94497-53-7Relevant academic research and scientific papers
Synthesis of Tamibarotene via Ullmann-Type Coupling
Bao, Xuefei,Qiao, Xuejun,Bao, Changshun,Liu, Yuting,Zhao, Xuan,Lu, Yi,Chen, Guoliang
, p. 748 - 753 (2017/05/29)
An effective process was developed for the preparation of tamibarotene via an Ullmann-type coupling in a nonpressurized l-proline/DMSO system. Notable features were the telescoping of reactions, avoiding environmentally hazardous materials, and an accepta
Design, synthesis and biological evaluation of novel tamibarotene derivative as multitarget anticancer agent
Jiang, Yuqi,Hou, Jinning,Li, Xiaoyang,Xu, Wenfang,Zhang, Yingjie
, p. 729 - 733 (2016/09/28)
A novel tamibarotene derivative was synthesized by coupling cytotoxic agent 5-Fluorouracil (5-FU) with tamibarotene via ester. This hybrid drug (compound 10) was evaluated for its antiproliferative activities against human leukemic U937, HL-60 and K562 cell lines in vitro. Results showed that compound 10 exhibited more potent anti-leukemic activity than the positive control tamibarotene. Furthermore, the preliminary stability test of compound 10 revealed that it could release tamibarotene and 5-FU significantly in vitro. These interesting results would be meaningful to develop more potent drugs for the treatment of human leukemia.
Synthesis of Am80 (tamibarotene) prodrug candidates, congeners and metabolites
Muratake, Hideaki,Amano, Yohei,Toda, Takahiro,Sugiyama, Kiyoshi,Shudo
, p. 846 - 852 (2013/09/12)
Compound 1 (IT-M-07000) was previously reported as a candidate prodrug of Am80 (Tamibarotene; used to treat acute promyelocytic leukemia), and shown to be efficiently metabolized to Am80 via β-oxidation. Here, we describe in detail the synthesis of 1, together with another tetradeuterated candidate prodrug, IT-YA-00616 (2), as well as two congeners, and several metabolic intermediates of 1 previously detected in mouse plasma.
Method for preparing benzoic acid derivatives
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, (2008/06/13)
This invention relates to a synthesis method favorable for the industrial production of a benzoic acid derivative having a retinoid activity of the general formula: STR1 wherein the derivative can be obtained by a simple procedure in safety with high yield.Specifically, this invention relates to a synthesis method characterized in that only one vessel is needed for several reactions in the different steps of subjecting acetanilide as a starting material, which is readily available and safe to handle, to Friedel-Crafts reaction with 2,5-dimethyl-2,5-dichlorohexane; subjecting the thus obtained compound to acyl exchange reaction with monomethyl ester terephthalic chloride, followed by hydrolysis; and recrystallizing from a mixture of methanol and water.Moreover, the crystals in novel form obtained by the synthesis method of this invention are suitable for formulation, because the amount of solvents remaining therein after recrystallization is small and the grain size thereof is uniform.
Retinobenzoic Acids. 1. Structure-Activity Relationships of Aromatic Amides with Retinoidal Activity
Kagechika, Hiroyuki,Kawachi, Emiko,Hashimoto, Yuichi,Himi, Toshiyuki,Shudo, Koichi
, p. 2182 - 2192 (2007/10/02)
Two types of aromatic amides, terephthalic monoanilides and (arylcarboxamido)benzoic acids, have been shown to possess potent retinoidal activities and can be classified as retinoids.The structure-activity relationships of these amides are discussed on the basis of differentiation-inducing activity on human promyelocytic leukemia cells HL-60.In generic formula 4 (X = NHCO or CONH), the necessary factors to elicit the retinoidal activities are a medium-sized alkyl group (isopropyl, tert-butyl, etc.) at the meta position and a carboxyl group at the para position of the other benzene ring.The bonding of the amide structure can be reversed, this moiety apparently having the role of locating the two benzene rings at suitable positions with respect to each other.Substitution at the ring position ortho to the amide group or N-methylation of the amido group caused loss of activity, presumably owing to the resultant change of conformation.It is clear that the mutual orientation of the benzylic methyl group(s) and the carboxyl group and their distance apart are essential factors determining the retinoidal activity.Among the synthesized compounds, 4-benzoic acid (Am80) and 4-benzoic acid (Am580) were several times more active than retinoic acid in the assay.They are structurally related to retinoic acid, as is clear from the biological activity of the hybrid compounds (M2 and R2).
