1980
DOI: 10.1021/jm00186a016
|View full text |Cite
|
Sign up to set email alerts
|

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

Abstract: 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.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
4
1

Citation Types

0
6
0

Year Published

1981
1981
2023
2023

Publication Types

Select...
7
1

Relationship

0
8

Authors

Journals

citations
Cited by 29 publications
(6 citation statements)
references
References 7 publications
0
6
0
Order By: Relevance
“…Similarly, this compound provides a different class of ethers as opposed to THAs 62 , 70 , 73 , and 89 – 93 , which contain alkyl ether substituents. Sulfoxide 101 and sulfone 102 were oxidized from THA 92 using aqueous hydrogen peroxide at 40 °C and m -CPBA in CHCl 3 at 0 °C, respectively . Finally, a small set of THAs was prepared in which the 2-position possessed a difluoromethylene unit.…”
Section: Resultsmentioning
confidence: 99%
“…Similarly, this compound provides a different class of ethers as opposed to THAs 62 , 70 , 73 , and 89 – 93 , which contain alkyl ether substituents. Sulfoxide 101 and sulfone 102 were oxidized from THA 92 using aqueous hydrogen peroxide at 40 °C and m -CPBA in CHCl 3 at 0 °C, respectively . Finally, a small set of THAs was prepared in which the 2-position possessed a difluoromethylene unit.…”
Section: Resultsmentioning
confidence: 99%
“…For example, the pyridinone carboxylic acid 1a displayed a high degree of antianaphylactic activity (Figure ). Moreover, the benzothiopyran derivative 1b was a very potent full agonist at dopamine D2 receptors and a partial agonist at dopamine D3 receptors . In addition, compound 1c showed a 192-fold more powerful acetylcholinesterase (AChE) inhibitory activity than its oxygen-containing analogues, rivastigmine, thereby possessing great potential for the treatment of Alzheimer’s disease .…”
Section: Introductionmentioning
confidence: 99%
“…Sulfur-containing heterocycles, such as thiochromanone, thioflavanone, thiochromone, thioflavone, and their derivatives ( Scheme 1 ) have been reported to display rich biological activities. For example, thioflavonoids, which are the sulfur analogues of flavonoids [ 12 , 13 , 14 , 15 , 16 , 17 , 18 ], display many biological activities, such as antimicrobial, antioxidant, inhibiting nitric oxide production, and antifungal et al [ 3 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ] Thiochroman-4-ones have been reported to display antifungal activities. Some thiochroman-4-one derivatives have been studied and shown to display the cytotoxic effect on tumor cells in vitro [ 28 ].…”
Section: Introductionmentioning
confidence: 99%
“…They are key precursors for certain bioactive antiproliferative agents [ 31 ]. Known as an important class of heterocycles [ 3 , 4 ], they are vital precursors of bioactive thiochroman-4-one 1,1-dioxanes, as well as benzothiazepins [ 20 , 21 , 32 , 33 , 34 , 35 , 36 , 37 , 38 ].…”
Section: Introductionmentioning
confidence: 99%