Microwave-Assisted Syntheses of Bioactive Seven-Membered, Macro-Sized Heterocycles and Their Fused Derivatives

被引:27
作者
Driowya, Mohsine [1 ]
Saber, Aziza [1 ]
Marzag, Hamid [1 ]
Demange, Luc [2 ,3 ,4 ]
Bougrin, Khalid [1 ]
Benhida, Rachid [2 ]
机构
[1] Univ Mohammed 5, Fac Sci, Lab Chim Plantes & Synth Organ & Bioorgan, URAC23, BP 1014, Rabat, Morocco
[2] Univ Cote Azur, Univ Nice Sophia Antipolis, CNRS, ICN,UMR,UNS 7272, Parc Valrose, F-06108 Nice 2, France
[3] Univ Paris 05, Sorbonne Paris Cite, UFR Sci Pharmaceut, Dept Chim, 4 Ave Observ, FR-75006 Paris, France
[4] UFR Biomed St Peres, 45 Rue St Peres, FR-75006 Paris, France
来源
MOLECULES | 2016年 / 21卷 / 08期
关键词
microwave irradiation; bioactive molecules; dipolar cycloaddition; cyclocondensations; multicomponent reactions; SOLID-PHASE SYNTHESIS; DIVERSITY-ORIENTED SYNTHESIS; DIFFICULT PEPTIDE SEQUENCES; SOLVENT-FREE SYNTHESIS; ONE-POT SYNTHESIS; METAL-FREE; PTAEROXYLIN DESOXYKARENIN; ANTIMICROBIAL ACTIVITY; CATALYZED SYNTHESIS; ENHANCED SYNTHESIS;
D O I
10.3390/molecules21081032
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
This review describes the recent advances in the microwave-assisted synthesis of 7-membered and larger heterocyclic compounds. Several types of reaction for the cyclization step are discussed: Ring Closing Metathesis (RCM), Heck and Sonogashira reactions, Suzuki-Miyaura cross-coupling, dipolar cycloadditions, multi-component reactions (Ugi, Passerini), etc. Green syntheses and solvent-free procedures have been introduced whenever possible. The syntheses discussed herein have been selected to illustrate the huge potential of microwave in the synthesis of highly functionalized molecules with potential therapeutic applications, in high yields, enhanced reaction rates and increased chemoselectivity, compared to conventional methods. More than 100 references from the recent literature are listed in this review.
引用
收藏
页数:47
相关论文
共 111 条
[41]   Design and microwave-assisted synthesis of novel macrocyclic peptides active at melanocortin receptors: Discovery of potent and selective hMC5R receptor antagonists [J].
Grieco, Paolo ;
Cai, Minying ;
Liu, Lu ;
Mayorov, Alexander ;
Chandler, Kevin ;
Trivedi, Dev ;
Lin, Guangxin ;
Campiglia, Pietro ;
Novellino, Ettore ;
Hruby, Victor J. .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (09) :2701-2707
[42]   New Alkaloids from Hippeastrum papilio (Ravenna) Van Scheepen [J].
Guo, Ying ;
de Andrade, Jean P. ;
Pigni, Natalia B. ;
Torras-Claveria, Laura ;
Tallini, Luciana R. ;
Borges, Warley de S. ;
Viladomat, Francesc ;
Nair, Jerald J. ;
Zuanazzi, Jose A. S. ;
Bastida, Jaume .
HELVETICA CHIMICA ACTA, 2016, 99 (02) :143-147
[43]   Efficient synthesis of antifungal active 9-substituted-3-aryl-5H, 13aH-quinolino[3,2-f][1,2,4]triazolo[4,3-b][1,2,4]triazepines in ionic liquids [J].
Gupta, Monika .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (16) :4919-4923
[44]   Efficient and novel one-pot synthesis of antifungal active 1-substituted-8-aryl-3-alkyl/aryl-4H-pyrazolo[4,5-f][1,2,4]triazolo[4,3-b][1,2,4]triazepines using solid support [J].
Gupta, Monika ;
Paul, Satya ;
Gupta, Rajive .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (02) :631-635
[45]  
Gupta M, 2009, INDIAN J CHEM B, V48, P460
[46]   Postmortem distribution of the novel antipsychotic drug quetiapine [J].
Hopenwasser, J ;
Mozayani, A ;
Danielson, TJ ;
Harbin, J ;
Narula, HS ;
Posey, DH ;
Shrode, PW ;
Wilson, SK ;
Li, R ;
Sanchez, LA .
JOURNAL OF ANALYTICAL TOXICOLOGY, 2004, 28 (04) :264-268
[47]   Macrocyclic peptidomimetics with antimicrobial activity: synthesis, bioassay, and molecular modeling studies [J].
Ibrahim, Mohamed A. ;
Panda, Siva S. ;
Oliferenko, Alexander A. ;
Oliferenko, Polina V. ;
Girgis, Adel S. ;
Elagawany, Mohamed ;
Kucukbay, F. Zehra ;
Panda, Chandramukhi S. ;
Pillai, Girinath G. ;
Samir, Ahmed ;
Tamm, Kaido ;
Hall, C. Dennis ;
Katritzky, Alan R. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (36) :9492-9503
[48]   Use of the 2-Chlorotrityl Chloride Resin for Microwave-Assisted Solid Phase Peptide Synthesis [J].
Ieronymaki, Matthaia ;
Androutsou, Maria Eleni ;
Pantelia, Anna ;
Friligou, Irene ;
Crisp, Molly ;
High, Kirsty ;
Penkman, Kirsty ;
Gatos, Dimitrios ;
Tselios, Theodore .
BIOPOLYMERS, 2015, 104 (05) :506-514
[49]   Synthesis of novel 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1,4]diazepines under microwave irradiation as potential anti-tumor agents [J].
Insuasty, Braulio ;
Garcia, Angelica ;
Quiroga, Jairo ;
Abonia, Rodrigo ;
Nogueras, Manuel ;
Cobo, Justo .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (07) :2841-2846
[50]   BENZODIAZEPINE PEPTIDOMIMETICS - POTENT INHIBITORS OF RAS FARNESYLATION IN ANIMAL-CELLS [J].
JAMES, GL ;
GOLDSTEIN, JL ;
BROWN, MS ;
RAWSON, TE ;
SOMERS, TC ;
MCDOWELL, RS ;
CROWLEY, CW ;
LUCAS, BK ;
LEVINSON, AD ;
MARSTERS, JC .
SCIENCE, 1993, 260 (5116) :1937-1942