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药物详细合成路线

Name Ebselen;DR-3305;PZ-51;Harmokisane
Chemical Name 2-Phenyl-1,2-benzisoselenazol-3(2H)-one
CAS 60940-34-3
Related CAS
Formula C13H9NOSe
Structure
Formula Weight 274.18278
Stage 中止开发
Company Aventis Pharma (Originator), Daiichi Pharmaceutical (Licensee)
Activity/Mechanism Antiallergy/Antiasthmatic Drugs, Asthma Therapy, CARDIOVASCULAR DRUGS, Cerebrovascular Diseases, Treatment of, NEUROLOGIC DRUGS, RESPIRATORY DRUGS, Restenosis Treatment of, Stroke, Treatment of, Treatment of Disorders of the Coronary Arteries and Atherosclerosis, Antioxidants, NADPH Oxidase Inhibitors, Protein Kinase C (PKC) Inhibitors
Syn. Route 3
Route 1
a new synthesis of ebselen has been published:the radical reaction of 2-(benzylseleno)-n-phenylbenzamide (i) with triphenyltin hydride (ii) and aibn in refluxing benzene gives n-phenyl-2-(triphenylstannylseleno)benzamide (iii), which is treated with dibenzoyl peroxide (iv) in refluxing benzene to yield the diselenide (v). finally, the diselenide (v) was treated with di-tert-butyl peroxide (vi) in chlorobenzene at 120 c. this reaction cannot be carried out in refluxing benzene due to the extreme insolubility of (v) in benzene.
List of intermediates No.
1-(4-cyclohexylphenyl)-1-ethanone (i)
3,5-dimethoxybenzaldehyde (iii)
2-(2,3-dihydro-1h-inden-2-yl)acetic acid (v)
Reference 1:
    fong, m.c.; schiesser, c.h.; reactions of 2,2-diselenobis(n-alkylbenzamides) with peroxides: a free-radical synthesis of ebselen and related analogues. tetrahedron lett 1995, 36, 40, 7329.

Route 2
a new synthesis of ebselen has been reported:the reaction of benzanilide (i) first with lithium diisopropylamide and then with butyllithium in thf gives the dianion (ii), which is treated with freshly sublimed selenium to afford the insertion dianion (iii). finally, this compound is cyclized with cubr2 in the same solvent. this reaction has also been carried out with 77se in order to obtain labeled ebselen.
List of intermediates No.
benzyl 2,3-dihydro-1h-inden-2-ylmethylcarbamate (i)
2,3-dihydro-1h-inden-2-ylmethylamine; 2,3-dihydro-1h-inden-2-ylmethanamine (ii)
4-chloro-n-(2,3-dihydro-1h-inden-2-ylmethyl)benzenesulfonamide (iii)
Reference 1:
    oppenheimer, j.; silks, l.a.; synthesis of 2-phenyl-1,2-benziso[se-77]selenazol-3(2h)-one: ebselen. j label compd radiopharm 1996, 38, 3, 281.

Route 3
the neutralized diazonium salt of anthranilic acid (i) is treated with sodium diselenide yielding diselenosalicylic acid (ii), which is treated with thionyl chloride to give the selenenyl chloride (iii). treatment of (iii) with aniline (iv) in the presence of a base affords pz-51.
List of intermediates No.
1-ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (iv)
1-[3-(benzyloxy)-6-methoxy-2-quinolinyl]-1-ethanone (i)
3-(benzyloxy)-6-methoxy-2-quinolinecarboxylic acid (ii)
3-hydroxy-6-methoxy-2-quinolinecarboxylic acid (iii)
Reference 1:
    renson, m.; etschenberg, e.; winkelmann, j. (a. nattermann & cie. gmbh); 2-phenyl-1,2-benzisoselenazol-3(2h)-one containing pharmaceutical preparations and process for the treatment or rheumatic diseases. de 3027073; ep 0044971; jp 8256427; us 4352799 .
Reference 2:
    graf, e.; dereu, n.; ebselen. drugs fut 1984, 9, 10, 741.

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依布硒;英文名Ebselen;DR-3305;PZ-51;Harmokisane;CAS[60940-34-3]

 
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