Synthesis of some novel pyrimidine, thiophene, coumarin, pyridine and pyrrole derivatives and their biological evaluation as analgesic, antipyretic and anti-inflammatory agents

Pyrimidine derivative 3 was afforded through the reaction of compound (1) with 5-ureidohydantion (2). Product 3 underwent a cyclization to produce fused pyrimidine derivative 7, although the latter product 7 was synthesized through one step via the reaction of compound (1) with 5-ureidohydantion (2) using another catalyst. Compound 3 was oriented to react with cyclic ketones 8a,b in the presence of elemental sulfur, salicylaldehyde (10), aryldiazonium chlorides 12a,b and ω-bromo-4-methoxy- acetophenone (14), which afforded, fused thiophene derivatives 9a,b, coumarin derivative 11, arylhdrazono derivatives 13a,b and 4-methoxyphenyl butenyl derivative 15, respectively. The latter product 15 was reacted with either potassium cyanide (16a) or potassium thiocyanide (16b) to form cyano and thiocyano derivatives 17a,b, respectively. Compound 17a underwent further cyclization to afford pyridopyrimidine derivative 19. Compound 15 was reacted with either hydrazine (20a) or phenylhydrazine (20b) to produce hydrazo derivatives 21a,b and these products were cyclize to produce pyrrole derivatives 23a,b. Finally, 5-ureidohydantion (2) was reacted with compounds 24a,b,c to afford pyrimidine derivatives 25a,b,c. The structures of the synthesized compounds were confirmed using IR, 1H NMR, 13C NMR and mass spectrometry techniques. Compounds 11 and 19 have promising as analgesic and antipyretic activities

Research on chemical constituents from Reduning Injection (IV) / 中草药

Objective: To study the antipyretic and anti-inflammatory constituents from the active fraction of Reduning Injection (RI). Methods: The active fraction of RI was screened by the LPS-induced mouse endotoxin shock model. The chemical constituents were isolated by chromatography on silica gel, ODS, Sephadex LH-20, Toyopearl HW-40 columns, reverse phase MPLC, and HPLC repeatedly, and their structures were identified by spectral data and physicochemical property. Results: The 95% ethanol eluate of RI on the macroporous adsorption resin column was proved to be the antipyretic and anti-inflammatory active fraction of RI. Fourteen compounds were isolated and identified as dibutyl phthalate (1), isovanillic acid (2), acetovanillone (3), phenylpropionic acid (4), geniposide (5), jasmigeniposide B (6), geniposidic acid (7), genipin-1-β-D-gentiobioside (8), 6″-O-trans-p-coumaroylgenipin gentiobioside (9), 6″-O-trans-feruloylgenipin gentiobioside (10), 6″-O-trans-sinapoylgenipin gentiobioside (11), jasmigeniposide A (12), 6″-O-trans-cinnamoylgenipin gentiobioside (13), and 2'-O-trans-caffeoylgardoside (14). Conclusion: Compounds 1-4 and 13 are reported from RI for the first time; And UPLC analyses and literature data showe that compounds 5 and 7-13 are originated from Gardenia jasminoides.