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Synthesis of Spirooxindole-O-Naphthoquinone-Tetrazolo[1,5-a]Pyrimidine Hybrids as Potential Anticancer Agents.

ABSTRACT: A series of novel spirooxindole-O-naphthoquinone-tetrazolo[1,5-a]pyrimidine hybrids were designed, synthesized and evaluated as potent antitumor agents. These hybrids exhibited relatively high cytotoxic activity against cancer cell line HepG2 (IC₅₀ = 2.86?36.34 ?M), while normal cell line LO2 was less sensitive to these hybrids (IC₅₀ = 36.37?248.39 ?M). On the whole, among all the compounds tested, compound 4e, with a mean IC₅₀ value of 2.86 ?M, was the most active. The novel hybrids may find their pharmaceutical applications after further investigations.

SUBMITTER: Wu L

PROVIDER: S-EPMC6225336 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Synthesis of Spirooxindole-O-Naphthoquinone-Tetrazolo[1,5-a]Pyrimidine Hybrids as Potential Anticancer Agents.

Wu Liqiang L Liu Yunxia Y Li Yazhen Y

Molecules (Basel, Switzerland) 20180912 9

A series of novel spirooxindole-O-naphthoquinone-tetrazolo[1,5-a]pyrimidine hybrids were designed, synthesized and evaluated as potent antitumor agents. These hybrids exhibited relatively high cytotoxic activity against cancer cell line HepG2 (IC50 = 2.86⁻36.34 μM), while normal cell line LO2 was less sensitive to these hybrids (IC50 = 36.37⁻248.39 μM). On the whole, among all the compounds tested, compound 4e, with a mean IC50 value of 2.86 ...[more]

PMID: 30213123

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Project description:The novel heterocyclization of 5-(2-aminophenyl)-1H-tetrazole with potassium ethylxanthogenate or carbon disulfide was proposed. The potassium salt of the tetrazolo[1,5-c]quinazoline-5-thione was subsequently modified by alkylation with proper halogen derivatives to (tetrazolo[1,5-c]quinazolin-5-ylthio)alkyls, N,N-dialkylethylamines, 1-aryl-2-ethanones, 1-(alkyl)aryl-2-ethanols, carboxylic acids, and esters. The structures of all newly synthesized compounds were confirmed by FT-IR, UV-vis, LC-MS, (1)H, (13)C NMR, and elemental analysis data. The substances were screened for antibacterial and antifungal activities (100 μg) against Escherichia coli, Staphylococcus aureus, Enterobacter aerogenes, Entrococcus faecalis, Pseudomonas aeruginosa, Klebsiella pneumoniae, and Candida albicans. Preliminary bioluminescence inhibition tests against Photobacterium leiognathi Sh1 showed that substances 5.2-5.4, 6.1, 7.1 with ethanone or carboxylic acid substituents showed toxicity against bacteria cells. The substances chosen by the US National Cancer Institute (NCI) were screened for their ability to inhibit 60 different human tumor cell lines, where 2-(tetrazolo[1,5-c]quinazolin-5-ylthio)-1-(4-tolyl)ethanone (5.2), 3-(tetrazolo[1,5-c]quinazolin-5-ylthio)propanoic and related 3-metyl-butanoic acids (6.2, 6.3), and ethyl tetrazolo[1,5-c]quinazolin-5-ylthio)acetate (7.2) showed lethal antitumor activity (1.0 μM) against the acute lymphoblastic leukemia cell line (CCRF-CEM), and substances 5.2 and 6.3 exhibited moderate anticancer properties inhibiting growth of the leukemia MOLT-4 and HL06-(TB) cell lines. The moderate antitumor activity was demonstrated in 1-(2,5-dimethoxyphenyl)-2-(tetrazolo[1,5-c]quinazolin-5-ylthio)ethanone (5.4) against the CNS cancer cell line SNB-75. Comparing the docking mode of the Gefitinib and synthesised substances on the ATP binding site of EGFR, it could be assumed that these compounds might act in the same way. The results of the investigation could be considered as a useful base for future development of potent antimicrobials and antitumor agents among tetrazolo[1,5-c]quinazoline-5-thione S-derivatives.

Dataset Information

Synthesis of Spirooxindole-O-Naphthoquinone-Tetrazolo[1,5-a]Pyrimidine Hybrids as Potential Anticancer Agents.

Publications

Synthesis of Spirooxindole-O-Naphthoquinone-Tetrazolo[1,5-a]Pyrimidine Hybrids as Potential Anticancer Agents.

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