Synthesis of novel bis-anthraquinone derivatives and their biological evaluation as antitumor agents

Abstract

Cancer has become a major worldwide problem and drug resistance now is one of the most important problems in treatment of cancer. Anthraquinone derivatives represent one of the most important drugs that can be used in treatment of many types of cancer. In this study two series of novel bis-anthraquinone derivatives have been synthesized. Five of these compounds were chosen to be evaluated for their antitumor activity against human cancer cell lines by the National Cancer Institute (NCI, USA). Marked activity was shown for the tested compounds(2-6). The most active one was compound 6 with mean value -67.00 against all cell lines. Compounds 7 and 8 were found inactive.

Synthesis, Docking and Biological Activities of Novel Hybrids Celecoxib and Anthraquinone Analogs as Potent Cytotoxic Agents

“…On the other hand 2-aminoanthraquinone 8 was reacted with the same series of chloroacyl chlorides or oxalyl dichloride to give the intermediates 2- or 4-chloro- N -(9,10-dihydro-9,10-dioxoanthracen-2-yl) alkanamides 9a – c , 9a was obtained according to a previously reported method [ 20 ] or 2-((9,10-dihydro-9,10-dioxoanthracen-2-yl)amino)-2-oxoacetyl chloride 9d according to the reported method [ 21 ], which on reaction with celecoxib 1 gave the target compounds 10a – d . Compound 8 was also reacted with 2-chloroethylisocyanate to give the intermediate 11 according to the reported method [ 12 ] which was then reacted with celecoxib 1 to give the final compound 12 ( Scheme 2 ). It is clear that compounds 3a – c are isomers for compounds 10a – c , while compound 10d can be obtained by applying the same method applied for preparation of compounds 3a – c .…”

“…Several new clinical studies were performed on celecoxib, a selective Cox-2 inhibitor which proved its effectiveness in many types of cancer including colorectal cancer, prostate cancer, breast cancer, non-small cell lung cancer [ 8 , 9 ], ovarian cancer [ 10 ], head and neck squamous cell carcinoma [ 11 ]. Another potential mechanism for anticancer agents is by targeting the DNA by intercalating agents such as anthraquinones [ 12 ]. These compounds have long been used as effective anticancer drugs against a broad spectrum of tumors.…”

Anticancer activity of some polyamine derivatives on human prostate and breast cancer cell lines

“…It results in higher DNA affinity and sequence selectivity in comparison to corresponding monointercalating agents (Brana et al, 2001;Lorente et al, 2004;Tse & Boger 2004). In addition, a positive correlation between cytotoxic potency and the strength of reversible DNA binding for bisintercalators has been observed (Taher & Hegazy, 2013).…”

Synthesis and cytotoxic activity of certain benzothiazole derivatives against human MCF‐7 cancer cell line

“…DNA has proven to be an important target in cancer therapy. The planar structure of DNA intercalating drugs can strongly bind to DNA resulting in the death of cancer cells …”

“…The planar structure of DNA intercalating drugs can strongly bind to DNA resulting in the death of cancer cells. [5] Although many classes of drugs are being used for the treatment of breast cancer, as axitinib, methotrexate, raloxifene, and doxorubicin, the need for more potent selective antitumor agents is still not precluded [6] (Figure 1). The benzothiazole ring system shows diversity of biological activities as anxiolytic, antiallergic, cardiovascular, antidiabetic, antipsychotic, and antioxidant effect.…”