Design, Synthesis and Anticancer Screening of Novel Pyrazole Derivatives Linking to Benzimidazole, Benzoxazole and Benzothiazole

Abstract

Substituted aromatic amines were diazotized followed by coupling with malononitrile to afford substituted phenyl hydrazono-malononitrile compounds 2a-c. Compounds 3a-c were prepared through the reaction of substituted phenyl hydrazono-malononitriles 2a-c with phenyl hydrazine, while the reaction of compounds 2a-c with hydrazine hydrate afforded diamino compounds 4a-c. The diamino compounds 4a-c was condensed with different substituted aromatic aldehydes to yield N-benzylidine pyrazole diamines 5a-i. The structure of the newly synthesized compounds was confirmed by IR, 1 H NMR, MS spectral data and elemental analysis. Twelve novel compounds 3a-c and 5a-i were screened for their anticancer activities against breast carcinoma (T47D) and human hepatocarcinoma cell lines (Huh-7) compared with Doxorubicin. The detailed synthesis, spectroscopic data and anticancer activities of the synthesized compounds were reported.

Antitumor activities on HL-60 human leukemia cell line, molecular docking, and quantum-chemical calculations of some sulfonamide-benzoxazoles

“…Recently, many efforts have been made to develop safer and more effective ways of treating cancers and to search for novel chemotherapeutic agents with minimal side effects (Caleta et al 2009). In this context, the major challenge is the development of more effective and less toxic new anticancer drugs (Abdelgawad et al 2014).…”

“…Through searching the literature, it was found that benzoxazole derivatives play an important role in the design of new drugs, since they present interesting biological and pharmacological activities, including antimicrobial (Padalkar et al 2012, Yildiz-Oren et al 2004a, antiviral (Plemper et al 2004), antituberculosis (Klimesov a et al 2009), antioxidant, antihelmintic (Satyendra et al 2011), and anticancer (Abdelgawad et al 2014, El-Hady and Abubshait 2015, Kamal et al 2010, Rida et al 2005, Sato et al 2001, Xiang et al 2012 activities.…”

Synthesis, Reactions and Antitumor Activity of Certain 1,3-diphenylpyrazole-4-carboxaldehyde Derivatives

“…Pyrazole showed promising anticancer effects [16][17][18][19][20][21][22]. In search for better antitumor treatment, a large number of pyrazole derivatives were synthesized and tested over the years, the use of this powerful pharmacophore is very popular and modern [23][24][25].…”

Formation of a nanorod shaped ionogel and its high catalytic activity for one-pot synthesis of benzothiazoles

“…[15][16][17] These heterocycles have shown numerous activities including antimicrobial, 18,19 antifungal, 20 anticancer, 21,22 and antitumor. [15][16][17] These heterocycles have shown numerous activities including antimicrobial, 18,19 antifungal, 20 anticancer, 21,22 and antitumor.…”