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We have designed and synthesized three pyrazole analogs (4, 5a, 5b), pyrazole-based chalcones (6a–6d) and (8a–8h), and N-formyl/acetyl 1,3,5-trisubstituted pyrazoline analogs (7a–7d), (9a–9d). FT-IR, 1H, 13C NMR, and mass spectrometry techniques were used to describe the structures of all the synthesized analogs. The single crystal X-ray method was used to identify the molecular structure of derivatives 4 and 5a. All synthesized analogs were screened by MTT assay on two cancer cell lines, the human lung cancer cell line (A549) and cervical cancer cell line (HeLa). Among all compounds, analog 9d demonstrates significant anticancer activity against HeLa (IC50 = 23.6 μM) and A549 (IC50 = 37.59 μM). The non-interactive interaction of active compound (9d) with Calf thymus DNA (Ct-DNA) has been investigated through various methods, such as UV-vis absorption, emission, cyclic voltammetry and circular …