Syntheses of HIV Protease Inhibitors Having a Peptide Moiety Which.

Asagarasu, Akira; Uchiyama, Taketo; Achiwa, Kazuo

doi:10.1248/cpb.46.697

Cited by 12 publications

(10 citation statements)

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“…The 1 H NMR spectrum of 10a demonstrated singlets at δ 2.44 and δ 2.84 that were attributed to CH 3 -Ar, whereas the doublets at δ 7. 26,7.43,7.49,7.81,8.06,and 8.20 (J ∼ 8.0 Hz) belonged to aromatic protons. The NH signal appeared at δ 10.54, which exchanged with D 2 O.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Anti–HIV, and Antifungal Activity of New Benzensulfonamides Bearing the 2,5-Disubstituted-1,3,4-Oxadiazole Moiety

Zareef

Iqbal

Al‐Masoudi

et al. 2007

Phosphorus, Sulfur, and Silicon and the Related Elements

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Section: Resultsmentioning

confidence: 99%

Synthesis, Anti–HIV, and Antifungal Activity of New Benzensulfonamides Bearing the 2,5-Disubstituted-1,3,4-Oxadiazole Moiety

Zareef

Iqbal

Al‐Masoudi

et al. 2007

Phosphorus, Sulfur, and Silicon and the Related Elements

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“…From the gradient selected HMBC spectrum 25 Next, other models of captopril derivatives bearing a thioether linkage were prepared, aiming to evaluate their anti-HIV activity. Roark et al 26 A suitable coupling method 27 was employed for the formation of peptides by reaction of the carboxylic acid group with acylated amino acid, using 1-hydroxybenzotriazole (HOBt) 28,29 and 30 as coupling reagents. HOBt 1 is currently the most frequently used activating agent for the carboxyl group of amino acids.…”

Section: Resultsmentioning

confidence: 99%

Amino acid derivatives. Part 6. New analogues of the angiotensin-converting enzyme 'Captopril'. Synthesis and anti-HIV activity

Al‐Masoudi¹,

Hamad²,

Hameed³

et al. 2010

Arkivoc

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The development of new HIV non-nucleoside reverse transcriptase inhibitors (NNRTIs) offers the possibility of generating structures of increased potency. On this basis, new derivatives of the angiotensin-converting enzyme 'Captopril' bearing benzimidazoles, benzothiazole, purine and pyridine residues were synthesized with the aim of developing new NNRTIs. Alternatively, the thioether analogs bearing carboxymethylthio, 2-amino-2-oxo-ethylthio, 2-(phthalimido-2-yl)-2-ethylthio, 1-benzyl-2-ethyl-4-nitro-imidazol-5-yl)-piperazin-1-yl)-2-oxo-ethylthio, and the carboxamide analogs were prepared from condensation of Captopril with various halide derivatives. The new compounds were assayed against HIV-1 and HIV-2 in MT-4 cells. The compound having a 4-chlorobenzimidazole group was the most active in inhibiting HIV-1, with EC 50 = 0.24 µg/ml, with therapeutic indexes (SI) of 21, is a leading candidate for further development.

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“…Subsequently, the corresponding acid 2b 25 was obtained by saponification of ester 2a. A suitable coupling method 26 was employed for the formation of peptides by the reaction of the carboxylic acid group with the L-amino acid methyl ester hydrochloride, using 1-hydroxybenzotriazole (HOBt) 27,28 and N,N`-dicyclohexylcarbodiimide (DCC) 29 as coupling reagent. Currently, HOBt is used very frequently as activating agent for the coupling of carboxylic acid group and amino group, not only because the coupling process is fast, but also it suppresses racemization, especially in the presence of DCC.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of chiral N-(2-(1-oxophthalazin-2(1H)-yl) ethanoyl)-α-amino acid derivatives as antitumor agents

El‐Nezhawy¹,

Radwan²,

Gaballah³

2009

Arkivoc

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A series of chiral α-amino acid derivatives conjugated with 1-oxophthalazine moiety 5a-e were synthesized by coupling of various L-acylated amino acid derivatives with 2-(1-oxophthalazin-2(1H)-yl)acetic acid in the presence of 1-hydroxybenzotriazole (HOBt) and N,N`-dicyclohexylcarbodiimide (DCC) as coupling reagent. Alternatively, compounds 5a-e were prepared by the reaction of the corresponding aizde 4, via the azide-coupling method, with Lacylated amino acid derivatives. The peptide esters 5a-d were converted into their corresponding amides 6a-d by treating with methanolic ammonia. Moreover, 5a was boiled with hydrazine hydrate to afford the corresponding hydrazide 7. Finally, the dipeptides 8a-c were prepared by coupling of 5a with the appropriate L-amino acid methyl ester. The synthesized compounds were tested against Caucasian breast adenocarcinoma MCF7 cell line.

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Syntheses of HIV Protease Inhibitors Having a Peptide Moiety Which.

Cited by 12 publications

References 0 publications

Synthesis, Anti–HIV, and Antifungal Activity of New Benzensulfonamides Bearing the 2,5-Disubstituted-1,3,4-Oxadiazole Moiety

Synthesis, Anti–HIV, and Antifungal Activity of New Benzensulfonamides Bearing the 2,5-Disubstituted-1,3,4-Oxadiazole Moiety

Amino acid derivatives. Part 6. New analogues of the angiotensin-converting enzyme 'Captopril'. Synthesis and anti-HIV activity

Synthesis of chiral N-(2-(1-oxophthalazin-2(1H)-yl) ethanoyl)-α-amino acid derivatives as antitumor agents

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