1‐Acetyl‐3,5‐diaryl‐4,5‐dihydro(1H)pyrazoles: Exhibiting Anticancer Activity through Intracellular ROS Scavenging and the Mitochondria‐Dependent Death Pathway

Abstract

A series of 17 analogs of 1-acetyl-4,5-dihydro(1H)pyrazoles (JP-1 to JP-17) bearing two aromatic rings at positions 3 and 5, either of which ought to be heterocyclic, were synthesized and evaluated for their anti-proliferative potential against breast cancer (MCF-7 and T-47D) and lung cancer (H-460 and A-549) cell lines for the first time. JP-1-7, -10, -11, -14, and -15 were observed to exhibit significant anti-proliferative activity against MCF-7 cells. Some notions about structure-activity relationships are reported. The investigated compounds were found to lower the intracellular reactive oxygen species in the H2 DCFDA assay and also caused mitochondria-dependent cell death in the MCF-7 cell line, indicating a plausible mechanism of their anticancer effect.

Larvicidal activity of substituted chalcones against Aedes aegypti (Diptera: Culicidae) and non‐target organisms

“…All the chalcone derivatives synthesized (3a-3f and 6a-6f) were characterized by 1 H-NMR, 13 C-NMR, and FTIR spectroscopy, and the results corroborated literature data. 30,34,[49][50][51][52][53][54][55][56][57][58][59][60]…”

Unanticipated Cleavage of 2-Nitrophenyl-Substituted N-Formyl Pyrazolines under Bechamp Conditions: Unveiling the Synthesis of 2-Aryl Quinolines and Their Mechanistic Exploration via DFT Studies

“…2-Pyrazoline and its derivatives such as N -alkanoyl/aroylpyrazolines find wide applications 1 as medicinal agents, 2 possess optical properties, 3 act as chemosensors in bioimaging, 4 and serve as synthetic intermediates. 5 A few literature reports are available on decomposition of 1-pyrazoline 6 ( a ) under thermal and photochemical conditions, which leads to the formation of (Scheme 1i) cyclopropane ( c ) via 1,3-biradical 6a ( b ) and the formation and extrusion of nitrogen gas (Scheme 1ii).…”

Pyrimidine containing epidermal growth factor receptor kinase inhibitors: Synthesis and biological evaluation

“…[12,13] However, early Phase I clinical trials of third-generation EGFR inhibitors are found to be promising and effective, but they are likely to produce off-target side-effects and toxicities after their prolonged use. [14,15] Thus, based on our previous experiences in anticancer drug discovery, [16][17][18][19][20][21][22][23][24] we have designed the target compounds (Figure 2) considering the common pharmacophoric features of erlotinib (reversible) and WZ4002 (irreversible) [25] with the assumptions that compounds should: (a) possess pyrimidine ring with 2-alkoxy/ hydroxyl aniline moiety for hydrogen bond interaction with MET793, (b) be able to selectively target hypoxic tumours by possessing nitro substituent on either or both the aromatic rings with/without solubility enhancer due to their bioreduction to yield electrophilic substances which are capable of damaging protein and nucleic acids [24,26] and have radiosensitizing ability, [27] (c) be reversible and non-covalent in nature as irreversible inhibitors not only make covalent interactions with CYS797 of target but also undergo conjugate addition with other nucleophiles in the body due to their Michael acceptor property, thereby leading to off-target side-effects and, (d) be easy to synthesize and cost-effective.…”