79442-34-5Relevant articles and documents
Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
Jeong, Eun Jeong,Lee, In-Sook Han
, p. 668 - 673 (2019/07/12)
A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.
Silver-catalyzed decarboxylative cross-coupling of α-keto acids with alkenes giving approach to chalcones
Wu, Shang,Yu, Hongheng,Hu, Qinzheng,Yang, Quanlu,Xu, Shouwang,Liu, Tian
supporting information, p. 4763 - 4765 (2017/12/01)
A silver-catalyzed decarboxylative cross-coupling of α-keto acids with alkenes is reported. The method, with a wide range of substrate tolerance and mild operational conditions, can produce various chalcone derivatives in moderate to high yields from easily available starting materials.
Domino-Fluorination-Protodefluorination Enables Decarboxylative Cross-Coupling of α-Oxocarboxylic Acids with Styrene via Photoredox Catalysis
Zhang, Muliang,Xi, Junwei,Ruzi, Rehanguli,Li, Nan,Wu, Zhongkai,Li, Weipeng,Zhu, Chengjian
, p. 9305 - 9311 (2017/09/25)
Domino-fluorination-protodefluorination decarboxylative cross-coupling of α-keto acids with styrene has been developed via photoredox catalysis. The critical part of this strategy is the formation of the carbon-fluorine (C-F) bond by the capture of a carbon-centered radical intermediate, which will overcome side reactions during the styrene radical functionalization process. Experimental studies have provided evidence indicating a domino-fluorination-protodefluorination pathway with α-keto acid initiating the photoredox cycle. The present catalytic protocol also affords a novel approach for the construction of α,β-unsaturated ketones under mild conditions.
Green synthesis of chalcones and microbiological evaluation
Ritter, Marina,Martins, Rosiane M.,Rosa, Silvana A.,Malavolta, Juliana L.,Lund, Rafael G.,Flores, Alex F. C.,Pereira, Claudio M.P.
, p. 1201 - 1210 (2015/06/16)
A green method was developed for the synthesis of chalcones using glycerin as solvent. Subsequently, the potential microbiology activity of these molecules was evaluated by testing them against the Gram-positive bacteria Staphylococcus aureus (S. aureus) ATCC 19095 and Enterococcus faecalis (E. faecalis) ATCC 4083, the Gram-negative bacteria Escherichia coli (E. coli) ATCC 29214 and Pseudomonas aeruginosa (P. aeruginosa) ATCC 9027, and the fungus Candida albicans (C. albicans), which includes ATCC 62342 and three clinical strains of C. albicans from human oral cavities. The results showed that some chalcones exhibited moderate inhibitory activity, the most prominent being those acting against the fluconazole-resistant strains of C. albicans.
ACETYL-COA CARBOXYLASE MODULATORS
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Paragraph 00169-00170; 00210-00214, (2015/01/09)
Provided herein are compounds that exhibit activity as acetyl-CoA carboxylase modulators (e.g., inhibitors) and are useful, for example, in methods for the control of fungal pathogens in plants.
Design and synthesis of spiro derivatives containing a thiophene ring and evaluation of their anti-microbial activity
Kanagaraju, Geethanjali,Thangamani, Arumugam
, p. 1619 - 1630 (2015/04/22)
Synthesis of a series of novel spiro pyrrolidines has been accomplished by 1, 3-dipolar cycloaddition reaction of azomethine ylide generated from phenylalanine and isatin with dipolarophiles in good yield. The reaction proceeded with high regio and stereoselectivity. The products have been characterized by elemental analyses and spectroscopic techniques, namely IR, 1H NMR and 13C NMR spectroscopies. Single crystal analysis of compounds 4k 2D-NMR analysis of compound 4k confirmed the structures of spiropyrrolidine derivatives. These compounds were evaluated for their antimicrobial activity. Most of the synthetic compounds exhibited good activity against microorganisms.
Regiospecific synthesis and biological evaluation of spirooxindolopyrrolizidines via [3+2] cycloaddition of azomethine ylide
Thangamani, Arumugam
experimental part, p. 6120 - 6126 (2011/01/13)
Reaction of (E)-3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones with azomethine ylide (generated in situ via decarboxylative condensation of isatin with l-proline) in refluxing methanol afforded 1′-(aryl)-2′-(2- thienylcarbonyl)-spiro[3H-indole-3,3′-[3H]pyrrolizin]-2-ones as the sole product in a regiospecific manner. The synthesized compounds have been characterized by their elemental, analytical and spectral studies. The synthesized compounds were screened for their antibacterial and antifungal activities against a spectrum of microbial organisms. These studies proved that compounds 1′-(p-chlorophenyl)-2′-(2-thienylcarbonyl)-spiro[3H- indole-3,3′-[3H]pyrrolizin]-2-one (4b), 1′-(p-fluorophenyl)- 2′-(2-thienylcarbonyl)-spiro[3H-indole-3,3′-[3H]pyrrolizin]-2-one (4d) and 1′-(p-methoxyphenyl)-2′-(2-thienylcarbonyl)-spiro[3H- indole-3,3′-[3H]pyrrolizin]-2-one (4h) against Staphylococcus aureus, 1′-(p-chlorophenyl)-2′-(2-thienylcarbonyl)-spiro[3H-indole-3, 3′-[3H]pyrrolizin]-2-one (4b), 1′-(p-methylphenyl)-2′-(2- thienylcarbonyl)-spiro[3H-indole-3,3′-[3H]pyrrolizin]-2-one (4c) and 1′-(p-fluorophenyl)-2′-(2-thienylcarbonyl)-spiro[3H-indole-3, 3′-[3H]pyrrolizin]-2-one (4d) against Salmonella typhi show maximum inhibition potency at low concentration (6.25 μg/mL) whereas 4d against Candida albicans and 4b and 4d against Rhizopus sp. showed beneficial antifungal activity at minimum concentration.
