Pot, atom and step-economic (PASE) synthesis of medicinally relevant spiro[oxindole-3,4′-pyrano[4,3-b]pyran] scaffold

2016 ◽  
Vol 22 (1) ◽  
pp. 11-15 ◽  
Author(s):  
Michail N. Elinson ◽  
Fedor V. Ryzhkov ◽  
Victor A. Korolev ◽  
Mikhail P. Egorov
Keyword(s):  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Large Scale ◽  
Potassium Fluoride ◽  
Environmentally Benign ◽  
Anti Hiv

AbstractFast (3 min) pot, atom and step economics (PASE) potassium fluoride catalyzed multicomponent reaction of isatins, malononitrile and 4-hydroxy-6-methyl-2H-pyran-2-one results in efficient formation of substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans in 92–96% yields. The developed ‘on-solvent’ approach to the substituted spirooxindole-3,4′-pyrano[4,3-b]pyrans – the pharmacologically perspective substances with known antiviral, antileishmanial, anticonvulsant and anti-HIV activities – is beneficial from the viewpoint of diversity-oriented large-scale processes and represents fast and environmentally benign synthetic concept for the multicomponent reactions strategy.

scholarly journals Synthesis of depsipeptides via isocyanide-based consecutive Bargellini/Passerini multicomponent reactions

SynOpen ◽  
2021 ◽  
Author(s):  
Hassan Farhid ◽  
Mohammad Mahdi Rostami ◽  
Ahmad Shaabani ◽  
Behrouz Notash
Keyword(s):  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Flexible Structures ◽  
Amide Bond ◽  
Environmentally Benign ◽  
Reaction Products ◽  
Reaction Conditions ◽  
New Class ◽  
High Yields ◽  
Straightforward Approach

An efficient and straightforward approach has been established for the preparation of new class of depsipeptide structures via isocyanide-based consecutive Bargellini/Passerini multicomponent reactions. 3-Carboxamido-isobutyric acids bearing an amide bond were supplied via Bargellini multicomponent reaction from isocyanides, acetone, and chloroform in the presence of sodium hydroxide. Next, via the Passerini multicomponent reaction strategy, a new class of depsipeptides was synthesized using the Bargellini reaction products, isocyanides, and aldehydes under environmentally benign reaction conditions. The prepared depsipeptides have more flexible structures than their pseudopeptidic analogs. Using cheap and readily available starting materials, mild reaction conditions, simple procedures, and high yields are the advantages of the present strategy.

scholarly journals An evaluation of credentials of a multicomponent reaction for the synthesis of isothioureas through the use of a holistic CHEM21 green metrics toolkit

2017 ◽  
Vol 19 (1) ◽  
pp. 249-258 ◽  
Author(s):  
S. Abou-Shehada ◽  
P. Mampuys ◽  
B. U. W. Maes ◽  
J. H. Clark ◽  
L. Summerton
Keyword(s):  
Organic Compounds ◽  
Multicomponent Reaction ◽  
Multicomponent Reactions ◽  
Materials Used

Multicomponent reactions (MCRs) are considered green and material efficient methods for the synthesis of organic compounds, however very few studies have investigated the metrics of the upstream processes involved to achieve the starting materials used in these reactions.

An Environmentally Benign Catalytic Method for Versatile Synthesis of 1,4-Dihydropyridines via Multicomponent Reactions

2015 ◽  
Vol 33 (5) ◽  
pp. 568-572 ◽  
Author(s):  
Shuo Cao ◽  
Shanshan Zhong ◽  
Changfeng Hu ◽  
Jie-Ping Wan ◽  
Chengping Wen
Keyword(s):  
Multicomponent Reactions ◽  
Environmentally Benign ◽  
Catalytic Method

scholarly journals Synthesis of Biologically Active Molecules through Multicomponent Reactions

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 505 ◽  
Author(s):  
Daniel Insuasty ◽  
Juan Castillo ◽  
Diana Becerra ◽  
Hugo Rojas ◽  
Rodrigo Abonia
Keyword(s):  
Multicomponent Reaction ◽  
Biological Property ◽  
Multicomponent Reactions ◽  
Organic Molecules ◽  
Biological Activities ◽  
Biologically Active ◽  
Vast Number ◽  
Key Points ◽  
Reported Data ◽  
Synthetic Approaches

Focusing on the literature progress since 2002, the present review explores the highly significant role that multicomponent reactions (MCRs) have played as a very important tool for expedite synthesis of a vast number of organic molecules, but also, highlights the fact that many of such molecules are biologically active or at least have been submitted to any biological screen. The selected papers covered in this review must meet two mandatory requirements: (1) the reported products should be obtained via a multicomponent reaction; (2) the reported products should be biologically actives or at least tested for any biological property. Given the diversity of synthetic approaches utilized in MCRs, the highly diverse nature of the biological activities evaluated for the synthesized compounds, and considering their huge structural variability, much of the reported data are organized into concise schemes and tables to facilitate comparison, and to underscore the key points of this review.

scholarly journals Concise Synthesis of Macrocycles by Multicomponent Reactions

Synthesis ◽  
2018 ◽  
Vol 50 (05) ◽  
pp. 1027-1038 ◽  
Author(s):  
Alexander Dömling ◽  
Eman Abdelraheem ◽  
Samad Khaksar
Keyword(s):  
Amino Acid ◽  
Multicomponent Reaction ◽  
Ring Opening ◽  
Multicomponent Reactions ◽  
Reaction Pathway ◽  
Ring Closure ◽  
Side Chains ◽  
Reaction Sequence ◽  
Cyclic Anhydride

A short reaction pathway was devised to synthesize a library of artificial 18–27-membered macrocycles. The five-step reaction sequence involves ring opening of a cyclic anhydride with a diamine, esterification, coupling with an amino acid isocyanide, saponification, and, finally, macro-ring closure using an Ugi or, alternatively, a Passerini multicomponent reaction. Three out of the five steps allow for the versatile introduction of linker elements, side chains, and substituents with aromatic, heteroaromatic, and aliphatic character. The versatile pathway is described for 15 different target macrocycles on a mmol scale. Artificial macrocycles have recently become of great interest due to their potential to bind to difficult post-genomic targets.

Chitosan: A Natural and Sustainable Polymeric Organocatalyst for C-C Bond Formation During the Synthesis of 5-amino-2,3-dihydrobenzo[d] thiazole-4,6-dicarbonitriles

2019 ◽  
Vol 6 (1) ◽  
pp. 69-76
Author(s):  
Km N. Shivhare ◽  
Ibadur R. Siddiqui
Keyword(s):  
Catalytic Activity ◽  
Multicomponent Reaction ◽  
Bond Formation ◽  
Environmentally Benign ◽  
One Pot ◽  
Reaction Condition ◽  
Three Component Reaction ◽  
Efficient Route

Background: A green, recyclable and reusable chitosan catalyst has been utilized for the synthesis of 5-amino-2,3-dihydrobenzo[d]thiazole-4,6-dicarbonitrile and its derivatives. Methods and Results: Three-component reaction protocol incorporates the reaction of aldehydes, malononitrile and rhodanine derivatives. This is examined as an efficient route for the synthesis of dicarbonitriles utilizing a green, biodegradable, environmentally benign, and easily available chitosan catalyst. In the reported protocol, catalyst can be recycled and not any substantial dropping in its catalytic activity during the recycling steps was obtained. Conclusion: A green and environmentally benign, one pot three-component protocol has been illustrated for the synthesis of 5-amino-2,3-dihydrobenzo[d]thiazole-4,6-dicarbonitrile derivatives. Adequately yield products were gained via the natural catalytic approach with the recyclability of the catalyst. The use of chitosan represents this procedure as an attractive substitute for the synthesis of biaryls complex by multicomponent reaction condition.

Anodic Oxidation as an Enabling Tool for the Synthesis of Natural Products

Synthesis ◽  
2020 ◽  
Vol 52 (19) ◽  
pp. 2781-2794
Author(s):  
Till Opatz ◽  
Leander Geske ◽  
Eisuke Sato
Keyword(s):  
Organic Synthesis ◽  
Large Scale ◽  
Bond Formation ◽  
Short Review ◽  
Natural Product Synthesis ◽  
Environmentally Benign ◽  
Full Potential ◽  
Future Prospects ◽  
Reaction Conditions ◽  
Chemical Oxidants

Electrochemistry provides a valuable toolbox for organic synthesis and offers an appealing, environmentally benign alternative to the use of stoichiometric quantities of chemical oxidants or reductants. Its potential to control current efficiency along with providing alternative reaction conditions in a classical sense makes electrochemistry a suitable method for large-scale industrial transformations as well as for laboratory applications in the synthesis of complex molecular architectures. Even though research in this field has intensified over the recent decades, many synthetic chemists still hesitate to add electroorganic reactions to their standard repertoire, and hence, the full potential of preparative organic electrochemistry has not yet been unleashed. This short review highlights the versatility of anodic transformations by summarizing their application in natural product synthesis.1 Introduction2 Shono-Type Oxidation3 C–N/N–N Bond Formation4 Aryl–Alkene/Aryl–Aryl Coupling5 Cycloadditions Triggered by Oxidation of Electron-Rich Arenes6 Spirocycles7 Miscellaneous Transformations8 Future Prospects

An environmentally benign and practical synthesis of sugar orthoesters promoted by potassium fluoride

2004 ◽  
Vol 45 (48) ◽  
pp. 8847-8848 ◽  
Author(s):  
Shin-ichiro Shoda ◽  
Masashi Moteki ◽  
Ryuko Izumi ◽  
Masato Noguchi
Keyword(s):  
Potassium Fluoride ◽  
Environmentally Benign ◽  
Practical Synthesis

scholarly journals Efficient Single Tobamoviral Vector-Based Bioproduction of Broadly Neutralizing Anti-HIV-1 Monoclonal Antibody VRC01 in Nicotiana benthamiana Plants and Utility of VRC01 in Combination Microbicides

2013 ◽  
Vol 57 (5) ◽  
pp. 2076-2086 ◽  
Author(s):  
Krystal Teasley Hamorsky ◽  
Tiffany W. Grooms-Williams ◽  
Adam S. Husk ◽  
Lauren J. Bennett ◽  
Kenneth E. Palmer ◽  
...  
Keyword(s):  
Reverse Transcriptase ◽  
Nicotiana Benthamiana ◽  
Large Scale ◽  
Neutralization Assay ◽  
Enzyme Linked Immunosorbent Assay ◽  
Scale Production ◽  
Gp120 Binding ◽  
Topical Microbicides ◽  
Anti Hiv ◽  
Hiv 1

ABSTRACTBroadly neutralizing monoclonal antibodies (bnMAbs) may offer powerful tools for HIV-1 preexposure prophylaxis, such as topical microbicides. However, this option is hampered due to expensive MAb biomanufacturing based on mammalian cell culture. To address this issue, we developed a new production system for bnMAb VRC01 inNicotiana benthamianaplants using a tobamovirus replicon vector. Unlike conventional two-vector-based expression, this system was designed to overexpress full-length IgG1 from a single polypeptide by means of kex2p-like enzyme recognition sites introduced between the heavy and light chains. An enzyme-linked immunosorbent assay (ELISA) revealed that gp120-binding VRC01 IgG1 was maximally accumulated on 5 to 7 days following vector inoculation, yielding ∼150 mg of the bnMAb per kg of fresh leaf material. The plant-made VRC01 (VRC01p) was efficiently purified by protein A affinity followed by hydrophobic-interaction chromatography. ELISA, surface plasmon resonance, and an HIV-1 neutralization assay demonstrated that VRC01p has gp120-binding affinity and HIV-1-neutralization capacity virtually identical to the human-cell-produced counterpart. To advance VRC01p's use in topical microbicides, we analyzed combinations of the bnMAb with other microbicide candidates holding distinct antiviral mechanisms in an HIV-1 neutralization assay. VRC01p exhibited clear synergy with the antiviral lectin griffithsin, the CCR5 antagonist maraviroc, and the reverse transcriptase inhibitor tenofovir in multiple CCR5-tropic HIV-1 strains from clades A, B, and C. In summary, VRC01p is amenable to robust, rapid, and large-scale production and may be developed as an active component in combination microbicides with other anti-HIV agents such as antiviral lectins, CCR5 antagonists, and reverse transcriptase inhibitors.

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