949023-16-9

Usage

Uses

Used in Pharmaceutical Industry:
(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid is used as a cytotoxic agent for its potent anticancer properties. It has been found to exhibit similar cytotoxic activities in the MCF-7 human tumor cell line as paclitaxel, a widely used chemotherapy drug. This makes it a potential candidate for the development of new cancer treatments.
Modification of (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic Acid:
(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid can be further modified to enhance its cytotoxic properties and improve its therapeutic potential. These modifications may involve changes to the benzoyl, 4-methoxyphenyl, or phenyl groups, or the introduction of additional functional groups to the oxazolidine ring. Such modifications can lead to the development of more effective and targeted cancer therapies.

InChI:InChI=1/C24H21NO5/c1-29-19-14-12-18(13-15-19)23-25(22(26)17-10-6-3-7-11-17)20(21(30-23)24(27)28)16-8-4-2-5-9-16/h2-15,20-21,23H,1H3,(H,27,28)/t20-,21+,23?/m0/s1

Upstream product

• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 129320-33-8 5-Ethyl (2R,3R)-2-benzyloxy-3-hydroxy-3-phenylpropanethioate 
• 202390-82-7 5-Ethyl (2R,3S)-3-amino-2-benzyloxy-3-phenylpropanethioate 
• 202390-83-8 5-Ethyl (2R,3S)-3-benzoylamino-2-benzyloxy-3-phenylpropanethioate 
• 10374-29-5 N-benzylidenebenzamide 
• 162189-17-5 N-[(1S,2R)-3-((1R,5S,7S)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-(4-methoxy-benzyloxy)-3-oxo-1-phenyl-propyl]-benzamide 
• 155396-70-6 N-<<(p-Methoxybenzyl)oxy>acetyl>-2,10-camphorsultam 
• 442850-34-2 (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoic acid benzyl ester 
• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 
• 98-88-4 benzoyl chloride 
• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 104-55-2 3-phenyl-propenal 
• 257947-27-6 threo-3-phenylisoserineamide 

Relevant academic research and scientific papers

Synthesis method of paclitaxel side chain and analogs thereof (by machine translation)

The invention discloses a synthesis method of a taxol side chain ((4S, 5R) -3 - benzoyl -2 - (4 - methoxyphenyl) -4 - phenyl -5 - oxazoline carboxylic acid) shown as a formula (f) and a series of reactions such as epoxidation, methyl esterification, ammonolysis, ester hydrolysis, condensation, configuration overturning, condensation and hydrolysis as well as analogues thereof. The invention discloses a synthesis method of the taxol side chain ((4S 5R) -3 -benzoyl -2 - (4 - methoxyphenyl) -4 - phenyl -5 - oxazoline carboxylic acid) and the like. The method has the advantages of short reaction time, high yield, good chiral selectivity, suitability for industrial production and the like. (by machine translation)

Synthetic method of paclitaxel side chain

The invention discloses a synthetic method of a paclitaxel side chain. The method comprises the steps of taking (2R, 3S)-3-phenyl isoserine hydrochloride as a raw material; carrying out esterificationreaction under the participation of methanol and thionyl chloride to obtain (2R, 3S)-phenyl isoserine methyl ester; then preparing (2R, 3S)-N-benzoyl-phenyl isoserine methyl ester through a benzoylation reaction; preparing (4S, 5R)-5-methoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-3-benzoyl-1,3-oxazolidine through a cyclization protection reaction; finally, obtaining a paclitaxel side chain crude product through hydrolysis, and further purifying the paclitaxel side chain crude product through recrystallization to obtain a paclitaxel side chain finished product. The method is simple and easy to operate, short in production period, low in cost, high in purification efficiency and suitable for industrial application and market popularization.

Synthesis and biological activity of C-7, C-9 and C-10 modified taxane analogues from 1-deoxybaccatin VI

A series of C-7, C-9 and C-10 modified taxane analogues were synthesized and their in vitro anticancer activities against three human cancer cell lines: A-549 (human lung cancer cell line), MDA-MB-231 (human breast cancer cell line), A-549/T (human lung c

Preparation method of side chain of paclitaxel

The invention discloses a preparation method of a side chain of paclitaxel shown as a formula II. The preparation method includes the following steps that in a solvent, under the temperature not higher than an atmospheric boiling point of the solvent, a c

The synthesis of novel taxoids for oral administration

A group of novel taxoids, with modifications at C-7, C-10, C-3′ and C-14 positions of paclitaxel, was synthesized in order to improve their biological profile by decreasing their affinity with P-glycoprotein (P-gp) and increasing cellular permeability. Most of the new taxoids demonstrated the similar potent cytotoxic activities in MCF-7 human tumor cell line as paclitaxel in vitro. In the permeability assay with monolayers of Caco-2 cells, most of the compounds demonstrated an increased trans-cellular transport in A-to-B direction in comparison with paclitaxel. Among them the compounds T-13, T-15 and T-26 showed the highest permeability, and with efflux ratios better than that of ortataxel. The interaction of the compounds T-13 and T-26 with P-gp was evaluated using Madin-Darby canine kidney (MDCK)-multidrug resistance-1(MDR1) and MDCK-wild-type (WT). The results indicated that T-13 and T-26 were poor substrates for P-gp and possessed inhibiting effects of P-gp mediated efflux. It was thus clear that simultaneous modifications at the C-7, C-10 and C-3′ positions of paclitaxel significantly impaired its interactions with P-gp and interfered with P-gp mediated efflux.

Asymmetric total synthesis of Taxol

The asymmetric total synthesis of Taxol was achieved by way of B to BC to ABC to ABCD ring construction. Optically active 8-membered ring enones 1 and 2 corresponding to the B ring of Taxol have been synthesized in high yields from the linear precursors 28 and 32, respectively, by intramolecular aldol cyclization using SmI2. The optically active linear polyoxy compounds 28 and 32 were obtained by way of diastereoselective aldol reaction between aldehyde 4 and ketene silyl acetal 8 catalyzed by MgBr2 · OEt2. The chiral pentanal 4 was synthesized either by asymmetric aldol reaction of achiral aldehyde 7 and ketene silyl acetal 8 by means of a chiral Lewis acid or by diastereoselective aldol reaction between the chiral aldehyde 16, derived from L-serine, and the lithium enolate derived from methyl isobutyrate. Optically active bicyclo[6.4.0]dodecanone 38β, corresponding to the BC ring system of Taxol, was prepared from 8-membered ring enone 2 in high yield by stereoselective Michael addition and successive intramolecular aldol cyclization. Furthermore, baccatin III, the ABCD ring system of Taxol, was efficiently synthesized from the BC ring system 38β by successive construction of the A and D rings by intramolecular pinacol coupling cyclization, introduction of the C-13 hydroxyl group and an oxetane-forming reaction. Finally, the total synthesis of Taxol was accomplished by dehydration condensation between a protected N-benzoylphenylisoserine 70 or 75 and 7-TES baccatin III, prepared from baccatin III. Taxol side chains 70, 73, 75, and 77, optically active protected N-benzoylphenylisoserines, were synthesized by enantioselective aldol reaction from two achiral starting materials, benzaldehyde and an enol silyl ether 65 derived from S-ethyl benzyloxyethanethioate.

Total asymmetric synthesis of taxol by dehydration condensation between 7-TES baccatin III and protected N-benzoylphenylisoserines prepared by enantioselective aldol reaction

Total asymmetric synthesis of Taxol was completed by dehydration condensation between a protected N-benzoylphenylisoserine 4 or 9 and 7-TES baccatin in which was prepared from 8-membered ring enone. Taxol side chains 4, 7, 9 and 11, optically active protected N-benzoylphenylisoserines, were successfully synthesized by enantioselective aldol reaction from two achiral starting materials, benzaldehyde and an enol silyl ether derived from S-ethyl benzyloxyethanethioate.

Process for the preparation of a 1,3-oxazolidine-5-carboxylic acid

Method for the preparation of 1,3-oxazolidin 5-carboxylic acid having the general formula (I) STR1 from a product having the general formula (II) STR2 In the general formulas (I) and (II), Ar is an aryl radical, R1 is a benzoyl radical or a rad

Process for preparing taxane derivatives

Method of preparing taxane derivatives of general formula (I) by esterification of protected baccatine III or 10-deacetyl-baccatine III by means of an acid of general formula (VII), deprotection of the side chain and elimination of the hydroxy function protection groupings. In general formulae (I) and (VII): Ar stands for aryl, R is hydrogen or acetyl, R1 is benzoyl or R2 --O--CO-- in which R2 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, phenyl or heterocyclyl, and R3 is hydrogen, alkoxy, optionally substituted aryl. STR1

Direct, Stereoselective Synthesis of the Protected Paclitaxel (Taxol) Side Chain and High-yield Transformation to Paclitaxel

A short, efficient approach to the p-methoxybenzylidene-protected paclitaxel (Taxol) side chain through benzaldehyde benzoylimine-chiral enolate condensation, followed by DDQ-mediated oxazolidine formation and hydrolysis is described; the C-7-triethylsily