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药物详细合成路线

Name Gossypol
Chemical Name 1,1,6,6,7,7-Hexahydroxy-3,3-dimethyl-5,5-diisopropyl-(2,2-binaphthalene)-8,8-dicarboxaldehyde;2,2-Bis(1,6,7-trihydroxy-3-methyl-5-isopropyl-8-formylnaphthalene)
CAS 303-45-7
Related CAS
Formula C30H30O8
Structure
Formula Weight 518.5688
Stage II 期临床
Company Xian Lijun Pharmaceutical (Originator), Bioenvision (Licensee)
Activity/Mechanism Bladder Cancer Therapy , Contraceptives, Disorders of Sexual Function and Reproduction, Treatment of, ENDOCRINE DRUGS, Male Contraceptives, Oncolytic Drugs, Prostate Cancer Therapy, Antimitotic Drugs, bcl-xl Inhibitors, Steroid 5alpha-Reductase Inhibitors
Syn. Route 2
Route 1
the condensation of 3,4-dimethoxy-2-isopropylbenzaldehyde (i) with diethyl succinate (ii) by means of nah in refluxing benzene gives 2-(2-isopropyl-3,4-dimethoxybenzylidene)succinic acid monoethyl ester (iii), which is cyclized by treatment with acetic anhydride and sodium acetate in refluxing acetic acid and hydrolyzed with naoh in refluxing methanol yielding acid (iv). the reduction of (iv) with lialh4 in ether affords 3-hydroxymethyl-5-isopropyl-6,7-dimethoxy-1-naphthol (v), which is hydrogenated with h2 over pd/c in methanol with some hcl giving 3-methyl-5-isopropyl-6,7-dimethoxy-1-naphthol (vi). thermal dimerization of (vi) by heating at 215 c yields 2,2-bis(3-methyl-5-isopropyl-6,7-dimethoxy-1-naphthol) (vii).
List of intermediates No.
propylene oxide; 2-methyloxirane (ii)
bromo[2,4-dichloro-6-ethyl-5-fluoro-1(6h)-pyrimidinyl]magnesium (i)
2,4-dichloro-6-ethyl-5-fluoropyrimidine (iii)
4-(aminooxy)-2-chloro-6-ethyl-5-fluoropyrimidine; o-(2-chloro-6-ethyl-5-fluoro-4-pyrimidinyl)hydroxylamine (iv)
1-(2-hydroxy-4,6-dimethoxyphenyl)-1-butanone (v)
1-[2,4-dimethoxy-6-[(triisopropylsilyl)oxy]phenyl]-1-butanone (vi)
1-[2-hydroxy-4-methoxy-6-[(triisopropylsilyl)oxy]phenyl]-1-butanone (vii)
Reference 1:
    cashaw, j.l.; edwards, j.d.jr.; studies in the naphtalene series. iii. synthesis of apogossypol hexamethyl ether. j am chem soc 1957, 79, 2283.
Reference 2:
    edwards, j.d.jr.; total synthesis of gossypol. j am chem soc 1958, 80, 3798.
Reference 3:
    el-nockrashy; j am oil chem soc 1963, 40, 1, 14.
Reference 4:
    leeson, p.; gossypol. drugs fut 1979, 4, 5, 338.

Route 2
intermediate (vii) is methylated with dimethylsulfate and koh in refluxing aqueous dioxane affording apogossypol hexamethyl ether (viii) . the cleavage of the methoxy groups with bbr3 and aqueous naoh yields apogossypol (ix), which by reaction with n,n-diphenylformamidine (x) affords gossypol bis(n-phenylimine) (xi), which is finally hydrolyzed.
List of intermediates No.
1-[2-hydroxy-4-methoxy-6-[(triisopropylsilyl)oxy]phenyl]-1-butanone (vii)
7-methoxy-4-propyl-5-[(triisopropylsilyl)oxy]-2h-chromen-2-one (viii)
tigloyl chloride; (e)-2-methyl-2-butenoyl chloride (ix)
7-methoxy-8-[(e)-2-methyl-2-butenoyl]-4-propyl-5-[(triisopropylsilyl)oxy]-2h-chromen-2-one (x)
5-hydroxy-7-methoxy-8-[(e)-2-methyl-2-butenoyl]-4-propyl-2h-chromen-2-one (xi)
Reference 1:
    cashaw, j.l.; edwards, j.d.jr.; studies in the naphtalene series. iii. synthesis of apogossypol hexamethyl ether. j am chem soc 1957, 79, 2283.
Reference 2:
    edwards, j.d.jr.; total synthesis of gossypol. j am chem soc 1958, 80, 3798.
Reference 3:
    el-nockrashy; j am oil chem soc 1963, 40, 1, 14.
Reference 4:
    leeson, p.; gossypol. drugs fut 1979, 4, 5, 338.

来源:药化网

作者:药化小编

摘要:本文合成路线介绍的是药物中文名棉籽酚;英文名Gossypol;CAS[303-45-7]

 
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