Catharanthine - CAS 2468-21-5
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Not Intended for Therapeutic Use. For research use only.
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Catharanthine inhibits nicotinic receptor mediated diaphragm contractions with IC50 of 59.6 μM.
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1. Interactions of vinca alkaloid subunits with chiral amido[4]resorcinarenes: a dynamic, kinetic, and spectroscopic study
Bruno Botta*, Caterina Fraschetti, Maurizio Speranza*. Org. Biomol. Chem., 2009, 7, 1798–1806
Insights into the structure and the dynamics of catharanthine and of the proton-bound [4R/S•H•C]+ complexes were obtained by using two computational methodologies implemented in MacroModel, that is i) the statistical conformational search/docking procedure Monte Carlo Multiple Minimum (MCMM) and ii) constant temperature MD runs. Each MCMM conformational search on catharanthine was started after having performed the MacroModel automatic setup to set all the search variables (torsions to be rotated, rings to be opened, etc.). Summing up, 3000 steps were invariably performed each time, in which a total number of 11 torsional degrees of freedom was analysed. A randomly variable number of rotatable bonds of the molecules ranging from 2 to 10 was varied in each step in the range 0o–180o.
2. Synthesis of fluorinated catharanthine analogues and investigation of their biomimetic coupling with vindoline
Emerson Giovanelli, Lionel Moisan, Eric Doris*. Org. Biomol. Chem., 2013, 11, 5885–5891
Ideally, an alternative pathway to vinflunine should avoid the drastic superacidic medium and start from a less valuable intermediate than anhydrovinblastine. Our rationale was guided by two facts: (i) in the course of the synthesis of vinflunine, only the velbenamine upper part of the dimer is affected by the fluorination, and (ii) the classical precursor of the velbenamine moiety is catharanthine. Consequently, we conceived that the direct introduction of the two fluorine atoms to catharanthine 6 could pave the way toward the synthesis of vinflunine 5. Actually, the biomimetic coupling of difluorinated catharanthine 10 with vindoline 7 could not only give access to vinflunine, but also to unsaturated analogues (e.g. difluoroanhydrovinblastine 11) whose formation in superacidic medium is prevented because of the inherent saturation of C3’=C4’ double bond. As part of our ongoing interest in Vinca alkaloid chemistry, we thus designed a synthetic scheme for the preparation of difluorocatharanthine (and congeners) and investigated its (their) biomimetic coupling with vindoline.
3. The radical cation mediated cleavage of catharanthine leading to the vinblastine type alkaloids: implications for total synthesis and drug design
Maryam Sadat Alehashem, Chuan-Gee Lim, Noel F. Thomas*. RSC Adv.,2016, 6, 18002–18025
This stereochemical outcome might well suggest a concerted mechanism, an alternative Kutney himself considered. On the other hand the stepwise azabenzfulvene mechanism would appear to be supported by Sundberg's observation that under Kutney's conditions N-methyl catharanthine is consumed, yet does not couple with vindoline most of which was recovered. On the other hand N-methyl catharanthine is recovered unchanged in the absence of vindoline which implies firstly, a catalytic role for vindoline and secondly, that the neutral azabenzfulvene may be the crucial intermediate.
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