Synthesis of Chiral Dispiro-indolinone-pyrrolidine-rhodanines Using (R)/(S)-1-(2,4-dimethoxyphenyl)ethylamine

被引:0
作者
Degtiarev, Anton D. [1 ]
Barashkin, Aleksandr A. [1 ]
Grishin, Yuri K. [1 ]
Roznyatovsky, Vitaly A. [1 ]
Tafeenko, Viktor A. [1 ]
Tarasenko, Elena A. [1 ]
Beloglazkina, Elena K. [1 ]
机构
[1] MV Lomonosov Moscow State Univ, Dept Chem, Moscow 119991, Russia
来源
CHEMISTRYSELECT | 2025年 / 10卷 / 25期
关键词
1; 3-dipolar cycloaddition; Azomethine ylides; Chiral amines; Rhodanines; Spiro-compounds; STAPHYLOCOCCUS-AUREUS MRSA; BIOLOGICAL EVALUATION; DERIVATIVES BEARING; ASYMMETRIC CONSTRUCTION; RHODANINE-3-ACETIC ACID; METHICILLIN-RESISTANT; AZOMETHINE YLIDES; INHIBITORS; DESIGN; PIOGLITAZONE;
D O I
10.1002/slct.202503393
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The use of (R) or (S)-1-(2,4-dimethoxyphenyl)ethylamines as starting compounds makes it possible to obtain the individual enantiomers of dispiro-indolinone-pyrrolidine-rhodanines with a yield of up to 53% based on a three-step synthesis through the formation of 5-arylidenrhodanines with a chiral substituent at N(3) atom, their subsequent 1,3-dipolar cycloaddition with azomethine ylide generated in situ from isatin and sarcosine and chromatographic separation of the resulting diastereomers.
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页数:7
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共 53 条
[1]   Comparative Analysis of Aducanumab, Zagotenemab and Pioglitazone as Targeted Treatment Strategies for Alzheimer's Disease [J].
Abyadeh, Morteza ;
Gupta, Vivek ;
Gupta, Veer ;
Chitranshi, Nitin ;
Wu, Yunqi ;
Amirkhani, Ardeshir ;
Meyfour, Anna ;
Sheriff, Samran ;
Shen, Ting ;
Dhiman, Kunal ;
Salekdeh, Ghasem H. ;
Haynes, Paul A. ;
Graham, Stuart L. ;
Mirzaei, Mehdi .
AGING AND DISEASE, 2021, 12 (08) :1964-1976
[2]   Molecular design and synthesis of HCV inhibitors based on thiazolone scaffold [J].
Al-Ansary, Ghada H. ;
Ismail, Mohamed A. H. ;
Abou El Ella, Dalal A. ;
Eid, Sameh ;
Abouzid, Khaled A. M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 68 :19-32
[3]   Novel imidazo[2,1-b][1,3,4]thiadiazole carrying rhodanine-3-acetic acid as potential antitubercular agents [J].
Alegaon, Shankar G. ;
Alagawadi, Kallanagouda R. ;
Sonkusare, Pranali V. ;
Chaudhary, Sagar M. ;
Dadwe, Dilip H. ;
Shah, Amol S. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (05) :1917-1921
[4]   Fluorescent rhodanine-3-acetic acids visualize neurofibrillary tangles in Alzheimer's disease brains [J].
Anumala, Upendra Rao ;
Gu, Jiamin ;
Lo Monte, Fabio ;
Kramer, Thomas ;
Heyny-von Haussen, Roland ;
Hoelzer, Jana ;
Goetschy-Meyer, Valerie ;
Schoen, Christian ;
Mall, Gerhard ;
Hilger, Ingrid ;
Czech, Christian ;
Herms, Jochen ;
Schmidt, Boris .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (17) :5139-5144
[5]   2H-chromene derivatives bearing thiazolidine-2,4-dione, rhodanine or hydantoin moieties as potential anticancer agents [J].
Azizmohammadi, Mohammad ;
Khoobi, Mehdi ;
Ramazani, Ali ;
Emami, Saeed ;
Zarrin, Abdolhossein ;
Firuzi, Omidreza ;
Miri, Ramin ;
Shafiee, Abbas .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 59 :15-22
[6]   Synthesis of Enantiomerically Pure Thioureas and Thiohydantoins Based on (R)- and (S)-1-(2,4-Dimethoxy-phenyl)ethan-1-amines [J].
Barashkin, A. A. ;
Polyakov, V. S. ;
Shikut, N. L. ;
Putilova, A. D. ;
Gorovoy, A. R. ;
Tafeenko, V. A. ;
Zyk, N., V ;
Beloglazkina, E. K. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 58 (09) :1362-1367
[7]   Diastereoselective cycloaddition of isatin azomethine ylides to 5-arylidene-2-thiohydantoins bearing 3-positioned chiral substituent [J].
Barashkin, Alexander A. ;
Polyakov, Vladislav S. ;
Shikut, Nikita L. ;
Putilova, Anastasia D. ;
Gorovoy, Anton R. ;
Degtiarev, Anton D. ;
Tafeenko, Victor A. ;
Tarasevich, Boris N. ;
V. Zyk, Nikolai ;
Beloglazkina, Elena K. .
MENDELEEV COMMUNICATIONS, 2022, 32 (02) :221-223
[8]   REACTIONS OF AMINES .2. DEGRADATION VIA TERTIARY AMINE OXIDES [J].
BAUMGARTEN, HE ;
BOWER, FA ;
OKAMOTO, TT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (12) :3145-3149
[9]   Synthesis and Biological Evaluation of Novel Dispiro Compounds based on 5-Arylidenehydantoins and Isatins as Inhibitors of p53-MDM2 Protein-Protein Interaction [J].
Beloglazkina, Anastasia ;
Barashkin, Alexander ;
Polyakov, Vladislav ;
Kotovsky, German ;
Karpov, Nikita ;
Mefedova, Sofia ;
Zagribelny, Bogdan ;
Ivanenkov, Yan ;
Kalinina, Marina ;
Skvortsov, Dmitry ;
Tafeenko, Victor ;
Zyk, Nikolay ;
Majouga, Alexander ;
Beloglazkina, Elena .
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (06) :747-755
[10]   Rhodanine-based tau aggregation inhibitors in cell models of tauopathy [J].
Bulic, Bruno ;
Pickhardt, Marcus ;
Khlistunova, Inna ;
Biernat, Jacek ;
Mandelkow, Eva-Maria ;
Mandelkow, Eckhard ;
Waldmann, Herbert .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9215-9219