58896-42-7Relevant academic research and scientific papers
1-Butyl-1-methylpyrrolidinium hydrogen sulfate-promoted preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one derivatives
Ghashang, Majid
, p. 2187 - 2195 (2013)
A convenient preparative approach for synthesis of various 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones promoted by 1-butyl-1- methylpyrrolidinium hydrogen sulfate is developed which involves cyclocondensation of aldehydes with amines and ethyl pyruvate under ambient conditions. Graphical abstract: A convenient preparative approach for synthesis of various 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones promoted by 1-butyl-1-methylpyrrolidinium hydrogen sulfate is developed which involves cyclocondensation of aldehydes with amines and ethyl pyruvate under ambient conditions.[Figure not available: see fulltext.]
3-Vinylazetidin-2-Ones: Synthesis, antiproliferative and tubulin destabilizing activity in MCF-7 and MDA-MB-231 Breast Cancer Cells
Wang, Shu,Malebari, Azizah M.,Greene, Thomas F.,O’Boyle, Niamh M.,Fayne, Darren,Nathwani, Seema M.,Twamley, Brendan,McCabe, Thomas,Keely, Niall O.,Zisterer, Daniela M.,Meegan, Mary J.
, (2019/08/12)
Microtubule-targeted drugs are essential chemotherapeutic agents for various types of cancer. A series of 3-vinyl-β-lactams (2-azetidinones) were designed, synthesized and evaluated as potential tubulin polymerization inhibitors, and for their antiproliferative effects in breast cancer cells. These compounds showed potent activity in MCF-7 breast cancer cells with an IC50 value of 8 nM for compound 7s 4-[3-Hydroxy-4-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-3-vinylazetidin-2-one) which was comparable to the activity of Combretastatin A-4. Compound 7s had minimal cytotoxicity against both non-tumorigenic HEK-293T cells and murine mammary epithelial cells. The compounds inhibited the polymerisation of tubulin in vitro with an 8.7-fold reduction in tubulin polymerization at 10 μM for compound 7s and were shown to interact at the colchicine-binding site on tubulin, resulting in significant G2/M phase cell cycle arrest. Immunofluorescence staining of MCF-7 cells confirmed that β-lactam 7s is targeting tubulin and resulted in mitotic catastrophe. A docking simulation indicated potential binding conformations for the 3-vinyl-β-lactam 7s in the colchicine domain of tubulin. These compounds are promising candidates for development as antiproiferative microtubule-disrupting agents.
Silica gel supported sodium hydrogen sulfate as an efficient and reusable heterogeneous catalyst for the synthesis of imines in solvent-free conditions under microwave irradiation
Gopalakrishnan, Mannathusamy,Sureshkumar, Purushothaman,Kanagarajan, Vijayakumar,Thanusu, Jeyaraman,Govindaraju, Ramalingam
, p. 299 - 303 (2007/10/03)
This synthesis of imines has been carried out efficiently by the condensation of carbonyl compounds with amines in the presence of silica gel supported sodium hydrogen sulfate (NaHSO4.SiO2) as a heterogeneous catalyst under microwave irradiation in solvent-free conditions. NaHSO4.SiO2 can be recovered and re-used up to ten times by simple washing with diethyl ether after each use and activated in an oven at 120°C for 1 h, thus rendering the process more economical.
Magnesium perchlorate as an efficient catalyst for the synthesis of imines and phenylhydrazones
Chakraborti, Asit K.,Bhagat, Srikant,Rudrawar, Santosh
, p. 7641 - 7644 (2007/10/03)
Magnesium perchlorate has been found to be an efficient catalyst for the synthesis of imines and phenylhydrazones by the reaction of carbonyl compounds with amines and phenylhydrazine in high yields at room temperatures and in short times. The condensation of less electrophilic carbonyl compounds with poorly nucleophilic amines affords the imines in excellent yields.
