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Said A Said et al.
European journal of medicinal chemistry, 44(12), 4787-4792 (2009-08-18)
A series of diazipine, pyrimidine, fused triazolopyrimidine and imide derivatives were newly synthesized using 4-phenyl-but-3-en-2-one 1 as a starting material and compounds 2 and 9 are intermediates. Initially the acute toxicity of the compounds was assayed via the determination of
Bin Cao et al.
Organic & biomolecular chemistry, 10(6), 1239-1245 (2011-12-20)
An efficient and easy procedure to synthesize the pyridinyl analogues of dibenzylideneacetone (pyr-dba) was developed by the condensation of substituted nicotinaldehyde and acetone in the presence of K(2)CO(3) in toluene-EtOH-H(2)O solvent system. Structurally diverse pyr-dba, including quinolinyl dba, can be
Jiyong Zhang et al.
The Journal of organic chemistry, 71(7), 2918-2921 (2006-03-25)
The first efficient asymmetric synthesis of obolactone 1 has been accomplished in 11 steps and with a 15% overall yield in which Brown's enantioselective allylation reactions and ring-closing metathesis reaction are key steps.
Chisako Yamagami et al.
Bioorganic & medicinal chemistry letters, 12(17), 2281-2285 (2002-08-06)
The inhibitory effect (IC(50)) of the title compounds on UV-induced mutagenesis in Escherichia coli WP2uvrA was analyzed quantitatively by using various quantum chemical descriptors and also by the CoMFA method: both approaches provided results of similar quality. The activity was
Phenylbutane Derivatives as Main Constituents of Monanthotaxis capea Essential Oil.
Lamaty G, et al.
J. Essent. Oil Res., 4(1), 33-39 (1992)
Ikuro Abe et al.
Organic letters, 4(21), 3623-3626 (2002-10-12)
[reaction: see text] Substrate specificities of plant polyketide synthases (PKSs) were investigated using analogues of malonyl-CoA, the extension unit of the polyketide chain elongation reactions. When incubated with methylmalonyl-CoA and 4-coumaroyl-CoA, plant PKSs (chalcone synthase from Scutellaria baicalensis, stilbene synthase
Jia Zhang et al.
Journal of mass spectrometry : JMS, 47(8), 1059-1064 (2012-08-18)
A mass spectrometric study of protonated warfarin and its derivatives (compounds 1 to 5) has been performed. Losses of a substituted benzylideneacetone and a 4-hydroxycoumarin have been observed as a result of retro-Michael reaction. The added proton is initially localized
Indrani Mitra et al.
Chemical biology & drug design, 73(5), 526-536 (2009-04-18)
We have modeled antioxidant activities of hydroxybenzalacetones against lipid peroxidation induced by t-butyl hydroperoxide (pC1), gamma-irradiation (pC2) and also their 1,1-diphenyl-2-picryl hydrazyl (DPPH) free radical scavenging activity (pC3) using quantitative structure-activity relationship technique. The quantitative structure-activity relationship models were developed
Highly asymmetric Michael addition to alpha,beta-unsaturated ketones catalyzed by 9-amino-9-deoxyepiquinine.
Jian-Wu Xie et al.
Angewandte Chemie (International ed. in English), 46(3), 389-392 (2006-12-13)
Toshiyuki Wakimoto et al.
Methods in enzymology, 515, 337-358 (2012-09-25)
Members of the chalcone synthase superfamily of type III polyketide synthases (PKSs) catalyze iterative condensations of CoA thioesters to produce a variety of polyketide scaffolds with remarkable structural diversity and biological activities. The homodimeric type III PKSs share a common
Dongjin Ji et al.
FEMS microbiology letters, 239(2), 241-248 (2004-10-13)
An entomopathogenic bacterium, Xenorhabdus nematophila, is known to have potent antibiotic activities to maintain monoxenic condition in its insect host for effective pathogenesis and ultimately for optimal development of its nematode symbiont, Steinernema carpocapsae. In this study we assess its
Mahesh Raj Nepal et al.
Toxicology letters, 289, 75-85 (2018-03-17)
Among many of the validated methods for testing skin sensitization, direct peptide reactivity assay (DPRA) employs no cells or animals. Although no immune cells are involved in this assay, it reliably predicts the skin sensitization potential of a chemical in
G Feron et al.
Letters in applied microbiology, 45(1), 29-35 (2007-06-28)
To investigate the enzymatic aldol reaction between acetone as a donor and 4-hydroxybenzaldehyde as a receptor to generate 4-(4-hydroxyphenyl)-but-3-ene-2-one or 4-hydroxybenzylidene acetone, the direct precursor of 4-(4-hydroxyphenyl)-butan-2-one or raspberry ketone, using different species of filamentous fungi and bacteria. Different classes
National Toxicology Program technical report series, (572)(572), 1-188 (2012-06-14)
Methyl trans-styryl ketone is used as a synthetic flavoring agent and a fragrance additive in food and personal care products. Methyl trans-styryl ketone was nominated for study by the National Cancer Institute due to widespread human exposure as a flavoring
Yoichi Kohno et al.
Drug metabolism and disposition: the biological fate of chemicals, 33(8), 1115-1123 (2005-05-03)
When chalcone and trans-4-phenyl-3-buten-2-one (PBO) were incubated with liver microsomes of untreated rats in the presence of NADPH, 4-hydroxychalcone and trans-4-(4-hydroxyphenyl)-3-buten-2-one (4-OH-PBO), respectively, were formed as major metabolites. Two minor metabolites of chalcone, 4'-hydroxychalcone and 2-hydroxychalcone, were also observed. The
Chrisitine Jisoo Song et al.
Journal of microbiology and biotechnology, 21(3), 317-322 (2011-04-06)
A monoterpenoid compound, benzylideneacetone (BZA), is identified from bacterial metabolites synthesized by an entomopathogenic bacterium, Xenorhabdus nematophila. It inhibits phospholipase A2 of target insects to shut down biosynthesis of various eicosanoids, which play significant roles in insect immunity. This study
Lisa Dalla Via et al.
European journal of medicinal chemistry, 44(7), 2854-2861 (2009-01-22)
A series of conjugates of alpha,beta-unsaturated ketone systems, phenyl-butenone and diaryl-propenones (chalcones), with the tricyclic planar pyrroloquinoline nucleus were synthesised and evaluated for their anticancer properties. The aim was to target DNA by butenone and chalcones, and determine the occurrence
Gábor Szántó et al.
Chirality, 20(10), 1120-1126 (2008-05-29)
Six active 4-aryl-5-nitro-pentan-2-ones were synthesized enantioselectively from the corresponding 5-aryl-butenones by asymmetric Michael addition of nitromethane using an imidazolidine-type enantioselective organocatalyst. The ee ratio of the products were between 67 and 100%, determined by HPLC with Chiracel OD. Molecular and
Samyeol Seo et al.
Applied and environmental microbiology, 78(11), 3816-3823 (2012-03-27)
The entomopathogenic bacteria Xenorhabdus nematophila and Photorhabdus temperata subsp. temperata suppress insect immune responses by inhibiting the catalytic activity of phospholipase A(2) (PLA(2)), which results in preventing biosynthesis of immune-mediating eicosanoids. This study identified PLA(2) inhibitors derived from culture broths
Bowon Kwon et al.
Journal of economic entomology, 101(1), 36-41 (2008-03-12)
Benzylideneacetone (BZA) is a metabolite of gram-negative entomopathogenic bacterium Xenorhabdus nematophila, and it acts as an enzyme inhibitor against phospholipase A2 (PLA2). PLA2 catalyzes a committed biosynthetic step of eicosanoids, which mediate insect immune reactions to infection by microbial pathogens.
Chisako Yamagami et al.
Bioorganic & medicinal chemistry letters, 14(22), 5629-5633 (2004-10-16)
Antioxidant activities for a series of hydroxybenzalacetones, OH-BZ, were evaluated by measuring inhibitory potencies of OH-BZ against lipid peroxidation induced by t-BuOOH or gamma-irradiation. Their quantitative structure-activity relationship (QSAR) studies indicated that the activities are mainly governed by electronic and
Hiroyuki Morita et al.
Proceedings of the National Academy of Sciences of the United States of America, 107(2), 669-673 (2010-01-19)
Benzalacetone synthase (BAS), a plant-specific type III polyketide synthase (PKS), catalyzes a one-step decarboxylative condensation of malonyl-CoA and 4-coumaroyl-CoA to produce the diketide benzalacetone. We solved the crystal structures of both the wild-type and chalcone-producing I207L/L208F mutant of Rheum palmatum
Jin Tatsuzaki et al.
Journal of natural products, 69(10), 1445-1449 (2006-10-28)
Twenty-eight compounds related to dehydrozingerone (1), isoeugenol (3), and 2-hydroxychalcone (4) were synthesized and evaluated in vitro against human tumor cell replication. Except for isoeugenol analogues 27-35, most compounds exhibited moderate or strong cytotoxic activity against KB, KB-VCR (a multidrug-resistant
Nitin H Patel et al.
ALTEX, 36(3), 373-387 (2019-03-14)
Chemical substances that induce an allergic response in skin upon contact are called skin allergens or sensitizers, while chemical substances that elicit an allergic response only in presence of light are called photoallergens or photo sensitizers. The Direct Peptide Reactivity
Hiroyuki Morita et al.
Acta crystallographica. Section F, Structural biology and crystallization communications, 64(Pt 4), 304-306 (2008-04-09)
Benzalacetone synthase (BAS) from Rheum palmatum is a plant-specific type III polyketide synthase that catalyzes the one-step decarboxylative condensation of 4-coumaroyl-CoA with malonyl-CoA to produce the diketide 4-(4-hydroxyphenyl)-but-3-en-2-one. Recombinant BAS expressed in Escherichia coli was crystallized by the sitting-drop vapour-diffusion
Noriko Motohashi et al.
Chemical & pharmaceutical bulletin, 53(8), 1003-1005 (2005-08-05)
Antioxidant activity of a series of hydroxybenzalacetones was determined against peroxynitrite-induced lipid peroxidation in red blood cell membrane and SOS response through DNA damage in bacterial cells. Hydroxybenzalacetone derivatives with hydroxy, methoxy, ethoxy or methyl substitution were analyzed and found
Organoleptic Characteristics of Flavor Materials
Mosciano, G.
Perfumer & Flavorist, 30, 51-51 (2005)
Aditya L Gottumukkala et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 17(11), 3091-3095 (2011-02-10)
Ace of base: A catalytic system is presented that, solely by choice of the base, selectively switches between conjugate addition and the Mizoroki-Heck reaction of aryl halides with Michael acceptors (see scheme; R, R' = alkyl, aryl). For conjugate addition
Tsuyoshi Abe et al.
Bioorganic & medicinal chemistry letters, 17(11), 3161-3166 (2007-03-27)
Benzalacetone synthase (BAS) is a plant-specific chalcone synthase (CHS) superfamily type III polyketide synthase (PKS) that catalyzes a one-step decarboxylative condensation of 4-coumaroyl-CoA with malonyl-CoA. The diketide forming activity of Rheum palmatum BAS is attributed to the characteristic substitution of
Mohammed I El-Gamal et al.
European journal of medicinal chemistry, 45(4), 1403-1414 (2010-01-19)
Herein, we report the design, synthesis, and pharmacological properties of a series of substituted benzylidene acetone oxime ether derivatives from the corresponding oxime derivatives. All the newly synthesized compounds were investigated in vivo for their anti-inflammatory activities using carrageenin-induced rat
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