- 1,7-Migration of benzyl group in 2-substituted N-benzylindoles
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It has been shown that when 2-substituted N-benzylindoles are heated above 100°C in polyphosphoric acid, the benzyl group is split off and undergoes 1,7-migration. 1997 Plenum Publishing Corporation.
- Samsoniya,Chikvaidze,Gogrichiani,Machaidze,Saliya
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- Synthesis of 2-substitued indoles via Pd-catalysed cyclization in an aqueous micellar medium
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The synthesis of 2-substituted indoles starting from the corresponding unprotected 2-alkynylanilines was made possible in 3% TPGS-750-M water using Pd(OAc)2 alone as the catalyst. The reaction was sensitive to the heating mode respect to the na
- Cini, Elena,Siciliano, Sofia,Taddei, Maurizio,Vinciarelli, Giorgia
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- Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors
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The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.
- Chen, Zhe-Sheng,Dai, Qing-Qing,Li, Guo-Bo,Liu, Hong-Min,Liu, Hui,Wang, Bo,Wang, Shaomeng,Yu, Bin,Yuan, Shuo,Zhang, Jing-Ya,Zhang, Xiao-Nan,Zuo, Jia-Hui
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p. 14895 - 14911
(2021/10/12)
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- Synthesis of 2-substituted indole with Hantzsch ester catalyzed by palladium
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An efficient reductive cyclization of o-nitrobenzyl ketone compounds was achieved by using a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. 2-Substituted indoles were obtained in good yields. Investigation of the mechanism suggests that palladium hydride promotes the reduction of nitro group, and acetic acid was beneficial for the loss of water to produce the intended product. This reaction system can not only broaden the use of Hantzsch 1,4-dihydropyridine ester, but it also provides a novel approach for preparing indole compounds.
- Li, Yanan,Wang, Bo,Xing, Ruiguang
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p. 295 - 303
(2019/08/01)
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- One-Pot Reaction between N-Tosylhydrazones and 2-Nitrobenzyl Bromide: Route to NH-Free C2-Arylindoles
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A one-pot Barluenga coupling between N-tosylhydrazones and nitro-benzyl bromide, followed by deoxygenation of ortho-nitrostyrenes, and subsequent cyclization has been developed, providing a new way to synthesize various C2-arylindoles. This method exhibits a good substrate scope and functional group tolerance, and it allows an access to NH-free indoles, which can present a potential utility in medicinal chemistry applications.
- Bzeih, Tourin,Zhang, Kena,Khalaf, Ali,Hachem, Ali,Alami, Mouad,Hamze, Abdallah
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p. 228 - 238
(2019/01/04)
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- Directed Decarbonylation of Unstrained Aryl Ketones via Nickel-Catalyzed C - C Bond Cleavage
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The nickel-catalyzed decarbonylation of unstrained diaryl ketones has been developed. The reaction is catalyzed by a combination of Ni(cod)2 and an electron-rich N-heterocyclic carbene ligand. High functional group tolerance and excellent yields (up to 98%) are observed. This strategy provides an alternative and versatile approach to construct biaryls using an inexpensive nickel catalyst.
- Zhao, Tian-Tian,Xu, Wen-Hua,Zheng, Zhao-Jing,Xu, Peng-Fei,Wei, Hao
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p. 586 - 589
(2018/01/26)
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- Efficient synthesis of 2-arylindoles, 2-arylimidazo[1,2-a]pyridines and 2-arylquinoxalines, and their bis-derivatives using [Hmim]OTf ionic liquid supported on nano-silica as a reusable catalyst
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Abstract An efficient and facile method for the synthesis of 2-arylindoles, 2-arylimidazo[1,2-a]pyridines and 2-arylquinoxalines by the reaction of various α-bromo ketones with anilines, 2-aminopyridine and 1,2-phenylenediamine, respectively, in the presence of N-methylimidazolium trifluoromethanesulfonate ionic liquid supported on nano-silica ([Hmim]OTf@nano-SiO2) as a reusable catalyst under solvent-free conditions has been developed. The bis-derivatives of these compounds were also prepared efficiently, for the first time, using this catalytic system. All products were obtained in high yields and in short reaction times.
- Soltani, Mohammad,Mohammadpoor-Baltork, Iraj,Khosropour, Ahmad R.,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah
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p. 1369 - 1380
(2015/06/22)
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- Oxidation of 2-arylindoles for synthesis of 2-arylbenzoxazinones with oxone as the sole oxidant
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A novel and efficient method for the oxidation of 2-arylindoles to synthesize 2-arylbenzoxazinones utilizing oxone as the sole oxidant has been developed. The reaction tolerates a wide range of functional groups and allows quick and atom-economical assembly of a variety of valuable 2-arylbenzoxazinones in high yields.
- Lian, Xiao-Li,Lei, Hao,Quan, Xue-Jing,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
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supporting information
p. 8196 - 8198
(2013/09/12)
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- Toward highly potent cancer agents by modulating the C-2 group of the arylthioindole class of tubulin polymerization inhibitors
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New arylthioindole derivatives having different cyclic substituents at position 2 of the indole were synthesized as anticancer agents. Several compounds inhibited tubulin polymerization at submicromolar concentration and inhibited cell growth at low nanomolar concentrations. Compounds 18 and 57 were superior to the previously synthesized 5. Compound 18 was exceptionally potent as an inhibitor of cell growth: it showed IC50 = 1.0 nM in MCF-7 cells, and it was uniformly active in the whole panel of cancer cells and superior to colchicine and combretastatin A-4. Compounds 18, 20, 55, and 57 were notably more potent than vinorelbine, vinblastine, and paclitaxel in the NCI/ADR-RES and Messa/Dx5 cell lines, which overexpress P-glycoprotein. Compounds 18 and 57 showed initial vascular disrupting effects in a tumor model of liver rhabdomyosarcomas at 15 mg/kg intravenous dosage. Derivative 18 showed water solubility and higher metabolic stability than 5 in human liver microsomes.
- La Regina, Giuseppe,Bai, Ruoli,Rensen, Whilelmina Maria,Di Cesare, Erica,Coluccia, Antonio,Piscitelli, Francesco,Famiglini, Valeria,Reggio, Alessia,Nalli, Marianna,Pelliccia, Sveva,Da Pozzo, Eleonora,Costa, Barbara,Granata, Ilaria,Porta, Amalia,Maresca, Bruno,Soriani, Alessandra,Iannitto, Maria Luisa,Santoni, Angela,Li, Junjie,Miranda Cona, Marlein,Chen, Feng,Ni, Yicheng,Brancale, Andrea,Dondio, Giulio,Vultaggio, Stefania,Varasi, Mario,Mercurio, Ciro,Martini, Claudia,Hamel, Ernest,Lavia, Patrizia,Novellino, Ettore,Silvestri, Romano
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p. 123 - 149
(2013/03/13)
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- Palladium-catalyzed synthesis of indoles via ammonia cross-coupling-alkyne cyclization
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The synthesis of indoles via the metal-catalyzed cross-coupling of ammonia is reported for the first time; the developed protocol also allows for the unprecedented use of methylamine or hydrazine as coupling partners. These Pd/Josiphos-catalyzed reactions proceed under relatively mild conditions for a range of 2-alkynylbromoarenes.
- Alsabeh, Pamela G.,Lundgren, Rylan J.,Longobardi, Lauren E.,Stradiotto, Mark
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supporting information; experimental part
p. 6936 - 6938
(2011/08/06)
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- 2-Phenyl-indole derivatives and process for preparing the same
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New stabilizers of polymers and co-polymers of vinyl chloride, the said stabilizers being 2-phenyl-indole derivatives corresponding to the formula: STR1 wherein R represents a phenyl radical, an amino group, optionally substituted by an acetyl or benzoyl
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