The Structure and Synthesis of Cytokinin Metabolites. 1. The 7- and 9-β-D-Glucofuranosides and Pyranosides of Zeatin and 6-Benzylaminopurine

1978 ◽  
Vol 31 (5) ◽  
pp. 1095 ◽  
Author(s):  
DE Cowley ◽  
CC Duke ◽  
AJ Liepa ◽  
JK Macleod ◽  
DS Letham
Keyword(s):  
Pyrimidine Ring ◽  
Ring Closure ◽  
Imidazole Derivative ◽  
High Yield ◽  
Ring Size ◽  
Plant Metabolites ◽  
One Pot ◽  
Synthetic Routes

The structures of the major stable plant metabolites of the cytokinins zeatin and 6-benzylaminopurine have been confirmed by synthesis to be 7- and 9-β-D-glucopyranosides. The small quantities of metabolites initially isolated (< 100 μg) precluded assignment of the glucose ring size or configuration of the anomeric linkage so that synthesis of both the furanose and pyranose forms of 7-β-D- and 9-β-D-glucosylzeatin and 6-benzylaminopurine was undertaken which allowed direct u.v., m.s. and t.l.c. comparison with the metabolites. Numerous synthetic routes to the unusual 7-glucosides of the two cytokinins were explored, the most successful utilizing a one-pot pyrimidine ring closure of an imidazole derivative to afford directly in high yield the required 7-glucosides of zeatin and 6-benzylaminopurine.

Synthesis of Highly Functionalized Quinazoline-2,4(1H,3H)-diones from Isocyanides, Aniline and Isocyanate via Cu-Catalyzed Intermolecular C-H Activation Reactions

2020 ◽  
Vol 17 (11) ◽  
pp. 832-836
Author(s):  
Manijeh Nematpour ◽  
Hossein Fasihi Dastjerdi ◽  
Mehdi Jahani ◽  
Sayyed Abbas Tabatabai
Keyword(s):  
13C Nmr ◽  
Reaction Times ◽  
High Yield ◽  
One Pot ◽  
1H And 13C Nmr ◽  
Activation Reaction ◽  
Elemental Analyses

A simple and appropriate procedure for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives from isocyanides, aniline and isocyanate via the Cu-catalyzed intramolecular C-H activation reaction is reported. The advantages of this method are one-pot conditions, accessible starting materials- catalyst, high yield of products, and short reaction times. The structures are confirmed spectroscopically (1H- and 13C-NMR, IR and EI-MS) and by elemental analyses.

Design, Synthesis, In vitro Cytotoxic Activity Evaluation, and Study of Apoptosis Inducing Effect of New Styrylimidazo[1,2-a]Pyridines as Potent Anti-Breast Cancer Agents

2019 ◽  
Vol 19 (2) ◽  
pp. 265-275 ◽  
Author(s):  
Faeze Khalili ◽  
Sara Akrami ◽  
Malihe Safavi ◽  
Maryam Mohammadi-Khanaposhtani ◽  
Mina Saeedi ◽  
...  
Keyword(s):  
Breast Cancer ◽  
Cytotoxic Activity ◽  
High Yield ◽  
Breast Cancer Cell Lines ◽  
Pyridine Derivatives ◽  
One Pot ◽  
Standard Drug ◽  
Three Component Reaction ◽  
Anti Cancer

Background: This paper reports synthesis, cytotoxic activity, and apoptosis inducing effect of a novel series of styrylimidazo[1,2-a]pyridine derivatives. Objective: In this study, anti-cancer activity of novel styrylimidazo[1,2-a]pyridines was evaluated. Methods: Styrylimidazo[1,2-a]pyridine derivatives 4a-o were synthesized through a one-pot three-component reaction of 2-aminopyridines, cinnamaldehydes, and isocyanides in high yield. All synthesized compounds 4a-o were evaluated against breast cancer cell lines including MDA-MB-231, MCF-7, and T-47D using MTT assay. Apoptosis was evaluated by acridine orange/ethidium bromide staining, cell cycle analysis, and TUNEL assay as the mechanism of cell death. Results: Most of the synthesized compounds exhibited more potent cytotoxicity than standard drug, etoposide. Induction of apoptosis by the most cytotoxic compounds 4f, 4g, 4j, 4n, and 4m was confirmed through mentioned methods. Conclusion: In conclusion, these results confirmed the potency of styrylimidazo[1,2-a]pyridines for further drug discovery developments in the field of anti-cancer agents.

scholarly journals 1,3-Diketone Calix[4]arene Derivatives—A New Type of Versatile Ligands for Metal Complexes and Nanoparticles

Molecules ◽  
2021 ◽  
Vol 26 (5) ◽  
pp. 1214
Author(s):  
Sergey N. Podyachev ◽  
Rustem R. Zairov ◽  
Asiya R. Mustafina
Keyword(s):  
Structural Diversity ◽  
Building Blocks ◽  
Structural Features ◽  
Structure Property ◽  
One Pot ◽  
Arene Ligands ◽  
Structure Property Relationships ◽  
New Type ◽  
Synthetic Routes ◽  
Magnetic Resonance Imaging Mri

The present review is aimed at highlighting outlooks for cyclophanic 1,3-diketones as a new type of versatile ligands and building blocks of the nanomaterial for sensing and bioimaging. Thus, the main synthetic routes for achieving the structural diversity of cyclophanic 1,3-diketones are discussed. The structural diversity is demonstrated by variation of both cyclophanic backbones (calix[4]arene, calix[4]resorcinarene and thiacalix[4]arene) and embedding of different substituents onto lower or upper macrocyclic rims. The structural features of the cyclophanic 1,3-diketones are correlated with their ability to form lanthanide complexes exhibiting both lanthanide-centered luminescence and magnetic relaxivity parameters convenient for contrast effect in magnetic resonance imaging (MRI). The revealed structure–property relationships and the applicability of facile one-pot transformation of the complexes to hydrophilic nanoparticles demonstrates the advantages of 1,3-diketone calix[4]arene ligands and their complexes in developing of nanomaterials for sensing and bioimaging.

Catalyst-Free One-Pot Synthesis of Novel Heteroarylamine Substituted Furo[3,2-c]coumarins

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1589-1592 ◽  
Author(s):  
Abolfazl Olyaei ◽  
Mahnaz Saraei ◽  
Reyhaneh Khoeiniha
Keyword(s):  
Michael Addition ◽  
Aldol Condensation ◽  
Ring Closure ◽  
Dehydration Reaction ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Tandem Process ◽  
First Time

A high-yielding cyclocondensation of 4-hydroxycoumarin, phenylglyoxal monohydrate, and heteroarylamines proceeds without catalysis, which gives novel functionalized furo[3,2-c]coumarins and heteroarylamino alkylation of coumarin products in acetonitrile under reflux, is reported for the first time. This tandem process involves sequentially an aldol condensation, Michael addition, a ring closure, and dehydration reaction.

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