- Study of Biological Activities and ADMET-Related Properties of Novel Chlorinated N-arylcinnamamides
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A series of eighteen 4-chlorocinnamanilides and eighteen 3,4-dichlorocinnamanilides were designed, prepared and characterized. All compounds were evaluated for their activity against gram-positive bacteria and against two mycobacterial strains. Viability on both cancer and primary mammalian cell lines was also assessed. The lipophilicity of the compounds was experimentally determined and correlated together with other physicochemical properties of the prepared derivatives with biological activity. 3,4-Dichlorocinnamanilides showed a broader spectrum of action and higher antibacterial efficacy than 4-chlorocinnamanilides; however, all compounds were more effective or comparable to clinically used drugs (ampicillin, isoniazid, rifampicin). Of the thirty-six compounds, six derivatives showed submicromolar activity against Staphylococcus aureus and clinical isolates of methicillin-resistant S. aureus (MRSA). (2E)-N-[3,5-bis(trifluoromethyl)phe-nyl]-3-(4-chlorophenyl)prop-2-enamide was the most potent in series 1. (2E)-N-[3,5-bis(Trifluoro-methyl)phenyl]-3-(3,4-dichlorophenyl)prop-2-enamide, (2E)-3-(3,4-dichlorophenyl)-N-[3-(trifluo-romethyl)phenyl]prop-2-enamide, (2E)-3-(3,4-dichloro-phenyl)-N-[4-(trifluoromethyl)phe-nyl]prop-2-enamide and (2E)-3-(3,4-dichlorophenyl)-N-[4-(trifluoromethoxy)phenyl]prop-2-en-amide were the most active in series 2 and in addition to activity against S. aureus and MRSA were highly active against Enterococcus faecalis and vancomycin-resistant E. faecalis isolates and against fast-growing Mycobacterium smegmatis and against slow-growing M. marinum, M. tuberculosis non-hazardous test models. In addition, the last three compounds of the above-mentioned showed insignificant cytotoxicity to primary porcine monocyte-derived macrophages.
- Cizek, Alois,Hosek, Jan,Jampilek, Josef,Kavanova, Lenka,Kos, Jiri,Lelakova, Veronika,Leva, Lenka,Michnova, Hana,Oravec, Michal,Pindjakova, Dominika,Strakova, Nicol,Strharsky, Tomas,Vrablova, Lucia
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- Synthesis of Linear α,β-Unsaturated Amides from Isocyanates and Alkenylaluminum Reagents
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A new approach has been developed for the synthesis of linear α,β-unsaturated amides by the direct coupling of isocyanates with alkenylaluminum reagents. At room temperature, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional-group tolerance in the absence of any catalyst or additive.
- Chen, Bo,Wu, Xiao-Feng
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supporting information
p. 788 - 792
(2020/05/19)
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- Palladium-catalyzed carbonylative synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent
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In this work, an interesting procedure for the synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent has been developed. With palladium as the catalyst and XPhos as the ligand under carbon monoxide pressure, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional group tolerance. Remarkably, this procedure also represents an example on addition of organometallic reagent to isocyanates for α,β-unsaturated amides synthesis.
- Chen, Bo,Wu, Xiao-Feng
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p. 160 - 163
(2020/02/11)
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- Green synthesis of isoxazoline derivatives using microwave irradiation and their antifungal activity
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Microwave irradiation method was used for synthesis of isoxazolines. Claisen Schmidt reaction of different aromatic aldehydes with acetanilide gave acrylamides (1a-1h) which on further reaction with hydroxylamine hydrochloride (in the presence of sodium hydroxide) afforded isoxazolines (2a-2h). Physical data of all the synthesized compounds were recorded. Isoxazolines were characterized by their IR and 1H NMR spectra. All the synthesized isoxazolines were screened for their antifungal activity against fungi namely Drechslera maydis and Rhizoctonia solani isolated from maize. Isoxazolines having chloro substitution on benzene ring found to be most effective followed by fluoro and nitro substituted compounds. None of the compound was registered as effective as Bavistin.
- Goyal, Akhil,Sharma, Sunita,Gaba, Jyoti,Kaur, Harleen
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p. 2169 - 2172
(2016/07/19)
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- Copper-catalyzed direct transformation of secondary allylic and benzylic alcohols into azides and amides: An efficient utility of azide as a nitrogen source
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A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has been successfully adapted to the preparation of azides directly from their corresponding alcohols and offers excellent chemoselectivity in the formation of ω-halo azides and the azidation of allylic alcohols in the presence of a benzyl alcohol moiety. In addition, this strategy provides an opportunity to synthesize azides that can serve as precursors to β-amino acids. A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has also been adapted to the preparation of azides directly from their corresponding alcohols.
- Rokade, Balaji V.,Gadde, Karthik,Prabhu, Kandikere Ramaiah
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p. 2706 - 2717
(2015/04/27)
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- Direct transformation of arylpropynes to acrylamides via a three-step tandem reaction
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A novel and metal-free acrylamides formation between arylpropynes and hydroxylamine hydrochloride through sp3 C-H and C-C bond cleavage has been achieved with DDQ as an oxidant. The mechanistic study shows that the acrylamides are formed through a three-step tandem sequence, including cross-dehydrogenative-coupling (CDC) reaction, aza-Meyer-Schuster rearrangement and Beckmann rearrangement. This journal is The Royal Society of Chemistry 2014.
- Qiu, Jun,Zhang, Ronghua
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p. 1556 - 1560
(2014/03/21)
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- Iron-catalyzed C-H and C-C bond cleavage: A direct approach to amides from simple hydrocarbons
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Something functional: The title reaction proceeds in the presence of azide and water to deliver amides in high yields, and it can be used in a ring-expansion strategy to generate lactams. A mechanism is proposed based on experimental results. This reaction offers a new approach to functionalizing simple and readily available hydrocarbons. DDQ=2,3-dichloro-5,6-dicyano-1,4- benzoquinone. Copyright
- Qin, Chong,Zhou, Wang,Chen, Feng,Ou, Yang,Jiao, Ning
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supporting information; experimental part
p. 12595 - 12599
(2012/01/15)
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- Nucleophilic substitution reactions of cinnamoyl chlorides with anilines in acetonitrile and acetonitrile-methanol mixtures
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Kinetic studies on the solvolysis (in MeOH-MeCN mixtures) and aminolysis (with anilines in MeCN) of cinnamoyl chlorides have been carried out at 25.0 deg C.The relatively large negative values of ρY+ = -0.9 ca. -1.5 for the methanolysis are consistent with a dissociative SN2-like mechanism.For the aminolysis, the ρy values are positive (ρY = 0.52 ca. 1.64) and ρX values range from -1.68 to -2.51 in acetonitrile.The positive values of βX = 0.6-0.9 and ρXY = 0.88 in acetonitrile, and isotope effect data suggest that the aminolysis proceeds by a stepwise mechanism with rate-limiting breakdown of the tetrahedral intermediate, T+/-.It is noted that in the acyl-transfer reactions proceeding by rate-limiting departure of the leaving group from the tetrahedral intermediate the signs of both ρY and ρXY are positive and the reactivity-selectivity principle (RSP) is valid in general.
- Kim, Tae-Hyoung,Huh, Chul,Lee, Bon-Su,Lee, Ikchoon
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p. 2257 - 2262
(2007/10/03)
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