106115-46-2

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 120-92-3 cyclopentanone 
• 23786-93-8 1,1-diethoxy-cyclopentane 
• 104-87-0 4-methyl-benzaldehyde 
• 14202-31-4 4-methoxybenzaldehyde-1,1-diacetate 
• 19980-43-9 1-(trimethylsilyloxy)cyclopentene 
• 58647-67-9 2-(4-methoxybenzylidene)cyclopentanone 

Downstream Products

• 1261032-47-6 1-N-methyl-spiro[2.3']oxindole-spiro[3.2]5-(4-methoxy)benzylidenecyclopentanone-4-(4-methoxy)phenyl-pyrrolidine 
• 1427056-48-1 3-(4-methoxybenzylidene)-9-(4-methoxyphenyl)-6,6-dimethyl-2,3,6,7-tetrahydrocyclopenta[b]chromen-8(1H,5H,9H)-one 
• 115592-00-2 2',3',6',7'-Tetrahydro-4'-(4-methoxyphenyl)-1',2,5-tris<(E)-(4-methoxyphenyl)methylen>spiro 
• 115591-97-4 2-(4-Methoxyphenyl)-5-<(E)-(4-methoxyphenyl)methylen>-1,1-dimethylspiro<2.4>heptan-4-on 
• 115591-91-8 1,3-Bis<(E)-(4-methoxyphenyl)methylen>-2-(phenylmethylen)cyclopentan 

Relevant academic research and scientific papers

Iodotrimethylsilane-Mediated Cross-Aldol Condensation: A Facile Synthesis of α,α′-Bis(substituted benzylidene)cycloalkanones

A facile and efficient method for the preparation of α, α′-bis(substituted benzylidene)cycloalkanones is described for the first time using iodotrimethylsilane generated in situ from chlorotrimethylsilane and sodium iodide in acetonitrile. The reaction proceeds rapidly at room temperature, giving high yields of products.

Second- and third-order nonlinear optical properties of Bis-chalcone derivatives

Bis-chalcone derivatives: 2,5-bis(benzylidene)-cyclopentanone (CP-DBA), 2,5-bis(4-methoxy-benzylidene)-cyclopentanone (CP-POME), 2,5-bis(4-isopropyl- benzylidene)-cyclopentanone (CP-ISO) and 2,5-bis(cinnamylidene)-cyclopentanone (CP-CAL) are synthesized by Claisen-Schmidt reaction and characterized using, FT-IR, 1H NMR, 13C NMR, and mass spectroscopic techniques. The second- and third-order nonlinear optical properties of these samples are studied using second harmonic generation and nanosecond open-aperture Z-scan methods. CP-POME has shown a very high second harmonic generation (SHG) efficiency (5.3 times that of urea). These molecules reveal a strong third-order nonlinear absorption (NLA) that is of optical limiting type, due to their peculiar D-π-A-π-D structure that leads to high polarization of the delocalized electron cloud. CP-CAL exhibits highest NLA activity with a β coefficient of 1 × 10-10 m/W. Through numerical simulations, the mechanism of NLA is found to be a two-photon absorption process in the case of all the samples.

Synthesis and synergistic antifungal effects of monoketone derivatives of curcumin against fluconazole-resistant Candida spp.

Twenty-three monoketone derivatives of curcumin were synthesized to investigate the synergy with fluconazole against fluconazole-resistant Candida spp. The minimal inhibitory concentration (MIC80) and the fractional inhibitory concentration index (FICI) of the antifungal synergist fluconazole were measured against fluconazole-resistant C. albicans, C. tropicalis and C. krusei in vitro. Most of these compounds showed good synergistic activities against C. tropicalis. Among them, compound 9 exhibited significant synergistic activities against Candida spp. SARs were also discussed. In particular, a cell growth test exhibited that a combination of 1 μg ml-1 fluconazole and 64 μg ml-1 or 128 μg ml-1 compound 9 showed the most potent fungicidal effect against C. tropicalis. The synergistic effect may be associated with the changes of the intracellular ATP content and cell membrane permeability. Our results provided a basis for future evaluation and development of these compounds as leads for therapeutics for fluconazole-resistant candidiasis.

Synthesis and spectroscopic and structural studies of cross-conjugated dienones derived from cyclic ketones and aromatic aldehydes

Cross-conjugated dienones were synthesized by the reactions of cyclic ketones with two equivalents of aromatic aldehydes under basic conditions. An NMR spectroscopic study and X-ray diffraction analysis demonstrated that all reaction products are formed as E,E isomers. Spontaneous photochemical trans-cis isomerization of cross-conjugated dienones under the scattered light in solution was observed for the first time. The degree of isomerization depends mainly on the nature of the central fragment of the dienone molecule. The previously unknown product of photochemical [2+2]-cycloaddition of 2,5-bis[(E)-(3-pyridyl)methylidene]cyclopentanone was synthesized and characterized by spectroscopic methods and X-ray diffraction. Under the conditions used, only one isomer of the cyclobutane adduct was obtained. Springer Science+Business Media, Inc. 2006.

Synthesis, structure, electrochemistry, and photophysics of 2,5-dibenzylidenecyclopentanones containing in benzene rings substituents different in polarity

A series of cross-conjugated dienones was synthesized to study the dependence of physicochemical characteristics on the nature of substituents in the aromatic groups of symmetric cyclopentanone dibenzylidene derivatives. The structure of compounds was established by electronic, IR, and NMR spectroscopy and X-ray diffraction study. All the compounds obtained possess the E,E-geometry. In the crystalline state, the arrangement of the dienone molecules is unfavorable for the intermolecular [2+2] photocycloaddition to take place. The low-temperature phases transition for unsubstituted diphenyl derivative of cyclopentanone was detected using variable-temperature X-ray diffraction and differential scanning calorimetry. Oxidation and reduction potentials of the dienones were measured by cyclic voltammetry. Their dependence on the nature and placement of substituents in the benzene rings was demonstrated. A linear correlation (R = 0.9343) between the difference of electrochemical oxidation and reduction potentials and the energy of the long-wavelength absorption maximum was found, that allows us to recommend the use of the data obtained in the correlation analysis of other compounds of this class.

Studies in the cycloproparene series: Cross-conjugated π-extended alkylidenecycloproparenes

The first simple and stable cross-conjugated π-extended alkylidenecycloproparenes 5, 6 and 15-22 have been prepared as coloured crystalline derivatives from use of (E,E)-1,5-diphenylpenta-2,4-dienone, (E,E)-1,5-diarylpenta-1,4-dien-3-ones and (E,E)-2,5-(d

Green, rapid, and highly efficient syntheses of α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones as potentially biologic compounds via solvent-free microwave-assisted Claisen–Schmidt condensation catalyzed by MoCl5

A new, green, and highly efficient protocol for the expeditious preparation of some α,α′-bis[(aryl or allyl)idene]cycloalkanones and 2-[(aryl or allyl)idene]-1-indanones via a simple microwave-assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent-free conditions, simple operation, use of a very inexpensive and available catalyst, low catalyst loading, short reaction times, high yields of the pure products, no harmful by-products, easy workup, and also the applicability of microwave irradiation as a clean source of energy. Furthermore, a gram-scale reaction was successfully conducted, proving the scalability of this current Claisen–Schmidt condensation reaction.

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.].

Diarylidenecyclopentanone derivatives as potent anti-inflammatory and anticancer agents

Cancer is often associated with chronic inflammation. In order to develop potential anticancer and anti-inflammatory agents a series of 26 diarylidenecyclopentanones (DACPs) Ia–Iv, II, III, and IV were synthesized. Five of the synthesized DACPs are novel (Ih, Ij, Ik, Is, and Iv), derivative Iv was characterized using single-crystal X-ray diffraction study. All the synthesized derivatives were tested for their anti-inflammatory as well as cytotoxicity properties. Compound Is is found to have the highest anti-inflammatory activity (93.67%) by inhibiting PGE2 (prostaglandin E2) production. Three of the DACPs (Io, It, and Iu) were observed to have high cytotoxicity with IC50 value of 8.73 ± 0.06 μM (Io), 12.55 ± 0.31 μM (It), and 11.47 ± 0.15 μM (Iu) against HeLa cells. Further staining and cell cycle analysis was done using these three DACPs to understand their mechanism of action. The G0/G1 phase was observed to be the longest one through which the cells undergo apoptosis.

Antiparasitic activity of synthetic curcumin monocarbonyl analogues against Trichomonas vaginalis

Trichomoniasis is a parasitic infection caused by Trichomonas vaginalis and it is considered to be the most common non-viral sexually transmitted infection in the world. Since the 1960s, nitroimidazoles such as metronidazole are the drugs of choice for the treatment of trichomoniasis, but many adverse effects and allergic reactions may result from their use. Reports of metronidazole-resistant infections also highlight the importance for the search of new anti-T. vaginalis agents. Considering this, herein we report the anti-T. vaginalis evaluation of 21 synthetic monocarbonyl analogues of curcumin, which itself has been reported to possess antiparasitic potential. From the in vitro analysis of the synthetic molecules, untreated trophozoites, and metronidazole at 100 μM, it was observed that three curcumin analogues (3a, 3e, and 5e) exhibited anti-T. vaginalis activity comparable to metronidazole (no significant statistical difference). Optimal antiparasitic concentrations were determined to be 80 μM and 90 μM for propanone derivatives 3a and 3e, respectively, and 200 μM for cyclohexanone derivative 5e. Kinetic growth curves showed that, after 24 h, the trophozoites were completely inhibited. At the tested concentrations, natural curcumin did not significantly inhibit the growth of trophozoites, therefore demonstrating that the designed synthetic molecules not only have better chemical stability, but also higher anti-T. vaginalis potential. Cytotoxicity analysis, performed on VERO cells, demonstrated low, moderate and high cytotoxic effects for analogues 3e, 5e and 3a, respectively. This study suggests that these analogues possess chemical features of interest to be further explored as alternatives for the treatment of trichomoniasis.