Synthesis and structure-activity relations of 5H,11H-[2]benzopyrano[4,3-g][1]benzopyran-9-carboxylic acids

Jp, Devlin; Freter, Kurt; Pb, Stewart

doi:10.1021/jm00212a004

Cited by 9 publications

(2 citation statements)

References 6 publications

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“…4-(4-0 xo-4H-[ 1 ]benzopy ran-3-y 1) -2,4-dioxobutanoic Acid and Its Ethyl Ester (4a, R5 = H, Et). A solution of 3a (1.8 g, 9.5 mmol) in anhydrous THF (20 mL) was added dropwise to a stirred suspension of NaH (57% oil suspension, 1.17 g, 29 mmol) in THF (30 mL) and the mixture was refluxed under N2 for 15 min. A solution of diethyl oxalate (1.39 g, 9.5 mmol) in THF (20 mL) was added dropwise at 60 °C and a gentle reflux was continued for 15 h.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and antiallergic properties of some 4H,5H-pyrano[3,2-c][1]benzopyran-4-one, 4H,5H-[1]benzothiopyrano[4,3-b]pyran-4-one, and 1,4-dihydro-5H-[1]benzothiopyrano[4,3-b]pyridin-4-one derivatives

Philipp¹,

Jirkovsky²,

Martel³

1980

J. Med. Chem.

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A series of novel 2-carboxylic acids of the title ring systems has been synthesized from the corresponding 3-acetyl-4H-[1]benzopyran-4-one and benzothiopyran-4-one. These acids were examined for their ability to inhibit the rat passive cutaneous anaphylaxis; the pyridinone carboxylic acids 6 displayed a higher degree of iv and ip anaphylactic activities than their pyranone analogues 5. The potassium salt 5a (R6 = K) was the only compound that exhibited a moderate oral activity.

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Section: Methodsmentioning

confidence: 99%

Synthesis and antiallergic properties of some 4H,5H-pyrano[3,2-c][1]benzopyran-4-one, 4H,5H-[1]benzothiopyrano[4,3-b]pyran-4-one, and 1,4-dihydro-5H-[1]benzothiopyrano[4,3-b]pyridin-4-one derivatives

Philipp¹,

Jirkovsky²,

Martel³

1980

J. Med. Chem.

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“…A new series of paeonol derivatives containing the 1,4-benzoxazinone and 1,2,3-triazole moieties were synthesized in five steps and the synthetic routine is shown in Scheme 1. Paeonol (1) was first selectively introduced nitro group by reacting with HNO 3 /H 2 SO 4 at the C-3 position to form compound 2, 29 which could be further converted to intermediate 3 by reduction with zinc powder in acetic acid. 30 After successfully synthesizing compound 3 via amidation and cyclization reaction, intermediate 4 containing the 1,4-benzoxazinone moiety was obtained.…”

Section: Chemistrymentioning

confidence: 99%

Design, synthesis, and antitumor activity of novel paeonol derivatives containing the 1,4-benzoxazinone and 1,2,3-triazole moieties

Yang

Shi

Guo

et al. 2019

Journal of Chemical Research

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A new series of paeonol derivatives containing the 1,4-benzoxazinone and 1,2,3-triazole moieties were synthesized and evaluated for their cytotoxicity in vitro against human non-small cell lung cancer NCI-H1299 cells and human cervical carcinoma HeLa cells. Among them, compared with that of paeonol, compounds 8-acetyl-4-{[(1-(5-chloro-2-nitrophenyl)-1 H-1,2,3-triazol-4-yl]methyl}-5-methoxy-2 H-1,4-benzoxazin-3(4 H)-one, 8-acetyl-4-[(1-mesityl-1 H-1,2,3-triazol-4-yl)methyl]-5-methoxy-2 H-1,4-benzoxazin-3(4 H)-one, and 8-acetyl-5-methoxy-4-{[(1-(naphthalen-1-yl)-1 H-1,2,3-triazol-4-yl]methyl}-2 H-1,4-benzoxazin-3(4 H)-one exhibited significant inhibitory activity toward the human non-small cell lung cancer NCI-H1299 cells (IC50 = 13.36 ± 0.003, 19.75 ± 0.3, 15.79 ± 0.05 μg mL−1). The last compound also exhibited significant inhibitory activity toward the human cervical carcinoma HeLa cells (IC50 = 19.73 ± 1.0 μg mL−1).

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Wessely‐Moser Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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The Wessely–Moser rearrangement is an acid‐ or a base‐promoted isomerization of flavones or flavonoids having an unprotected hydroxy group at position 5, involving an opening of the flavone heterocycle and ring closure of the β‐diketone intermediate. It has been reported that the Wessely–Moser rearrangement also occurs for natural products containing a flavone component. In addition, the Wessely–Moser rearrangement has also been observed during the acidic hydrolysis of glycosides with flavone as an aglycone and the acidic demethylation of flavones and xanthones. It has also been observed that the 5‐hydroxy group is necessary for the occurrence of Wessely–Moser rearrangement. This rearrangement has certain applications in organic synthesis and is useful for the structural rationalization of the natural products.

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Synthesis and structure-activity relations of 5H,11H-[2]benzopyrano[4,3-g][1]benzopyran-9-carboxylic acids

Cited by 9 publications

References 6 publications

Synthesis and antiallergic properties of some 4H,5H-pyrano[3,2-c][1]benzopyran-4-one, 4H,5H-[1]benzothiopyrano[4,3-b]pyran-4-one, and 1,4-dihydro-5H-[1]benzothiopyrano[4,3-b]pyridin-4-one derivatives

Synthesis and antiallergic properties of some 4H,5H-pyrano[3,2-c][1]benzopyran-4-one, 4H,5H-[1]benzothiopyrano[4,3-b]pyran-4-one, and 1,4-dihydro-5H-[1]benzothiopyrano[4,3-b]pyridin-4-one derivatives

Design, synthesis, and antitumor activity of novel paeonol derivatives containing the 1,4-benzoxazinone and 1,2,3-triazole moieties

Wessely‐Moser Rearrangement

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