Wiley
Helvetica Chimica Acta
,  volume 86 ,  issue 6 ,  pages 2082-2089

New Tetracyclic Colchicinoids from the Reaction of N-Deacetylthiocolchicine and N-Deacetylcolchicine with Nitrous Acid and tert-Butyl Nitrite

Bruno Danieli 1, 2
, 
Giordano LESMA 1, 2
, 
Daniele Passarella 1, 2
, 
Davide Prosperi 1, 2
, 
Alessandro Sacchetti 1, 2
, 
Alessandra Silvani 1, 2
, 
Riccardo Destro 3
, 
Emanuela May 3
, 
Ezio Bombardelli 4
1
 
2
 
fax: +39‐2‐50314078)
3
 
4
 
Indena S.p.A., Via Ortles 12, I‐20122 Milano
Publication type: Journal Article
Publication date: 2003-06-01
Wiley
scimago Q2
wos Q3
SJR: 0.491
CiteScore: 3.0
Impact factor: 1.8
ISSN: 0018019X, 15222675
Catalysis
Organic Chemistry
Drug Discovery
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Abstract
Reaction of N-deacetylthiocolchicine (3) and N-deacetylcolchicine (4) with nitrous acid (HONO) furnished the new tetracyclic colchicinoids 5 and 6, as well as the Demyanov-rearrangement products 7 and 8. Starting from 3, the pyrazole-containing tetracycle 9 was obtained. The novel compounds were characterized spectroscopically, and an X-ray crystal-structure analysis of 5 allowed us to establish the absolute configurations at the stereogenic centers.
Found 
3 citations
Fedorov Alexey
DSc in Chemistry, associate member of the Russian Academy of Sciences 
93 publications,  2 825 citations,  10 reviews
h-index: 27
Lobachevsky State University of Nizhny Novgorod
Lobachevsky State University of Nizhny Novgorod
1 citation
Beloglazkina Elena
DSc in Chemistry, professor
296 publications,  3 248 citations,  11 reviews
h-index: 29
Lomonosov Moscow State University
Lomonosov Moscow State University
1 citation
Vil' Vera
PhD in Chemistry
86 publications,  1 967 citations,  3 reviews
h-index: 24
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Organic Chemistry
1 citation
Yaremenko Ivan
PhD in Chemistry
60 publications,  1 567 citations,  5 reviews
h-index: 24
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Organic Chemistry
1 citation
Gorbunova Yuliya
DSc in Chemistry, professor, full member of the Russian Academy of Sciences 
284 publications,  4 398 citations,  65 reviews
h-index: 34
Lomonosov Moscow State University
Lomonosov Moscow State University
Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
A.N. Frumkin Institute of Physical Chemistry and Electrochemistry of the Russian Academy of Sciences
Research interests
Coordination Chemistry
Lanthanides
Supramolecular chemistry
Tetrapyrrolic compounds
1 citation
Volcho Konstantin
DSc in Chemistry, professor of the Russian Academy of Sciences 
279 publications,  3 898 citations,  65 reviews
h-index: 31
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences
1 citation
Danilkina Natalia
44 publications,  625 citations
h-index: 14
Saint Petersburg State University
Saint Petersburg State University
Research interests
Bioorganic chemistry
Click chemistry
Heterocyclic compounds
Medicinal Chemistry
Organic Chemistry
1 citation
Osipov Sergey
DSc in Chemistry
138 publications,  2 739 citations,  3 reviews
h-index: 29
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
A.N.Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences
1 citation
Gazizov Almir
🥼
DSc in Chemistry
157 publications,  889 citations,  23 reviews
h-index: 14
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Heterocyclic compounds
Organic Chemistry
Organophosphorus chemistry
1 citation
Karasik Andrey
DSc in Chemistry, professor, associate member of the Russian Academy of Sciences 
224 publications,  2 599 citations
h-index: 26
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Coordination Chemistry
Luminescence
Phosphorus ligands
1 citation
Dotsenko Viktor
DSc in Chemistry, professor
244 publications,  2 741 citations,  2 reviews
h-index: 22
North Caucasus Federal University
North Caucasus Federal University
Kuban State University
Kuban State University
Research interests
Active methylene compounds
Biological activity
Heterocyclic compounds
Malononitrile
Selenoamides
Thioamides
1 citation
Zagidullin Almaz
🥼 🤝
PhD in Chemistry
81 publications,  884 citations
h-index: 17
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
A.E. Arbuzov Institute of Organic and Physical Chemistry of the Kazan Scientific Center of the Russian Academy of Sciences
Research interests
Asymmetric metal complex catalysis
Chemistry of organic and organoelement compounds; chemistry of polymers; production of materials
Coordination chemistry of phosphorus
Organoelement chemistry
Organophosphorus chemistry
Synthesis of chiral phosphorus-containing ligands
1 citation
Aksenov Aleksandr
🥼 🤝
DSc in Chemistry, professor
243 publications,  2 187 citations,  15 reviews
h-index: 24
North Caucasus Federal University
North Caucasus Federal University
Research interests
Medicinal Chemistry
Organic Chemistry
1 citation
Sosnovskikh Vyacheslav
DSc in Chemistry, professor
355 publications,  4 721 citations
h-index: 30
Ural Federal University
Ural Federal University
1 citation
Ilkin Vladimir
PhD in Chemistry
16 publications,  187 citations
h-index: 7
Ural Federal University
Ural Federal University
Research interests
Catalysis
Heterocyclic compounds
Organic Chemistry
Synthetic Organic Chemistry
1 citation
Krylov Igor
PhD in Chemistry
78 publications,  1 885 citations,  18 reviews
h-index: 25
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
Research interests
Green chemistry
Organic Chemistry
Organic electrochemistry
Organic synthesis
Photochemistry
Plant protection
1 citation
Tikhomirov Alexander
🥼 🤝
DSc in Chemistry, associate professor
59 publications,  920 citations
h-index: 17
Mendeleev University of Chemical Technology of Russia
Mendeleev University of Chemical Technology of Russia
Gause Institute of New Antibiotics
Gause Institute of New Antibiotics
Research interests
Medicinal Chemistry
1 citation
Ivanov Andrey
54 publications,  534 citations
h-index: 12
A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
A.E. Favorsky Irkutsk Institute of Chemistry of the Siberian Branch of the Russian Academy of Sciences
1 citation
Buev Evgeny
PhD in Chemistry
31 publications,  346 citations,  2 reviews
h-index: 9
Ural Federal University
Ural Federal University
Research interests
Chemistry of nitrogen-containing heterocycles
Organic Chemistry
Organic synthesis

Top-30

Journals

1
2
European Journal of Organic Chemistry
European Journal of Organic Chemistry, 2, 33.33%
European Journal of Organic Chemistry
2 publications, 33.33%
Journal of Medicinal Chemistry
Journal of Medicinal Chemistry, 1, 16.67%
Journal of Medicinal Chemistry
1 publication, 16.67%
ACS Omega
ACS Omega, 1, 16.67%
ACS Omega
1 publication, 16.67%
Natural Product Reports
Natural Product Reports, 1, 16.67%
Natural Product Reports
1 publication, 16.67%
Russian Chemical Reviews
Russian Chemical Reviews, 1, 16.67%
Russian Chemical Reviews
1 publication, 16.67%
1
2

Publishers

1
2
American Chemical Society (ACS)
American Chemical Society (ACS), 2, 33.33%
American Chemical Society (ACS)
2 publications, 33.33%
Wiley
Wiley, 2, 33.33%
Wiley
2 publications, 33.33%
Royal Society of Chemistry (RSC)
Royal Society of Chemistry (RSC), 1, 16.67%
Royal Society of Chemistry (RSC)
1 publication, 16.67%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii, 1, 16.67%
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 16.67%
1
2
  • We do not take into account publications without a DOI.
  • Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
6
Share
Cite this
GOST |
Cite this
GOST Copy
Danieli B. et al. New Tetracyclic Colchicinoids from the Reaction of N-Deacetylthiocolchicine and N-Deacetylcolchicine with Nitrous Acid and tert-Butyl Nitrite // Helvetica Chimica Acta. 2003. Vol. 86. No. 6. pp. 2082-2089.
GOST all authors (up to 50) Copy
Danieli B., LESMA G., Passarella D., Prosperi D., Sacchetti A., Silvani A., Destro R., May E., Bombardelli E. New Tetracyclic Colchicinoids from the Reaction of N-Deacetylthiocolchicine and N-Deacetylcolchicine with Nitrous Acid and tert-Butyl Nitrite // Helvetica Chimica Acta. 2003. Vol. 86. No. 6. pp. 2082-2089.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1002/hlca.200390164
UR - https://doi.org/10.1002/hlca.200390164
TI - New Tetracyclic Colchicinoids from the Reaction of N-Deacetylthiocolchicine and N-Deacetylcolchicine with Nitrous Acid and tert-Butyl Nitrite
T2 - Helvetica Chimica Acta
AU - Danieli, Bruno
AU - LESMA, Giordano
AU - Passarella, Daniele
AU - Prosperi, Davide
AU - Sacchetti, Alessandro
AU - Silvani, Alessandra
AU - Destro, Riccardo
AU - May, Emanuela
AU - Bombardelli, Ezio
PY - 2003
DA - 2003/06/01
PB - Wiley
SP - 2082-2089
IS - 6
VL - 86
SN - 0018-019X
SN - 1522-2675
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2003_Danieli,
author = {Bruno Danieli and Giordano LESMA and Daniele Passarella and Davide Prosperi and Alessandro Sacchetti and Alessandra Silvani and Riccardo Destro and Emanuela May and Ezio Bombardelli},
title = {New Tetracyclic Colchicinoids from the Reaction of N-Deacetylthiocolchicine and N-Deacetylcolchicine with Nitrous Acid and tert-Butyl Nitrite},
journal = {Helvetica Chimica Acta},
year = {2003},
volume = {86},
publisher = {Wiley},
month = {jun},
url = {https://doi.org/10.1002/hlca.200390164},
number = {6},
pages = {2082--2089},
doi = {10.1002/hlca.200390164}
}
MLA
Cite this
MLA Copy
Danieli, Bruno, et al. “New Tetracyclic Colchicinoids from the Reaction of N-Deacetylthiocolchicine and N-Deacetylcolchicine with Nitrous Acid and tert-Butyl Nitrite.” Helvetica Chimica Acta, vol. 86, no. 6, Jun. 2003, pp. 2082-2089. https://doi.org/10.1002/hlca.200390164.