An Eco‐friendly Synthesis and Biological Screening of Fused Heterocyclic Compounds Containing a Thiophene Moiety via Gewald Reaction

Abstract

5‐Amino‐3‐phenyl‐1‐(2,4,6‐trichlorophenyl)‐1H‐thieno[3,2‐c]pyrazole‐6‐carbonitrile (2) was designed and synthesized by one‐pot multicomponent reaction. Compound 2 was reacted with different reagents to obtain new condensed moieties with our thienopyrazole skeleton. The compounds were prepared by using environmentally benign techniques as microwave irradiation, ultrasonic irradiation, and ball‐milling. The structure of the prepared compounds was elucidated through spectroscopic methods. The new compounds were evaluated for their in vitro antibacterial and antifungal potentialities.

New Pyrazolothiazole as Potential Wnt/β‐Catenin Inhibitors: Green Synthesis, Characterization, Antimicrobial, Antioxidant, Antineoplastic Evaluation, and Molecular Docking Study

“…Microwave‐assisted multicomponent reactions have proved to be the most effective method for the organic synthesis of novel heterocyclic compounds with high yield, short reaction time, high selectivity, atom economy, and simplified purification processes, which can help accelerate the drug development process [34] . In this work, we report an environmentally benign microwave irradiation approach, as part of our research on using eco‐friendly techniques [35–38] . The results (Table 1) showed shorter reaction time, higher yield and purer products compared to conventional ones.…”

“…[34] In this work, we report an environmentally benign microwave irradiation approach, as part of our research on using eco-friendly techniques. [35][36][37][38] The results (Table 1) showed shorter reaction time, higher yield and purer products compared to conventional ones.…”

Ultrasonic‐Assisted condensation of aromatic and aliphatic aldehydes with 3‐(Thiophen‐2‐yl)‐5‐Pyrazolone: Synthesis, characterization and Stereoselective application

“…As a continuation of our research interest in the application of ecofriendly techniques [15, 33, 34], we report an environmentally benign condition (ultrasonic irradiation). The ultrasonic technique afforded the same compounds obtained from the conventional method (melting point, mixed melting point, thin‐layer chromatography [TLC], and spectral analyses).…”

“…Pyrazolone-containing drugs as phenazone, propyphenazone, ampyrone, and metamizole are useful antipyretic and analgesic drugs [11], while edaravone (MCI-186) has been used to treat brain [12] and myocardial ischemia [13,14] (Figure 1). Owning to their wide distribution in nature and essentiality, we have published many papers in this field [15][16][17][18]. In addition to its biological activities, pyrazolone is extensively involved in the manufacture of commercial dyes, such as photographic and textile dyes [19][20][21].…”

Synthesis and cytotoxic activity of some new heterocycles incorporating cyclohepta[b]thiophene‐3‐carboxamide derivatives

“…[7] Such type of scaffolds display attractive feature, due to their ability to act as intermediate for the synthesis of conjugates and hybrid biological active thiophene-containing heterocycles. [8,9] Many therapeutic products such as antipsychotic drug olanzapine I (Figure 1), the non-steroidal anti-inflammatory tinoridine II and the promising anticancer agent Raltitrexed (Tomudex) III are 2-aminothiophene derivatives which, appeared on the market or underwent wide-ranging pharmacological studies, [10][11][12][13][14] also 2-Aminothiophene derivatives exhibited a large spectrum of biological properties that include; Antiplatelet, [15] anxiolytic, [16] anti-diabetes, [15] antioxidant, [17] anti-inflammatory, [18] and antianxiety. [19] In light of the remarkable variety of biological activities realized in thiophene and attached heterocyclic compounds, we reported here the modification of thiophene ring into a variety of novels condensed thiophene derivatives incorporating thiazole, pyrazole, pyridazine, pyridine, and thiophene and investigated their activity as potent anticancer.…”