- Synthesis of Chiral Polycyclic Tetrahydrocarbazoles by Enantioselective Aminocatalytic Double Activation of 2-Hydroxycinnamaldehydes with Dienals
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An efficient aminocatalytic enantioselective double-activation strategy has been developed that combines several different aminocatalytic modes in a cascade process, such as iminium ion, vinylogous iminium ion, trienamine, and dienamine activations. By using this strategy, 2-hydroxycinnamaldehydes worked well with various dienals via [4 + 2] cycloaddition and the oxa-Michael reaction-initiated cascade, respectively, leading to chiral polycyclic tetrahydrocarbazole and chromane derivatives with excellent diastereo- and enantioselectivities.
- Ming, Yong-Chao,Lv, Xue-Jiao,Liu, Ming,Liu, Yan-Kai
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supporting information
p. 6515 - 6519
(2021/09/02)
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- Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives
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A simple and effective one-pot synthesis of substituted indolo[1,2-a]quinolines has been developed. The desired products were obtained in up to 98% yield when substituted 2-methyindoles were treated with 2-iodobenzaldehyde in the presence of Cs2CO3, CuI and L-proline. Our mechanistic study confirmed that the reaction sequence involved an intermolecular Knoevenagel reaction followed by an intramolecular Ullmann-type coupling reaction. Moreover, some of the synthesized compounds were found to be active against human breast (MCF-7) and colorectal (HCT-116) cancer cells with IC50 values of 27.96 μM and in the range of 6.21–46.91 μM, respectively.
- Borwornpinyo, Suparerk,Chuanopparat, Nutthawat,Jearawuttanakul, Kedchin,Kanjanasirirat, Phongthon,Ngernmeesri, Paiboon,Rattanarat, Hassayaporn,Seemakhan, Sawinee,Thanetchaiyakup, Adisak
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- Direct construction of carbazoles from 2-methyl-indole-3-carbaldehydes and enals
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The direct and rapid construction of carbazoles was achieved via the reaction of 2-methyl-indole-3-carbaldehydes with enals promoted by LiCl/DBU in a single operation. This mild and green reaction proceeds through a [4 + 2] cycloaddition/dehydration/oxidative aromatization cascade to generate carbazoles in good to excellent yields. The reaction features mild reaction conditions, a broad substrate scope, and excellent functional group tolerance, using O2 (1 atm) as the sole oxidant and affording H2O as the only by-product. More importantly, 4-fluoroquinocarbazole, a significant bioactive compound, was generated in 80% yield in only one step from the obtained carbazole.
- Liu, Dehai,Huang, Jie,Fu, Zhenqian,Huang, Wei
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supporting information
p. 968 - 972
(2019/04/17)
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- One-pot synthesis of substituted indolo[1,2-a]quinolines under transition-metal-free conditions
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A simple and efficient one-pot synthesis of substituted indolo[1,2-a]quinolines under transition-metal-free conditions has been developed. When 2-fluorobenzaldehyde was treated with substituted 2-methylindoles in the presence of Cs2CO3, the desired products were typically obtained in good to excellent yields. This reaction sequence involves a nucleophilic aromatic substitution and a Knoevenagel condensation reaction. Our mechanistic investigation revealed that both reactions could proceed as an intermolecular reaction in the first step.
- Thanetchaiyakup, Adisak,Rattanarat, Hassayaporn,Chuanopparat, Nutthawat,Ngernmeesri, Paiboon
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supporting information
p. 1014 - 1018
(2018/02/23)
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- Selective nickel-catalyzed dehydrogenative-decarboxylative formylation of indoles with glyoxylic acid
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Herein we present a new strategy for the dehydrogenative-decarboxylative coupling of indoles with glyoxylic acid. A broad range of indoles were transformed into the corresponding 3-formylindoles in moderate to good yields and excellent functional group tolerance. Notably, no N-formylation product was detected under our conditions.
- Yin, Zhiping,Wang, Zechao,Wu, Xiao-Feng
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supporting information
p. 3707 - 3710
(2018/05/31)
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- Exploiting the Distal Reactivity of Indolyl Methylenemalononitriles: An Asymmetric Organocatalyzed [4+2] Cycloaddition with Enals Enables the Assembly of Elusive Dihydrocarbazoles
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An unprecedented technique for the in situ generation of indolyl ortho-quinodimethanes from 2-methylindole-based methylenemalononitriles by amine-mediated remote C(sp3)?H deprotonation was developed. These intermediates were efficiently trapped by diverse enals to provide a rapid entry to 2,9-dihydro-1H-carbazole-3-carboxyaldehyde structures through a formal asymmetric [4+2] eliminative cycloaddition governed by a α,α-diphenylprolinol trimethylsilyl ether catalyst.
- Rassu, Gloria,Curti, Claudio,Zambrano, Vincenzo,Pinna, Luigi,Brindani, Nicoletta,Pelosi, Giorgio,Zanardi, Franca
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supporting information
p. 12637 - 12640
(2016/08/30)
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- Structural Characterization and Computer-Aided Optimization of a Small-Molecule Inhibitor of the Arp2/3 Complex, a Key Regulator of the Actin Cytoskeleton
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CK-666 (1) is a recently discovered small-molecule inhibitor of the actin-related protein 2/3 (Arp2/3) complex, a key actin cytoskeleton regulator with roles in bacterial pathogenesis and cancer cell motility. Although 1 is commercially available, the crystal structure of Arp2/3 complex with 1 bound has not been reported, making its mechanism of action uncertain. Furthermore, its relatively low potency increases its potential for off-target effects invivo, complicating interpretation of its influence in cell biological studies and precluding its clinical use. Herein we report the crystal structure of 1 bound to Arp2/3 complex, which reveals that 1 binds between the Arp2 and Arp3 subunits to stabilize the inactive conformation of the complex. Based on the crystal structure, we used computational docking and free-energy perturbation calculations of monosubstituted derivatives of 1 to guide optimization efforts. Biochemical assays of ten newly synthesized compounds led to the identification of compound 2, which exhibits a threefold increase in inhibitory activity invitro relative to 1. In addition, our computational analyses unveiled a surface groove at the interface of the Arp2 and Arp3 subunits that can be exploited for additional structure-based optimization.
- Baggett, Andrew W.,Cournia, Zoe,Han, Min Suk,Patargias, George,Glass, Adam C.,Liu, Shih-Yuan,Nolen, Brad J.
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scheme or table
p. 1286 - 1294
(2012/07/17)
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- 2-Indolyl Imidazo [4,5-d] Phenanthroline Derivatives and Their Use in the Treatment for Cancer
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2-indolyl imidazo[4,5-d]phenanthroline compounds of Formula I that are capable of intracellular chelation of transition metals and of exerting antiproliferative effects in cancer cells, that are cytostatic and/or cytotoxic, are provided. Compounds of Form
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Page/Page column 30
(2010/07/08)
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- Indanediones-1,3 VIII. Hydroxy-2 indolyl-2 indanediones-1,3, (indolyl-3 methylene)-2 indanediones-1,3 et derives: recherche d'une activite anti-inflammatoire
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1,3-Indandiones VIII. 2-Hydroxy-2-indolyl-1,3-indandiones, 2-(indol-3-ylmethylene indandione and derivatives: search for anti-inflammatory activity.A series of 2-hydroxy-2-indolyl-1,3-indandiones, diversely substituted on the heterocycle were synthetized in order to study their anti-inflammatory activity.Catalytic hydrogenation gave 2,3-dihydroxy-1 indanones 6 and NaBH4 reduction of 3i led to the corresponding indanetriol 7i.Base-catalyzed isomerization of hydroxy-β-diketones 3 furnished 3-indololylcarbonyl phthalides 9.Only compound 3d exhibited a significant inhibition of mouse paw edema.Experimentation in the rat paw edema test confirmed the anti-inflammatory effect of 3d, but it was associated with an anti-coagulant activity. ω-Amino-alkylation of the indole nitrogen of 3d led to loss of anti-inflammatory activity.Introduction of a double bond between the indandione and indole nuclei, leading to 2-(indol-3-ylmethylene)-1,3 indandiones 12, proved ineffective in raising this activity. 2-hydroxy-2-indolyl-1,3-indandiones/ 2,3-dihydroxyindanones/ 1,2,3-indantriols/ 3-indolylcarbonyl-phthalides/ 2-(indol-3-ylmethylene)-1,3-indandiones/ anti-inflammatory activity/ anti-coagulant activity
- Courant, Jacqueline,Leblois, Danielle,Tandon, Manju,Robert-Piessard, Sylvie,le Baut, Guillaume,et al.
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p. 145 - 154
(2007/10/02)
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