13235-60-4Relevant articles and documents
Design, synthesis and biological evaluation of 4-methoxy diaryl isophthalates as antiplatelet agents
Xiu-jie, Liu,Chao-qing, Wang,Jie, Meng,xin-xin, Shi,ya-nan, Yan,Xu-guang, Liu
, p. 488 - 496 (2018)
A series of 4-methoxy diphenyl isophthalates, which are the isosturctural analogs of picotamide, were designed and synthesized using the concept of isosterism. The structures of these new analogs were characterized by all means of spectroscopy, including 1H NMR, 13C NMR, and MS spectra. In vitro antiplatelet aggregation activities of these compounds were investigated by using Born’s test method. Among the 19 compounds tested for both ADP and collagen inducers, six of them (P216–P219 and P220–P221) were found to exhibit higher activity in vitro antiplatelet aggregation than Picotamide. In particular, the compound P220 bearing a nitrooxyl group showed the highest acitivity 72.1% (induced by collagen) and 72.5% (induced by ADP), with IC50 values of 0.30 μM/L induced by ADP (1.3 μM/L) and LD50 CloseSPigtSPi 2500 mg/kg, could have dual mechanism of action. Evaluation of cytotoxic activity of the compounds against L929 cell line revealed that none of the compounds have significant cytotoxicity. Through the careful analysis of in vitro activity data, the SAR of these compounds was preliminarily deduced. The results of this study showed that 4-methoxy diaryl isophthalates derivatives are potential to become an antiplatelet aggregation agents.
Preparation method of picotamide
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Paragraph 0027; 0036-0038, (2021/01/25)
The invention provides a method for preparing picotamide, which comprises the following steps: taking dimethyl 4-hydroxyl isophthalate as a raw material, carrying out methyl etherification reaction toobtain dimethyl 4-methoxy isophthalate; then, carrying out hydrolysis reaction to obtain 4-methoxy isophthalic acid; and finally, carrying out amidation reaction to obtain picotamide. Compared with atraditional method, the preparation method has the advantages of short synthesis steps, simplicity and convenience in operation, high reaction speed, high yield and the like. Besides, the raw materials required by the method are extracted from waste residues generated in industrial production, the extraction method is simple, the resource utilization rate is increased, the environmental pollutionis reduced, the production cost is reduced, and the method is suitable for large-scale industrial production.
Synthesis and in vitro activities on anti-platelet aggregation of 4-methoxy-1,3-phthalamidesamides and benzenedisulfonamides
Chen, Guangling,Wang, Chaoqing,Zhang, Zhihao,Liu, Xiujie
, p. 1413 - 1424 (2019/06/20)
Cardiovascular diseases are the most frequent cause of morbidity and mortality worldwide. In order to discover novel compounds with anti-platelet aggregation activities, a series of novel 4-methoxy-1,3-phthalamidesamides (1a–1i) and a series of novel 4-methoxy-1,3-benzenedisulfon-amides (2a–2i) were synthesized and their anti-platelet aggregation activities were evaluated by the turbidimetric method in response to the following agonists: adenosine diphosphate (ADP), arachidonic acid (AA), and Collagen. Those compounds that have better in vitro activities were subjected to cell toxicity tests via cell counting kit-8 (CCK-8) assay. The inhibition rates of anti-platelet in vitro of five compounds 1g (39.45%), 2d (38.87%), 2g (38.55%), 2h (44.56%), and 2i (43.93%) were higher than that of two reference drugs picotamide (36.12%) and aspirin (38.45%) when ADP was selected as an inducer. The inhibition rates of seven compounds 1c (43.63%), 1d (40.02%), 1g (47.42%), 1i (40.45%), 2c (40.11%), 2d (40.45%), and 2i (49.05%) were higher than that of picotamide (34.89%) and aspirin (39.43%) when AA was selected as inducer. And the inhibition rates of five compounds 1d (47.22%), 1i (45.01%), 2d (38.74%), 2e (42.21%), and 2f (39.94%) were higher than picotamide (38.45%) and aspirin (37.08%) when collagen was selected as inducer. Moreover, the effect of cell toxicity exhibited that none of the compounds had obvious cell toxicity against L-929 cells. Therefore, 4-methoxy-1,3-phthalamidesamides (1a–1i) and 4-methoxy-1,3-benzenedisulfon-amides (2a–2i) have the potential to become a novel kind of anti-platelet drugs and deserve further study.
He pyrrole testsamine synonym, preparation method and its application
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Paragraph 0030; 0041; 0042, (2017/03/08)
The invention relates to the field of medicinal chemistry and particularly relates to picotamide analogues (I), a preparation method and a pharmaceutical composition containing the picotamide analogues, wherein R represents hydrogen, 3, 5, 6- trimethyl, 5-methyl or 6-methyl. The picotamide analogues provided by the invention can be used for treating or preventing thromboembolic diseases.
Design, synthesis and in vitro activities on anti-platelet aggregation of 4-methoxybenzene-1,3-isophthalamides
Liu, Xiu Jie,Shi, Xin Xin,Zhong, Yong Liang,Liu, Ning,Liu, Kai
, p. 6591 - 6595,5 (2012/12/12)
On the purpose of searching for the structure-activity relationship (SAR) and obtaining novel anti-platelet drugs, 41 4-methoxybenzene-1,3-isophthalamides have been described the synthesis process and in vitro activities on anti-platelet aggregation. The target compounds have been classified into four series: series 1 (ortho-substituted phenyl: 1a-1j), series 2 (meta-substituted phenyl: 2a-2k), series 3 (para-substituted phenyl: 3a-3l) and series 4 (aromatic of no substituted group and aromatic heterocyclic substituted groups: 4a-4h). The chemical structures of the target compounds were confirmed by MS, IR, 1H NMR, and their in vitro activities on anti-platelet aggregation were tested and assessed by using Born test. The result showed that thirteen compounds 1c, 1d, 1i, 1j, 2g, 3a, 3c, 3d, 3f, 3h, 3l, 4b and 4c have superior anti-platelet aggregation activities than the reference drug Picotamide.
Synthesis and in vitro activities on anti-platelet aggregation of N,N′-di(2-substituted-phenyl)-4-methoxy isophthalamides and benzene-1,3-disulfonamides
Liu, Xiu Jie,He, Xin,Shi, Cheng Ling,Meng, Jie,Shao, Ying Lu,Si, Hong Qiang,Hu, Tao
, p. 1139 - 1142 (2012/01/06)
On the propose of searching for the SAR and obtaining novel antiplatelet aggregating drugs, we have described the synthesis procedure and the activities in vitro on antiplatelet aggregation of two series of derivatives, which contain both 18 N,N′-di(2-substitutedphenyl)-4-methoxyisophthalamides (2a-2r) of the 2 series and nine N,N′-di(2-substitutedphenyl)-4-methoxybenzene-1,3- disulfonamides (3a-3i) of the 3 series. The results showed that three compounds 2e, 2i and 3g emerged as significant activities of antiplatelet aggregation, superior to two reference drugs picotamide and aspirin, and eight compounds 2j, 2k, 2l, 2o, 2p, 2q, 2r and 3i merely superior to picotamide. The preliminary SAR shows that it is favorable for the 2 series to increase the activities via the steric hindrance substituents attached to the two side chain benzene rings at 2-positions. And the arylamides of the 2 series have better the activity values than the arylsulfonamides of the 3 series respective except for 3b and 3g. On the contrary, electrostatic factors would not contribute evidently to the activities of the two series. The structures of 15 compounds newly synthesized have been established by MS and 1H NMR and been first reported in this paper.
Synthesis and mesomorphism of 1,3-benzenedicarboxylic acid derivatives
Novikova,Kilimenchuk,Yarkova,Meshkova,Topilova
body text, p. 1602 - 1607 (2009/05/06)
4-Methoxy-l,3-benzenedicarboxylic acid esters and 4-(4- hexyloxybenzoylamino)phenyl 1,3-benzenedicarboxylate, each containing five aromatic rings, were synthesized. The influence of the structure of the synthesized banana-like compounds on their mesogenic activity was examined.
