The diketopiperazine-fused tetrahydro-β-carboline scaffold as a model peptidomimetic with an unusual α-turn secondary structure

Francesco Airaghi, Andrea Fiorati, Giordano Lesma, Manuele Musolino, Alessandro Sacchetti and Alessandra Silvani
Beilstein J. Org. Chem. 2013, 9, 147–154. https://doi.org/10.3762/bjoc.9.17

Cite the Following Article

The diketopiperazine-fused tetrahydro-β-carboline scaffold as a model peptidomimetic with an unusual α-turn secondary structure
Francesco Airaghi, Andrea Fiorati, Giordano Lesma, Manuele Musolino, Alessandro Sacchetti and Alessandra Silvani
Beilstein J. Org. Chem. 2013, 9, 147–154. https://doi.org/10.3762/bjoc.9.17

How to Cite

Airaghi, F.; Fiorati, A.; Lesma, G.; Musolino, M.; Sacchetti, A.; Silvani, A. Beilstein J. Org. Chem. 2013, 9, 147–154. doi:10.3762/bjoc.9.17

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Calcaterra, A.; Mangiardi, L.; Delle Monache, G.; Quaglio, D.; Balducci, S.; Berardozzi, S.; Iazzetti, A.; Franzini, R.; Botta, B.; Ghirga, F. The Pictet-Spengler Reaction Updates Its Habits. Molecules (Basel, Switzerland) 2020, 25, 414. doi:10.3390/molecules25020414
  • Sun, S.; He, M.; VanPatten, S.; Al-Abed, Y. Mechanistic insights into high mobility group box-1 (HMGb1)-induced Toll-like receptor 4 (TLR4) dimer formation. Journal of biomolecular structure & dynamics 2018, 37, 3721–3730. doi:10.1080/07391102.2018.1526712
  • Martínez-Crespo, L.; Escudero-Adán, E. C.; Costa, A.; Rotger, C. The Role of N-Methyl Squaramides in a Hydrogen-Bonding Strategy to Fold Peptidomimetic Compounds. Chemistry (Weinheim an der Bergstrasse, Germany) 2018, 24, 17802–17813. doi:10.1002/chem.201803930
  • Rossetti, A.; Sacchetti, A.; Gatti, M.; Pugliese, A.; Roda, G. RAPID ACCESS TO REVERSE-TURN PEPTIDOMIMETICS BY A THREE-COMPONENT UGI REACTION OF 3,4-DIHYDROISOQUINOLINE. Chemistry of Heterocyclic Compounds 2017, 53, 1214–1219. doi:10.1007/s10593-018-2202-5
  • Berthet, M.; Lebrun, A.; Martel, A.; Cheviet, T.; Martinez, J.; Parrot, I. Oxa–diketopiperazines: Access and Conformational Analysis of Potential Turn Inducers. ChemistrySelect 2017, 2, 5824–5827. doi:10.1002/slct.201701393
  • Petersen, R.; Komnatnyy, V. V.; Nielsen, T. E. Synthesis of Constrained Peptidomimetics via the Pictet-Spengler Reaction. Topics in Heterocyclic Chemistry; Springer International Publishing, 2016; pp 81–103. doi:10.1007/7081_2015_190
  • Zhao, Q.; Schafmeister, C. E. Diketopiperazine-Based Peptide Mimic Scaffolds. Topics in Heterocyclic Chemistry; Springer International Publishing, 2015; pp 51–80. doi:10.1007/7081_2015_165
  • Martínez, L. A.; Martorell, G.; Sampedro, A.; Ballester, P.; Costa, A.; Rotger, C. Hydrogen Bonded Squaramide-Based Foldable Module Induces Both β- and α-Turns in Hairpin Structures of α-Peptides in Water. Organic letters 2015, 17, 2980–2983. doi:10.1021/acs.orglett.5b01268
  • Sano, S.; Nakao, M. Chemistry of 2,5-Diketopiperazine and Its Bis-Lactim Ether: A Brief Review. HETEROCYCLES 2015, 91, 1349. doi:10.3987/rev-15-820
  • Nair, R. V.; Baravkar, S. B.; Ingole, T. S.; Sanjayan, G. J. Synthetic turn mimetics and hairpin nucleators: Quo Vadimus?. Chemical communications (Cambridge, England) 2014, 50, 13874–13884. doi:10.1039/c4cc03114h
  • Baek, J.; Kang, S. Y.; Im, C.; Park, Y. S. Asymmetric Synthesis of 3,4,6‐Trisubstituted 2,5‐Diketopiperazines by Using Dynamic Kinetic Resolution of α‐Bromo Tertiary Acetamides. European Journal of Organic Chemistry 2014, 2014, 2780–2789. doi:10.1002/ejoc.201301936
  • Jida, M.; Tourwé, D.; Ballet, S. Highly stereoselective one-pot construction of trisubstituted tetrahydro-β-carboline-fused diketopiperazines: a synthetic route towards cialis analogues. RSC Adv. 2014, 4, 38159–38163. doi:10.1039/c4ra05981f
  • Lesma, G.; Cecchi, R.; Cagnotto, A.; Gobbi, M.; Meneghetti, F.; Musolino, M.; Sacchetti, A.; Silvani, A. Tetrahydro-β-carboline-Based Spirocyclic Lactam as Type II′ β-Turn: Application to the Synthesis and Biological Evaluation of Somatostatine Mimetics. The Journal of organic chemistry 2013, 78, 2600–2610. doi:10.1021/jo302737j
Other Beilstein-Institut Open Science Activities