Abstract:
:A facile procedure is described for the conversion of morphine, via the diphosphate ester derivative 1 followed by catalytic reduction and treatment with Li/NH3, to 3-deoxy-7,8-dihydromorphine (3). Oxidation with benzophenone tert-butoxide converted 3 to the ketone 4, which on treatment with Zn/NH4Cl formed (-)-4-hydroxymorphinan-6-one 5. Reaction of 5 with diazomethane formed the methyl ether 6. The N-cyclopropylmethyl analogues of 4 and 5 were also prepared, i.e., 8c and 9 from 4. The antinociceptive activity of these compounds was tested. Compounds 5, 6, 8c, and 9 showed potent antiwrithing activity and, based on these data, a structure-activity relationship in morphinans is discussed.
journal_name
J Med Chemjournal_title
Journal of medicinal chemistryauthors
Manmade A,Dalzell HC,Howes JF,Razdan RKdoi
10.1021/jm00144a013subject
Has Abstractpub_date
1981-12-01 00:00:00pages
1437-40issue
12eissn
0022-2623issn
1520-4804journal_volume
24pub_type
杂志文章abstract::A series of trans-platinum(IV) complexes with functionalized aromatic carboxylate ligands, cis,cis,trans-Pt(NH3)2Cl2(CO2C6H4R)2 (R = H (3), p-vinyl (4), p-methoxy (5), p-iodo (6), p-cyano (7), or o-carboxyl (8)) was synthesized and characterized by spectroscopic methods. Crystal structures of 3, 4, 7, and 8 were obtai...
journal_title:Journal of medicinal chemistry
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更新日期:2005-12-15 00:00:00
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journal_title:Journal of medicinal chemistry
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abstract::On the basis of structural data gathered during our ongoing HIV-1 protease inhibitors program, from which our clinical candidate TMC114 9 was selected, we have discovered new series of fused heteroaromatic sulfonamides. The further extension into the P2' region was aimed at identifying new classes of compounds with an...
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journal_title:Journal of medicinal chemistry
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abstract::The syntheses of three new cyclosporin A (CsA) analogues that contain novel MeBmt derivatives in the 1-position are described. The MeBmt analogue that contains an additional methyl group on C4, (2S,3R,6E)-4,4-dimethyl-3-hydroxy-2-(N-methylamino)-6-octenoic acid (MeBm2t), was synthesized in four steps beginning with th...
journal_title:Journal of medicinal chemistry
pub_type: 杂志文章
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journal_title:Journal of medicinal chemistry
pub_type: 杂志文章
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abstract::Inosine monophosphate dehydrogenase (IMPDH) is a key enzyme that is involved in the de novo synthesis of purine nucleotides. Novel 2-aminooxazoles were synthesized and tested for inhibition of IMPDH catalytic activity. Multiple analogues based on this chemotype were found to inhibit IMPDH with low nanomolar potency. O...
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更新日期:2002-05-23 00:00:00
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journal_title:Journal of medicinal chemistry
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更新日期:1999-11-18 00:00:00
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journal_title:Journal of medicinal chemistry
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更新日期:2012-08-09 00:00:00
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更新日期:2011-01-13 00:00:00
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journal_title:Journal of medicinal chemistry
pub_type: 杂志文章
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更新日期:2009-11-12 00:00:00
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journal_title:Journal of medicinal chemistry
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journal_title:Journal of medicinal chemistry
pub_type: 杂志文章
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journal_title:Journal of medicinal chemistry
pub_type: 杂志文章
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更新日期:1993-06-11 00:00:00
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