- Bioactive 4-substituted-6-methyl-2-pyrones with promising cytotoxicity against A2780 and K562 cell lines.
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Bioactive synthetic 4-substituted-6-methyl-2-pyrones are reported. Various 4-substitutents have been incorporated using Pd-catalysed carbon-carbon bond coupling procedures. Preliminary screening of the 2-pyrones against human ovarian carcinoma (A2780) and
- Marrison, Lester R,Dickinson, Julia M,Fairlamb, Ian J S
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Read Online
- An efficient synthesis of 4-alkenyl/alkynyl-6-methyl-2-pyrones via Pd-catalysed coupling on 4-bromo-6-methyl-2-pyrone
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We herein report the efficient syntheses of biologically active 4-alkenyl- and 4-alkynyl-6-methyl-2-pyrones using Pd-catalysed coupling procedures. A palladium on carbon/triphenylphosphine combination is shown to be the most effective catalyst for Sonogas
- Marrison, Lester R.,Dickinson, Julia M.,Ahmed, Razwan,Fairlamb, Ian J.S.
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Read Online
- PI3K INHIBITORS AND USES THEREOF
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The development of a new, targeted drug delivery paradigm coupled to improved PI3K inhibitors (e.g., PI3Kα inhibitors) represents a significant advance in cancer therapy. Provided herein are compounds, such as compounds of Formula (I) and (II), and pharmaceutically acceptable salts, hydrates, solvates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrugs thereof. The compounds provided herein are PI3K (e.g., PI3Kα) inhibitors and are therefore useful for the treatment and/or prevention of various diseases (e.g., proliferative diseases such as cancer). Also provided herein are nanoparticles and nanogels (e.g., P-selectin targeting nanoparticles) comprising PI3K inhibitors, such a compound described herein. In certain embodiments, a nanoparticle or nanogel described herein encapsulates a compound described herein for targeting delivery to cancer cells or tumors.
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Paragraph 00423-00424
(2020/05/15)
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- Unexpected C-N bond formation via Smiles rearrangement: One pot synthesis of N -arylated coumarin/pyran derivatives
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A conceptually new and one-pot method for the synthesis of N-arylated coumarin/pyran derivatives via Smiles rearrangement. The reaction of 4-bromocoumarin/pyran with 2-amino phenols affords O-arylated coumarin/pyran which subsequently rearranges into N-arylated coumarin/pyran under mild reaction conditions in good yields.
- Kumar, K. Shiva,Ramulu, Meesa Siddi,Kumar, N. Praveen
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supporting information
p. 11276 - 11279
(2018/07/25)
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- Synthesis of trifluoromethylthiolated and trifluoromethylselenolated pyrones
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Trifluoromethylthiolation and trifluoromethylselenolation of 3- or 4-iodo(bromo)-2-pyrones with (bpy)CuSCF3 and [(bpy)CuSeCF3]2 provide a convenient method for the synthesis of trifluoromethylthio(seleno)lated 4-alkoxy-, aryloxy-, and benzyloxy-2-pyrones in high yields.
- Zhang, Yunxiao,Yang, Ding-Yah,Weng, Zhiqiang
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supporting information
p. 3853 - 3859
(2017/06/13)
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- Cyclization of 4-Phenoxy-2-coumarins and 2-Pyrones via a Double C-H Activation
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Aryl-heteroaryl coupling via double C-H activation is a powerful transformation that avoids the installation of activating groups. A double C-H activation of privileged biological scaffolds, 2-coumarins and 2-pyrones, is reported. Despite the rich chemistry of these molecular frameworks, the yields are very good. Excellent regioselectivity was achieved on the pyrones. This methodology was applied to the synthesis of flemichapparin C in three steps. Isotope effect experiments were carried out, and a mechanism is proposed.
- Mackey, Katrina,Pardo, Leticia M.,Prendergast, Aisling M.,Nolan, Marie-T.,Bateman, Lorraine M.,McGlacken, Gerard P.
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supporting information
p. 2540 - 2543
(2016/06/15)
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- Intramolecular Direct Arylation of 3-Halo-2-pyrones and 2-Coumarins
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Direct arylation represents a favorable alternative to traditional cross-coupling and has found widespread use with simple aryls and robust heterocycles. Herein a direct arylation protocol has been optimized and applied to 2-pyrones, which are delicate an
- Nolan, Marie-T.,Pardo, Leticia M.,Prendergast, Aisling M.,McGlacken, Gerard P.
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p. 10904 - 10913
(2015/11/18)
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- Evaluation of α-pyrones and pyrimidones as photoaffinity probes for affinity-based protein profiling
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α-Pyrones and pyrimidones are common structural motifs in natural products and bioactive compounds. They also display photochemistry that generates high-energy intermediates that may be capable of protein reactivity. A library of pyrones and pyrimidones was synthesized, and their potential to act as photoaffinity probes for nondirected affinity-based protein profiling in several crude cell lysates was evaluated. Further "proof-of-principle" experiments demonstrate that a pyrimidone tag on an appropriate scaffold is equally capable of proteome labeling as a benzophenone.
- Battenberg, Oliver A.,Nodwell, Matthew B.,Sieber, Stephan A.
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scheme or table
p. 6075 - 6087
(2011/10/09)
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- An economical access to 3,4-diaryl-2(5H)-furanones and 4-aryl-6-methyl- 2(2H)-pyranones by pd-catalyzed Suzuki-type arylation of 3-aryl-4-tosyloxy-2(5H) -furanones and 6-methyl-4-tosyloxy-2(2H)-pyranones, respectively
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Both symmetrical and unsymmetrical 3,4-diaryl-substituted 2(5H)-furanones have been efficiently synthesized using an inexpensive procedure involving the Pd(OAc)2/PCy3-catalyzed Suzuki-type arylation of readily available 3-aryl-4-tosy
- Bellina, Fabio,Marchetti, Chiara,Rossi, Renzo
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body text
p. 4685 - 4690
(2009/12/07)
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- ANTIBACTERIAL CONDENSED THIAZOLES
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Compound of formula (I) have antibacterial activity: wherein: m is 0 or 1; Q is hydrogen or cyclopropyl; AIk - is an optionally substituted, divalent C1-C6 alkylene, alkenylene or alkynylene radical which may contain an ether (-0-), thioether (-S-) or amino (-NR)- link, wherein R is hydrogen, -CN or C1-C3 alky!; X is -C(=O)NR6-, or -C(=O)O- wherein R6 is hydrogen, optionally substituted C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl; Z1 is -N= or -CH= Z2 is -N= or -C(R1)=; R1 is hydrogen, methyl, ethyl, ethenyl, ethynyl, methoxy, mercapto, mercaptomethyl halo, fully or partially fluorinated (C1-C2)alkyl, (C1-C2JaIkOXy or (C1-C2)alkylthio, nitro, or nitrile (-CN); R2 is a group Q1 -[Alk1]q-Q2 -, wherein q is 0 or 1; AIkl is an optionally substituted, divalent, straight chain or branched C1-C6 alkylene, or C2-C6 alkenylene or C2-C6 alkynylene radical which may contain or terminate in an ether (-O-), thioether (-S-) or amino (-NR)- link; Q2 is an optionally substituted divalent monocyclic carbocyclic or heterocyclic radical having 5 or 6 ring atoms or an optionally substituted divalent bicyclic carbocyclic or heterocyclic radical having 9 or 10 ring atoms; Q1 is hydrogen, an optional substituent or an optionally substituted carbocyclic or heterocyclic radical having 3-7 ring atoms
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Page/Page column 28-29; 50
(2009/07/17)
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- Preparation and decarboxylative rearrangement of (Z)-enyne esters
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A method to assemble (Z)-enyne esters via palladium-catalyzed cross coupling reactions of enol tosylates is reported. A base-mediated one-pot decarboxylative rearrangement of the enynes to enones is described. The scope of this process is examined.
- Woo, Jacqueline C.S.,Walker, Shawn D.,Faul, Margaret M.
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p. 5679 - 5682
(2008/02/10)
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- Synthesis of gerfelin and related analogous compounds
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Gerfelin, an inhibitor of human geranylgeranyl diphosphate (GGPP) synthase that has been isolated from a culture broth of Beauveria felina QN22047, was synthesized in 4 and 3 steps starting from 2,4-dihydroxy-6-methylbenzoic acid and 3,4,5-trihydroxytolue
- Islam, Md. Sadequl,Kitagawa, Mitsuhiro,Imoto, Masaya,Kitahara, Takeshi,Watanabe, Hidenori
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p. 2523 - 2528
(2008/02/05)
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- Methods of treating cataracts and diabetic retinopathy with tricyclic pyrones
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Water-soluble, cell permeable aldose reductase inhibitors are presented. These compounds prevent the effects of galactosemia in patients. The compounds prevent both the accumulation of polyols and the change in levels of protein kinase C gamma observed du
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Page/Page column 35
(2008/06/13)
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- 2-Pyrones possessing antimicrobial and cytotoxic activities
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The 2-pyrone sub-unit is found in a number of natural products possessing broad spectrum biological activity. Such compounds are validated as being capable of binding to specific protein domains and able to exert a remarkable range of biological effects. In an effort to identify synthetic 2-pyrones with interesting biological effects, herein we report the synthesis and biological evaluation of 4-substituted-6-methyl-2-pyrones. Synthetic routes to 4-alkyl/alkenyl/aryl/alkynyl-6-methyl-2-pyrones have been developed utilising Sonogashira, Suzuki and Negishi cross-coupling starting from readily available 4-bromo-6-methyl-2-pyrone. Specific conditions for each organometallic protocol were required for successful cross-coupling. In particular, a triethylamine/acetonitrile - base/solvent mixture was crucial to Sonogashira alkynylation of 4-bromo-6-methyl-2-pyrone, whereas thallium carbonate was a mandatory base for the Suzuki cross-coupling of trialkylboranes. The 2-pyrones demonstrate potent inhibitory activity against Bacillus subtilis, Escherichia coli, Staphylococcus aureus, Schizosaccharomyces pombe and Botrytis cinerea. The growth inhibitory activities of selected 2-pyrones were determined in A2780 human ovarian carcinoma and K562 human chronic myelogenous leukaemia cell lines using an in vitro cell culture system (MTT assay). These studies demonstrate that 4-phenylethynyl-, 4-tetrahydropyranylpropargyl ether- and 4-ethynyl-6-methyl-2-pyrones have excellent potential as a new class of anticancer agents.
- Fairlamb, Ian J. S.,Marrison, Lester R.,Dickinson, Julia M.,Lu, Feng-Ju,Schmidt, Jan Peter
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p. 4285 - 4299
(2007/10/03)
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- A facile bromination of hydroxyheteroarenes
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Bromination of hydroxyheteroarenes using P2O5/Bu4NBr proceeds under mild conditions to afford high yields of various bromoheteroarenes. This procedure is successfully applied to large-scale syntheses of bromoheteroarenes.
- Kato, Yoshiaki,Okada, Shigemitsu,Tomimoto, Koji,Mase, Toshiaki
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p. 4849 - 4851
(2007/10/03)
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- 4-AMINO-6-METHYL-2H-PYRAN-2-ONE. PREPARATION AND REACTIONS WITH AROMATIC ALDEHYDES.
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Bis(4-amino-6-methyl-2-oxo-2H-pyran-3-yl)arylmethanes, 1, are synthesized by reaction of 4-amino-6-methyl-2H-pyran-2-one, 10, with aromatic aldehydes.The aminopyrone 10 is obtained in three steps from 4-hydroxy-6-methyl-2H-pyran-2-one (triacetic acid lact
- Cervera,Maria,Moreno-Manas, Marcial,Pleixats, Roser
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p. 7885 - 7892
(2007/10/02)
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