- Facile Synthesis of Potent HIV-1 Protease Inhibitors containing a Novel Pseudo-symmetric Dipeptide Isostere
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A series of potent inhibitors of the HIV-1 protease containing a novel pseudo-symmetric dipeptide isostere 3 was synthesized via ring opening of a protected epoxide with various substituted hydrazines.
- Sham, Hing L.,Betebenner, David A.,Zhao, Chen,Wideburg, Norman E.,Saldivar, Ayda,et al.
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- Antiviral drug and drug composition thereof
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The invention relates to an antiviral drug and a drug composition thereof, specially relates to a drug against human immunodeficiency virus (HIV) and a drug composition thereof, and particularly relates to a drug capable of serving as a retrovirus proteas
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Paragraph 0114
(2019/01/08)
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- Antiviral drug and its pharmaceutical composition
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The invention relates to an antiviral medicine and a medicine composition thereof, in particular relates to an anti-human immunodeficiency virus (HIV) medicine and a medicine composition thereof, and especially relates to a medicine which can be taken as
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Paragraph 0203-0204
(2017/03/21)
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- Synthesis of optically active α-aminoalkyl α′-halomethyl ketone: A cross-claisen condensation approach
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(Equation presented) A simple and versatile method was developed for the synthesis of α-aminoalkyl α′-halomethyl ketone derivatives, which are useful intermediates of protease inhibitors. It involves selective halogenation of the α-position on a β-ketoester, which is prepared by cross-Claisen condensation using N-protected amino acid ester. The title compound is obtained in high yield after decarboxylation of the α-halo-β-ketoester.
- Honda, Yutaka,Katayama, Satoshi,Kojima, Mitsuhiko,Suzuki, Takayuki,Izawa, Kunisuke
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p. 447 - 449
(2007/10/03)
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- Process for producing 3-amino-2-oxo-1-halogenopropane derivatives
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Compounds formed by reacting a protected amino acid with an alkali metal enolate of an alkyl acetate are reacted with a halogenating agent for halogenation of the 2-position, or a protected amino acid is reacted with an alkali metal enolate of an alkyl halogenoacetate, to form a 4-amino-3-oxo-2-halogenobutanoic acid ester derivative, and hydrolysis and decarboxylation are conducted to produce a 3-amino-2-oxo-1-halogenopropane derivative or its salt. The present method is a useful process for producing a 3-amino-2-oxo-1-halogenopropane derivatives which can easily be converted to a 3-amino-1,2-epoxypropane.
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- Studies toward the Large-Scale Synthesis of the HIV Proteinase Inhibitor Ro 31-8959
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Ro 31-8959 (1), a potent and selective inhibitor of HIV proteinase, is currently in phase III clinical trials.Six approaches for the large-scale synthesis of this compound have been studied.All routes employ an initial disconnection to an electrophilic L-phenylalanine homologue equivalent 13 and the decahydroisoquinoline derivative 5.They differ in adopting either an epoxide, a cyclic sulfate, or an aldehyde as the electrophilic entity and develop chirality from L-phenylalanine, dimethyl D-tartrate, or a Sharpless epoxidation.The preferred route starts from N-phthaloyl-L-phenylalaninyl chloride and uses tris((trimethylsilyl)oxy)ethene to effect homologation to hydroxy ketone 30, which is elaborated in a five-step two-pot procedure to N-phthaloyl epoxide 33 and hence 1.Kilogram quantities of Ro 31-8959 have been prepared using this route.
- Parkes, Kevin E. B.,Bushnell, David J.,Crackett, Peter H.,Dunsdon, Stephen J.,Freeman, Andrew C.,et al.
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p. 3656 - 3664
(2007/10/02)
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- Stereocontrolled synthesis of erythro N-protected α-amino epoxides and peptidyl epoxides
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N-protected α-amino epoxides of erythro configuration, derived from α-amino acids, were synthesized in a stereoselective manner. The erythro (2S,3S), configuration was achieved by the synthetic sequence: amino acid -> haloketone -> halohydrin -> epoxide. A mechanistic explanation for the observed stereoselectivity is presented. This stereoselective synthetic approach was applied to the synthesis of a variety of short peptidyl epoxides, bearing a predefined absolute configuration of the chiral epoxide moiety.
- Albeck, Amnon,Persky, Rachel
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p. 6333 - 6346
(2007/10/02)
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