442850-34-2

Upstream product

• 911199-15-0 C₂₅H₃₃NO₆S 
• 196929-85-8 (R)-N-benzylidene-2-methylpropane-2-sulfinamide 
• 98-88-4 benzoyl chloride 
• 195624-97-6 (2R,3S)-3-acetylamino-2-hydroxy-3-phenylpropanoic acid isopropyl ester 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 60512-85-8 (E)-isopropyl cinnamate 

Downstream Products

• 442850-35-3 (4S,5S)-2,4-diphenyl-2-oxazoline-5-carboxylic acid benzyl ester 
• 949023-16-9 (4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid 
• 442850-37-5 (2R,3S)-2-acetylthio-3-benzoylamino-3-phenylpropanoic acid p-methoxybenzyl ester 
• 442850-36-4 (4S,5S)-2,4-diphenyl-2-oxazoline-5-carboxylic acid p-methoxybenzyl ester 
• 235432-37-8 (4S,5S)-2,4-diphenyl-1,3-oxazoline-5-carboxylic acid 

Relevant academic research and scientific papers

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.

Preparation of β-amino-α-mercapto acids and amides: Stereocontrolled syntheses of 2′-sulfur analogues of the taxol C-13 side chain, both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine

Stereoselective syntheses of both syn and anti S-acetyl-N-benzoyl-3-phenylisocysteine as coupling-ready reagents via the ring-opening reactions of trans- and cis-oxazoline-5-carboxylates with thiolacetic acid were demonstrated. In addition, we report upon ring-opening reactions of oxazoline-5-carboxamides. Ab initio molecular calculations were used to explain the different reactivities of these oxazolines with respect to the ring-opening reaction.