- Rh-Catalyzed aldehydic C-H alkynylation and annulation
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Novel Rh-catalyzed aldehydic C-H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C-H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-
- Ramakrishna, Boddu S.,Rao, Maddali L. N.
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p. 1402 - 1411
(2020/03/03)
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- 2-Styrylchromone derivatives as potent and selective monoamine oxidase B inhibitors
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A series of eighteen 2-styrylchromone derivatives (see Chart 1) were synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activities. Many of the derivatives inhibited MAO-B comparable to pargyline (a positive control), and most of them inhibited MAO-B selectively. Of the eighteen derivatives, compound 9 having methoxy group at R1 and chlorine at R4 showed both the best MAO-B inhibitory activity (IC50 = 17 ± 2.4 nM) and the best MAO-B selectivity (IC50 for MAO-A/IC50 for MAO-B = 1500). The mode of inhibition of compound 9 against MAO-B was competitive and reversible. Quantitative structure–activity relationship (QSAR) analyses of the 2-styrylchromone derivatives were conducted using their pIC50 values with the use of Molecular Operating Environment (MOE) and Dragon, demonstrating that the descriptors of MAO-B inhibitory activity and MAO-B selectivity were 1734 and 121, respectively, that showed significant correlations (P 50 value indexes for MAO-B exhibited a determination coefficient (R2) of 0.873 as well as a Leave-One-Out cross-validated determination coefficient (Q2) of 0.675. These data suggested that the 2-styrylchromone structure might be a useful scaffold for the design and development of novel MAO-B inhibitors.
- Takao, Koichi,Endo, Saki,Nagai, Junko,Kamauchi, Hitoshi,Takemura, Yuri,Uesawa, Yoshihiro,Sugita, Yoshiaki
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- Soft-enolization Baker-Venkataraman Rearrangement Enabled Total Synthesis of Dirchromones and Related 2-Substituted Chromones
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A seven-step total synthesis of the original scaffold of cytotoxic dirchromones involving an unprecedented soft-enolization Baker-Venkataraman rearrangement was designed. The methodology enabled access to naturally occurring dirchromone 1 (21% overall yield) at gram-scale, which was screened for cytotoxicity against 13 cancer cell lines. The scope of the soft-enolization Baker-Venkataraman rearrangement encompasses diversely substituted dirchromones, including flavonoids, 2-styrylchromones, and 2-phenylethylchromones.
- St-Gelais, Alexis,Alsarraf, Jér?me,Legault, Jean,Gauthier, Charles,Pichette, André
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p. 7424 - 7428
(2019/01/03)
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- Discovery, Structure-Activity Relationship, and Antiparkinsonian Effect of a Potent and Brain-Penetrant Chemical Series of Positive Allosteric Modulators of Metabotropic Glutamate Receptor 4
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The metabotropic glutamate receptor 4 (mGluR4) is an emerging target for the treatment of Parkinson's disease (PD). However, since the discovery of its therapeutic potential, no ligand has been successfully developed enough to be tested in the clinic. In the present paper, we report for the first time the medicinal chemistry efforts conducted around the pharmacological tool (-)-PHCCC. This work led to the identification of compound 40, a potent and selective mGluR4 positive allosteric modulator (PAM) with good water solubility and demonstrating consistent activity across validated preclinical rodent models of PD motor symptoms after intraperitoneal administration: haloperidol-induced catalepsy in mouse and the rat 6-hydroxydopamine (6-OHDA) lesion model. Moreover, we also describe the identification of compound 60 a close analogue of compound 40 with improved pharmacokinetic profile after oral administration. On the basis of its favorable and unique preclinical profile, compound 60 (PXT002331, now foliglurax) was nominated as a candidate for clinical development.
- Charvin, Delphine,Pomel, Vincent,Ortiz, Millan,Frauli, Mélanie,Scheffler, Sophie,Steinberg, Edith,Baron, Luc,Deshons, Laurène,Rudigier, Rachel,Thiarc, Delphine,Morice, Christophe,Manteau, Baptiste,Mayer, Stanislas,Graham, Danielle,Giethlen, Bruno,Brugger, Nadia,Hédou, Ga?l,Conquet, Fran?ois,Schann, Stephan
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p. 8515 - 8537
(2017/11/03)
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- Synthesis of functionalized chromones via organocatalysis
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A facile and versatile organocatalytic approach to access 2-substituted and 2,3-disubstituted chromone derivatives under mild conditions was developed, which was effectively catalyzed by novel proline phenylsulphonylhydrazide or pyrrolidine. As a result, diversely functionalized chromones were obtained in up to 99% yield. In addition, further modification of the corresponding chromones afforded novel polycyclic chromones.
- Wen, Sai-Shuai,Wang, Jing,Luo, Yi-Ming,Yang, Hua
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p. 9314 - 9320
(2015/03/05)
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- Synthesis of (E)-2-styrylchromones and flavones by base-catalyzed cyclodehydration of the appropriate β-diketones using water as solvent
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A low cost, safe, clean and environmentally benign base-catalyzed cyclodehydration of appropriate β-diketones affording (E)-2-styrylchromones and flavones in good yields is disclosed. Water was used as solvent and the reactions were heated using classical
- Pinto, Joana,Silva, Vera L. M.,Silva, Ana M. G.,Silva, Artur M. S.
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p. 11418 - 11431
(2015/08/06)
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- Structure-activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells
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The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI50 value of 1.3 μM. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.
- Lin, Chen,Lu, Pei-Jung,Yang, Chia-Ning,Hulme, Christopher,Shaw, Arthur Y.
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p. 2385 - 2394
(2013/07/26)
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- Synthesis and evaluation of antioxidant activity of 2-styrylchromones
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Antioxidants are emerging as potential prophylactic and therapeutic agents which scavenge free radicals otherwise reactive oxygen species and prevent the damage caused by them. Free radicals have been associated with pathogenesis of various disorders like
- Pawar, Shrinivas P.,Kondhare, Dasharath D.,Zubaidha
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p. 753 - 757
(2013/04/10)
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- (E)-3-Halo-2-styryl-4H-chromen-4-ones: Synthesis and transformation to novel pyrazoles
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New methods for the synthesis of (E)-3-halo-2-styryl-4H-chromen-4-ones were established. The reaction of these compounds with hydrazine hydrate afforded new and unexpected 3(5)-aryl-5(3)-[2-(2-hydroxyphenyl)-2-hydrazonoethyl]-1H- pyrazoles, which upon aci
- Ferreira, Joana P.A.,Silva, Vera L.M.,Elguero, José,Silva, Artur M.S.
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p. 9701 - 9709
(2013/10/22)
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- (E)-2-Styrylchromones as potential anti-norovirus agents
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Human noroviruses (NoV) are now recognized as the most frequent cause of outbreaks and sporadic cases of acute gastroenteritis. Despite the significant economic impact and considerable morbidity of norovirus disease, no drug or vaccine is currently available to treat or prevent this disease, therefore the discovery of anti-norovirus drugs is urgent. In the present work, a total of 12 structure related chromone and (E)-2-styrylchromones were evaluated for their potential anti-norovirus activity using the murine norovirus (MNV) as a surrogate model for human NoV. From the 12 compounds studied, six (E)-2-styrylchromones were found to have with interesting anti-norovirus activity. The best compounds of the series were (E)-5-hydroxy-2-styrylchromone and (E)-4′-methoxy-2-styrylchromone with an IC50 ≈ 7 μM. A first insight into the mechanism of action of these compounds was possible. An interesting relationship between the anti-norovirus activity and the chemical structure was observed. The present study points out that the (E)-2-styrylchromones skeleton is an important one which deserves to be developed and further explored as new antiviral drugs against NoV.
- Rocha-Pereira, Joana,Cunha, Ricardo,Pinto, Diana C.G.A.,Silva, Artur M.S.,Nascimento, Maria Sao Jose
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scheme or table
p. 4195 - 4201
(2010/09/12)
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- Microwave assisted synthesis of 1-(2-hydroxyphenyl)-5-phenyl pent-4-ene-1,3-diones and their conversion to 2-styryl chromones
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A simple and efficient method has been developed for the rapid synthesis of 1-(2-hydroxyphenyl)-5-phenyl pent-4-ene-1,3-diones 3a-g in a single pot reaction under microwave irradiation. These β-diketones are further converted into 2-styryl chromones again
- Goel, Sharda,Ritu,Makrandi
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p. 1278 - 1281
(2007/10/03)
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- Studies on unimolecular and bimolecular photoprocesses of a newly synthesized selenium compound, 7-chloro-2-phenyl-9H-[1]-benzopyrano[3,2-b]-selenophene-9-one (SeP)
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Using steady state/time resolved spectroscopic and electrochemical techniques the spectroscopic and photophysical studies were made on a novel synthesized selenophene compound SeP in nonpolar methylcyclohexane (MCH), polar aprotic acetonitrile (ACN) and p
- De,De,Mallik,Ganguly
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p. 1427 - 1441
(2007/10/03)
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- Novel (E)- and (Z)-2-styrylchromones from (E,E)-2′-hydroxycinnamylideneacetophenones - Xanthones from daylight photooxidative cyclization of (E)-2-styrylchromones
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The oxidative cyclization of (E,E)-2′-hydroxycinnamylideneacetophenones 1a-e, and (E,E)-2′-benzyloxy-6′-hydroxycinnamylideneacetophenones 1i-1 with DMSO/ iodine, gave (E)-2-styrylchromones 3a-e,i-1. However, in the case of (E,E)-γ-alkyl-2′-hydroxycinnamyl
- Silva, Artur M. S.,Pinto, Diana C. G. A.,Tavares, Hilario R.,Cavaleiro, Jose A. S.,Jimeno, M. Luisa,Elguero, Jose
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p. 2031 - 2038
(2007/10/03)
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- Synthesis of 4-Aryl-3-(2-chromonyl)-2-pyrazolines by the 1,3-Dipolar Cycloaddition of 2-Styrylchromones with Diazomethane
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The first reported 1,3-dipolar cycloaddition of 2-styrylchromones with diazomethane afforded 4-aryl-3-(2-chromonyl)-2-pyrazolines. However, 3-aryl-4-(2-chromonyl)-1-pyrazolines have been also found as minor products of this reaction. These two series of p
- Pinto, Diana C.G.A.,Silva, Artur M.S.,Almeida, Lucia M.P.M.,Cavaleiro, Jose A.S.,Levai, Albert,Patonay, Tamas
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p. 217 - 224
(2007/10/03)
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- Oxidative cyclization of o-hydroxy-ω-cinnamylideneacetophenones to 2-styrylchromones with potassium iodate-dimethyl sulphoxide
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o-Hydroxy-ω-cinnamylideneacetophenones (1) have been found to undergo oxidative cyclization to the corresponding 2-styrylchromones (2) in satisfactory yields by heating them with potassium iodate in dimethyl sulphoxide.
- Singhi, Manasi,Grover, S. K.
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p. 1083 - 1084
(2007/10/02)
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- New route to styrylchromones via [1-(2-hydroxybenzoyl)alkylidene]triphenylphosphoranes
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Several [1-(2-hydroxybenzoyl)alkylidene]triphenylphosphoranes have been obtained in good yields through acylation of the corresponding alkylidenetriphenylphosphoranes, prepared in situ, by the easily available methyl 2-hydroxybenzoates. These ylides prove
- Zammattio,Brion,Le Baut,Ducrey
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p. 375 - 376
(2007/10/02)
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- A modified synthesis of 2-styrylchromones
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2-Hydroxy-ω-cinnamylideneacetophenones (3a-e) have been obtained by condensation of 2-hydroxyacetophenones (1) with cinnamaldehyde (2) in the presence of barium hydroxide.Oxidative cyclisation of the compounds 3a-e with iodine in dimethyl sulphoxide provi
- Makrandi, J. K.,Seema
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p. 788 - 789
(2007/10/02)
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- A CONVENIENT SYNTHESIS OF 2-STYRYLCHROMONES BY MODIFIED BAKER-VENKATARAMAN TRANSFORMATION USING PHASE TRANSFER CATALYSIS.
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Condensation of 2-hydroxyacetophenones 1 with cinnamic anhydrides 2 in the presence of tetra-n-butyl ammonium hydrogen sulfate in benzene-aqueous potassium carbonate biphase medium give 1-(2-hydroxyphenyl)-5-phenyl-4-pentene-1,3-diones 3 which on cyclodeh
- Makrandi, J. K.,Kumari, Vandna
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p. 1919 - 1922
(2007/10/02)
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- 53. Acid-Catalyzed Cyclization Rections of Substituted Acetylenic Ketones: A New Approach for the Synthesis of 3-Halofurans, Flavones, and Styrylchromones
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Acetylenic acetals of type I (Scheme 1) and acetylenic ketones of type III (Scheme 1), 37 and 38 (Scheme 7) are versatile synthetic precursors for the synthesis of various heterocycles by acid-catalyzed cyclization reactions.By this way, substituted 3-halofurans of type II and IV (Scheme 1) and flavones and styrylchromones (Scheme 7) can be synthesized in good-to-excellent yields.The high degree of regioselectivity in the synthesis of the 3-halofurans (Scheme 4) is the result of the regioselective β-addition of HX (X = Cl, Br, I) to the acetylenic aldehyde and acetylenic ketone moieties.A possible mechanism is depicted in Scheme 5.Since 3-halofurans can easily be metalated and substituted, this approach constitutes a new synthesis of highly substituted furans.
- Obrecht, Daniel
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p. 447 - 456
(2007/10/02)
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- Synthesis and Reactions of 1,5-Disubstituted 4-Pentene-1,3-diones
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The title compounds (III) have been synthesised by the base-catalysed Baker-Venkataraman transformation of cinnamoyl and p-methoxycinnamoyl esters (II) of substituted 2-hydroxyacetophenones (I).The cyclodehydration of III with AcOH-H2SO4 affords 2-styrylc
- Gaggad, H. L.,Wadodkar, K. N.,Ghiya, B. J.
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p. 1244 - 1247
(2007/10/02)
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- Reactions with 2-Methyl- and 2-Styryl-4-thiochromones
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Diazoalkanes react with 2-methyl- and 2-styryl-4-thiochromones to yield the 1,3-dithiolanes 1 and/or ethylenes 2-4.The latter are cleaved with thionyl chloride to give the corresponding ketones, while on fusion with sulfur they afford the corresponding thioketones.By condensation with compounds containing active hydrogen, such as malononitrile and ethyl cyanoacetate, the 2-methyl- and 2-styryl-4-thiochromones yield the compounds 5.Oxidation of 2-methyl- and 2-styryl-4-thiochromones was accomplished by yellow mercury(II) oxide as well as with tetrahalo-o-benzoquinones to give the corresponding ketones.The biological activity of some selected comounds prepared during this work has been tested towards Gram-positive and Gram-negative bacteria.
- Zeid, Ibrahim,El-Bary, Hamed Abd,Yassin, Salah,Zahran, Magdy
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p. 186 - 190
(2007/10/02)
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