Synthesis and pharmacological properties of polysubstituted 2-amino-4 H -pyran-3-carbonitrile derivatives
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COMPREHENSIVE REVIEW
Synthesis and pharmacological properties of polysubstituted 2‑amino‑4H‑pyran‑3‑carbonitrile derivatives Zahra Tashrifi1 · Mohammad Mohammadi‑Khanaposhtani2 · Haleh Hamedifar3,4 · Bagher Larijani5 · Samira Ansari3,4 · Mohammad Mahdavi5 Received: 17 July 2019 / Accepted: 9 September 2019 © Springer Nature Switzerland AG 2019
Abstract 2-Amino-3-cyano-4H-chromenes are structural core motifs that received increasing attention in the last years due to their interesting potential pharmacological properties. In this review, the synthetic methods for these compounds are classified based on the type of catalyst in the pertinent reactions. In addition, the wide range of pharmacological properties of these compounds is covered in a separate section. Graphic Abstract
Keywords 2-Amino-4H-pyran-3-carbonitriles · Pharmacological properties · Polysubstituted · Malononitrile · Catalysts
Introduction Polysubstituted 2-amino-4H-pyran-3-carbonitrile derivatives are among very important heterocyclic compounds with a wide range of interesting biological activities (Table 1) * Samira Ansari [email protected] * Mohammad Mahdavi [email protected] Extended author information available on the last page of the article
[1–9]. Their huge potential in drug discovery has inspired a wide array of synthetic work, and the conception of a new modified polycyclic framework based on this core structure has stimulated an extensive effort and attention. Furthermore, because of their orthogonal functional groups, these compounds can be considered as key intermediates for subsequent transformations. Several strategies toward the synthesis of 2-amino4H-pyran-3-carbonitriles in racemic or enantiomerically pure form have been described. The most useful and preferred
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Molecular Diversity
Table 1 Examples of biologically active molecules having 2-amino-4H-pyran-3-carbonitriles moieties
Structure
Effect
Effect
Antibacterial, Anti-inflammatory [1]
Inhibitor of xanthine oxidase [6]
Antibacterial, Antituberculosis, Antimalarial [2]
Apoptosis Inducer, Anticancer [7]
Inducer apoptosis, Anticancer [3]
Antibacterial, Antifungal [8]
Antibacterial [4]
Inhibitor of diabetic vascular dysfunction [9]
Inhibitor of the Excitatory Amino Acid Transporters (EAATs) [5]
Drug: Anti Anaplastic Thyroid Cancer (ATC)
method for the construction of these heterocyclic compounds is the multicomponent reaction (MCR) of aldehydes or isatin with malononitrile and β-ketoesters, diverse enolizable C-Hactivated acidic compounds and phenols in the presence or absence of a catalyst (Scheme 1). In 2015, a review article was published describing the different organocatalyzed synthetic strategies for the construction of chiral 2-amino-3-cyano-4H-chromene derivatives [10]. But despite their importance in synthetic, biological and medicinal chemistry, a comprehensive summary on the synthetic methodologies and different applications of polysubstituted 2-amino-4H-pyran-3-carbonitrile derivatives has not been reported. Hence, in th
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