PMID- 12736457 OWN - NLM STAT- MEDLINE DCOM- 20040105 LR - 20190706 IS - 0009-2363 (Print) IS - 0009-2363 (Linking) VI - 51 IP - 5 DP - 2003 May TI - Synthesis and biological activity of novel 5-(omega-aryloxyalkyl)oxazole derivatives as brain-derived neurotrophic factor inducers. PG - 565-73 AB - A novel series of 5-(omega-aryloxyalkyl)oxazole derivatives was prepared and their effects on brain-derived neurotrophic factor (BDNF) production were evaluated in human neuroblastoma (SK-N-SH) cells. Syntheses were performed by construction of an oxazole ring as a key reaction. Most of the 5-(omega-aryloxyalkyl)oxazole derivatives markedly increased BDNF production in SK-N-SH cells. 4-(4-Chlorophenyl)-2-(2-methyl-1H-imidazol-1-yl)-5-[3-(2-methoxyphenoxy)propyl]-1, 3-oxazole, one of the most promising compounds, showed potent activity (EC(50)=7.9 microM) and the improvement of the motor nerve conduction velocity and the tail-flick response accompanied by a recovery of the brain-derived neurotrophic factor level in the sciatic nerve of streptozotocin (STZ)-diabetic rats. FAU - Maekawa, Tsuyoshi AU - Maekawa T AD - Medicinal Chemistry Research Laboratories II, Pharmaceutical Research Division, Takeda Chemical Industries, Ltd., Osaka, Japan. Maekawa_Tsuyoshi@takeda.co.jp FAU - Sakai, Nozomu AU - Sakai N FAU - Tawada, Hiroyuki AU - Tawada H FAU - Murase, Katsuhito AU - Murase K FAU - Hazama, Masatoshi AU - Hazama M FAU - Sugiyama, Yasuo AU - Sugiyama Y FAU - Momose, Yu AU - Momose Y LA - eng PT - Journal Article PL - Japan TA - Chem Pharm Bull (Tokyo) JT - Chemical & pharmaceutical bulletin JID - 0377775 RN - 0 (Alkanes) RN - 0 (Blood Glucose) RN - 0 (Brain-Derived Neurotrophic Factor) RN - 0 (Indicators and Reagents) RN - 0 (Oxazoles) SB - IM MH - Alkanes/*chemical synthesis/pharmacology MH - Animals MH - Blood Glucose/metabolism MH - Body Weight/drug effects MH - Brain Chemistry/*drug effects MH - Brain Neoplasms/metabolism MH - Brain-Derived Neurotrophic Factor/*biosynthesis MH - Cell Line, Tumor MH - Diabetes Mellitus, Experimental/complications MH - Diabetic Neuropathies/drug therapy MH - Humans MH - Indicators and Reagents MH - Magnetic Resonance Spectroscopy MH - Male MH - Neural Conduction/drug effects MH - Neuroblastoma/metabolism MH - Oxazoles/*chemical synthesis/pharmacology MH - Rats MH - Rats, Sprague-Dawley MH - Reaction Time/drug effects MH - Stimulation, Chemical MH - Structure-Activity Relationship MH - Subcellular Fractions/chemistry EDAT- 2003/05/09 05:00 MHDA- 2004/01/06 05:00 CRDT- 2003/05/09 05:00 PHST- 2003/05/09 05:00 [pubmed] PHST- 2004/01/06 05:00 [medline] PHST- 2003/05/09 05:00 [entrez] AID - 10.1248/cpb.51.565 [doi] PST - ppublish SO - Chem Pharm Bull (Tokyo). 2003 May;51(5):565-73. doi: 10.1248/cpb.51.565.