618-73-5Relevant articles and documents
Manning,Nierenstein
, p. 1547 (1912)
Design and synthesis of pyrazole–pyrazoline hybrids as cancer-associated selective COX-2 inhibitors
Akhtar, Wasim,Marella, Akranth,Alam, Mohammad Mumtaz,Khan, Mohemmed F.,Akhtar, Mymoona,Anwer, Tariq,Khan, Farah,Naematullah, Md.,Azam, Faizul,Rizvi, Moshahid A.,Shaquiquzzaman, Mohammad
, (2020/10/09)
In continuation of our previous work on cancer and inflammation, 15 novel pyrazole–pyrazoline hybrids (WSPP1–15) were synthesized and fully characterized. The formation of the pyrazoline ring was confirmed by the appearance of three doublets of doublets in 1H nuclear magnetic resonance spectra exhibiting an AMX pattern for three protons (HA, HM, and HX) of the pyrazoline ring. All the synthesized compounds were screened for their in vitro anticancer activity against five cell lines, that is, MCF-7, A549, SiHa, COLO205, and HepG2 cells, using the MTT growth inhibition assay. 5-Fluorouracil was taken as the positive control in the study. It was observed that, among them, WSPP11 was found to be active against A549, SiHa, COLO205, and HepG2 cells, with IC50 values of 4.94, 4.54, 4.86, and 2.09 μM. All the derivatives were also evaluated for their cytotoxicity against HaCaT cells. WSPP11 was also found to be nontoxic against normal cells (cell line HaCaT), with an IC50 value of more than 50 μM. The derivatives were also evaluated for their in vitro anti-inflammatory activity by the protein (egg albumin) denaturation assay and the red blood cell membrane stabilizing assay, using diclofenac sodium and celecoxib as standard. Compounds that showed significant anticancer and anti-inflammatory activities were further studied for COX-2 inhibition. The manifestation of a higher COX-2 selectivity index of WSPP11 as compared with other derivatives and an in vitro anticancer activity against four cell lines further established that compounds that were more selective toward COX-2 also exhibited a better spectrum of activity against various cancer cell lines.
Synthesis, characterization and antibacterial evaluation of 2, 3dihydroquinazolin-4 (1h)-ones and some new bis 2, 3-dihydroquinazolin-4 (1h)-ones using pre-made pyrazole carbaldehyde derivatives
Mahmoodi, Nosrat Ollah,Sina, Kiana Faraji,Yahyazadeh, Asieh
, p. 176 - 182 (2021/03/19)
2, 3-Dihydroquinazolinones are of popular compounds with the diversification of biological and pharmacological activities. Among many discovered methods, there are efficient and convenient methods used for the synthesis of 2, 3-dihydroquinazoline-4 (1H)-one and some new bis 2, 3-dihydroquinazoline-4 (1H)-one derivatives which are reported in this study. The mentioned methods include the two-component condensation of one molecule of anthranilamide and one molecule of pyra-zole carbaldehyde using montmorillonite-K10 as a catalyst for the preparation of 2, 3 dihydroquinazo-line-4 (1H)-ones. Also, one-pot pseudo-five-component reaction (5MCRs) of two molecules of isatoic anhydride, two molecules of pyrazole carbaldehydes and one molecule of ethan-1, 2-diamine in the presence of the r catalyst (montmorillonite-K10) for the synthesis of bis 2, 3-dihydroquinazoline-4 (1H)-ones. Despite the short times of reactions, high yields of products were obtained, which were val-idated using FT-IR,1HNMR,13CNMR, and elemental analysis. Moreover, the compounds were screened for their antimicrobial activities against two-gram-positive bacterial strains: Staphylococcus aureus and Micrococcus Luteus; and against two-gram-negative bacterial strains, as well: Escherichia coli and Pseudomonas aeruginosa, which all were utilized for antibacterial investigations. The results showed moderate or significant antibacterial activities.
