5447-53-0

Basic information

• Product Name: 2,5-bis(4-methoxybenzylidene)cyclopentanone
• Synonyms: 2,5-bis(4-methoxybenzylidene)cyclopentanone
• CAS NO: 5447-53-0
• Molecular Formula: C₂₁H₂₀O₃
• Molecular Weight: 320.3817
• Mol File: 5447-53-0.mol
• Article Data: 70

Chemical Properties

• Boiling Point: 538.4°Cat760mmHg
• Flash Point: 272°C
• Appearance: /
• Density: 1.191g/cm³
• Vapor Pressure: 1.16E-11mmHg at 25°C
• Refractive Index: 1.648
• CAS DataBase Reference: 2,5-bis(4-methoxybenzylidene)cyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-bis(4-methoxybenzylidene)cyclopentanone(5447-53-0)
• EPA Substance Registry System: 2,5-bis(4-methoxybenzylidene)cyclopentanone(5447-53-0)

Safety Data

• Hazardous Substances Data: 5447-53-0(Hazardous Substances Data)

Usage

General Description

2,5-bis(4-methoxybenzylidene)cyclopentanone is a compound that belongs to the class of organic chemicals known as benzylideneacetophenones. Its molecular structure consists of a cyclopentanone ring with two 4-methoxybenzylidene groups attached to it. 2,5-bis(4-methoxybenzylidene)cyclopentanone is used in organic synthesis as a starting material for the preparation of various pharmaceuticals, agrochemicals, and other organic compounds. It has been studied for its potential biological activities and has shown to exhibit antioxidant, antimicrobial, anti-inflammatory, and anticancer properties. Additionally, it has been used as a building block in the development of new materials for various industrial applications.

InChI:InChI=1/C21H20O3/c1-23-19-9-3-15(4-10-19)13-17-7-8-18(21(17)22)14-16-5-11-20(24-2)12-6-16/h3-6,9-14H,7-8H2,1-2H3

Upstream product

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

Downstream Products

• 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 
• 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 

Relevant articles and documents

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.

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.

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.