36394-75-9Relevant articles and documents
Synthesis, pharmacological evaluation and molecular docking of novel R-/S-2-(2-hydroxypropanamido)-5-trifluoromethyl benzoic acid as dual anti-inflammatory anti-platelet aggregation agents
Rong, Rong,Zhang, Rui-zhen,Wang, Xin,Dan, Yu-han,Zhao, Yun-li,Yu, Zhi-guo
, p. 967 - 978 (2019/12/12)
R-/S-2-(2-hydroxypropanamido) benzoic acid (R-/S-HPABA), marine-derived anti-inflammatory antiplatelet drugs, were initially synthesised in our group. However, preliminary research showed that R-/S-HPABA were eliminated rapidly because of extensive hydroxylation metabolism of phenyl ring in vivo. In order to reduce significant hydroxylation metabolism to improve pharmacological activity and bioavailability, trifluoromethyl group was incorporated into R-/S-HPABA to synthesise R-/S-2-(2-hydroxypropanamido)-5-trifluoromethyl benzoic acid (R-/S-HFBA), respectively. The purposes of this study were to report the synthesis of R-/S-HFBA and compare the anti-inflammatory antiplatelet effect and pharmacokinetic properties of R-/S-HFBA with those of R-/S-HPABA. Carrageenan-induced rat paw edema assay was used for the evaluation of the anti-inflammatory activity. R-/S-HFBA showed better results in inhibiting edema and were able to prolong the anti-inflammatory effect after carrageenan injection. The antiplatelet aggregation activity of R-/S-HFBA and R-/S-HPABA was studied on arachidonic acid-induced platelet aggregation of rabbit platelet-rich plasma. The aggregation inhibition rate of R-/S-HFBA was significantly (p max, larger AUC0-∞, and longer t1/2, which, as expected, are more metabolically stable.
Preparation method and application of 2-lactoyl aminobenzoic acid
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Paragraph 0039; 0040, (2017/08/30)
The invention relates to a new medicinal application of a chiral compound. The chiral compound is chemically named as R-/S-2-lactoyl aminobenzoic acid and has a structural formula as follows: formula (shown in the description). The compound is initially extracted and separated from secondary metabolite of microorganisms and can be obtained by virtue of a chemical synthetic method. An initial pharmacology experiment shows that the compound has good pain-easing and anti-inflammation activities and relatively low stimulation to gastrointestinal tracts. Recent researches prove that the compound has relatively good anti-platelet aggregation and anti-thrombus activities and is expected to be a novel non-steroidal anti-platelet aggregation and anti-thrombus drug.
3-Aminoquinazolinones as chiral ligands in catalytic enantioselective diethylzinc and phenylacetylene addition to aldehydes
Karabuga, Semistan,Karakaya, Idris,Ulukanli, Sabri
, p. 851 - 855 (2014/06/23)
A series of readily known enantiomerically pure 3-aminoquinazolinones 1a-d were synthesised from easily accessible chiral pool α-hydroxy acids and α-amino acids in only four steps without any requirement of chromatography. These quinazolinones were examined as chiral ligands for catalytic enantioselective diethylzinc and phenylacetylene additions to aldehydes. For enantioselective alkylations, the effects of temperature, solvent, diethylzinc and ligand criteria were analysed, and the desired chiral alcohols were obtained in up to 86% ee. 3-Aminoquinazolinones 1a-d were also shown to be very useful ligands in enantioselective alkynylations of aldehydes. Based upon the optimised conditions, the corresponding propargylic alcohols were obtained in up to 94% ee.