【药物名称】DIBRT
化学结构式(Chemical Structure):
参考文献No.54872
标题:Nuclear receptor ligands and ligand binding domains
作者:Brenneisen,P.; et al. (Ciba Geigy Corp.)
来源:DE 1932690; DE 1935338; US 3839582
合成路线图解说明:

By reaction of 4-nitro-4?aminodiphenylamine (I) with N,N-diethylthiocarbamoyl chloride (II), ammonium thiocyanate (III), thiophosgene (IV), or bis-(N,N-diethylthiocarbamoyl)disulfide (V) in the appropriate solvent

合成路线图解说明:

Methylation of 2,6-diisopropylphenol (I) with iodomethane and K2CO3 provides ether (II). Subsequent treatment with iodine and nitric acid gives rise to the diaryl iodonium compound (III), isolated as the corresponding tetrafluoroborate salt. 3,5-Dibromo-4-hydroxybenzoic acid (IV) is esterified with methanol and thionyl chloride to produce (V). Copper-promoted coupling between hydroxybenzoate (V) and the diaryl iodonium salt (III) leads to diaryl ether (VI). Finally, simultaneous cleavage of the methyl ether and ester groups of (VI) is achieved by means of boron tribromide in cold CH2Cl2

参考文献No.54873
标题:Nuclear receptor ligands and ligand binding domains
作者:Baxter, J.D.; Scanlan, T.S.; Fletterick, R.J.; Wagner, R.L.; Kushner, P.J.; West, B.L.; Shiau, A.K.; Apriletti, J.W. (University of California, Oakland)
来源:CA 2314096; EP 1034184; US 6266622; WO 9926966
合成路线图解说明:

Methylation of 2,6-diisopropylphenol (I) with iodomethane and K2CO3 provides ether (II). Subsequent treatment with iodine and nitric acid gives rise to the diaryl iodonium compound (III), isolated as the corresponding tetrafluoroborate salt. 3,5-Dibromo-4-hydroxybenzoic acid (IV) is esterified with methanol and thionyl chloride to produce (V). Copper-promoted coupling between hydroxybenzoate (V) and the diaryl iodonium salt (III) leads to diaryl ether (VI). Finally, simultaneous cleavage of the methyl ether and ester groups of (VI) is achieved by means of boron tribromide in cold CH2Cl2

参考文献No.651501
标题:Structure-based design and synthesis of a thyroid hormone receptor (TR) antagonist
作者:Baxter, J.D.; Goede, P.; Apriletti, J.W.; West, B.L.; Feng, W.; Mellstrom, K.; Fletterick, R.J.; Wagner, R.L.; Kushner, P.J.; Ribeiro, R.C.; Webb, P.; Scanlan, T.S.; Nilsson, S.
来源:Endocrinology 2002,143(2),517
合成路线图解说明:

Methylation of 2,6-diisopropylphenol (I) with iodomethane and K2CO3 provides ether (II). Subsequent treatment with iodine and nitric acid gives rise to the diaryl iodonium compound (III), isolated as the corresponding tetrafluoroborate salt. 3,5-Dibromo-4-hydroxybenzoic acid (IV) is esterified with methanol and thionyl chloride to produce (V). Copper-promoted coupling between hydroxybenzoate (V) and the diaryl iodonium salt (III) leads to diaryl ether (VI). Finally, simultaneous cleavage of the methyl ether and ester groups of (VI) is achieved by means of boron tribromide in cold CH2Cl2

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