Anticancer activity of novel Schiff bases and azo dyes derived from 3-amino-4-hydroxy-2H-pyrano[3,2-c]quinoline-2,5(6H)-dione

Abstract

New Schiff bases and azo dyes derivatives have been synthesized via appropriate conventional methods using pyranoquinolinone as a starting material. The compounds obtained were characterized by spectral analysis and evaluated for anticancer activity in several human tumor cell lines: MCF-7 breast cancer, HepG2 liver cancer and HCT-116 colon carcinoma. 5-fluorouracil was used as a reference drug. The in vitro cytotoxicity screening results revealed that all tested compounds showed promising activity against MCF-7 cells. In particular, compounds 6a, 6b, and 7b showed excellent activity against the three human tumor cell lines. Structure-activity relationship studies indicated that the azo derivative with a trifluoromethoxy group (compound 7b) was the most potent candidate against the three human tumor cell lines (IC50, 1.82-8.06 μg/mL). Our findings highlight pyranoquinolinone analogues as a promising class of compounds for new anticancer therapies.

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“…The physical properties of prepared compounds are listed in Table 1. The FT-IR spectrum (Table 2) for compounds (11)(12)(13)(14)(15)(16)(17) showed a stretching new band in range of 1446-1521 cm -1 due to N-N triazole and N-H amide appearance at the range of 3159-3286 cm -1 .…”

“…2 drops of glacial acetic acid (0.1 mL) was added to different derivatives of aldehydes (2 mmol) and refluxed for 15-20 min, then N,N'-bis (2-amino aceto hydrazide) pyromellitic diimide compound (3) (0.4 g, 1 mmol) was added and refluxed for 3-6 h, controlled by TLC; the product was dried and washed with ether, recrystallized from di ethyl ether and petroleum ether (Scheme 1). (11)(12)(13)(14)(15)(16)(17) Benzonitrile (0.2 mL, 2 mmol) was added to Shiff basses compounds (11)(12)(13)(14)(15)(16)(17)(18)(19) dissolved in (butanol or ethanol) in presence of K2CO3 and refluxed for 24 h. The product was dried and recrystallized from petroleum ether (Scheme 1).…”

“…Scheme 1:The chemical steps for the synthesis of compounds(1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) …”

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“…Although sulfonamides were used before penicillin, they are still utilized today to prevent bacterial development [13,14]. These drugs, known as sulfa drugs, are pharmacologically important compounds with numerous clinical applications and are successfully applied to treat both Gram-positive and Gram-negative bacteria [15][16][17]. Sulfonamides have been utilized to treat cancer as a chemotherapeutic agent and a number of diseases greater than antifungals, non-peptide vasopressin receptor antagonists, antihypertensive agents, anti-inflammatory, antibacterial, translation initiation inhibitors, antineoplastic agents, diuretics, thyroid inhibitors, antitumor, carbonic anhydrase inhibitors, and glucocorticoid inhibitors are among the 30 sulfonamide derivatives in clinical use [18][19][20][21].…”

Physicochemical Properties of a Bi-aromatic Heterocyclic-Azo/BSA Hybrid System at the Air–Water Interface

“…Azo-heterocyclic compounds have been tremendously developed in the last few decades having valuable activity in biological fields. 11 − 13 But the amount of literature on mixed N-heterocyclic azo compounds is limited in literature. 14 − 16 In these azo-biheterocyclic compounds, the presence of a −N=N–C=N- azo–imine, functional group between two N-heterocyclic substances promotes their activity.…”