Synthesis of ferrocenyl pyrazole-containing chiral aminoethanol derivatives and their inhibition against A549 and H322 lung cancer cells.
A series of novel ethyl 3-ferrocenyl-1-(2-hydroxy-3-(phenylamino)propyl)-1H-pyrazole-5-carboxylate derivatives with optical activity (4) was synthesized by microwave-assisted reaction of substituted aniline and ethyl 3-ferrocenyl-1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylate that was prepared from ethyl 3-ferrocenyl-1H-pyrazole-5-carboxylate and (R)- or (S)-oxiran-2-ylmethyl 4-methylbenzenesulfonate. Structures of the compounds were characterized by means of IR, (1)H NMR and mass spectroscopy. Preliminary biological evaluation showed that all of the compounds could suppress the growth of A549 and H322 lung cancer cells. Among all of the tested compounds 4a, 4b and 4d were more effective and might perform their action through cell cycle arrest. Moreover, although the inhibition differences between R and S enantiomers are mostly not so significant, (R)-4b displayed more effective inhibition than (S)-4b.
Institute of Organic Chemistry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, PR China.
Shi-Li
SL
Shen
Jian
J
Zhu
Meng
M
Li
Bao-Xiang
BX
Zhao
Jun-Ying
JY
Miao
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004983:Ethanolamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005296:Ferrous Compounds / Q000737:chemistry*; D006801:Humans; D008175:Lung Neoplasms / Q000473:pathology*; D000075163:Metallocenes; D055620:Optical Phenomena; D011720:Pyrazoles / Q000737:chemistry*; D012995:Solubility; D013237:Stereoisomerism; D013816:Thermodynamics; D014867:Water / Q000737:chemistry
D000970:Antineoplastic Agents; D004983:Ethanolamines; D005296:Ferrous Compounds; D000075163:Metallocenes; D011720:Pyrazoles; D014867:Water; C031280:pyrazole; C004998:ferrocene