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药物详细合成路线

Name Curcumin
Chemical Name (E,E)-1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione
CAS 458-37-7
Related CAS
Formula C21H20O6
Structure
Formula Weight 368.38995
Stage I/II 期临床
Company Central Drug Research Institute (Originator)
Activity/Mechanism AIDS Medicines, Alzheimers Dementia, Treatment of , Antiarthritic Drugs, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Chemopreventive Agents, Cognition Disorders, Treatment of, NEUROLOGIC DRUGS, ONCOLYTIC DRUGS, TREATMENT OF MUSCULOSKELETAL & CONNECTIVE TISSUE DISEASES, Antioxidants, CCND1 Expression Inhibitors, HIV Integrase Inhibitors
Syn. Route 3
Route 1
synthesis of curcumin was first described by lampe et al. in our laboratory curcumin has been synthesized by condensing vanillin (i) and acetyl acetone (ii) in a medium of ethyl acetate using tributylborate as boron complex to avoid knoevenagel condensation at c-3 of acetyl acetone. curcumin is isolated from the reaction mixture by acidification and extraction with ethyl acetate. the organic layers are washed until neutral, dried and the solvent is removed. purified by chromatography over silica gel using ether/petroleum ether as the solvent.
List of intermediates No.
bis(chlorosulfonyl)imide (ii)
4-fluoro-2-hydroxy-n-(3-nitrobenzyl)benzamide (i)
Reference 1:
    scrimal, r.c.; curcumin. drugs fut 1987, 12, 4, 331.

Route 2
the protection of 4-bromo-2-methoxyphenol (i) with ethyl vinyl ether (ii) and tsoh in dichloromethane gives the ethoxyethyl ether (iii), which is treated with n-buli in thf to yield the phenyl lithium compound (iv). the reaction of (iv) with 2h-labeled dmf (v), followed by hydrolysis with hcl, affords the labeled 4-hydroxy-3-methoxybenzaldehyde (vi), which is finally condensed with pentane-2,4-dione (vii) by means of b2o3 and tetrahydroquinoline in dmf.
List of intermediates No.
n-benzoyl-n-(2-hydroxy-4-methylphenyl)thiourea (vii)
1-[(2r,4s,5r)-4-(benzyloxy)-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1h,3h)-pyrimidinedione (ii)
4-fluoro-2-hydroxy-n-(3-nitrobenzyl)benzamide (vi)
(2r,3r,4s,5r,6r)-2-(hydroxymethyl)-6-[(2-tetradecylhexadecyl)oxy]tetrahydro-2h-pyran-3,4,5-triol (v)
(3ar,12bs)-2-(bromomethyl)-3,3a,8,12b-tetrahydro-2h-dibenzo[3,4:6,7]cyclohepta[1,2-b]furan (i)
tert-butyl (3s)-3-[(4-methyl-1h-imidazol-1-yl)methyl]-1-piperidinecarboxylate (iii)
(3r)-3-[(4-methyl-1h-imidazol-1-yl)methyl]piperidine (iv)
7-hydroxy-4-methyl-2h-pyrano[2,3-b]pyridin-2-one (v)
o-(4-methyl-2-oxo-2h-pyrano[2,3-b]pyridin-7-yl) dimethylcarbamothioate (vi)
Reference 1:
    threadgill, m.d.; parveen, i.; labelled compounds of interest as antitumour agents - vii. [h-2]- and [c-14]-curcumin. j label compd radiopharm 2000, 43, 9, 883.

Route 3
the protection of 4-bromo-2-methoxyphenol (i) with ethyl vinyl ether (ii) and tsoh in dichloromethane gives the ethoxyethyl ether (iii), which is treated with n-buli in thf to yield the phenyl lithium compound (iv). the reaction of (iv) with 14c-labeled dmf (v), followed by hydrolysis with hcl, affords the labeled 4-hydroxy-3-methoxybenzaldehyde (vi), which is finally condensed with pentane-2,4-dione (vii) by means of b2o3 and tetrahydroquinoline in dmf.
List of intermediates No.
n-benzoyl-n-(2-hydroxy-4-methylphenyl)thiourea (vii)
1-[(2r,4s,5r)-4-(benzyloxy)-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1h,3h)-pyrimidinedione (ii)
4-fluoro-2-hydroxy-n-(3-nitrobenzyl)benzamide (vi)
(2r,3r,4s,5r,6r)-2-(hydroxymethyl)-6-[(2-tetradecylhexadecyl)oxy]tetrahydro-2h-pyran-3,4,5-triol (v)
(3ar,12bs)-2-(bromomethyl)-3,3a,8,12b-tetrahydro-2h-dibenzo[3,4:6,7]cyclohepta[1,2-b]furan (i)
tert-butyl (3s)-3-[(4-methyl-1h-imidazol-1-yl)methyl]-1-piperidinecarboxylate (iii)
(3r)-3-[(4-methyl-1h-imidazol-1-yl)methyl]piperidine (iv)
s-(4-methyl-2-oxo-2h-pyrano[2,3-b]pyridin-7-yl) dimethylcarbamothioate (v)
4-methyl-7-sulfanyl-2h-pyrano[2,3-b]pyridin-2-one (vi)
Reference 1:
    threadgill, m.d.; parveen, i.; labelled compounds of interest as antitumour agents - vii. [h-2]- and [c-14]-curcumin. j label compd radiopharm 2000, 43, 9, 883.

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姜黄素;英文名Curcumin;CAS[458-37-7]

 
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