59401-45-5

Upstream product

• 108-94-1 cyclohexanone 
• 100-10-7 4-dimethylamino-benzaldehyde 

Downstream Products

• 83391-11-1 (3R,3aS)-3-(4-Dimethylamino-phenyl)-7-[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-3,3a,4,5,6,7-hexahydro-indazole-2-carbaldehyde 
• 83391-18-8 C₂₄H₂₉N₅O 
• 83391-08-6 {(3R,3aS)-3-(4-Dimethylamino-phenyl)-7-[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-3,3a,4,5,6,7-hexahydro-indazol-2-yl}-methanol 
• 83391-13-3 (3R,3aS)-3-(4-Dimethylamino-phenyl)-7-[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-3,3a,4,5,6,7-hexahydro-indazole-2-carbodithioic acid 
• 83391-20-2 (3R,3aS)-3-(4-Dimethylamino-phenyl)-7-[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-3,3a,4,5,6,7-hexahydro-indazole-2-carboxylic acid ethyl ester 
• 1313510-73-4 2-amino-4-[4-(dimethylamino)phenyl]-8-(E)-[4-(dimethylamino)phenyl]methylidene-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 1428653-82-0 (E)-4-(7-(4-(dimethylamino)benzylidene)-2-phenyl-3,3a,4,5,6,7-hexahydro-2H-indazol-3-yl)-N,N-dimethylaniline 
• 1428653-77-3 (E)-1-(7-(4-(dimethylamino)benzylidene)-3-(4-(dimethylamino)phenyl)-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl)ethanone 
• 1228750-18-2 [7-(4-dimethylaminobenzylidene)-3-(4-dimethylaminophenyl)-2-oxo-2,3,4,5,6,7-hexahydro-2λ5-benzo[d][1,2]oxaphosphol-2-yl]dimethylamine 
• 1228750-19-3 [7-(4-dimethylaminobenzylidene)-3-(4-dimethylaminophenyl)-2-oxo-2,3,4,5,6,7-hexahydro-2λ5-benzo[d][1,2]oxaphosphol-2-yl]diethylamine 
• 118816-11-8 2,6-Bis-[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-cyclohexanol 
• 57770-89-5 C₂₄H₃₀N₄ 
• 129116-61-6 1-(4-Dimethylamino-phenyl)-5-[1-(4-dimethylamino-phenyl)-meth-(E)-ylidene]-3-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalene-2-carboxylic acid (4-chloro-phenyl)-amide 

Relevant academic research and scientific papers

Ash of pomegranate peels (APP): A bio-waste heterogeneous catalyst for sustainable synthesis of α,α′-bis(substituted benzylidine)cycloalkanones and 2-arylidene-1-tetralones

Abstract: α,α′-bis(substituted benzylidene)cycloalkanones were efficiently prepared from variously substituted aldehydes and cycloalkanones in water by using ash of pomegranate peels (APP) as a catalyst. The APP-catalyst was obtained from bio-waste by simple thermal treatment to dry peels of pomegranate fruit and formation of its active phase was confirmed by FT-IR, XRD, XRF, EDX, SEM, DSC-TGA and BET techniques. The analysis revealed that the present catalyst has basic sites which promote the synthesis of desired products. The main attractions of our protocol are utilization of highly abundant bio-waste-derived catalyst and good-to-excellent yield in shortest reaction time. This green protocol was further extended for structurally diverse 2-arylidene-1-tetralones by condensation of equimolar quantity of aromatic aldehydes and 1-tetralone at low temperature. The catalyst could be quantitatively recovered and reused effectively for five times. Graphic abstract: [Figure not available: see fulltext.].

Synthesis of diarylidenecyclohexanone derivatives as potential anti-inflammatory leads against COX-2/mPGES1 and 5-LOX

Inflammation is a pathophysiological condition which progresses through the prostaglandin (PG) and leukotriene (LT) pathways channelized by the enzymes COX/mPGES1 and 5-LOX respectively. Diarylidenecyclohexanone (DAC) derivatives (Ia-j, IIa-c, IIIa and IVa) were synthesized, characterized and screened for their in vitro anti-inflammatory activity via inhibition of 5-LOX and COX-2/mPGES1 enzymes. Compound Ic inhibited PGE2 production exhibiting an IC50 of 6.7 ± 0.19 μM, comparable to the standard inhibitor, licofelone (IC50 of 5.4 ± 0.02 μM). Compounds Ie and Ig showed maximum in vitro inhibitory activity against 5-LOX, exhibiting an IC50 of 1.4 ± 0.1 μM and 1.5 ± 0.13 μM, respectively, and these are comparable to that of the standard drug, zileuton (IC50 = 1.2 ± 0.11 μM). Ie and Ig do not possess radical scavenging properties and may not be disrupting the redox cycle of the enzyme. Hence they may be inhibiting the enzyme by a competitive mode. One of the compounds in the DAC series (IIc) containing a heterocyclic thienyl ring inhibited all the three enzymes. It inhibited 5-LOX and COX-2/mPGES1 with an IC50 of 1.8 ± 0.12 μM and 7.5 ± 0.4 μM respectively. An RT-PCR based mRNA expression study highlighted that Ic predominantly inhibited the expression of COX-2 rather than mPGES1. No toxicity towards the HeLa cell line indicated that the DACs could serve as structural templates towards lead optimization of compounds for discovery of novel, potent, safe and affordable drugs as anti-inflammatory agents.

An efficient green approach to aldol and cross-aldol condensations of ketones with aromatic aldehydes catalyzed by nanometasilica disulfuric acid in water

Aldol and cross-aldol condensations of aromatic aldehydes with various ketones in the presence of nanometasilica disulfuric acid (NMSDSA) as heterogeneous catalyst are presented. The catalyst was prepared according to the developed earlier method using inexpensive and readily available starting materials. The highly active catalyst gave excellent yields of the desired aldol products without self-condensation reaction taking place. Reaction times were short, the procedure and work-up were simple, and no volatile or hazardous organic solvents were involved. The catalyst could be recovered three times with only slight reduction in activity.

Solvent-free catalytic preparation of 2,6-dibenzylidenecycloalkanones using 2-hydroxyethylammonium acetate ionic liquid as catalyst

Various 2,6-dibenzylidenecycloalkanones were readily prepared in a condensation reaction catalyzed by 2-hydroxyethylammonium acetate ionic liquid under solvent-free conditions in excellent yields. The major advantages of the present method are high yields, short reaction times, lack of solvent, simplicity of performance, and low cost. Graphical abstract: [Figure not available: see fulltext.]

Synthesis, docking, and in vitro studies of some substituted bischalcones on acid and alkaline phosphatases

A series of bischalcones was synthesized and screened for their effect on acid and alkaline phosphatases. In addition, molecular modeling and docking of these compounds into alkaline phosphatase using iGemdock was performed in order to predict the affinity and orientation of the designed compounds at the active site and was compared with the established inhibitor levamisole. The iGemdock docking fitness resulted in decrease in total energy (ranging from -75.50 to -100.84) for all the synthesized compounds which were less than levamisole (-50.69) revealing higher binding with the enzyme. The compounds were synthesized by Clasien-Schimdt condensation and their effect was observed on the activity of acid and alkaline phosphatases. The results showed that synthesized bischalcones were inhibitory to alkaline phosphatases, whereas an activating effect was observed on the activity of acid phosphatase. The type of inhibition and Ki values of bischalcones on alkaline phosphatase were also determined. Springer Science+Business Media 2013.

Synthesis and evaluation of the antiparasitic activity of bis-(arylmethylidene) cycloalkanones

A series of bis-(arylmethylidene)-cycloalkanones was synthesized by cross-aldol condensation. The activity of the compounds was evaluated against amastigotes forms of Trypanosoma cruzi and promastigotes forms of Leishmania amazonensis. The cytotoxicity of the active compounds on uninfected fibroblasts or macrophages was established in vitro to evaluate the selectivity of their antiparasitic effects. Six compounds displayed trypanocidal activity against amastigotes intracellular forms of T. cruzi with IC50 values ranging from 7.0 to 249 μM. Besides these six compounds, eight other molecules exhibited significant leishmanicidal activity (IC50 values ranging from 0.6 to 110.4 μM). Two compounds can be considered as promising antiparasitic lead molecules because they showed IC50 values in the low-micromolar range (≤1.2 μM) with an adequate SI (≥19.9). To understand the mechanism of action of these compounds, two possible molecular targets were investigated: trypanothione reductase (TR) and cruzain.

Efficient method for the synthesis of, ′-bis(arylmethylidene) cycloalkanones catalyzed by bromodimethylsulfonium bromide

Bromodimethylsulfonium bromide (BDMS)-catalyzed crossed aldol condensation between aromatic aldehydes and ketones is reported to access ′-bis(arylmethylidene) cycloalkanones at room temperature in good yields within 3-10 min. The salient features of this method are the simplicity of the procedure, the ready accessibility of the catalyst, and greater yields in relatively short reaction times. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

New spiro (thio) barbiturates based on cyclohexanone and bicyclo [3.1.1]heptan-6-one by nonconcerted [1+5] cyclo addition reaction and their conformational structures

Crossed-aldol condensation reaction of aromatic aldehydes with ketones such as; acetone and cyclohexanone leads to the efficient formation of cross conjugated α,β-unsaturated ketones in excellent yield. The intermolecular and then intramolecular Michael addition reaction of α,β-unsaturated ketones derived from acetone and cyclohexanone with (thio)barbituric acids lead to synthesis new type of 7,11-diaryl-2,4-diazaspiro[5.5]undecane-1,3,5,9-tetraone and 2,4-diaryl-1'H-spiro[bicyclo[3.3.l]nonane-3,5'-pyrimidine]-2',4',6',9(3'H)-tetraone, respectively in good yield. Structure elucidation is carried out by 1H NMR, 13C NMR, FT-IR, UV-Visible, mass spectroscopy and X-ray crystallography techniques. A possible mechanism of the formation is discussed. The structural conformation also demonstrated by coupling constants derived from dihedral angles between vicinal and geminal protons. The 1H NMR spectra of NH protons of spiro compounds derived from barbituric acid show a broad singlet peak instead, these protons in the spiro compounds derived from thiobarbituric acid show two distinct peaks.

Study of in situ generation of carbocationic system from trityl chloride (Ph3CCl) which efficiently catalyzed cross-aldol condensation reaction

Organocatalyst trityl chloride (Ph3CCl), by in situ formation of trityl carbocation with inherent instability, efficiently promotes the cross-aldol condensation reaction between cycloalkanones and arylaldehydes in solvent-free and homogeneous media to afford α,α′- bis(arylidene)cycloalkanones in high yields. Moreover, an attractive and plausible mechanism based on observations and the literature is proposed for the reaction.

Sulfuric acid-modified PEG-6000 (PEG-SO3H): An efficient, bio-degradable and reusable catalyst for synthesis of α, α′ bis(arylidene) cycloalkanones under solvent-free conditions

A green and efficient method for synthesis of α, α′ -bis (arylidene) cycloalkanones, starting from aromatic aldehydes in reaction with ketones using sulfonated polyethylene glycol 6000 (PEG-SO3H) as a stable, reusable and biodegradable catalyst under solvent-free conditions at 80 °C is described. The use of a nontoxic, inexpensive, easily available and recyclable catalyst makes this protocol practical, environmentally friendly and economically attractive.