18269-12-0Relevant academic research and scientific papers
Hydrophobic mesoporous poly(ionic liquid)s towards highly efficient and contamination-resistant solid-base catalysts
Wang, Xiaochen,Li, Jing,Chen, Guojian,Guo, Zengjing,Zhou, Yu,Wang, Jun
, p. 993 - 1003 (2015)
Mesoporous poly(ionic liquid)s were synthesized by radical copolymerization of the ionic liquid 1-aminoethyl-3-vinylimidazolium bromide with divinylbenzene plus the ion exchange of bromide anions with hydroxyls. Characterizations revealed the high ionic l
One-Pot Knoevenagel and [4 + 2] Cycloaddition as a Platform for Calliviminones
Roy, Pritam,Anjum, S. Rehana,Ramachary, Dhevalapally B.
supporting information, p. 2897 - 2901 (2020/04/15)
Bioactive compounds featuring an unusual core of spiro[5.5]undecenes and calliviminones were synthesized in very good yield with good regio- and diastereoselectivities through a one-pot Knoevenagel and [4 + 2] cycloaddition from the readily available aldehydes, cyclic-1,3-diones, dienes, and a catalytic amount of (s)-proline.
Synthesis, antitumor activity and molecular docking studies on seven novel thiazacridine derivatives
Almeida, Marcel L.,Dos Santos, Flaviana A.,Pereira, Michelly C.,Pitta, Ivan R.,Pitta, Maira G. R.,Pitta, Marina G. R.,Viana, Douglas C. F.,da Costa, Valécia C. M.,de Melo Rêgo, Moacyr J. B.
, p. 359 - 368 (2020/07/16)
Aim and Objective: In the last decades, cancer has become a major problem in public health all around the globe. Chimeric chemical structures have been established as an important trend on medicinal chemistry in the last years. Thiazacridines are hybrid molecules composed of a thiazolidine and acridine nucleus, both pharmacophores that act on important biological targets for cancer. By the fact it is a serious disease, seven new 3-acridin-9-ylmethyl-thiazolidine-2,4-dione derivatives were synthesized, characterized, analyzed by computer simulation and tested in tumor cells. In order to find out if the compounds have therapeutic potential. Materials and Methods: Seven new 3-acridin-9-ylmethyl-thiazolidine-2,4-dione derivatives were synthesized through Michael addition and Knoevenagel condensation strategies. Characterization was performed by NMR and Infrared spectroscopy techniques. Regarding biological activity, thiazacridines were tested against solid and hematopoietic tumoral cell lines, namely Jurkat (acute T-cell leukemia); HL-60 (acute promyelocytic leukemia); DU 145 (prostate cancer); MOLT-4 (acute lymphoblastic leukemia); RAJI (Burkitt's lymphoma); K562 (chronic myelogenous leukemia) and normal cells PBMC (healthy volunteers). Molecular docking analysis was also performed in order to assess major targets of these new compounds. Cell cycle and clonogenic assay were also performed. Results: Compound LPSF/AA-62 (9f) exhibited the most potent anticancer activity against HL-60 (IC50 3,7±1,7 μM), MOLT-4 (IC50 5,7±1,1 μM), Jurkat (IC50 18,6 μM), Du-145 (IC50 20±5 μM) and Raji (IC50 52,3±9,2 μM). While the compound LPSF/AA-57 (9b) exhibited anticancer activity against the K562 cell line (IC50 51,8±7,8 μM). Derivative LPSF/AA-62 (9f) did not interfere in the cell cycle phases of the Molt-4 lineage. However, the LPSF/AA-62 (9f) derivative significantly reduced the formation of prostate cancer cell clones. The compound LPSF/AA-62 (9f) has shown strong anchorage stability with enzymes topoisomerases 1 and 2, in particular due the presence of chlorine favored hydrogen bonds with topoisomerase 1. Conclusion: The 3-(acridin-9-ylmethyl)-5-((10-chloroanthracen-9-yl)methylene)thiazolidine-2,4-dione (LPSF/AA-62) presented the most promising results, showing anti-tumor activity in 5 of the 6 cell types tested, especially inhibiting the formation of colonies of prostate tumor cells (DU-145).
DABCO-catalyzed Knoevenagel condensation of aldehydes with ethyl cyanoacetate using hydroxy ionic liquid as a promoter
Meng, Dan,Qiao, Yongsheng,Wang, Xin,Wen, Wei,Zhao, Sanhu
, p. 30180 - 30185 (2018/09/11)
N-(2-Hydroxy-ethyl)-pyridinium chloride ([HyEtPy]Cl) was synthesized and explored as a novel promoter for 1,4-diazabicyclo [2.2.2] octane (DABCO)-catalyzed Knoevenagel condensation reactions, which showed better catalytic activity compared to other ionic liquid (IL) that had no hydroxyl group attached to the IL scaffold. The effect of hydrogen bond formation between the hydroxyl group of [HyEtPy]Cl and the carbonyl group of aldehyde played an important role in the Knoevenagel condensation reaction. In the [HyEtPy]Cl-H2O-DABCO composite system, Knoevenagel condensation reactions proceeded smoothly and cleanly, and the corresponding Knoevenagel condensation products were obtained in good to excellent yields in all cases examined. This protocol provides a versatile solvent-catalyst system, which has notable advantages such as being eco-friendly, ease of work-up and convenient reuse of the ionic liquid.
An efficient Knoevenagel condensation of aldehydes with active methylene compounds over novel, robust CeZrO4?δ catalyst
Sahani, Amber J.,Burange, Anand S.,Jayaram, Radha V.
, p. 7805 - 7814 (2018/09/12)
Abstract: In the present work, we explored novel CeZrO4?δ as a catalyst for Knoevenagel condensation of aldehydes with reactive methylene compounds like malononitrile and ethylcyanoacetate. For the present study, ceria, zirconia and CeZrO4
Mn-MOF@Pi composite: synthesis, characterisation and an efficient catalyst for the Knoevenagel condensation reaction
Rambabu, Darsi,Ashraf, Mohammad,Pooja,Gupta, Ankush,Dhir, Abhimanew
supporting information, p. 4691 - 4694 (2017/11/17)
We have synthesised new Mn-MOF@Pi composite by encapsulation of piperidine in desolvated Mn-MOF and investigated its catalytic performance in Knoevenagel condensation reaction. The newly developed composite is compatible with various aromatic aldehydes an
Highly stable naphthalene core based novel cleft-shaped strain molecule: Influence of intermolecular H-bonding architectures
Panja, Sumit Kumar,Dwivedi, Nidhi,Saha, Satyen
, p. 59574 - 59581 (2016/07/06)
The significance of intermolecular classical and non-classical H-bonding interactions in the stabilization of a naphthalene core based conformationally rigid cleft-shaped 1,5-dioxocin (BNAP) is presented here. The importance of H-bonding interactions to a
First report of the application of simple molecular complexes as organo-catalysts for Knoevenagel condensation
Panja, Sumit Kumar,Dwivedi, Nidhi,Saha, Satyen
, p. 65526 - 65531 (2015/08/18)
A series of molecular complexes have been designed, synthesized and used as organo-catalysts for the first time for very efficient Knoevenagel condensation. Molecular complexes are thermally stable, easily recyclable, and have a low cost of preparation. T
Stereoselective synthesis of vic-halohydrins and an unusual Knoevenagel product from an organocatalyzed aldol reaction: A non-enamine mode
Thorat,Goswami,Sondankar,Bhusare
, p. 1093 - 1100 (2015/07/01)
Stereoselective synthesis by an aldol reaction between chloroacetone and aldehyde was studied using a synthesized chiral organocatalyst and triethylamine. The reaction gave α-chloro-β-hydroxy ketones in excellent yield with high anti selectivity and enantioselectivity. The chiral organocatalyst was also used in the Knoevenagel reaction, which gave α-cyano-β-hydroxy ketones at a low temperature and the usual Knoevenagel product at a high temperature. Both products were obtained in good to moderate yield with good anti selectivity in the case of α-cyano-β-hydroxy ketone derivatives.
Synthesis and antibacterial activity of ethyl 2-amino-6-methyl-5-oxo-4- aryl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate
Asghari, Sakineh,Ramezani, Samaneh,Mohseni, Mojtaba
, p. 431 - 434 (2014/03/21)
The three-component reaction of 4-hydroxy-1-methyl-2(1H)-quinolinone, aromatic aldehydes and ethyl cyanoacetate was carried out in the presence of a catalytic amount of 4-dimethyl aminopyridine (DMAP) in aqueous ethanol. The reactions result in the format
