- Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones
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A copper-catalyzed asymmetric 1,3-dipolar cycloaddition of glycine iminoesters with alkyl substituted 3-methylene-2-oxindoles is described. By usingde novodesign of P-stereogenic phosphines as ligands, spiro[pyrrolidin-3,3'-oxindole]s are generated in good to excellent yields with high asymmetric induction. A further reduced catalyst loading of 0.1 mol% is sufficient to achieve a satisfactory enantioselectivity of 90% ee. The DFT calculations suggest the second Michael addition of the 1,3-dipole to be the rate- andenantio-determining step. A key feature of this 1,3-dipolar cycloaddition is the wide substrate applicability, even with alkyl aldehyde-derived azomethine ylide; thus it has streamlined a highly enantioselective access to a new class of antiproliferative agents, MDM2-p53.
- Cui, Hao,Duan, Zheng,Li, Er-Qing,Li, Ke,Mathey, Fran?ois,Song, Manman,Wang, Congcong,Wang, Yue,Wei, Donghui
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supporting information
p. 3740 - 3746
(2020/06/03)
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- Asymmetric Synthesis of 3,3′-Piperidinoyl Spirooxindoles and Discovery of Stereospecific Cycloadducts as Novel Hedgehog Pathway Modulators
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An enantioselective hetero-Diels-Alder reaction of alkylidene oxindoles and 2-aza-3-silyloxy-1,3-butadienes, catalyzed by divalent transition metal complexes with N, N ′-dioxide ligands offered an efficient access to natural-product-based 3,3′-piperidinoyl spirooxindole class of small molecules. exo -Cycloadducts formed via stereospecific cycloaddition with Z -olefin displayed potent activity in modulation of hedgehog pathway.
- Flegel, Jana,Heitkamp, Franziska,Kumar, Kamal,Otte, Felix,Pergomet, Jorgelina L.,Rehan, Mohammad,Strohmann, Carsten
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supporting information
p. 3140 - 3152
(2020/09/07)
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- Facile synthesis of pyrroloindoles: Via a rhodium(II)-catalyzed annulation of 3-benzylidene-indolin-2-ones and α-imino carbenes
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The annulation of 3-benzylidene-indolin-2-ones with α-imino rhodium carbenes generated in situ from N-sulfonyl-1,2,3-triazoles is presented. Through the appropriate choice of catalyst, the reactions can be reasonably modulated, and consequently, a number of pyrroloindole derivatives were constructed in moderate to excellent yields.
- Ma, Xueji,Xie, Xuemei,Liu, Li,Xia, Ran,Li, Tongyu,Wang, Hangxiang
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supporting information
p. 1595 - 1598
(2018/02/14)
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- 2-indolinone derivatives as potent urease inhibitors
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Background: 2-Indolinone is a bicycle, heterocyclic compound analogous of indole skeleton containing a carbonyl group at 2-position of the 5-membered ring. Recently, different biological evaluations of oxindole derivatives have been reported. A variety of compounds with oxindoles moiety exhibit useful pharmaceutical properties like anti-inflammatory, anti-bacterial, anticancer, anti-proliferative, anti-hypertensive, anti-HIV and anti-convulsant activities. Methods: In the present study, fifteen 6-chloro-3-oxindole derivatives (1-15) were screened for urease inhibitory activity. The binding mode of the synthesized compounds was studied by molecular docking and found good results. 6-Chloro-3-oxindole derivatives 1-15 were synthesized from 6-chlorooxindole by refluxing with different aromatic aldehydes in ethanol in the presence of piperidine in high yields. Docking was carry out of the ligands into HCV NS3/4A protein. The software package MOE (Molecular Operating Environment) was used for docking. Results: Our present study has shown that compound 6 (IC50 = 13.34 ± 1.75 μM), 2 (IC50 = 16.67 ± 1.73 μM), and 5 (IC50 = 17.85 ± 2.21 μM) were found to be the most potent urease inhibitors as compared to the standard thiourea (IC50 = 21.1 ± 0.11 μM). Conclusion: Our present study has shown that Compounds 6 (IC50 = 13.34 ± 1.75 μM), 2 (IC50 = 16.67 ± 1.73 μM), and 5 (IC50 = 17.85 ± 2.21 μM) were found to be the most potent urease inhibitors as compared to the standard thiourea (IC50 = 21.1 ± 0.11 μM). These may serve as lead compounds for better urease inhibitors after fine tuning in the structure and further studies in future.
- Khan, Momin,Yousaf, Muhammad,Wadood, Abdul,Hussain, Zahid,Naeem, Muhammad,Zaman, Khair,Shah, Sana,Khan, Khalid Mohammed,Perveen, Shahnaz
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p. 814 - 821
(2018/07/03)
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- In?vitro targeting of colon cancer cells using spiropyrazoline oxindoles
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We report on the synthesis and biological evaluation of a library of twenty-three spiropyrazoline oxindoles. The antiproliferative activity of the chemical library was evaluated in HCT-116 p53(+/+) human colon cancer cell line with eight deriva
- Nunes, Rute C.,Ribeiro, Carlos J.A.,Monteiro, ?ngelo,Rodrigues, Cecília M.P.,Amaral, Joana D.,Santos, Maria M.M.
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p. 168 - 179
(2017/08/10)
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- Synthesis and evaluation of spiroisoxazoline oxindoles as anticancer agents
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Restoring p53 levels through disruption of p53-MDM2 interaction has been proved to be a valuable approach in fighting cancer. We herein report the synthesis and evaluation of eighteen spiroisoxazoline oxindoles derivatives as p53-MDM2 interaction inhibito
- Ribeiro, Carlos J.A.,Amaral, Joana D.,Rodrigues, Cecília M.P.,Moreira, Rui,Santos, Maria M.M.
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p. 577 - 584
(2014/01/17)
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- Synthesis of novel spiropyrazoline oxindoles and evaluation of cytotoxicity in cancer cell lines
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A series of novel spiropyrazoline oxindole derivatives was synthesized by 1,3-dipolar cycloaddition reaction. The compounds were screened for their in vitro cytotoxic activity against MCF-7 breast cancer cell line (estrogen receptor positive (ER+) and hum
- Monteiro, ?ngelo,Gon?alves, Lídia M.,Santos, Maria M.M.
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p. 266 - 272
(2014/05/06)
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