6524-20-5Relevant academic research and scientific papers
1,3-CYCLOHEXANEDIONE DERIVATIVES AND 1,3-CYCLOPENTANEDIONE DERIVATIVES AS BUFFERING MOLECULES IN NON-AQUEOUS SOLUTIONS
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Paragraph 0062, (2021/04/23)
This invention relates to 1,3-cyclohexanedione derivatives and 1,3-cyclopentanedione derivatives that have buffering function in non-aqueous solutions and to the use thereof for tuning the conditions to control chemical events in non-aqueous solutions. One aspect of the invention is a method for buffering a non-aqueous solution, including adding a buffering molecule to the non-aqueous solution, in which the non-aqueous solution contains an organic solvent, the buffering molecule is a 1,3-cyclohexanedione derivative or a 1,3-cyclopentanedione derivative, and the buffering molecule is optionally conjugated to a solid support.
Enantioselectivity-switchable organocatalytic [4 + 2]-annulation to access the spirooxindole?norcamphor scaffold
Wang, Jing,Zheng, Xian-Zhou,Xiao, Jun-An,Chen, Kai,Xiang, Hao-Yue,Chen, Xiao-Qing,Yang, Hua
, p. 963 - 968 (2021/02/06)
An organocatalyzed enantiodivergent synthesis of a multifunctionalized spirooxindole?norcamphor scaffold via a [4 + 2]-annulation between cyclicα, β-unsaturated ketone and methylene indolinones has been established. The presence of CaCl2 in DMF could reverse the enantioselectivity to facilely deliver the enantiomers of the corresponding spirooxindoles. Both enantiomers of the corresponding spirooxindoles were obtained in excellent yield and diastereo-/enantioselectivity by employing one single prolinosulfonamide catalyst.
Organocatalytic Aza-Michael/Michael Cyclization Cascade Reaction: Enantioselective Synthesis of Spiro-oxindole Piperidin-2-one Derivatives
Tang, Qing-Gang,Cai, Sen-Lin,Wang, Chuan-Chuan,Lin, Guo-Qiang,Sun, Xing-Wen
supporting information, p. 3351 - 3355 (2020/04/21)
A simple, direct, and highly enantioselective synthesis of spiro-oxindole piperidin-2-one derivatives was achieved through an aza-Michael/Michael cyclization cascade sequence using a squaramide catalyst. The desired products were obtained in excellent yields (up to 99%) and good to high stereoselectivities (up to >20:1 dr and up to 99% ee) under mild conditions.
Access to 3-Prenylated Oxindoles by α-Regioselective Prenylation: Application to the Synthesis of (±)-Debromoflustramine e
Li, De-Feng,Liu, Kun,Jiang, Yi-Xuan,Gu, Yan,Zhang, Jing-Ru,Zhao, Li-Ming
supporting information, p. 1122 - 1125 (2018/02/23)
The development of a rapid, highly efficient, and one-pot synthesis of C3-α-prenylated oxindoles with simple reagents is described. The process is based on zinc-mediated α-regioselective prenylation of 3-acylidene-oxindole with commercially available pren
Construction of highly enantioenriched spirocyclopentaneoxindoles containing four consecutive stereocenters via thiourea-catalyzed asymmetric Michael–Henry cascade reactions
Du, Yonglei,Li, Jian,Chen, Kerong,Wu, Chenglin,Zhou, Yu,Liu, Hong
supporting information, p. 1342 - 1349 (2017/07/18)
The thiourea-catalyzed asymmetric synthesis of highly enantioenriched spirocyclopentaneoxindoles containing chiral amide functional groups using simple 3-substituted oxindoles and nitrovinylacetamide as starting materials was achieved successfully. This protocol features operational simplicity, high atom economy, and high catalytic asymmetry, thus representing a versatile approach to the synthesis of highly enantioenriched spirocyclopentaneoxindoles.
Synthesis and evaluation of oxindoles as promising inhibitors of the immunosuppressive enzyme indoleamine 2,3-dioxygenase 1
Paul, Saurav,Roy, Ashalata,Deka, Suman Jyoti,Panda, Subhankar,Srivastava, Gopal Narayan,Trivedi, Vishal,Manna, Debasis
, p. 1640 - 1654 (2017/08/22)
Indoleamine 2,3-dioxygenase 1 (IDO1) is considered as an important therapeutic target for the treatment of cancer, chronic infections and other diseases that are associated with immune suppression. Recent developments in understanding the catalytic mechanism of the IDO1 enzyme revealed that conversion of l-tryptophan (l-Trp) to N-formylkynurenine proceeded through an epoxide intermediate state. Accordingly, we synthesized a series of 3-substituted oxindoles from l-Trp, tryptamine and isatin. Compounds with C3-substituted oxindole moieties showed moderate inhibitory activity against the purified human IDO1 enzyme. Their optimization led to the identification of potent compounds, 6, 22, 23 and 25 (IC50 = 0.19 to 0.62 μM), which are competitive inhibitors of IDO1 with respect to l-Trp. These potent compounds also showed IDO1 inhibition potencies in the low-micromolar range (IC50 = 0.33-0.49 μM) in MDA-MB-231 cells. The cytotoxicity of these potent compounds was trivial in different model cancer (MDA-MB-231, A549 and HeLa) cells and macrophage (J774A.1) cells. Stronger selectivity for the IDO1 enzyme (124 to 210-fold) over the tryptophan 2,3-dioxygenase (TDO) enzyme was also observed for these compounds. These results suggest that the oxindole moiety of the compounds could mimic the epoxide intermediate state of l-Trp. Therefore, the structural simplicity and low-micromolar inhibition potencies of these 3-substituted oxindoles make them quite attractive for further investigation of IDO1 function and immunotherapeutic applications.
Chemistry of phosphorus ylides. Part 37. The reaction of phosphonium ylides with indoles and naphthofurans. Synthesis of phosphanylidenes, pyrans, cyclobutenes, and pyridazine as antitumor agents
Maigali, Soher S.,El-Hussieny, Marwa,Soliman, Fouad M.
, p. 15 - 23 (2015/02/05)
The reaction of the stabilized phosphonium ylides 2a, b with indolinones 1a, b and naphthofuranone 13 afforded the corresponding propylidene and ethylidene derivatives 4a-d and 14a, b. On the other hand, the active phosphacumulenes 5a, b react with compounds 4a-d by [4 + 2]-cycloaddition to give the stable phosphanylidene indole pyranones 6a-h. Although compounds 14a, b afforded the naphthofuropyrans 16a-d and triphenylphosphane. Moreover, the phosphallene ylide 7 react with compounds 4a-d and 14a, b to give phosphanylidenecyclobuteneindoline 9a-d and naphthalenones 18a, b, respectively. In addition, the naphthofuropyridazine 21 was obtained from the reaction of the hydrazone 19 and the phosphacumulene 5a. The antitumor activity of some of the new compounds was evaluated, in vitro, against colon and hepatocellular carcinoma cell lines. They showed values closed to that recorded by the reference drug Doxorubicin.
Assembly of spirooxindole derivatives containing four consecutive stereocenters via organocatalytic Michael-Henry cascade reactions
Albertshofer, Klaus,Tan, Bin,Barbas III, Carlos F.
supporting information; experimental part, p. 1834 - 1837 (2012/07/03)
A novel organocatalytic strategy for the synthesis of highly substituted spirocyclopentaneoxindoles was developed employing simple nitrostyrenes and 3-substituted oxindoles as starting materials. Michael-Henry cascade reactions, enabled through cinchona alkaloid organocatalysis, provided products in high yield and excellent enantioselectivity in a single step.
