CuI/amino acid catalysis in coupling and cyclization of β‐bromo‐α,β‐unsaturated carboxylic acids with terminal alkynes leading to alkylidenefuranones

Ho, Son Long; Cho, Chan Sik; Choi, Heung‐Jin; Sohn, Ho‐Sang

doi:10.1002/aoc.2963

Cited by 8 publications

(5 citation statements)

References 44 publications

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“…Many furanone-containing compounds are known to show interesting biological activities [24] such as antibacterial, cytotoxic, antimicrobial, antibiotic, and antitumor activities. Prior work has shown the need for expensive transition metal catalysts for each transformation desired, posing potential drawbacks for the synthesis of these functionalized alkylidenefuranones [25]. The researchers conducted studies on the functional group tolerability for this transformation using this MOF catalyst with a wide substrate scope (Scheme 14a-i).…”

Section: Mof Recyclable Catalystsmentioning

confidence: 99%

Recyclable Catalysts for Alkyne Functionalization

2021

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In this review, we present an assessment of recent advances in alkyne functionalization reactions, classified according to different classes of recyclable catalysts. In this work, we have incorporated and reviewed the activity and selectivity of recyclable catalytic systems such as polysiloxane-encapsulated novel metal nanoparticle-based catalysts, silica–copper-supported nanocatalysts, graphitic carbon-supported nanocatalysts, metal organic framework (MOF) catalysts, porous organic framework (POP) catalysts, bio-material-supported catalysts, and metal/solvent free recyclable catalysts. In addition, several alkyne functionalization reactions have been elucidated to demonstrate the success and efficiency of recyclable catalysts. In addition, this review also provides the fundamental knowledge required for utilization of green catalysts, which can combine the advantageous features of both homogeneous (catalyst modulation) and heterogeneous (catalyst recycling) catalysis.

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Section: Mof Recyclable Catalystsmentioning

confidence: 99%

Recyclable Catalysts for Alkyne Functionalization

2021

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“…The 1 H NMR monitoring data for the other arylidenes and parent compounds 1a,b are given in Section IV in the ESI. As can be seen from Figure 2, only Z/E-isomerization is observed under UV light (365 nm), as follows from the downfield shift of the arylidene proton signal (by 5.94 ppm for the Z-isomer and by 6.95 ppm for the E-isomer), 42 and conversely, the signals of methoxy groups are shifted upfield. In the case of UV irradiation (365 nm), the content of the E-isomer in PSS reaches 45% (Figure 2), whereas it increases to 58% under solar irradiation (Figure S26).…”

Section: ■ Results and Discussionmentioning

confidence: 86%

“…Figure shows the structurally valuable NOESY correlations observed for the Z -isomer of the arylidene moiety. In addition, it should be noted that the signal of the arylidene proton in the Z -isomer is usually observed in the range of 5.9–6.5 ppm, while for the E -isomer, it is shifted downfield and appears at ∼7 ppm …”

Section: Resultsmentioning

confidence: 99%

“…In addition, it should be noted that the signal of the arylidene proton in the Z-isomer is usually observed in the range of 5.9−6.5 ppm, while for the E-isomer, it is shifted downfield and appears at ∼7 ppm. 42 The photosensitivity of all of the new compounds was studied before estimating their antiproliferative activity by UV−visible spectroscopy and NMR monitoring under irradiation of their solutions with UV and sunlight (the experiments were carried out at the latitude of Moscow at room temperature in April 2022, UV index − 3-4). It was found that the photochemical transformations of arylidenes strongly depended on the nature of ring B. Arylidenes 2a-j containing a 4-methoxyphenyl residue as ring B, in contrast to 1a, undergo only Z/E-isomerization upon exposure to UV or sunlight (Table 1).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Photostability and Antiproliferative Activity of Furan Analogues of Combretastatin A-4

Scherbakov¹,

Zakharov

Mikhaevich³

et al. 2022

Chem. Res. Toxicol.

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Cancer is one of the most serious health problems that usually require heavy medical treatment. It is important to ensure that no additional burden is placed on patients due to the modes of administration and/or poor quality of pharmaceuticals. In this regard, understanding, quantifying, and improving the photostability (resistance to UV light or sunlight) of drugs is among the important elements that can improve the patient's quality of life. In this work, the photochemical properties of a wide range of furanone analogues of combretastatin A-4 and their antiproliferative activity against A-431 epidermoid carcinoma cells were studied in a search for compounds with improved photostability and antiproliferative activity. It was found that the incorporation of an arylidene moiety led to a significant improvement in photostability, while the antiproliferative activity strongly depends on the nature of the aryl residue in the arylidene moiety. The high photostability of arylidenes was achieved due to the delocalization of the central double bond of the 1,3,5-hexatriene system, which limited the 6π-electrocyclization. The best results in terms of antiproliferative activity were obtained for thiophene arylidene (IC 50 = 0.6 μM) and 3,4-diarylfuran (IC 50 = 0.047 μM). The obtained results address the lack of data available now in scientific literature on the photodegradation of combretastatin A-4 analogues and should be taken into account in studies of the side effects of pharmaceuticals based on them.

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“…The authors have cited additional references within the Supporting Information. [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31]…”

Section: Supporting Informationmentioning

confidence: 99%

1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene (TBD): An Organocatalyst for Rapid Access to 3‐Hydroxyisoindolin‐1‐ones

Lan,

Auclair

2024

Eur J Org Chem

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The readily available organocatalyst 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD) was used for the rapid synthesis of 3‐hydroxyisoindolin‐1‐ones from 3‐alkylidenephthalides. The transformation occurs at room temperature and requires less solvent than traditional methods, providing a more sustainable synthetic option to access 3‐hydroxyisoindolin‐1‐ones with broad scope. Elaboration of the products to diverse scaffolds as well as synthesis of biologically active compounds are demonstrated.

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CuI/amino acid catalysis in coupling and cyclization of β‐bromo‐α,β‐unsaturated carboxylic acids with terminal alkynes leading to alkylidenefuranones

Cited by 8 publications

References 44 publications

Recyclable Catalysts for Alkyne Functionalization

Recyclable Catalysts for Alkyne Functionalization

Photostability and Antiproliferative Activity of Furan Analogues of Combretastatin A-4

1,5,7‐Triazabicyclo[4.4.0]dec‐5‐ene (TBD): An Organocatalyst for Rapid Access to 3‐Hydroxyisoindolin‐1‐ones

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