- Paclitaxel compounds with modified C-13 and C-14 position structure and preparing method of paclitaxel compounds
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The invention relates to a paclitaxel analogue with modified C-13 and C-14 positions and a preparing method of the paclitaxel analogue. The structural formula of the analogue is shown in the description. Different side chains are introduced into the C-13 position and the C-14 position of taxanes of 1-dehydroxybaccatin VI, the annular framework and necessary functional groups of paclitaxel are reserved, paclitaxel compounds are enriched, the obtained compounds have the natural anti-cancer biological activity of natural paclitaxel, certain application prospects on the aspect of reducing the toxic and side effects of natural paclitaxel are achieved, and meanwhile it is highly beneficial for studying the activity structure-function relationship of the compounds. The compounds a, b, c, d and taxol have a suppressing effect on the in-vitro proliferation of the A 549 lung cancer cells, A 2780 ovarian carcinoma cells and HL-60 promyelocytic leukemia cells of the human body.
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Page/Page column 17
(2017/10/09)
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- Substituent effect on the asymmetric induction with (1R,2S,5R)-and (1S,2R,5S)-menthol auxiliaries
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Substituted benzaldehydes reacts in cis-diastcrcoselective manner with mentliyl haloacetates in the presence of phase transfer catalyst and a base in THF at room temperature to give the corresponding 3-arvloxirane-2-carboxvlates (2/3a-h) in moderate to high yields The magnitude of asymmetric induction in the latter reaction was quantified by a Hammett type equation log(2/3)x = ρσr - log(2/3)X-H The stereochemistry of compounds 2 and 3 was elucidated b correlation with (4S. 5R)-2.4-diphenyll-4,5- dihydrooxazole-5-carboxylic acid (+)-8 as well as its enantiomer (-)-8.
- Er, Mustafa,Coskun, Necdet
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experimental part
p. 198 - 208
(2011/10/04)
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- Synthesis and Antifeedant Properties of N-Acylphenylisoserinates of Lactarius Sesquiterpenoid Alcohols
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The esterification of various sesquiterpenoid alcohols of Lactarius origin with N-benzoyl-[2R,3S]-phenylisoserine (side chain of Taxol), N-acetyl-[2R,3S]-phenylisoserine and N-tert-butoxy-[2R,3S]-phenylisoserine (side chain of Taxotere) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium, Sitophylus granarius and Rhizoperta dominica were measured. The introduction of the ester moiety in these molecules, in comparison to original compounds, moderately enhanced their antifeedant activities, as well as changed their selectivity of activity towards the test insects.
- Kopczacki,Gumulka,Masnyk,Sarosiek,Barycki,Ignacak,Zochowski,Grabarczyk,Nowak,Daniewski
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- Enantioselective synthesis of 1-aryl-2-propenylamines: A new approach to a stereoselective synthesis of the Taxol side chain
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A variety of substituted 1-aryl-2-propenylamines of high enantiomeric purity were prepared via lipase-catalysed resolution of the corresponding racemates. (R)-1-Phenyl-2-propenylamine was further synthesised into (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoic acid methyl ester, the side chain of Taxol.
- Castagnolo, Daniele,Armaroli, Silvia,Corelli, Federico,Botta, Maurizio
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p. 941 - 949
(2007/10/03)
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- Improved large-scale synthesis of phenylisoserine and the taxol C-13 side chain
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Dihydrodihydroxycinnamic acids and their esters react with acetonitrile or benzonitrile in the presence of sulfuric acid to afford the corresponding syn-β-amino-α-hydroxypropionic acid derivatives. High yields and diastereoselectivity of this transformation allows preparation of various phenylisoserine derivatives on a practical scale.
- Voronkov, Michael V.,Gontcharov, Alexander V.,Wang, Zhi-Min
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p. 407 - 409
(2007/10/03)
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- Synthesis and antifeedant properties of N-benzoylphenylisoserinates of Lactarius sesquiterpenoid alcohols
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The esterification of various sesquiterpenoid alcohols of Lactarius origin with N-benzoyl-[2R,3S]-phenylisoserine (side chain of Taxol) produced compounds whose antifeedant properties against storage pests Tribolium confusum, Trogoderma granarium and Sitophylus granarius were measured. The introduction of the taxol side chain in these molecules, in comparison to original compounds, moderately enhanced their antifeedant activities, as well as changed their selectivity of activity towards the test insects.
- Kopczacki, Piotr,Gumulka, Maria,Masnyk, Marek,Grabarczyk, Halina,Nowak, Gerard,Daniewski, Wlodzimierz M.
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p. 775 - 787
(2007/10/03)
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- Synthesis of N-benzoylphenylisoserinates of lactarorufin B (a sesquiterpene of Lactarius origin) and its derivatives
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Lactarorufin B, which is a Lactarius sesquiterpene possessing primary, secondary and tertiary hydroxyl groups on its lactarane skeleton, was selectively transformed into (2′R,3′S)-N-benzoylphenylisoserinates, using protective group methodology described below.
- Daniewski,Gumulka,Kopczacki,Masnyk
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p. 1287 - 1296
(2007/10/03)
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- Intermediary compounds for the hemisynthesis of taxanes and preparation processes therefor
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The present invention relates to new intermediates for the semisynthesis of taxanes and their preparation processes. It relates to derivatives of oxazolidines or oxazolidinones, as well as to new derivatives of baccatine III. The general process for the synthesis of taxanes according to the invention enables to obtain a product such as PACLITAXEL in only five steps from products available in the market, compared to nine steps in general, for processes of the prior art.
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- Process for the preparation of oxazoline compound
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The present invention relates to a process for the preparation of an oxazoline compound which is easily chemically converted to a beta-amino-alpha-hydroxy acid or a gamma-amino-beta-hydroxy acid. The method comprises producing a compound of the following formula (4) using alpha -amino acid. The produced compound (4) is subjected to an intramolecular cyclization to produce an oxazoline compound of the following formula (3). The oxazoline compound (3) is oxidized at a vinyl group with RuCl3 or NaIO4 to produce an oxazoline compound of the following formula (1) which is easily chemically converted to a beta-amino-alpha-hydroxy acid. Alternatively, the oxazoline compound (3) may also be treated with 9-borabiclo[3.3.1]nonane such that a hydroxy group is introduced into the end of the vinyl group of the oxazoline compound(3). The introduced end hydroxy group is oxidized with RuCl3 or NaIO4 to produce an oxazoline compound of the following formula (2) which is easily chemically converted to a gamma-amino-hydroxy acid.
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- An enantiocontrolled synthesis of the masked taxol C-13 side chain, oxazoline carboxylic acid
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Oxazoline carboxylic acid 6 as the taxol side chain precursor has been efficiently synthesized via the intramolecular iodoamidation of allylic trichloroacetimidate derived from trans-olefinic diol 1.
- Kang, Sung Ho,Kim, Cheol Min,Youn, Joo-Hack
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p. 3581 - 3582
(2007/10/03)
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- Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via π-allylpalladium complex catalyzed by Pd(0)
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The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis and Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same π-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of β- amino-α-hydroxy acids 1 and γ-amino-β-hydroxy acids 2, conveniently protected as oxazoline.
- Lee, Kee-Young,Kim, Yong-Hyun,Park, Min-Sung,Oh, Chang-Young,Ham, Won-Hun
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p. 9450 - 9458
(2007/10/03)
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- Synthesis of (4S, 5R) -2, 4-diphenyl-5-carboxy-oxazoline derivative as taxol side-chain precursor
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The present invention provides a process for preparing a (4S,5R)-2,4-diphenyl-5-carboxy-oxazoline derivative, which can serve as a taxol side-chain precursor, from the treatment of a (2R,3S)-alkyl trans-3-phenyl-2,3-epoxypropionate derivative with benzonitrile in the presence of a strong acid.
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- A highly stereocontrolled asymmetric synthesis of the Taxol C-13 side chain; (4S, 5R)-2,4-Diphenyloxazoline-5 carboxylic acid
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A stereoselective synthesis of (4S, 5R)-2,4-diphenyloxaline-5-carboxylic acid, a precursor of the Taxol C-13 side chain was achieved using palladium- catalyzed oxazoline formation reaction from commercially available amino acid.
- Lee, Kee-Young,Kim, Yong-Hyun,Park, Min-Sung,Ham, Won-Hun
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p. 8129 - 8132
(2007/10/03)
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- Synthesis of Taxol from Baccatin III via an Oxazoline Intermediate
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Taxol (1) can be prepared in good yield by coupling the oxazoline carboxylic acid 5 with 7-(triethylsilyl)baccatin III, followed by hydrolysis.The oxazolines 7 and 8 can also be prepared directly from taxol.
- Kingston, David G. I.,Chaudhary, Ashok G.,Gunatilaka, A. A. Leslie,Middleton, Mark L.
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p. 4483 - 4484
(2007/10/02)
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