PMID- 31963860
OWN - NLM
STAT- MEDLINE
DCOM- 20201007
LR  - 20240328
IS  - 1420-3049 (Electronic)
IS  - 1420-3049 (Linking)
VI  - 25
IP  - 2
DP  - 2020 Jan 19
TI  - The Pictet-Spengler Reaction Updates Its Habits.
LID - 10.3390/molecules25020414 [doi]
LID - 414
AB  - The Pictet-Spengler reaction (P-S) is one of the most direct, efficient, and 
      variable synthetic method for the construction of privileged pharmacophores such 
      as tetrahydro-isoquinolines (THIQs), tetrahydro-beta-carbolines (THBCs), and 
      polyheterocyclic frameworks. In the lustro (five-year period) following its 
      centenary birthday, the P-S reaction did not exit the stage but it came up again 
      on limelight with new features. This review focuses on the interesting results 
      achieved in this period (2011-2015), analyzing the versatility of this reaction. 
      Classic P-S was reported in the total synthesis of complex alkaloids, in 
      combination with chiral catalysts as well as for the generation of libraries of 
      compounds in medicinal chemistry. The P-S has been used also in tandem reactions, 
      with the sequences including ring closing metathesis, isomerization, Michael 
      addition, and Gold- or Bronsted acid-catalyzed N-acyliminium cyclization. 
      Moreover, the combination of P-S reaction with Ugi multicomponent reaction has 
      been exploited for the construction of highly complex polycyclic architectures in 
      few steps and high yields. The P-S reaction has also been successfully employed 
      in solid-phase synthesis, affording products with different structures, including 
      peptidomimetics, synthetic heterocycles, and natural compounds. Finally, the 
      enzymatic version of P-S has been reported for biosynthesis, biotransformations, 
      and bioconjugations.
FAU - Calcaterra, Andrea
AU  - Calcaterra A
AUID- ORCID: 0000-0001-7036-6620
AD  - Department of Chemistry and Technology of Drugs, "Department of Excellence 
      2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
FAU - Mangiardi, Laura
AU  - Mangiardi L
AUID- ORCID: 0000-0002-9937-4365
AD  - Department of Chemistry and Technology of Drugs, "Department of Excellence 
      2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
AD  - Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Viale 
      Regina Elena 291, 00161 Rome, Italy.
FAU - Delle Monache, Giuliano
AU  - Delle Monache G
AD  - Department of Chemistry and Technology of Drugs, "Department of Excellence 
      2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
FAU - Quaglio, Deborah
AU  - Quaglio D
AD  - Department of Chemistry and Technology of Drugs, "Department of Excellence 
      2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
FAU - Balducci, Silvia
AU  - Balducci S
AD  - Department of Chemistry and Technology of Drugs, "Department of Excellence 
      2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
FAU - Berardozzi, Simone
AU  - Berardozzi S
AUID- ORCID: 0000-0002-3352-9811
AD  - Department of Chemistry and Applied Biosciences, ETH-Zurich, Vladimir-Prelog Weg 
      4, 8093 Zurich, Switzerland.
FAU - Iazzetti, Antonia
AU  - Iazzetti A
AUID- ORCID: 0000-0002-7792-774X
AD  - Department of Chemistry and Technology of Drugs, "Department of Excellence 
      2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
FAU - Franzini, Roberta
AU  - Franzini R
AD  - Department of Chemistry and Technology of Drugs, "Department of Excellence 
      2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
FAU - Botta, Bruno
AU  - Botta B
AUID- ORCID: 0000-0001-8707-4333
AD  - Department of Chemistry and Technology of Drugs, "Department of Excellence 
      2018-2022", Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
FAU - Ghirga, Francesca
AU  - Ghirga F
AD  - Center for Life Nano Science@Sapienza, Istituto Italiano di Tecnologia, Viale 
      Regina Elena 291, 00161 Rome, Italy.
LA  - eng
GR  - ARS01_00432/Ministero dell'Istruzione, dell'Universita e della Ricerca/
GR  - Progetto grande di ricerca di Ateneo 2017/Sapienza Universita di Roma/
GR  - PRIN 2017/Ministero dell'Istruzione, dell'Universita e della Ricerca/
GR  - ESF COST Action CM1407/European Cooperation in Science and Technology/
GR  - Dipartimenti di Eccellenza - L.232/2016/Ministero dell'Istruzione, 
      dell'Universita e della Ricerca/
PT  - Journal Article
PT  - Review
DEP - 20200119
PL  - Switzerland
TA  - Molecules
JT  - Molecules (Basel, Switzerland)
JID - 100964009
RN  - 0 (Alkaloids)
RN  - 0 (Biological Products)
RN  - 7UI0TKC3U5 (Ruthenium)
SB  - IM
MH  - Alkaloids/chemical synthesis/chemistry
MH  - Biological Products/chemical synthesis/chemistry
MH  - Cyclization
MH  - *Models, Molecular
MH  - Ruthenium/chemistry
PMC - PMC7024544
OTO - NOTNLM
OT  - Pictet-Spengler
OT  - THBC
OT  - THIQ
OT  - alkaloid
OT  - cascade reaction
OT  - multicomponent reaction
OT  - natural products
OT  - tetrahydro-beta-carboline
OT  - tetrahydroisoquinoline
OT  - total synthesis
COIS- The authors declare no conflict of interest.
EDAT- 2020/01/23 06:00
MHDA- 2020/10/08 06:00
PMCR- 2020/01/19
CRDT- 2020/01/23 06:00
PHST- 2019/12/13 00:00 [received]
PHST- 2020/01/05 00:00 [revised]
PHST- 2020/01/09 00:00 [accepted]
PHST- 2020/01/23 06:00 [entrez]
PHST- 2020/01/23 06:00 [pubmed]
PHST- 2020/10/08 06:00 [medline]
PHST- 2020/01/19 00:00 [pmc-release]
AID - molecules25020414 [pii]
AID - molecules-25-00414 [pii]
AID - 10.3390/molecules25020414 [doi]
PST - epublish
SO  - Molecules. 2020 Jan 19;25(2):414. doi: 10.3390/molecules25020414.