- MeONH 2·hCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonylo-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones
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A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o -hydroxyacetophenones with methyl sulfoxides via a MeONH 2·HCl-mediated sequential methylenation/ conjugate addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated.
- Chang, Meng-Yang,Chen, Kuan-Ting
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p. 135 - 145
(2020/09/07)
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- C-H bond cleavage-enabled aerobic ring-opening reaction of: In situ formed 2-aminobenzofuran-3(2 H)-ones
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A C-H bond cleavage-enabled aerobic ring-opening reaction of 2-aminobenzofuran-3(2H)-ones formed in situ by hemiacetals with a variety of amines is reported. This simple one-pot reaction provides an alternative approach to obtain o-hydroxyaryl glyoxylamides in excellent yields of up to 97%. Alkylamines react with hemiacetals via a catalyst-free dehydration condensation to generate 2-aminobenzofuran-3(2H)-ones. The in situ formed semicyclic N,O-acetals undergo the same amine-initiated C-H bond hydroxylation in air under mild conditions to afford ring-opening products. Similarly, arylamines were investigated as substrates for a two-step tandem process involving a DPP-catalyzed condensation followed by a Et2NH-mediated C-H hydroxylation. Unlike the previously reported functionalization of N,O-acetals via a C-O or C-N cleavage, the aerobic oxidative C-H hydroxylation in this reaction, which is promoted by using stoichiometric amounts of alkylamines as both a Lewis base and a reductant at room temperature under atmospheric air, proceeds via α-carbonyl-stabilized carbanion intermediates from the C-H cleavage of N,O-acetals. This journal is
- Jiang, Zhihong,Lao, Chichou,Wang, Yingwei,Yang, Mingrong
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supporting information
p. 9448 - 9459
(2021/11/17)
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- Temperature-Controlled Desulfonylative Condensation of α-Sulfonyl o-Hydroxyacetophenones and 2-Formyl Azaarenes: Synthesis of Azaaryl Aurones and Flavones
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Temperature-controlled intermolecular desulfonylative condensation of α-sulfonyl o-hydroxyacetophenones with 2-formyl azaarenes (pyridines and quinolones) provides azaaryl (pyridyl and quinolyl) aurones and flavones under warming and refluxing toluene reaction conditions via the formation of the intermediate of sulfonyl chroman-4-one. The uses of various solvents are investigated for facile and efficient transformation. A plausible mechanism is proposed.
- Chang, Meng-Yang,Chen, Han-Yu,Tsai, Yu-Lin
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p. 326 - 337
(2019/01/08)
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- Discovery of clinical candidate (1 R,4 r)-4-((R)-2-((S)-6-Fluoro-5 H-imidazo[5,1-A[isoindol-5-yl)-1-hydroxyethyl)cyclohexan-1-ol (Navoximod), a potent and selective inhibitor of indoleamine 2,3-dioxygenase 1
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A novel class of 5-substituted 5H-imidazo[5,1-a]isoindoles are described as potent inhibitors of indoleamine 2,3-dioxygenase 1 (IDO1). A structure-based drug design approach was used to elaborate the 5H-imidazo[5,1-a]isoindole core and to improve potency and pharmacological properties. Suitably placed hydrophobic and polar functional groups in the lead molecule allowed improvement of IDO1 inhibitory activity while minimizing off-target liabilities. Structure-activity relationship studies focused on optimizing IDO1 inhibition potency and a pharmacokinetic profile amenable to oral dosing while controlling CYP450 and hERG inhibitory properties.
- Kumar, Sanjeev,Waldo, Jesse P.,Jaipuri, Firoz A.,Marcinowicz, Agnieszka,Van Allen, Clarissa,Adams, James,Kesharwani, Tanay,Zhang, Xiaoxia,Metz, Richard,Oh, Angela J.,Harris, Seth F.,Mautino, Mario R.
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p. 6705 - 6733
(2019/08/20)
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- 3-Hydroxychromone structure-based Raf kinase inhibitor, and preparation method and use thereof
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The invention relates to the field of pharmaceutical chemistry, and concretely relates to 3-hydroxychromone compounds (A). R1-R9, X1 and X2 in the compounds (A) are as defined in the description. The invention also discloses preparation methods of the compounds represented by general formula (A), a medicinal composition containing the compounds, and a medicinal use of the compounds, especially a use of the compounds as a Raf kinase inhibitor and a tumor inhibitor.
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Paragraph 0056-0058; 0110-0112
(2017/02/02)
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- Dehydrozingerone Inspired Styryl Hydrazine Thiazole Hybrids as Promising Class of Antimycobacterial Agents
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Series of styryl hydrazine thiazole hybrids inspired from dehydrozingerone (DZG) scaffold were designed and synthesized by molecular hybridization approach. In vitro antimycobacterial activity of synthesized compounds was evaluated against Mycobacterium tuberculosis H37Rv strain. Among the series, compound 6o exhibited significant activity (MIC = 1.5 μM; IC50 = 0.48 μM) along with bactericidal (MBC = 12 μM) and intracellular antimycobacterial activities (IC50 = 0.098 μM). Furthermore, 6o displayed prominent antimycobacterial activity under hypoxic (MIC = 46 μM) and normal oxygen (MIC = 0.28 μM) conditions along with antimycobacterial efficiency against isoniazid (MIC = 3.2 μM for INH-R1; 1.5 μM for INH-R2) and rifampicin (MIC = 2.2 μM for RIF-R1; 6.3 μM for RIF-R2) resistant strains of Mtb. Presence of electron donating groups on the phenyl ring of thiazole moiety had positive correlation for biological activity, suggesting the importance of molecular hybridization approach for the development of newer DZG clubbed hydrazine thiazole hybrids as potential antimycobacterial agents.
- Hampannavar, Girish A.,Karpoormath, Rajshekhar,Palkar, Mahesh B.,Shaikh, Mahamadhanif S.,Chandrasekaran, Balakumar
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supporting information
p. 686 - 691
(2016/07/26)
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- Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect
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2-(2′-Hydroxyphenyl)imidazo[1,2-a]pyridine (HPIP, 1) and its derivatives are synthesized, and their fluorescence properties are studied. Although all the compounds show faint dual emission (Φ ≈ 0.01), which is assigned to the normal and excited-state intr
- Mutai, Toshiki,Sawatani, Hirotaka,Shida, Toshihide,Shono, Hideaki,Araki, Koji
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p. 2482 - 2489
(2013/04/24)
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- A radical-based approach to hydroxytetralones from unprotected phenols
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Xanthates derived from unprotected 2-hydroxyacetophenones undergo smooth intermolecular addition to unactivated alkenes and subsequent cyclisation to give hydroxytetralones in good yield. The Royal Society of Chemistry 2010.
- Petit, Laurent,Zard, Samir Z.
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supporting information; experimental part
p. 5148 - 5150
(2010/10/19)
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- Regioselective synthesis of tetrasubstituted pyrroles by 1,3-dipolar cycloaddition and spontaneous decarboxylation
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We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of α,β-unsaturated benzofuran-3(2H)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).
- Kim, Yongju,Kim, Jonghoon,Park, Seung Bum
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supporting information; experimental part
p. 17 - 20
(2009/08/07)
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