Organoantimony(III) halide complexes with azastibocine framework as potential antitumor agents: Correlation between cytotoxic activity and N→Sb inter-coordination

A novel organoantimony complex of 6‐cyclohexyl‐6,7‐dihydrodibenzo[c,f] [1,5]azastibocin‐12(5H)‐yl nitrate (2) was synthesized and systematically characterized by techniques such as NMR spectra, TG‐DSC, and X‐ray diffraction. It was found that the complex 2 exhibits relatively strong Lewis acidity (3.3 < Ho ≤ 4.8) and could be employed as a water tolerant Lewis acid catalyst for the synthesis of synthetically valuable benzimidazole derivatives starting from aldehydes and arylenediamines. This catalytic system shows excellent tolerance toward a wide variety of functional groups, such as methyl, methoxyl, fluoro, chloro, bromo, nitro, cyan, trifluoromethyl, 1‐naphthaldehyde, furfural and n‐butyl, together with facile reusability in 5 times scale enlarged synthesis.

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An organoantimony nitrate complex with azastibocine framework as water tolerant Lewis acid catalyst for the synthesis of 1,2‐disubstitued benzimidazoles

Zhou

Lei

Liu

et al. 2020

Applied Organom Chemis

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Syntheses and characterization of novel antimony (III) and bismuth (III) derivatives containing β‐enamino ester along with antimicrobial evaluation, DFT calculation, and cytotoxic study

Sangwan,

Beniwal,

Gaur

et al. 2023

J Biochem & Molecular Tox

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Four novel antimony (III) and bismuth(III) complexes of the kind Cl–Sb–O–C(OR)–CH(CH3)C–NH–(CH2)2–NH–C(CH3)CH:C(OR)–O [where R = ‐CH3, M = Sb (1a); R = –C2H5, M = Sb (1b); R = –CH3, M = Bi (1c); R = –C2H5, M = Bi (1d)] were successfully prepared by reacting antimony(III)chloride and bismuth(III)chloride with sodium salt of β‐enamino esters in 1:1 stoichiometry, which were further structurally characterized by physicochemical and IR, 1H, 13C NMR spectral and mass spectrometry. Structural analysis revealed that all four derivatives of both antimony and bismuth display octahedarl geometry which has been optimized through computational studies. These derivatives along with their parent ligands were subsequently assayed in vitro for antibacterial (Bacillus subtilis, Pseudomonas aeruginosa) and antifungal (Aspergillus niger and Candida albicans) activities. Synthesized complexes were more efficacious in terms of biological activities as compared to parent ligands Further synthesized compounds were evaluated for their in vitro cytotoxic activity against lung cancer cell line A549 using MTT method. IC50 value for all four complexes was determined and all of them are found active. Computational studies of the representative complexes have been done using B3LYP/631‐G* basis sets to provide optimized geometry.

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Pd-catalyzed oxidative Heck-type arylation of vinyl ketones, alkenes, and acrylates with Sb-aryl-tetrahydrodibenz[c,f][1,5]azastibocines

Murata

Kakusawa

Arakawa

et al. 2020

Journal of Organometallic Chemistry

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Organoantimony(III) halide complexes with azastibocine framework as potential antitumor agents: Correlation between cytotoxic activity and N→Sb inter-coordination

Cited by 10 publications

References 37 publications

An organoantimony nitrate complex with azastibocine framework as water tolerant Lewis acid catalyst for the synthesis of 1,2‐disubstitued benzimidazoles

An organoantimony nitrate complex with azastibocine framework as water tolerant Lewis acid catalyst for the synthesis of 1,2‐disubstitued benzimidazoles

Syntheses and characterization of novel antimony (III) and bismuth (III) derivatives containing β‐enamino ester along with antimicrobial evaluation, DFT calculation, and cytotoxic study

Pd-catalyzed oxidative Heck-type arylation of vinyl ketones, alkenes, and acrylates with Sb-aryl-tetrahydrodibenz[c,f][1,5]azastibocines

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