On January 22, 1998, Shimizu, Hideaki; Abe, Atsuhiro; Yaegashi, Takashi; Sawada, Seigo; Nagata, Hiroshi published a patent.HPLC of Formula: 53788-12-8 The title of the patent was Preparation of taxane derivatives as antitumors and pharmaceuticals containing them. And the patent contained the following:
The title compounds [I; X, Y = CO-A-B; A = bond, -R-CO-, -R-OCO-, -R-NHCO-; R = alkylene, phenylene; B = (un)substituted heterocyclyl, e.g., piperazin-1-yl; Z = H, trialkylsilyl, trihaloalkoxycarbonyl; Bz = benzoyl], II [R7 = H, alkoxycarbonyl, aralkyloxycarbonyl; R8, R9 = H, alkyl, haloalkyl, etc.] or their salts are prepared Thus, 7-O-triethylsilyl-10-deacetylbaccatin III was reacted with 4-(dimethylamino)piperidinocarbonyl chloride (also prepared) in THF-hexane containing BuLi at -40° to room temperature to give 90% 10-O-(4-dimethylaminopiperidinocarbonyl)-7-O-triethylsilyl-10-deacetylbaccatin III. This was reacted with (4S,5R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid to give the title compound III. These compounds exhibit a high solubility in water and showed excellent antitumor activity. In an ELISA screening using human oral cancer KB cells, the GI50 for 13-O-[3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionyl]-10-O-(4-dipropylaminopiperidinocarbonyl)-10-deacetylbaccatin III (also prepared) was 0.78 ng/mL vs. 2.0 ng/mL for taxol. The solubility of 13-O-[3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionyl]-10-O-(4-dimethylaminopiperidinocarbonyl)-10-O-deacetylbaccatin III (also prepared) in water was 1260 μg/mL vs. 0.4 μg/mL for taxol. The experimental process involved the reaction of 4-Ethyl-piperazine-1-carbonyl chloride(cas: 53788-12-8).HPLC of Formula: 53788-12-8
The Article related to taxane derivative preparation antitumor solubility, Terpenes and Terpenoids: Diterpenes (C20), Including Gibberellins, Retinoids, Quassinoids, and Tocopherols and other aspects.HPLC of Formula: 53788-12-8
Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics