【药物名称】Darbufelone mesilate, PD-136095-0073, CI-1004
化学结构式(Chemical Structure):
参考文献No.16002
标题:3,5-Di-tertiary-butyl-4-hydroxyphenyl-methylene derivs. of 2-substd. thiazolidinones, oxazolidinones, and imidazolidinones as antiinflammatory agents
作者:Cetenko, W.A.; Connor, D.T.; Sircar, J.C.; Sorenson, R.J.; Unangst, P.C. (Pfizer Inc.)
来源:EP 0449216; JP 1992221371; US 5143928
合成路线图解说明:

The condensation of 3,5-bis(tert-butyl)-4-hydroxybenzaldehyde (I) with 2-iminothiazolidin-4-one (II) in refluxing acetic acid gives darbufelone (III), which is then treated with methanesulfonic acid in THF.

合成路线图解说明:

Knoevenagel condensation of benzaldehyde (I) with rhodanine (II) by means of sodium acetate in acetic acid afforded benzylidenethione (III). Alkylation with iodomethane in the presence of triethylamine gave methylthioether (IV), which was finally condensed with methoxamine hydrochloride and potassium tert--butoxide in refluxing ethanol to yield the title compound.

参考文献No.245779
标题:Synthesis and biological evaluation of 5-[[3,5-bis(1, 1-dimethylethyl)-4-hydroxyphenyl]methylene]oxazoles, -thiazoles, and -imidazoles: Novel dual 5-lipoxygenase and cyclooxygenase inhibitors with antiinflammatory activity
作者:Unangst, P.C.; Connor, D.T.; Cetenko, W.A.; Sorenson, R.J.; Kostlan, C.R.; Sircar, J.C.; Wright, C.D.; Schrier, D.J.; Dyer, R.D.
来源:J Med Chem 1994,37(2),322
合成路线图解说明:

The condensation of 3,5-bis(tert-butyl)-4-hydroxybenzaldehyde (I) with 2-iminothiazolidin-4-one (II) in refluxing acetic acid gives darbufelone (III), which is then treated with methanesulfonic acid in THF.

合成路线图解说明:

Knoevenagel condensation of benzaldehyde (I) with rhodanine (II) by means of sodium acetate in acetic acid afforded benzylidenethione (III). Alkylation with iodomethane in the presence of triethylamine gave methylthioether (IV), which was finally condensed with methoxamine hydrochloride and potassium tert--butoxide in refluxing ethanol to yield the title compound.

参考文献No.245781
标题:Oxazole, thiazole, and imidazole derivatives of 2, 6-di-tert-butylphenol as dual 5-lipoxygenase and cyclooxygenase inhibitors
作者:Schrier, D.J.; Sircar, J.C.; Connor, D.T.; Dyer, R.D.; Cetenko, W.A.; Wright, C.D.; Sorenson, R.J.; Unangst, P.C.
来源:Bioorg Med Chem Lett 1993,3(8),1729
合成路线图解说明:

The condensation of 3,5-bis(tert-butyl)-4-hydroxybenzaldehyde (I) with 2-iminothiazolidin-4-one (II) in refluxing acetic acid gives darbufelone (III), which is then treated with methanesulfonic acid in THF.

参考文献No.532526
标题:Combination phase II study of irinotecan (CPT 11) and raltitrexed (Tomudex) in advanced colorectal cancer
作者:Nobile, M.T.; et al.
来源:Proc Amer Soc Clin Oncol 1999,1818
合成路线图解说明:

The condensation of 3,5-bis(tert-butyl)-4-hydroxybenzaldehyde (I) with 2-iminothiazolidin-4-one (II) in refluxing acetic acid gives darbufelone (III), which is then treated with methanesulfonic acid in THF.

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