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      A new vinyl selenone-based domino approach to spirocyclopropyl oxindoles endowed with anti-HIV RT activity

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          Abstract

          A flexible synthesis of spirocyclopropyl oxindoles from vinyl selenones and oxindoles via a domino Michael addition/proton transfer/cyclization sequence has been developed.

          Abstract

          Herein, we disclose a general and flexible access to spirocyclopropyl oxindoles by a domino Michael/intramolecular nucleophilic substitution pathway with variously substituted vinyl selenones and enolizable oxindoles in aqueous sodium hydroxide solution. The spirocyclopropyl oxindole being a privileged scaffold, some of the synthesized compounds were selected for biological evaluation. Compound 3m showed selective anti-HIV-1 activity thanks to its ability to inhibit the reverse transcriptase.

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          Rapid and automated tetrazolium-based colorimetric assay for the detection of anti-HIV compounds.

          Rudi Pauwels, Jan Balzarini, Masanori Baba … (1988)
          A rapid, sensitive and automated assay procedure was developed for the in vitro evaluation of anti-HIV agents. An HTLV-I transformed T4-cell line, MT-4, which was previously shown by Koyanagi et al. (1985) to be highly susceptible to, and permissive for, HIV infection, served as the target cell line. Inhibition of the HIV-induced cytopathic effect was used as the end point. The viability of both HIV- and mock-infected cells was assessed spectrophotometrically via the in situ reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT). The procedure was optimized as to make optimal use of multichannel pipettes, microprocessor-controlled dispensing and optical density reading. The absorbance ratio of the mock-infected control to the HIV-infected samples was about 20. This allowed an accurate determination of the 50% effective doses, as demonstrated for 3'-azido-2',3'-dideoxythymidine (AZT), 2',3'-dideoxycytidine (ddCyd), dextran sulfate and heparin. The technique significantly reduced labor time as compared to the trypan blue exclusion method, and permits the evaluation of large numbers of compounds for their anti-HIV activity.
          Article 0 comments Cited 185 times – based on 0 reviews     Review now
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            The use of spirocyclic scaffolds in drug discovery.

            Yajun Zheng, Colin Tice, Suresh Singh (2014)
            Owing to their inherent three-dimensionality and structural novelty, spiro scaffolds have been increasingly utilized in drug discovery. In this brief review, we highlight selected examples from the primary medicinal chemistry literature during the last three years to demonstrate the versatility of spiro scaffolds. With recent progress in synthetic methods providing access to spiro building blocks, spiro scaffolds are likely to be used more frequently in drug discovery.
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              Detection, isolation, and continuous production of cytopathic retroviruses (HTLV-III) from patients with AIDS and pre-AIDS.

              M G Sarngadharan, M. Popovic, R Gallo … (1984)
              A cell system was developed for the reproducible detection of human T-lymphotropic retroviruses (HTLV family) from patients with the acquired immunodeficiency syndrome (AIDS) or with signs or symptoms that frequently precede AIDS (pre-AIDS). The cells are specific clones from a permissive human neoplastic T-cell line. Some of the clones permanently grow and continuously produce large amounts of virus after infection with cytopathic (HTLV-III) variants of these viruses. One cytopathic effect of HTLV-III in this system is the arrangement of multiple nuclei in a characteristic ring formation in giant cells of the infected T-cell population. These structures can be used as an indicator to detect HTLV-III in clinical specimens. This system opens the way to the routine detection of HTLV-III and related cytopathic variants of HTLV in patients with AIDS or pre-AIDS and in healthy carriers, and it provides large amounts of virus for detailed molecular and immunological analyses.
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                Author and article information

                Journal
                Journal ID (publisher-id): OBCRAK
                Title: Organic & Biomolecular Chemistry
                Abbreviated Title: Org. Biomol. Chem.
                Publisher: Royal Society of Chemistry (RSC)
                ISSN (Print): 1477-0520
                ISSN (Electronic): 1477-0539
                Publication date Created: 2016
                Publication date (Print): 2016
                Volume: 14
                Issue: 6
                Pages: 2015-2024
                Article
                DOI: 10.1039/C5OB02451J
                SO-VID: fbef12b4-1eba-486b-b3ee-4badbb34b16c
                Copyright © © 2016
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