Natural-Like Spirocyclic Δ

5-endo-dig cyclization Michael acceptors spirobutenolides synthetic methods thioredoxin reductase

Journal

Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783

Informations de publication

Date de publication:
01 Jun 2021
Historique:
received: 09 03 2021
pubmed: 14 4 2021
medline: 14 4 2021
entrez: 13 4 2021
Statut: ppublish

Résumé

α-Diazo homophotalimides were reacted with various propiolic acids on Rh

Identifiants

pubmed: 33848018
doi: 10.1002/chem.202100880
doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

8221-8227

Subventions

Organisme : Russian Science Foundation
ID : 20-13-00024
Organisme : Российский Фонд Фундaментaльных Исследовaний (РФФИ)
ID : 19-33-60010

Informations de copyright

© 2021 Wiley-VCH GmbH.

Références

S. K. Sartori, M. A. Diaz, G. Diaz-Munoz, Tetrahedron 2021, 84, 132001.
 
E. Chupakhin, O. Babich, A. Prosekov, L. Asyakina, M. Krasavin, Molecules 2019, 24, 4165;
H. Avcibasi, H. Anil, M. Toprak, Phytochemistry 1987, 26, 2852-2854;
N. S. Reddy, U. Venkatesham, T. P. Rao, Y. Venkateswarlu, Ind. J. Chem. 2000, 39B, 393-395;
B. R. Laible, S. D. J. Med. 2014, 67, 30-31;
H. Oh, J. B. Gloer, C. A. Shearer, J. Nat. Prod. 1999, 62, 497-501.
 
P. Yadav, R. Pratap, V. Ji Ram, Asian J. Org. Chem. 2020, 9, 1377-1409;
A. Leonardi, C. Riva, P. Tavecchia, G. Sironi, PCT Int. Appl. 2007025780; Chem. Abstr. 2007, 146, 296129;
R. Chib, B. A. Shah, N. Anand, A. Pandey, B. Kapoor, S. Bani, V. L. Gupta, Rajnikant, V. K. Sethi, S. C. Taneja, Bioorg. Med. Chem. Lett. 2011, 21, 4847-4851;
A. G. Stephen, K. M. Worthy, E. Towler, J. A. Mikovits, S. Sei, P. Roberts, Q.-E. Yang, R. K. Akee, P. Klausmeyer, T. G. McCloud, L. Henderson, A. Rein, D. G. Covell, M. Currens, R. H. Shoemaker, R. J. Fisher, Biochem. Biophys. Res. Commun. 2002, 296, 1228-1237;
A. Ali, J. M. Balkovec, R. Beresis, S. L. Colletti, D. W. Graham, G. F. Patel, C. J. Smith, PCT Int. Appl. 2004093805; Chem. Abstr. 2004, 141, 395547.
T. J. Ritchie, S. J. F. Macdonald, Drug Discovery Today 2009, 14, 1011-1020.
Y. Zheng, C. M. Tice, S. B. Singh, Bioorg. Med. Chem. Lett. 2014, 24, 3673-3682.
Y.-J Zheng, C. M. Tice, Exp. Opin. Drug Discov. 2016, 11, 831-834.
F. Lovering, J. Bikker, C. Humblet, J. Med. Chem. 2009, 52, 6752-6756.
F. M. Tajabadi, M. R. Campitelli, R. J. Quinn, Springer Sci. Rev. 2013, 1, 141-151.
S. Mandal, B. Thirupathi, Org. Biomol. Chem. 2020, 18, 5287-5314.
G. Kantin, D. Dar′in, M. Krasavin, Eur. J. Org. Chem. 2018, 4857-4859.
N. Guranova, D. Dar′in, G. Kantin, A. Novikov, O. Bakulina, M. Krasavin, J. Org. Chem. 2019, 84, 4534-4542.
J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734-736.
W.-G. Li, B. Cai, H.-B. Xiao, S.-F. Pi, H.-Z. Sun, Synlett 2016, 27, 794-798.
A. C. Hunter, S. C. Shlitzer, I. Sharma, Chem. Eur. J. 2016, 22, 16062-16065.
 
M. D. Aparece, P. A. Vadola, Org. Lett. 2014, 16, 6008-6011;
A. H. Bansode, S. R. Shaikh, R. G. Gonnade, N. T. Patil, Chem. Commun. 2017, 53, 9081-9084.
A. C. Hunter, K. Chinthapally, I. Sharma, Eur. J. Org. Chem. 2016, 2260-2263.
K. Matsuo, Y. Hasuike, Chem. Pharm. Bull. 1989, 37, 2803-2806.
J. B. Baell, J. W. M. Nissink, ACS Chem. Biol. 2018, 13, 36-44.
J. B. Baell, M. A. Walters, Nature 2014, 513, 481.
X. Deng, L. Kong, Y. Zhao, J. He, L.-Y. Peng, Y. Li, Q.-S. Zhao, Nat. Prod. Bioprospect. 2012, 2, 210.
K. Selvaraju, A. Mofers, P. Pellegrini, J. Solomonsson, A. Ahlner, V. Morad, E.-K. Hillert, B. Espinosa, E. S. J. Arner, L. Jensen, J. Molamstroem, M. V. Turkina, P. D′Arcy, M. A. Walters, M. Sunnerhagen, S. Linder, Sci. Rep. 2019, 9, 9841.
F.-F. Gan, K. K. Kaminska, H. Yang, C.-Y. Liew, P.-C. Leow, C.-L. So, L. N. L. Tu, A. Roy, C.-W. Yap, T.-S. Kang, W.-K. Chui, E.-H. Chew, Antioxid. Redox Signaling 2013, 19, 1149.
M. Jovanović, D. Zhukovsky, A. Podolski-Renić, I. Domračeva, R. Žalubovskis, M. Senćanski, S. Glišić, V. Sharoyko, T. Tennikova, D. Dar'in, M. Pešić, M. Krasavin, Eur. J. Med. Chem. 2019, 181, 111580.
M. Jovanović, D. Zhukovsky, A. Podolski-Renić, R. Žalubovskis, D. Dar'in, V. Sharoyko, T. Tennikova, M. Pešić, M. Krasavin, Eur. J. Med. Chem. 2020, 191, 112119.
A. Inyutina, E. Chupakhin, D. Dar′in, M. Krasavin, Synlett 2020, 31, 1487-1490.
V. M. Labunskyy, D. L. Hatfield, V. N. Gladyshev, Physiol. Rev. 2014, 4, 739-777.
B. Zhang, Y. Liu, X. Li, J. Xu, J. Fang, Chem. Asian J. 2018, 13, 3593-3600.
E. S. Arner, L. Zhong, A. Holmgren, Methods Enzymol. 1999, 300, 226-239.
B. Zhang, J. Zhang, S. Peng, R. Liu, X. Li, Y. Hou, X. Han, J. Fang, Exp. Opin. Ther. Pat. 2017, 27, 547-556.
F. Tan, X. Liu, X. Hao, Y. Tang, L. Lin, X. Feng, ACS Catal. 2016, 6, 6930-6934.
D. Dar′in, G. Kantin, M. Krasavin, Chem. Commun. 2019, 55, 5239-5242.

Auteurs

Dmitry Dar'in (D)

Chair of Natural Products Chemistry, Saint Petersburg State University, Saint-Petersburg, 199034, Russian Federation.

Grigory Kantin (G)

Chair of Natural Products Chemistry, Saint Petersburg State University, Saint-Petersburg, 199034, Russian Federation.

Evgeny Chupakhin (E)

Chair of Natural Products Chemistry, Saint Petersburg State University, Saint-Petersburg, 199034, Russian Federation.
Immanuel Kant Baltic Federal University, Kaliningrad, 236041, Russian Federation.

Vladimir Sharoyko (V)

Chair of Natural Products Chemistry, Saint Petersburg State University, Saint-Petersburg, 199034, Russian Federation.
Laboratory for Cell Biotechnology, Saint Petersburg State Institute of Technology (University), Saint Petersburg, 190013, Russian Federation.

Mikhail Krasavin (M)

Chair of Natural Products Chemistry, Saint Petersburg State University, Saint-Petersburg, 199034, Russian Federation.
Immanuel Kant Baltic Federal University, Kaliningrad, 236041, Russian Federation.

Classifications MeSH