57845-08-6Relevant articles and documents
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 and Anti-Proliferative Activity of New α-Amino Phosphonate Derivatives Bearing Heterocyclic Moiety
Abdelwahed, Ramzy E.,Awad, Hanem M.,El Gokha, Ahmed A.,El Sayed, Ibrahim El-Tantawy,Goda, Adel E-S.,Radhi, Ahmed Habeeb
, (2021/06/17)
Condensation of 4-chloroacetophenone 1 with phenyl hydrazine 2 afforded hydrazone 3. Further reaction of 3 with Vilsmeier reagent yielded the pyrazolaldehyde 4 in excellent yield. A one-pot, three-component reaction between aldehyde 4, triphenylphosphite 5, and appropriate amines in the presence of lithium perchlorate as Lewis acid catalyst gave the corresponding α-amino phosphonates 7-12(a-d) in good yields. The chemical structures of all new compounds were established by IR, 1H NMR, and mass spectroscopy analysis. The anti-proliferative activity of the synthesized compounds against HCT-116, HepG2 and MCF-7 human cancer cells using the MTT assay was evaluated, and revealed higher anticancer activity when compared with reference drug doxorubicin. Among the tested compounds, pyrazole derivatives 4 and 9 exhibited the highest anticancer activity against breast (MCF-7), and colon (HCT-116) cancer cell lines with IC50 = 2.7 and 3.3 μM, respectively.
B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions
Yuan, Wenkai,Huang, Jie,Xu, Xin,Wang, Long,Tang, Xiang-Ying
supporting information, p. 7139 - 7143 (2021/09/14)
An efficient B(C6F5)3-catalyzed aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed, affording a wide range of diaryl sulfides in good yields. An electron donor-acceptor complex between B(C6F5)3 and indoles was formed, facilitating the photoinduced single-electron transfer (SET) from indole substrates to the B(C6F5)3 catalyst. This protocol demonstrates a new reaction model using B(C6F5)3 as a single-electron oxidant.
