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Journal articles on the topic 'Synthesis of Allocolchicine'

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Author: Grafiati
Published: 6 September 2023

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1

Fedorov, Alexey, Ekaterina Shchegravina, Elena Svirshchevskaya, and Hans-Günther Schmalz. "A Facile Synthetic Approach to Nonracemic Substituted Pyrrolo-allocolchicinoids Starting from Natural Colchicine." Synthesis 51, no. 07 (December 13, 2018): 1611–22. http://dx.doi.org/10.1055/s-0037-1610673.

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A six-step semisynthetic approach towards chiral nonracemic pyrrolo-allocolchicinoids starting from naturally occurring colchicine was developed. The synthetic scheme includes an electrocyclic tropolone ring contraction to afford allocolchicinic acid followed by the Curtius reaction, giving the corresponding aniline. The Sandmeyer reaction and copper-mediated hydrazination gave hydrazine-substituted allocolchicine. This was introduced into the Fischer indole synthesis, affording libraries of regioisomeric indole-based allocolchicine congeners.
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2

Sitnikov, Nikolay S., Alexander V. Sinzov, Diane Allegro, Pascale Barbier, Sebastien Combes, Liliane Abodo Onambele, Aram Prokop, Hans-Günther Schmalz, and Alexey Yu Fedorov. "Synthesis of indole-derived allocolchicine congeners exhibiting pronounced anti-proliferative and apoptosis-inducing properties." MedChemComm 6, no. 12 (2015): 2158–62. http://dx.doi.org/10.1039/c5md00320b.

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3

Djurdjevic, Sinisa, Fei Yang, and James R. Green. "Intramolecular Nicholas Reactions in the Synthesis of Dibenzocycloheptanes. Synthesis of Allocolchicine NSC 51046 and Analogues and the Formal Synthesis of (−)-Allocolchicine." Journal of Organic Chemistry 75, no. 23 (December 3, 2010): 8241–51. http://dx.doi.org/10.1021/jo101953n.

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4

Fedorov, Alexey, Iuliia Gracheva, Elena Svirshchevskaya, Vladimir Faerman, and Irina Beletskaya. "Synthesis and Antiproliferative Properties of Bifunctional Allocolchicine Derivatives." Synthesis 50, no. 14 (May 28, 2018): 2753–60. http://dx.doi.org/10.1055/s-0037-1610146.

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Based on the natural antimitotic agent colchifoline as a lead structure, a series of novel bifunctional allocolchicine congeners were synthesized from commercial colchicine. The new derivatives maintain good cytotoxicity against T3M4, MiaPaCa-2, and PANC-1 cell lines. The presence of functional groups simplifies further modifications of the prepared structures and the design of novel colchicine-derived antitumor compounds with desired pharmacological properties.
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5

Zotov, A. S., E. S. Shchegravina, and A. Yu Fedorov. "Synthesis of Allocolchicine Conjugates with a Cetirizine Analog." Russian Journal of Organic Chemistry 54, no. 10 (October 2018): 1498–504. http://dx.doi.org/10.1134/s107042801810010x.

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6

Banwell, MG, JM Cameron, M. Corbett, JR Dupuche, E. Hamel, JN Lambert, CM Lin, and MF Mackay. "Synthesis and Tubulin-Binding Properties of Some AC- and ABC-Ring Analogs of Allocolchicine." Australian Journal of Chemistry 45, no. 12 (1992): 1967. http://dx.doi.org/10.1071/ch9921967.

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Fourteen analogues [compounds (8), (9) and (11)-(22)] of the powerful antimitotic agent allocolchicine (5) have been prepared and evaluated for their ability to prevent tubulin polymerization. The X-ray structure of one of the more active compounds, tricycle (20), is reported.
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7

Djurdjevic, Sinisa, Fei Yang, and James R. Green. "ChemInform Abstract: Intramolecular Nicholas Reactions in the Synthesis of Dibenzocycloheptanes. Synthesis of Allocolchicine NSC 51046 (IVa) and Analogues and the Formal Synthesis of (-)-Allocolchicine (V)." ChemInform 42, no. 11 (February 17, 2011): no. http://dx.doi.org/10.1002/chin.201111108.

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8

Joncour, Agnès, Anne Décor, Jian-Miao Liu, Marie-Elise Tran Huu Dau, and Olivier Baudoin. "Asymmetric Synthesis of Antimicrotubule Biaryl Hybrids of Allocolchicine and Steganacin." Chemistry - A European Journal 13, no. 19 (June 25, 2007): 5450–65. http://dx.doi.org/10.1002/chem.200601764.

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9

Krasniqi, Besir, and Wim Dehaen. "Synthesis of 1,2,3-Triazolo-Fused Allocolchicine Analogs via Intramolecular Oxidative Biaryl Coupling." Organic Letters 21, no. 13 (June 26, 2019): 5002–5. http://dx.doi.org/10.1021/acs.orglett.9b01707.

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10

Sitnikov, Nikolay, Janna Velder, Liliane Abodo, Nicole Cuvelier, Jörg Neudörfl, Aram Prokop, Günter Krause, Aleksey Y. Fedorov, and Hans-Günther Schmalz. "Total Synthesis of Indole-Derived Allocolchicine Analogues Exhibiting Strong Apoptosis-Inducing Activity." Chemistry - A European Journal 18, no. 38 (August 27, 2012): 12096–102. http://dx.doi.org/10.1002/chem.201200083.

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11

Zhang, Yan, Zhenzhi Cai, Julia Struwe, Chanchan Ma, Wangyu Zeng, Xinyi Liao, Min Xu, and Lutz Ackermann. "Dibenzocycloheptanones construction through a removable P-centered radical: synthesis of allocolchicine analogues." Chemical Science 12, no. 47 (2021): 15727–32. http://dx.doi.org/10.1039/d1sc05404j.

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12

Sitnikov, Nikolay S., Antonina S. Kokisheva, Georgy K. Fukin, Jörg-Martin Neudörfl, Hannah Sutorius, Aram Prokop, Valery V. Fokin, Hans-Günther Schmalz, and Alexey Yu Fedorov. "Synthesis of Indole-Derived Allocolchicine Congeners through Pd-Catalyzed Intramolecular C-H Arylation Reaction." European Journal of Organic Chemistry 2014, no. 29 (September 4, 2014): 6481–92. http://dx.doi.org/10.1002/ejoc.201402850.

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13

Paymode, Dinesh J., and Chepuri V. Ramana. "Total Synthesis of (±)-Allocolchicine and Its Analogues Using Co-Catalyzed Alkyne [2 + 2 + 2]-Cyclotrimerization." ACS Omega 2, no. 9 (September 8, 2017): 5591–600. http://dx.doi.org/10.1021/acsomega.7b00980.

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14

Vorogushin, Andrei V., Alexander V. Predeus, William D. Wulff, and Hans-Jürgen Hansen. "Diels−Alder Reaction−Aromatization Approach toward Functionalized Ring C Allocolchicinoids. Enantioselective Total Synthesis of (−)-7S-Allocolchicine." Journal of Organic Chemistry 68, no. 15 (July 2003): 5826–31. http://dx.doi.org/10.1021/jo034420t.

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15

Schmalz, Hans-Günther, and Norman Nicolaus. "Synthesis of Novel Allocolchicine Analogues with a Pyridine C-Ring through Intermolecular Vollhardt Diyne-Nitrile Cyclotrimerization." Synlett 2010, no. 14 (July 22, 2010): 2071–74. http://dx.doi.org/10.1055/s-0030-1258512.

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16

BANWELL, M. G., J. M. CAMERON, M. CORBETT, J. R. DUPUCHE, E. HAMEL, J. N. LAMBERT, C. M. LIN, and M. F. MACKAY. "ChemInform Abstract: Synthesis and Tubulin-Binding Properties of Some AC- and ABC-Ring Analogues of Allocolchicine." ChemInform 24, no. 13 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199313279.

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17

Sitnikov, Nikolay S., Antonina S. Kokisheva, Georgy K. Fukin, Joerg-Martin Neudoerfl, Hannah Sutorius, Aram Prokop, Valery V. Fokin, Hans-Guenther Schmalz, and Alexey Yu Fedorov. "ChemInform Abstract: Synthesis of Indole-Derived Allocolchicine Congeners Through Pd-Catalyzed Intramolecular C-H Arylation Reaction." ChemInform 46, no. 12 (March 2015): no. http://dx.doi.org/10.1002/chin.201512277.

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18

Nicolaus, Norman, and Hans-Guenther Schmalz. "ChemInform Abstract: Synthesis of Novel Allocolchicine Analogues with a Pyridine C-Ring Through Intermolecular Vollhardt Diyne-Nitrile Cyclotrimerization." ChemInform 42, no. 2 (December 16, 2010): no. http://dx.doi.org/10.1002/chin.201102204.

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19

Corrie, Tom J. A., and Guy C. Lloyd-Jones. "Formal Synthesis of (±)-Allocolchicine Via Gold-Catalysed Direct Arylation: Implication of Aryl Iodine(III) Oxidant in Catalyst Deactivation Pathways." Topics in Catalysis 60, no. 8 (April 19, 2017): 570–79. http://dx.doi.org/10.1007/s11244-017-0742-z.

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Abstract A concise formal synthesis of racemic allocolchicine has been developed, centred on three principal transformations: a retro-Brook alkylation reaction to generate an arylsilane, a gold-catalysed arylative cyclisation to generate the B-ring via biaryl linkage, and a palladium-catalysed carbonylation of an aryl chloride to generate an ester. 1H NMR monitoring of the key gold-catalysed cyclisation step reveals that a powerful catalyst deactivation process progressively attenuates the rate of catalyst turnover. The origins of the catalyst deactivation have been investigated, with an uncatalysed side-reaction, involving the substrate and the iodine(III) oxidant, identified as the source of a potent catalyst poison. The side reaction generates 1–4% of a diaryliodonium salt, and whilst this moiety is shown not to be an innate catalyst deactivator, when it is tethered to the arylsilane reactant, the inhibition becomes powerful. Kinetic modelling of processes run at two different catalyst concentrations allows extraction of the partitioning of the gold catalyst between the substrate and its diaryliodonium salt, with a rate of diaryliodonium salt generation consistent with that independently determined in the absence of catalyst. The high partition ratio between substrate and diaryliodonium salt (5/1) results in very efficient, and ultimately complete, diversion of the catalyst off-cycle. Graphical Abstract
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20

Bhowmik, Subhendu, Shruti Khanna, Kumkum Srivastava, Mohammad Hasanain, Jayanta Sarkar, Sandeep Verma, and Sanjay Batra. "An Efficient Combinatorial Synthesis of Allocolchicine Analogues via a Triple Cascade Reaction and their Evaluation as Inhibitors of Insulin Aggregation." ChemMedChem 8, no. 11 (September 5, 2013): 1767–72. http://dx.doi.org/10.1002/cmdc.201300302.

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21

Corrie, Tom J. A., and Guy C. Lloyd-Jones. "Correction to: Formal Synthesis of (±)-Allocolchicine Via Gold-Catalysed Direct Arylation: Implication of Aryl Iodine(III) Oxidant in Catalyst Deactivation Pathways." Topics in Catalysis 63, no. 19-20 (February 24, 2020): 1766. http://dx.doi.org/10.1007/s11244-020-01243-w.

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22

Bhowmik, Subhendu, Shruti Khanna, Kumkum Srivastava, Mohammad Hasanain, Jayanta Sarkar, Sandeep Verma, and Sanjay Batra. "ChemInform Abstract: An Efficient Combinatorial Synthesis of Allocolchicine Analogues via a Triple Cascade Reaction and Their Evaluation as Inhibitors of Insulin Aggregation." ChemInform 45, no. 13 (March 14, 2014): no. http://dx.doi.org/10.1002/chin.201413048.

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23

Djurdjevic, Sinisa, and James R. Green. "Allocolchicines via Intramolecular Nicholas Reactions: The Synthesis of NSC 51046." Organic Letters 9, no. 26 (December 2007): 5505–8. http://dx.doi.org/10.1021/ol7024422.

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24

Boyer, François-Didier, and Issam Hanna. "Synthesis of Allocolchicines Using Sequential Ring-Closing Enyne Metathesis−Diels−Alder Reactions." Organic Letters 9, no. 4 (February 2007): 715–18. http://dx.doi.org/10.1021/ol0630548.

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25

Jain, Nishant, Divya Yada, Thokhir B. Shaik, Galanki Vasantha, P. Surendra Reddy, Shasi V. Kalivendi, and B. Sreedhar. "Synthesis and Antitumor Evaluation of Nitrovinyl Biphenyls: Anticancer Agents Based on Allocolchicines." ChemMedChem 6, no. 5 (April 6, 2011): 859–68. http://dx.doi.org/10.1002/cmdc.201100019.

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26

Gracheva, Iuliia A., Hans Günther Schmalz, Elena V. Svirshchevskaya, Ekaterina S. Shchegravina, and Alexey Fedorov. "Design of an Aryne-Platform for the Synthesis of Non-Racemic Heterocyclic Allocolchicinoids." Organic & Biomolecular Chemistry, 2023. http://dx.doi.org/10.1039/d3ob00827d.

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A four-step semisynthetic approach towards a highly versatile allocolchicine-related chiral aryne intermediate starting from naturally occurring colchicine was developed, and some of its synthetic transformations were studied. The in situ...
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27

"Synthesis of Allocolchicine Analogues through Construction and Removal of P-centered Radicals." Synfacts 18, no. 03 (February 16, 2022): 0251. http://dx.doi.org/10.1055/s-0041-1737884.

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28

Pollok, Dennis, Florian U. Rausch, Sebastian B. Beil, Peter Franzmann, and Siegfried R. Waldvogel. "Allocolchicines─Synthesis with Electro-organic Key Transformations." Organic Letters, May 3, 2022. http://dx.doi.org/10.1021/acs.orglett.2c01084.

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29

Djurdjevic, Sinisa, and James R. Green. "ChemInform Abstract: Allocolchicines via Intramolecular Nicholas Reactions: The Synthesis of NSC 51046." ChemInform 39, no. 22 (May 27, 2008). http://dx.doi.org/10.1002/chin.200822201.

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30

Boyer, Francois-Didier, and Issam Hanna. "Synthesis of Allocolchicines Using Sequential Ring-Closing Enyne Metathesis—Diels—Alder Reactions." ChemInform 38, no. 26 (June 26, 2007). http://dx.doi.org/10.1002/chin.200726160.

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