Photochemical synthesis and anticancer activity of barbituric acid, thiobarbituric acid, thiosemicarbazide, and isoniazid linked to 2-phenyl indole derivatives

Abstract

2-Phenyl-1H-indole-3-carbaldehyde-based barbituric acid, thiobarbituric acid, thiosemicarbazide, isoniazid, and malononitrile derivatives were synthesized under photochemical conditions. The antitumor activities of the synthesized compounds were evaluated on three different human cancer cell lines representing prostate cancer cell line DU145, Dwivedi (DWD) cancer cell lines, and breast cancer cell line MCF7. All the screened compounds possessed moderate anticancer activity, and out of all the screened compounds, 5-{1[2-(4-chloro-phenyl)2-oxo-ethyl]-2-phenyl-1H-indole-3-ylmethylene}-2-thioxo-dihydro-pyrimidine-4,6-dione (2b) and 5-{1[2-(4-methoxy-phenyl)2-oxo-ethyl]-2-phenyl-1H-indole-3-ylmethylene}-2-thioxo-dihydro-pyrimidine-4,6-dione (2d) exhibited marked antitumor activity against used cell lines. Additionally, barbituric acid derivatives were selective to inhibit cell line DWD and breast cancer cell lines.

Contribution of Knoevenagel Condensation Products toward the Development of Anticancer Agents: An Updated Review

“…(NMP‐1) (Figure 5). Similarly, Rao and his group [76] synthesised 3‐barbituric or thiobarbituric acid condensed indole derivatives via Knoevenagel reaction and evaluated against three cancer cell lines. The most potent compound 35 is thiobarbituric acid derivative and showed significant activity with a GI 50 value of 28.43 and 38 μM against MCF‐7 and DU145 (Human prostate cancer) cell lines, respectively (Figure 5).…”

Antifibrotic Effects of a Barbituric Acid Derivative on Liver Fibrosis by Blocking the NF-κB Signaling Pathway in Hepatic Stellate Cells

“…Although barbituric acid is not pharmacologically active, it can form a large variety of derivatives called barbiturates that have been used in many ways (Shahzad et al, 2016). Barbituric acid derivatives possess different biological activities, such as hypnotic (Shonle and Moment, 1923;Wisner, 1925), sedative (Kliethermes et al, 2004), anticonvulsant (Srivastava and Kumar, 2004), antimicrobial (Dhorajiya et al, 2014), antiviral (Marecki et al, 2019), anti-inflammatory (Xu et al, 2016), anticancer, and antitumor properties (Singh et al, 2009;Penthala et al, 2015;Laxmi et al, 2016). In 2011, a study showed that a novel barbituric and thiobarbituric acid derivative inhibited high-fat/high-calorie diet-induced nonalcoholic fatty liver disease in male Wistar rats .…”

Dihydropyrimidines as Precursors for Synthesizing of Oxoketene gem-Dithiol and 1,2-Dithiol-3-Thione, a Facile Synthesis and Convenient Reaction Transformations

“…[17] On the other hand indole containing heterocycles were used as antiinflammatory, anticonvulsant agents, antitumor agents in the human cell line and cardioselective antiischemic ATP-sensitive potassium channel (KATP) opener activity. [18,19] Anticancer activity of various tricyclic and tetracyclic indoles, against human Egyptian Journal of Chemistry http://ejchem.journals.ekb.eg/ nasopharyngeal carcinoma (HONE-1) and gastric adenocarcinoma (NUGC-3) cell lines were studied by Hong et al [3,20] Khaledi et al [21], synthesized some indole derivatives which have antioxidant activities on DPPH radical scavenging and inhibition of lipid peroxidation. [21] The in vitro cytotoxic activities of the compounds bearing indole nucleus were evaluated against HCT-116 (human colon cancer cell line) and MCF-7 (estrogen dependent human breast cancer cell line).…”