52835-63-9Relevant academic research and scientific papers
Design, synthesis of novel pyrazolopyridine derivatives and CREBBP bromodomain inhibitors docking and molecular dynamics
Aruna, S.,Girija, R.,Saamanthi, M.,Vinod, D.
, p. 746 - 754 (2021/09/28)
A sequence of novel compounds pyrazolopyridine have been prepared by a general synthetic method. Due to high efficiency and selectivity, anticancer agents consisting of combined molecules have gained great interests. The IC50 values have been determined against cell line U937, the results obtained indicate the potential effects against cancer cell line. The cell potency of cell line is best for compounds 4a IC50 = 62.5 μM, 5b IC50 = 62.5 μM,4b IC50 = 31.2 μM, 4e IC50 = 31.2 μM), selectivity and in vivo. Further, the molecular docking studies indicate that substituted pyrazolo[4,3-c]pyridine derivatives show good anticancer activity in the medicinal field. The ease of synthesis and the significant biological activities make these compounds potential new frameworks for progress of cancer therapeutics. Compound 4f shows anticancer effect in cancer cell lines and in vivo that corresponds with antitumor activity in an AML cancer type. For the molecular docking with the ligands, the RMSD value has been calculated, the protein with the least RMSD is found to be 5KTU screening with 20 small molecules.
Application of monocarbonyl curcumin compound in preparation of medicine for preventing and treating periodontitis
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Paragraph 0024-0026; 0031, (2021/06/22)
The invention belongs to the technical field of medicines, and particularly relates to application of a specific monocarbonyl curcumin analogue in preparation of a medicine for preventing and treating periodontitis. Experiments prove that the monocarbonyl curcumin analogues not only can play a better anti-oxidation protection role by activating an Nrf2/HO-1 signal channel, but also can play an anti-inflammatory role by inhibiting release of inflammatory factors TNF alpha and IL1-beta, so that the monocarbonyl curcumin analogues have a remarkable prevention and treatment effect on rat periodontitis, have good potential value and significance for prevention and treatment of periodontitis, and have a good research and development prospect.
Synthesis and antiproliferative activity of cyclic arylidene ketones: a direct comparison of monobenzylidene and dibenzylidene derivatives
Huber, Imre,Zupk, Istvn,Kovcs, Ida J.,Minorics, Renta,Gulys-Fekete, Gergely,Masz, Gbor,Perjsi, Pl
, p. 973 - 981 (2015/02/19)
Abstract To give further insight into the influence of the structural modifications of enones and dienones on their antiproliferative properties, 25 derivatives of enones: (E)-2-benzylidene-1-cyclohexanones, (E)-2-benzylidene-1-tetralones, (E)-2-benzylidene-1-indanone, and dienones: (E,E)-2,5- or 2,6-dibenzylidene-1-cyclanones, (E,E)-3,5-dibenzylidene-4-piperidones were synthesized using a newly developed "one-pot" synthetic method. Due to the fact that all of them have the same aryl substituents (phenyl or 4-chlorophenyl) in the arylidene moiety, it is possible to compare the relevant contribution of the single-point structural modifications (type of ring or N-substitution) on their potency on the basis of their IC 50 values. Their antiproliferative activity was evaluated against the following four human adherent cancer cell lines: HeLa, A431, A2780, and MCF7. The cytotoxicity screen has revealed that the dibenzylidene dienones in general dominate the monobenzylidene enones in this respect. The nitrogen-containing heterocyclic dienones at the same time displayed higher inhibitory properties toward these human carcinoma cell lines compared with their homocyclic dienone analogs. One of the eight newly prepared 4-piperidone derivatives, N-(γ-oxobutyl)-(E,E)-3,5-bis(p-chlorobenzylidene)-4-piperidone is as potent a cell growth inhibitor (IC 50 of 0.438-1.409 μM) as the N-methyl-(E,E)-3,5-bis(p-chlorobenzylidene)-4-piperidone (IC 50 of 0.447-1.048 μM), one of the most active among the previously described compounds in this series. Catalytic hydrogen-transfer isomerization of compounds with two exocyclic benzylidene double bonds to derivatives with endocyclic double bonds results in the complete loss of antiproliferative activity. The structural modifications and 50 % inhibitory concentration (IC 50) values resulted in correlations which can promote the design of more potent derivatives of the 4-piperidone dienones.
Montmorillonite clay-promoted, solvent-free cross-aldol condensations under focused microwave irradiation
Rocchi, Damiano,Gonzalez, Juan F.,Menendez, J. Carlos
supporting information, p. 7317 - 7326 (2014/07/08)
An environmentally benign, clean and general protocol was developed for the synthesis of aryl and heteroaryl trans-chalcones. This method involved solvent-free reaction conditions under microwave irradiation in the presence of a clay-based catalyst, and afforded the target compounds in good yields and short reaction times. Furthermore, the same conditions allowed the synthesis of symmetrical, diarylmethylene-a,a-unsaturated ketones from aromatic aldehydes and ketones.
Amino functionalized mesoporous silica decorated with iron oxide nanoparticles as a magnetically recoverable nanoreactor for the synthesis of a new series of 2,4-diphenylpyrido[4,3-d]pyrimidines
Shadjou, Nasrin,Hasanzadeh, Mohammad
, p. 18117 - 18126 (2014/05/20)
(Fe2O3)-MCM-41-nPrNH2 as a magnetically recoverable nanoreactor, was prepared through the reaction of (Fe 2O3)-MCM-41 with 3-aminopropyltriethoxysilane in refluxing dry toluene. The catalyst with 10 wt% of loaded iron oxide nanoparticles was found to be a highly efficient nanocatalyst for the synthesis of a new class of 2,4-diphenylpyrido[4,3-d]pyrimidines under solvent free conditions in high to quantitative yields. By using an external magnet the catalyst was recovered and reused several times without any loss of efficiency. The prepared catalyst was characterized by transmission electron microscopy (TEM), Fourier transform infrared (FT-IR) spectroscopy, X-ray powder diffraction (XRD), and nitrogen physisorption measurements.
Application of MCM-41-SO3H as an advanced nanocatalyst for the solvent free synthesis of pyrano[3,2-c]pyridine derivatives
Rostamizadeh, Shahnaz,Shadjou, Nasrin,Hasanzadeh, Mohammad
experimental part, p. 866 - 871 (2012/08/07)
MCM-41-SO3H, an ordered mesoporous silica material in which MCM-41 with covalently anchored sulfonic acid groups was used as an acidic catalyst for the rapid and 'green' synthesis of pyrano[3,2-c]pyridine derivatives under solvent-free conditions. Reusability of the catalyst, high yields, short reaction times, simplicity and easy workup are advantages of this novel synthetic procedure compared to the conventional methods reported in the literature.
A highly atom economic, chemo-, regio- and stereoselective synthesis and evaluation of spiro-pyrrolothiazoles as antitubercular agents
Karthikeyan, Subramanian Vedhanarayanan,Bala, Balasubramanian Devi,Raja, Velanganni Paul Alex,Perumal, Subbu,Yogeeswari, Perumal,Sriram, Dharmarajan
supporting information; experimental part, p. 350 - 353 (2010/04/05)
The 1,3-dipolar cycloaddition of azomethine ylides derived from substituted isatins and 1,3-thiazolane-4-carboxylic acid to a series of 1-methyl-3,5-bis[(E)-arylmethylidene]-tetrahydro-4(1H)-pyridinones afforded novel spiro-pyrrolothiazoles chemo-, regio- and stereoselectively in quantitative yields. These compounds were screened for their in vitro activity against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB) using agar dilution method. Among the synthesized compounds, spiro[5.3′′]-5′′-nitrooxindole-spiro-[6.3′]-1′-methyl-5′-(2,4-di-chlorophenylmethylidene)tetrahydro-4′(1H)-pyridinone-7-(2,4-dichlorophenyl)tetra-hydro-1H-pyrrolo[1,2-c][1,3]thiazole (9k) was found to be the most active with a minimum inhibitory concentration (MIC) of 0.6 μM against MTB and MDR-TB.
The cytotoxic properties and preferential toxicity to tumour cells displayed by some 2,4-bis(benzylidene)-8-methyl-8-azabicyclo[3.2.1] octan-3-ones and 3,5-bis(benzylidene)-1-methyl-4-piperidones
Pati, Hari N.,Das, Umashankar,Das, Swagatika,Bandy, Brian,De Clercq, Erik,Balzarini, Jan,Kawase, Masami,Sakagami, Hiroshi,Quail, J. Wilson,Stables, James P.,Dimmock, Jonathan R.
experimental part, p. 54 - 62 (2009/04/07)
This study demonstrated that replacement of the axial protons on the C2 and C6 atoms of various 1-methyl-3,5-bis(benzylidene)-4-piperidones 3 by a dimethylene bridge leading to series 2 lowered cytotoxic potencies. Four compounds 2a and 3a-c emerged as lead molecules based on their toxicity towards different neoplasms and their selective toxicity for malignant rather than normal cells. Some possible reasons for the disparity between the IC50 values in the two series of compounds are presented based on molecular modeling, log P values and respiration in rat liver mitochondria.
Links between through-bond interactions and assembly structure in simple piperidones
Yuan, Ling,Sumpter, Bobby G.,Abboud, Khalil A.,Castellano, Ronald K.
scheme or table, p. 1924 - 1934 (2009/02/07)
3,5-Disubstituted piperidones provide an opportunity to explore donor-acceptor through-bond interactions in the context of molecular and supramolecular structure. The crystal structure of cis-3,5-dibenzyl-1- phenylpiperidin-4-one 3 is disordered and the lattice accommodates a ～3:1 ratio of the N-Ph equatorial (3-eq) and N-Ph axial (3-ax) epimers, based on refined values of occupancy factors. The fortuitous result allows a side-by-side comparison of the two configurations with respect to their donor-acceptor through-bond interactions. The energy difference between 3-ax and 3-eq (ΔEax-eq) has been evaluated in the gas phase using extensive first principles calculations, and for many levels of theory this difference parallels the experimentally-observed configurational ratio in the solid state (where the epimers share nearly identical packing environments). The calculations further show a difference in the through-bond stabilization for 3-ax and 3-eq, with larger contributions for 3-ax. Natural bond order (NBO) analysis quantifies the delocalization of the donor nitrogen lone pair into the adjacent carbon-carbon bonds and carbonyl acceptor for the 3-ax epimer. The work concludes that molecular-level structural perturbations that arise from or otherwise influence through-bond donor-acceptor interactions have consequences on solid-state and supramolecular assembly structure. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2008.
Discovery of antimycobacterial spiro-piperidin-4-ones: An atom economic, stereoselective synthesis, and biological intervention
Kumar, Raju Ranjith,Perumal, Subbu,Senthilkumar, Palaniappan,Yogeeswari, Perumal,Sriram, Dharmarajan
experimental part, p. 5731 - 5735 (2009/09/25)
An atom economic and stereoselective synthesis of several spiro-piperidin-4-ones through 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatin and α-amino acids viz. proline, phenylglycine, and sarcosine to a series of 1-methyl-3,5-bis[(E)- arylmethylidene]tetrahydro-4(1H)-pyridinones is described. These compounds were evaluated for their in vitro and in vivo activity against Mycobacterium tuberculosis H37Rv (MTB), multidrug resistant Mycobacterium tuberculosis (MDR-TB), and Mycobacterium smegmatis (MC2). Compound 4-(4-fluorophenyl)-5-phenylpyrrolo(spiro[2.3″]oxindole)spiro[3.3′] -1′-methyl-5′-(4-fluorophenylmethylidene)piperidin-4′-one (4e) was found to be the most active in vitro with a MIC value of 0.07 μM against MTB and was 5.1 and 67.2 times more potent than isoniazid and ciprofloxacin, respectively. In vivo, compound 4e decreased the bacterial load in lung and spleen tissues with 1.30 and 3.73-log 10 protections respectively and was considered to be promising in reducing bacterial count in lung and spleen tissues.
