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Volumn 19, Issue 18, 2009, Pages 5329-5333

Discovery of a novel class of isoxazoline voltage gated sodium channel blockers

Author keywords

Amide replacement; Heterocycles; Inflammatory pain; Isoxazoline; Neuropathic pain; Voltage gated sodium channel blocker

Indexed keywords

CDA 54; ISOXAZOLINE DERIVATIVE; SODIUM CHANNEL BLOCKING AGENT; UNCLASSIFIED DRUG; VOLTAGE GATED SODIUM CHANNEL;

EID: 68949108017     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.07.125     Document Type: Article
Times cited : (16)

References (13)
  • 5
    • 68949141369 scopus 로고    scopus 로고
    • note
    • Conformations of N-benzylacetamide, 2-methyl-4-phenyl-1,3-oxazole and 2-methyl-4-phenyl-4,5-dihydro-1,3-oxazole were optimized using the MMFFs force field with a distance-dependent dielectric of 4r. For 2-methyl-4-phenyl-4,5-dihydro-1,3-oxazole, two conformations were found which differed in ring pucker; the lower-energy conformation was used for the overlay shown in Figure 2. Molecules were superimposed by minimizing RMSD between the methyl carbon; the N, C, and O of the heterocycle or amide; and the phenyl ring centroid.
  • 6
    • 68949151467 scopus 로고    scopus 로고
    • note
    • Intermediate I was extracted into basic aqueous layer, while diamide by-product was washed away with EtOAc. Aqueous portion was then acidified and intermediate I was extracted into EtOAc. Since unreacted diacid starting material has higher aqueous solubility, this workup gave essentially pure intermediate I.
  • 9
    • 68949140485 scopus 로고    scopus 로고
    • note
    • v1.7 channels.
  • 12
    • 68949160557 scopus 로고    scopus 로고
    • note
    • Chiral OJ column, 15 × 250 mm; mobile phase: 12% IPA, 88% heptane; flow rate: 9 ml/min. Retention time for the four isomers: 17, 23, 31, 37 min.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.