Synthesis and properties of 5-methylidene-3,5-dihydro-4H-imidazol-4-ones (microreview)

被引:30
作者
Baleeva, Nadezhda S. [1 ,2 ]
Baranov, Mikhail S. [1 ,2 ]
机构
[1] Russian Acad Sci, MM Shemyakin & Yu A Ovchinnikov Inst Bioorgan Che, 16-10 Miklukho Maklaya St, Moscow 117997, Russia
[2] Russian Natl Res Med Univ, 1 Ostrovityanova St, Moscow 117997, Russia
基金
俄罗斯基础研究基金会;
关键词
GREEN FLUORESCENT PROTEIN; GFP CHROMOPHORE; DERIVATIVES; IMIDAZOLONES; PHOTOPHYSICS; EMISSION; ANALOGS; AGENTS;
D O I
10.1007/s10593-016-1909-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This microreview presents the key methods of synthesis of 5-methylidene-3,5-dihydro-4H-imidazol-4-ones together with analysis of the relative efficiency for the substituent introduction at different positions of the ring. Also, examples of reactions typical for these compounds presented in the literature over the last seven years are given.
引用
收藏
页码:444 / 446
页数:3
相关论文
共 32 条
[1]   Synthesis of Some More Fluorine Heterocyclic Nitrogen Systems Derived From Sulfa Drugs as Photochemical Probe Agents for Inhibition of Vitiligo Disease-Part I [J].
Abdel-Rahman, Reda M. ;
Makki, Mohammad Saleh I. T. ;
Bawazir, Wafa A. .
E-JOURNAL OF CHEMISTRY, 2011, 8 (01) :405-414
[2]  
[Anonymous], 2013, SCI SIN CHIM, V16
[3]   Efficient Synthesis of New 4-Arylideneimidazolin-5-ones Related to the GFP Chromophore by 2+3 Cyclocondensation of Arylideneimines with Imidate Ylides [J].
Baldridge, Anthony ;
Kowalik, Janusz ;
Tolbert, Laren M. .
SYNTHESIS-STUTTGART, 2010, (14) :2424-2436
[4]   Synthesis of the chromophores of fluorescent proteins and their analogs [J].
Baranov, M. S. ;
Lukyanov, K. A. ;
Yampolsky, I. V. .
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2013, 39 (03) :223-244
[5]   Red-Shifted Fluorescent Aminated Derivatives of a Conformationally Locked GFP Chromophore [J].
Baranov, Mikhail S. ;
Solntsev, Kyril M. ;
Baleeva, Nadezhda S. ;
Mishin, Alexander S. ;
Lukyanov, Sergey A. ;
Lukyanov, Konstantin A. ;
Yampolsky, Ilia V. .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (41) :13234-13241
[6]   Ring-expanding rearrangement of 2-acyl-5-arylidene-3,5-dihydro-4H-imidazol-4-ones in synthesis of flutimide analogs [J].
Baranov, Mikhail S. ;
Fedyakina, Irina T. ;
Shchelkanov, Mikhail Yu. ;
Yampolsky, Ilia V. .
TETRAHEDRON, 2014, 70 (23) :3714-3719
[7]   A synthetic approach to GFP chromophore analogs from 3-azidocinnamates. Role of methyl rotors in chromophore photophysics [J].
Baranov, Mikhail S. ;
Solntsev, Kyril M. ;
Lukyanov, Konstantin A. ;
Yampolsky, Ilia V. .
CHEMICAL COMMUNICATIONS, 2013, 49 (51) :5778-5780
[8]   Conformationally Locked Chromophores as Models of Excited-State Proton Transfer in Fluorescent Proteins [J].
Baranov, Mikhail S. ;
Lukyanov, Konstantin A. ;
Borissova, Alexandra O. ;
Shamir, Jordan ;
Kosenkov, Dmytro ;
Slipchenko, Lyudmila V. ;
Tolbert, Laren M. ;
Yampolsky, Ilia V. ;
Solntsev, Kyril M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (13) :6025-6032
[9]   Multicolor Fluorescent Polymers Inspired from Green Fluorescent Protein [J].
Deng, Hongping ;
Su, Yue ;
Hu, Minxi ;
Jin, Xin ;
He, Lin ;
Pang, Yan ;
Dong, Ruijiao ;
Zhu, Xinyuan .
MACROMOLECULES, 2015, 48 (16) :5969-5979
[10]   Microwave-assisted synthesis and antimicrobial screening of new imidazole derivatives bearing 4-thiazolidinone nucleus [J].
Desai, N. C. ;
Joshi, V. V. ;
Rajpara, K. M. ;
Vaghani, H. V. ;
Satodiya, H. M. .
MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (04) :1893-1908