PMID- 26719050
OWN - NLM
STAT- MEDLINE
DCOM- 20161221
LR  - 20190728
IS  - 1873-4286 (Electronic)
IS  - 1381-6128 (Linking)
VI  - 22
IP  - 12
DP  - 2016
TI  - The Pictet-Spengler Reaction Still on Stage.
PG  - 1808-50
AB  - Today, in spite of being older than a century (born in 1911), the Pictet-Spengler 
      two component reaction (PS-2CR) is still one of the most popular reactions, not 
      only for the synthesis of tetrahydroisoquinolines (THIQs), 
      tetrahydro-beta-carbolines (THBCs), or more complex structures containing these two 
      privileged moieties, but also for the construction of novel scaffolds, available 
      for structure-activity relationship (SAR) studies and/or for combinatorial 
      libraries targeted at drug discovery. The prominence of the P-S cyclization is 
      brought about by the inheritance from analogous enzyme-catalyzed reactions of the 
      biogenetic pathways of natural products, mainly indole alkaloids, with a broad 
      range of biological activities. This knowledge has been the starting point for 
      the biomimetic synthesis or the bio-engineering production of pharmacologically 
      important drugs. The long-lasting life of the P-S reaction depends on the 
      discovery of its multiple facets, the modifications of its parameters and 
      components, as well as the continuous renovation of solutions for the challenging 
      stereochemical outcome of the transformation. This paper deals with an updated 
      visit to the P-S reaction aiming to find the threads of the story without 
      forgetting the numerous facets of the prism. It is organized as a theater piece, 
      with a prologue and the main scene (namely, Act 1) where the readers can follow 
      the parade of the two above-mentioned very recurring motifs (namely, THIQ and 
      THBC) by moving from one step to another (a cyclization, an intramolecular 
      attack, a stereoselective passage) to find the way out of the labyrinth of the 
      P-S reaction.
FAU - Ingallina, Cinzia
AU  - Ingallina C
FAU - D'Acquarica, Ilaria
AU  - D'Acquarica I
FAU - Delle Monache, Giuliano
AU  - Delle Monache G
FAU - Ghirga, Francesca
AU  - Ghirga F
FAU - Quaglio, Deborah
AU  - Quaglio D
FAU - Ghirga, Patrizio
AU  - Ghirga P
FAU - Berardozzi, Simone
AU  - Berardozzi S
FAU - Markovic, Violeta
AU  - Markovic V
FAU - Botta, Bruno
AU  - Botta B
AD  - Dipartimento di Chimica e Tecnologie del Farmaco, Faculty of Pharmacy and 
      Medicine, Sapienza University of Rome, P.le A. Moro 5, 00185 Roma, Italy. 
      bruno.botta@uniroma1.it.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
PT  - Review
PL  - United Arab Emirates
TA  - Curr Pharm Des
JT  - Current pharmaceutical design
JID - 9602487
RN  - 0 (Indole Alkaloids)
RN  - EC 4.3.- (Carbon-Nitrogen Lyases)
RN  - EC 4.3.3.2 (strictosidine synthetase)
SB  - IM
MH  - Bioengineering
MH  - Carbon-Nitrogen Lyases/*metabolism
MH  - Cyclization
MH  - Humans
MH  - Indole Alkaloids/chemistry/*metabolism
MH  - Molecular Structure
MH  - Stereoisomerism
EDAT- 2016/01/01 06:00
MHDA- 2016/12/22 06:00
CRDT- 2016/01/01 06:00
PHST- 2015/10/30 00:00 [received]
PHST- 2015/12/30 00:00 [accepted]
PHST- 2016/01/01 06:00 [entrez]
PHST- 2016/01/01 06:00 [pubmed]
PHST- 2016/12/22 06:00 [medline]
AID - CPD-EPUB-72814 [pii]
AID - 10.2174/1381612822666151231100247 [doi]
PST - ppublish
SO  - Curr Pharm Des. 2016;22(12):1808-50. doi: 10.2174/1381612822666151231100247.