical Pincer N-Heterocyclic Carbene–Nitrogen–Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp2–H Arylation of Benzoxazoles

Unsymmetrical Pincer N-Heterocyclic Carbene–Nitrogen–Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp2–H Arylation of Benzoxazoles

The Impact of Incorporation Piperazine on Biological Activities of Benzazoles

Heterocyclic Compounds and their Derivatives with Potential Anticancer Activity

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Product

Resources

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Unsymmetrical Pincer N-Heterocyclic Carbene–Nitrogen–Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp²–H Arylation of Benzoxazoles

Unsymmetrical Pincer N-Heterocyclic Carbene–Nitrogen–Phosphine Chelated Palladium(II) Complexes: Synthesis, Structure, and Reactivity in Direct Csp²–H Arylation of Benzoxazoles