Green Expedient Synthesis of Pyrimidine Derivatives via Chalcones and Evaluation of their Anthelmintic Activity

Abstract

Objective: In the present study, we focused on the environment-friendly processes used for the preparation of pyrimidine derivatives with pharmacological properties. In this regard, microwave heating is used as the alternative energy sources to synthesize a series of pyrimidine derivatives by the condensation of chalcones with urea under basic conditions. Chalcones were synthesized by Claisen-Schimidt condensation of acetophenone with various substituted benzaldehyde in the presence of ethanolic potassium hydroxide solution. Methods: The IR, 1 H-NMR, mass spectra and CHN analyses confirmed the structure of the prepared compounds. Shorter reaction time, environment friendly procedure and excellent yields are the advantages of microwave synthesis. The newly synthesized pyrimidine derivatives were screened for their anthelmintic activity and found to have moderate to considerable activity as compared to the standard drug. Results: Some of the synthesized compounds exhibited significant anthelmintic activity. Compound 4e with electron withdrawing groups was found to be highly potent among the series. This attempt will lead to an increased number of new and sustainable methods for the synthesis of biologically-active pyrimdine derivatives.

Recent Advances in Chalcones: Synthesis, Transformation and Pharmacological Activities

“…Meanwhile, Aswin et al reported pyrimidine-2(1H)-thione 20 from the condensation of chalcone 19 with thiourea using triphenylphosphine (PPh 3 ) as a catalyst [10]. Pyrimidine derivatives 22 were also reported from chalcones 21 with urea in the presence of ethanolic potassium hydroxide solution [11] (Scheme 4).…”

“…Chalcones transformation might proceed either by 1,4-addition or 1,2-addition. Examples of heterocyclic compounds from chalcones are pyrazoles [1,2], pyrroles [3][4][5], pyrazoline [6], isoxazoles [7][8][9], pyrimidines [10,11], pyridines [12][13][14][15][16], indoles, indazoles, triazoles [17,18], imidazoles [19,20], thiazines [21], 1,5-benzodiazepines, 1,3,4-thiadiazepines, benzoazepines, and 1,5-benzodiazepines [22]. Chalcones are multifunctional molecules that possess promising pharmacological activities.…”

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

“…[53,54] antifungal, [55,56] antiviral, [57][58][59] antibacterial, [60] antimalarial, [61] anti-HIV, [62,63] antiulcer, [64] insecticide, [65] antineoplastic, [66] antiepileptic, [67] analgesic, [68] and anthelmintic. [69] Several commercially available drugs derived from pyrimidine are sildenafil (viagra), formycin A, [70] sulfadiazine, [71] pyrimethamine, [72] roscovitine, [73] indiplon, zaleplon, [74] ocinaplon, [75] dinaciclib, [75] fluorastrol, [76] 5-fluorouracil, [77] ispinesib, [78] volasertib, [79] pictilisib, monastrol, [80] and etravirine [81] (Figure 2).…”

Solvent-free synthesis of new chalcone derivatives from 3-nitro phthalic acid and evaluation of their biological activities

“…Chalcones can be produced by biosynthesis, and chemical synthesis [4]. They possess a wide spectrum of biological activities such as amoebicidal [5], antiviral [6], antiprotozoal [7], anticancer [8], antihelmintic [9], antiulcer, insecticidal [10], antioxidative [11], antibacterial [12], and cytotoxic [13]. The relationship between different composition of chalcones with improved good pharmacological properties became rich substance to work for many years ago.…”