157796-99-1Relevant articles and documents
Ultrasound-assisted rapid synthesis of 2-aminopyrimidine and barbituric acid derivatives
Bayramo?lu, Duygu,Kurtay, Gülbin,Güllü, Mustafa
, p. 649 - 658 (2020)
Novel, inexpensive, and relatively expeditious procedure to achieve the synthesis of different 2-aminopyrimidine and barbituric acid derivatives is presented here, starting from readily available compounds such as guanidine hydrochloride, urea, 1,3-dialkylurea, or thiourea. Under ultrasonic irradiation, base-driven (Na2CO3, NaOH, or NaOC2H5) heterocyclization reactions of the aforementioned substrates with diethyl malonate, diethyl-2-alkyl malonate, pentane-2,4-dione, or ethyl-3-oxobutanoate yielded corresponding products. Significant advantages of this sonochemical synthetic protocol with regard to the conventional thermal methods include easy reaction setup and work-up steps, reasonably mild conditions, shorter reaction times (～30 min) and comparably high product yields. The characterization of the synthesized compounds was based on melting points, FT-IR, GC-MS, 1H-NMR techniques, and the obtained data were also checked from the previously published studies.
Design and synthesis of some barbituric and 1,3-dimethylbarbituric acid derivatives: A non-classical scaffold for potential PARP1 inhibitors
Eldin A. Osman, Essam,Hanafy, Noura S.,George, Riham F.,El-Moghazy, Samir M.
, (2020/09/16)
Six series based on barbituric acid 5a-e, 10a-d; thiobarbituric acid 6a-e, 11a-d and 1,3-dimethylbarbituric acid 7a-e, 12a-d were prepared and screened for their in vitro PARP1 inhibition. They revealed promising inhibition at nanomolar level especially compounds 5c, 7b, 7d and 7e (IC50 = 30.51, 41.60, 41.53 and 36.33 nM) with higher potency than olaparib (IC50 = 43.59 nM). Moreover, compounds 5b, 5d, 7a, 12a and 12c exhibited good comparable activity (IC50 = 65.93, 58.90, 66.57, 45.40 and 50.62 nM, respectively). Furthermore, the most active compounds 5c, 7b, 7d, 7e, 12a and 12c against PARP1 in vitro were evaluated in the BRCA1 mutated triple negative breast cancer cell line MDA-MB-436 where 5c and 12c showed higher potency compared to olaparib and result in cell cycle arrest at G2/M phase. 5c and 12c showed apoptotic effects in MDA-MB-436 and potentiated the cytotoxicity of temozolomide in A549 human lung epithelial cancer cell line. Compounds 5c and 12c represent interesting starting points towards PARP1 inhibitors.
Synthesis, characterization, solvatochromic properties, and antimicrobial evaluation of 5-acetyl-2-thioxo-dihydro-pyrimidine-4,6-dione-based chalcones
Dhorajiya, Bhaveshkumar D.,Bhakhar, Bhimji S.,Dholakiya, Bharatkumar Z.
, p. 4075 - 4086 (2013/09/02)
A new series of chalcone analogs namely 5-(3-phenyl-acryloyl)-2-thioxo- dihydro-pyrimidine-4,6-dione have been synthesized from the key intermediate 5-acetyl-2-thioxo-dihydro-pyrimidine-4,6-dione 4′ with different aldehyde derivatives were performed to get the target compounds as thiobarbituric acid-based chalcones 5(a′-k′) and they were obtained in excellent yields. The newly synthesized compounds were characterized by spectral analysis (FT-IR, 1H NMR, 13C NMR, and UV spectroscopy) and elemental analysis. The synthesized compounds were evaluated for their antimicrobial activity against five bacterial strains (S. aureus, S. pyogenes, E. coli, K. pneumoniae, and P. aeruginosa) and four fungal strains (C. albicans, A. clavatus, T. rubrum, and Penicillium wild strain). Among the screened compounds, 5e′ and f′ showed comparable activity (minimum inhibitory concentration = 500 μg/mL) nearly to that of standard antibiotics griseofulvin.
