Preparation of Benzoyloxy Benzophenone Derivatives and Their Inhibitory Effects of ICAM-1 Expression

Kwon, Eun-Mi; Kim, CheolGi; Goh, Ah-Ra; Park, Jin-Seu; Jun, Jong‐Gab

doi:10.5012/bkcs.2012.33.6.1939

Cited by 15 publications

(10 citation statements)

References 12 publications

(3 reference statements)

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“…To further demonstrate the practicality of the photocatalytic oxidation, four one-pot sequential organic syntheses starting from benzyl alcohol or 1-phenethylalcohols were performed ( Scheme 3 b). The crude alcohol underwent smooth hydrazidation ( 1a → 5a ) [ 49 ], esterification ( 1a → 5b ) [ 50 ], oximation ( 1a → 5c ) [ 51 ], and Claisen–Schmidt condensation ( 1a → 5d ) [ 52 ] in the desired yields.…”

Section: Resultsmentioning

confidence: 99%

External Catalyst- and Additive-Free Photo-Oxidation of Aromatic Alcohols to Carboxylic Acids or Ketones Using Air/O2

Luo

et al. 2023

Molecules

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We present an environment-friendly and highly efficient method for the oxidation of aromatic alcohols to carboxylic acids or ketones in air via light irradiation under external catalyst-, additive-, and base-free conditions. The photoreaction system exhibits a wide substrate scope and the potential for large-scale applications. Most of the desired products are easily obtained via recrystallization and separation from low-boiling reaction medium acetone in good yields, and the products can be subsequent directly transformed without further purification.

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Section: Resultsmentioning

confidence: 99%

External Catalyst- and Additive-Free Photo-Oxidation of Aromatic Alcohols to Carboxylic Acids or Ketones Using Air/O2

Luo

et al. 2023

Molecules

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“…Two key coumarin precursors, 8‐acetyl‐7‐hydroxy‐4‐methylcoumarin 4 and 3‐acetylcoumarin 6 , were required. Precursor 4 was synthesized according to Pechmann reaction by reacting resorcinol 1 and ethyl acetoacetate in the presence of acid catalyst to give 7‐hydroxy‐4‐methylcoumarin 2 , which upon acetylation and Fries rearrangement gave 8‐acetyl‐7‐hydroxy‐4‐methylcoumarin 4 [ 38–40 ] (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of new coumarin derivatives as cytotoxic agents

Ragab

Eissa

Fahim

et al. 2021

Archiv der Pharmazie

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New coumarin derivatives 9a–f, 10a–e, and 11a–f were synthesized and evaluated for their cytotoxic activity against a human breast cancer cell line (MCF‐7). All compounds exhibited good activity in the nanomolar range, using doxorubicin and erlotinib as positive controls. The most active compound 9d with IC50 of 21 nM was tested against the HCT‐116, HepG‐2, A549, and SGC‐7901 cell lines, with IC50 values of 0.021, 0.170, 0.028, and 0.11 µM, respectively. Compound 9d was further investigated for its ability to suppress the expression of epidermal growth factor receptor (EGFR). Compound 9d decreased the concentration of EGFR by 87%, using erlotinib as a positive control. A docking study revealed similar or higher scores than for erlotinib and similar binding poses providing interactions with the hinge region of the tyrosine kinase (TK). Besides the effect on expression, this in silico investigation predicts the possibility of direct binding between the new coumarin derivatives and the EGFR TK. Moreover, computational calculation for ADME properties for the most active compounds 9d, 9e, 10c, and 11c revealed the expected high gastrointestinal tract absorption, moderate water solubility with no central nervous system toxicity, and druglikeness.

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“…In order to prove such an operational superiority, several classical chemical processes were conducted. The crude reaction mixture could smoothly perform esterification (1a → 3a), 59 Friedel-crafts acylation (1a → 3b), 60 and cyanation (1a → 3c) 61 in good to excellent yield.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Green and Efficient: Oxidation of Aldehydes to Carboxylic Acids and Acid Anhydrides with Air

Liu

Xie

et al. 2018

ACS Sustainable Chem. Eng.

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An economic, safe, practical, and environmentally benign protocol for the oxidation of aldehydes to carboxylic acids and acid anhydrides with ambient air as the sole oxidant was developed. This oxidation is operationally simple and external catalyst-, initiator-, and base-free, with outstanding functional group tolerance (moisture-, acid-, base-, and oxidant-sensitive groups). It also provides a practical protocol for large scale synthesis (>100 g), late-stage modification of polyfunctional compounds, and one-pot sequential transformation starting from aldehydes.

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Preparation of Benzoyloxy Benzophenone Derivatives and Their Inhibitory Effects of ICAM-1 Expression

Cited by 15 publications

References 12 publications

External Catalyst- and Additive-Free Photo-Oxidation of Aromatic Alcohols to Carboxylic Acids or Ketones Using Air/O2

External Catalyst- and Additive-Free Photo-Oxidation of Aromatic Alcohols to Carboxylic Acids or Ketones Using Air/O2

Synthesis and biological evaluation of new coumarin derivatives as cytotoxic agents

Green and Efficient: Oxidation of Aldehydes to Carboxylic Acids and Acid Anhydrides with Air

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