Blocking group-directed diastereoselective total synthesis of (±)-α-noscapine

Ni, Jizhi; Xiao, Heping; Weng, Lipeng; Wei, Xiaofeng; Xu, Youjun

doi:10.1016/j.tet.2011.05.060

Cited by 14 publications

(8 citation statements)

References 31 publications

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“…Additionally, it was a potential natural product against SARS-CoV-2 ( Kumar N. et al, 2020 ). Apart from the natural source Papaver somniferum L. ( Dang and Facchini, 2012 ) from which it is abundantly isolated, there is enough literature available on noscapine and the synthesis of its derivatives ( Zhou et al, 2003 ; Ni et al, 2011 ; Devine et al, 2018 ).…”

Section: Natural Products Against Sars-cov-2: Computational To Preclinical Studiesmentioning

confidence: 99%

Natural Products for the Prevention and Control of the COVID-19 Pandemic: Sustainable Bioresources

Singla

Chopra

et al. 2021

Front. Pharmacol.

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Background: The world has been unprecedentedly hit by a global pandemic which broke the record of deadly pandemics that faced humanity ever since its existence. Even kids are well-versed in the terminologies and basics of the SARS-CoV-2 virus and COVID-19 now. The vaccination program has been successfully launched in various countries, given that the huge global population of concern is still far behind to be vaccinated. Furthermore, the scarcity of any potential drug against the COVID-19-causing virus forces scientists and clinicians to search for alternative and complementary medicines on a war-footing basis.Aims and Objectives: The present review aims to cover and analyze the etiology and epidemiology of COVID-19, the role of intestinal microbiota and pro-inflammatory markers, and most importantly, the natural products to combat this deadly SARS-CoV-2 virus.Methods: A primary literature search was conducted through PubMed and Google Scholar using relevant keywords. Natural products were searched from January 2020 to November 2020. No timeline limit has been imposed on the search for the biological sources of those phytochemicals. Interactive mapping has been done to analyze the multi-modal and multi-target sources.Results and Discussion: The intestinal microbiota and the pro-inflammatory markers that can serve the prognosis, diagnosis, and treatment of COVID-19 were discussed. The literature search resulted in yielding 70 phytochemicals and ten polyherbal formulations which were scientifically analyzed against the SARS-CoV-2 virus and its targets and found significant. Retrospective analyses led to provide information about 165 biological sources that can also be screened if not done earlier.Conclusion: The interactive analysis mapping of biological sources with phytochemicals and targets as well as that of phytochemical class with phytochemicals and COVID-19 targets yielded insights into the multitarget and multimodal evidence-based complementary medicines.

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Section: Natural Products Against Sars-cov-2: Computational To Preclinical Studiesmentioning

confidence: 99%

Natural Products for the Prevention and Control of the COVID-19 Pandemic: Sustainable Bioresources

Singla

Chopra

et al. 2021

Front. Pharmacol.

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“…The target compounds were reached as follows. Compounds 12(a–h) were prepared by substituted benzoic acid and aromatic amine, in the presence of SOCl 2 . Intermediates 13(a–h) were gained by reacting 12(a–h) with substituted benzaldehyde in the presence of POCl 3 (Bischler–Napieralski reaction), which were then reduced by NaBH 4 to achieve 14(a–h) .…”

Section: Chemistrymentioning

confidence: 99%

“…Compounds 12(a-h) were prepared by substituted benzoic acid and aromatic amine, in the presence of SOCl 2 . [20] Intermediates 13(a-h) were gained by reacting 12(a-h) with substituted benzaldehyde in the presence of POCl 3 (Bischler-Napieralski [21] reaction), which were then reduced by NaBH 4 to achieve 14(a-h) . Compounds 16(a-l) were obtained from different substituted cinnamic acid via SOCl 2 -catalyzed amidation reaction [22] followed by hydrolyzation to achieve compounds 17(a-k) .…”

mentioning

confidence: 99%

Design, synthesis, and biological evaluation of novel tetrahydroisoquinoline derivatives as potential antitumor candidate

Zhu

et al. 2016

Chem Biol Drug Des

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A novel class of tetrahydroisoquinoline derivatives was designed and synthesized as antitumor agents and evaluated for their in vitro and in vivo biological activities. The antiproliferative activities of all the target compounds on HUVEC, MCF-7, and HT-29 were evaluated. Compared with colchicine (1.04 × 10 μm), 17d and 17e exhibited outstanding activity on MCF-7 with IC values 0.26 × 10 μm and 0.89 × 10 μm in cell cytotoxicity assay. The tubulin polymerization assay demonstrated that 17d and 17e exhibited better inhibition rate. In the MCF-7-xenograft mouse model that was treated with 17d and 17e by intraperitoneal injection, the tumor weight was decreased at same rate with tamoxifen, and relative tumor proliferation rates were 59.48% and 41.33%, while tamoxifen was 45.08% with a daily dose of 20 mg/kg, which were demonstrated potent in vivo efficacy.

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“…However, despite significant progress, general de novo syntheses of isoquinolinone and tetrahydroisoquinoline (THIQ) motifs remain limited, with many modern techniques relying on well-established classical methodologies mimicking known biosyntheses of these structures. , The most prominent examples are more than a century old and include the Pictet–Spengler cyclization, , Bischler–Napieralski dihydroisoquinoline cyclization, Pomeranz–Fritsch–Bobbitt isoquinoline synthesis, Dieckmann cyclization [(a), Scheme ], and approaches based on Friedel–Crafts alkylation . These venerable reactions proceed via an electrophilic aromatic substitution (S E Ar) mechanism and thus are well-suited to the archetypal electron-rich catechol and mescalin motifs found in myriad natural products and pharmaceuticals.…”

mentioning

confidence: 99%

Lithioarene Cycliacylation and Pd-Catalyzed Aminoethylation/Cyclization to Access Electronically Diverse Saturated Isoquinoline Derivatives

et al. 2021

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We report operationally facile methods for the synthesis of substituted dihydroisoquinolinones and tetrahydroisoquinolines from readily accessible o-bromobenzyl bromides and o-bromobenzaldehydes, respectively. While classical electrophilic aromatic substitution reactions are tailored to the construction of saturated isoquinolines derived from electron-rich precursors, we demonstrate efficient syntheses from electronically diverse substrates to produce cyclized products as single regioisomers.

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Blocking group-directed diastereoselective total synthesis of (±)-α-noscapine

Cited by 14 publications

References 31 publications

Natural Products for the Prevention and Control of the COVID-19 Pandemic: Sustainable Bioresources

Natural Products for the Prevention and Control of the COVID-19 Pandemic: Sustainable Bioresources

Design, synthesis, and biological evaluation of novel tetrahydroisoquinoline derivatives as potential antitumor candidate

Lithioarene Cycliacylation and Pd-Catalyzed Aminoethylation/Cyclization to Access Electronically Diverse Saturated Isoquinoline Derivatives

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