Antagonists of slow reacting substance of anaphylaxis. Synthesis of a series of chromone-2-carboxylic acids

Appleton, R. A.; Bantick, John R.; Chamberlain, T. R.; Hardern, David N.; Lee, T B; Pratt, A.D.

doi:10.1021/jm00213a012

Cited by 55 publications

(22 citation statements)

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“…Next, the synthesis of the 2‐substituted amino‐chromones ( IV ) was undertaken whereby 2′‐hydroxyacetophenone ( 10 ) was first subjected to Kostanecki conditions to give ethyl ester 11 , which was then nitrated to give 6‐nitro‐chromone 12 in 90% yield over the two steps (Scheme ) . A Claisen condensation between acetophenone 10 and ethyl cyclopropane‐carboxylate then afforded chromone 13 , which after nitration gave cyclopropyl‐substituted nitro‐chromone 14 in 65% yield over the two steps.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalised Chromonyl‐pyrimidines and Their Potential as Antimycobacterial Agents

et al. 2020

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Drug-resistant strains of Mycobacterium tuberculosis are on the rise and have resulted in an urgent need to develop new tuberculosis (TB) drugs. Herein, the development of chromonylpyrimidines as a new TB drug scaffold is presented. A library of eleven chromonyl-pyrimidines was synthesised, from which lead compound 6-((2-amino-6-methylpyrimidin-4-yl)amino)-3benzoyl-2-phenyl-4H-chromen-4-one (MIC = 36 μM against M. tuberculosis) was identified. A second-generation library of seven aryl-substituted chromonyl-pyrimidines was then prepared, with six chromonyl-pyrimidines exhibiting an improved M. tuberculosis growth inhibition (MIC = 12.5 μM). From this work, the potential of chromonyl-pyrimidines as therapeutics for TB is demonstrated.[a] Dr.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Functionalised Chromonyl‐pyrimidines and Their Potential as Antimycobacterial Agents

et al. 2020

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“…As starting materials, 2'-hydroxyacetophenone (3a) is commercially available and 5'-benzyl-2'-hydroxyacetophenone (3b) was readily prepared by the reaction of 4-benzylphenol with acetic anhydride in the presence of boron trifluoride-acetic acid complex (Appleton et al, 1977). Claisen condensation of acetophenones (3a~b) with diethyl oxalate using NaH as a base afforded 1,3-diketo esters 4a~b.…”

Section: Resultsmentioning

confidence: 99%

Chromone and chromanone derivatives as strand transfer inhibitors of HIV-1 integrase

et al. 2008

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HIV-1 integrase catalyzes terminal cleavage at the 3' end of the proviral DNA, removing a pair of bases and causing strand transfer by joining the 3' end to 5'-phosphates in the target DNA. Several aryl 1,3-diketo acids that can inhibit the strand transfer reaction of HIV-1 IN have been identified. Here we synthesized a new series of compounds with a chromone or chromanone ring as conformationally constrained scaffolds of 1,3-diketo acids, and then tested their ability to inhibit HIV-1 IN-mediated strand transfer. All compounds moderately inhibited HIV-1 IN activity, indicating that the conformational restriction of one keto group into a chromone or chromanone ring decreases inhibition of the HIV-1 IN strand transfer.

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“…Application of FPL-55712, a leukotriene antagonist – sodium 7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-2-hydroxypropoxy]-4-oxo-8-propyl- 4H-1-benzopyran-2-carboxylate [23]with indomethacin reduced the muscle tone and allowed a steady level to be obtained [22]. Therefore, we performed experiments in the presence of FPL-55712 (10 –6 M ) and indomethacin (10 –6 M ), as in previous studies [20, 22, 24].…”

Section: Methodsmentioning

confidence: 99%

Histamine-Induced Increase in Isometric Tension of Smooth Muscle Is Mediated by Local Vagus Nerve in Human Bronchus

Aizawa

Inoue²,

Miyazaki³

et al. 2000

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Background: The vagus nerve is reported to play an important role in the regulation of airway responsiveness. Objective: In the present study, we investigated the role of the local vagus nerve in the changes in isometric tension of smooth muscle induced by histamine in the human airway. Methods: Eight human lung tissue specimens were obtained at thoracic surgery, and 24 bronchial smooth muscle strips were used for isometric tension recording. The changes in isometric tension were induced by histamine in the presence or absence of physostigmine (10^–6 M), atropine (10^–6 M), and/or tetrodotoxin (10^–6 M). Results: We found that: (1) histamine induced a dose-dependent increase in the isometric tension in human bronchial smooth muscle; (2) physostigmine (10^–6 M) significantly potentiated the amplitude of the histamine-induced increase in isometric tension; (3) atropine (10^–6 M) significantly suppressed the histamine-induced increase in isometric tension; (4) tetrodotoxin (10^–6 M), did not affect the histamine-induced increase in isometric tension of smooth muscle, and (5) in the presence of tetrodotoxin, atropine significantly suppressed the histamine-induced increase in isometric tension. Conclusion: These findings suggest that the histamine-induced increase in isometric tension is mediated partly by acetylcholine, presumably released by the direct action of histamine on the vagus efferent nerve terminals without the central reflex via vagus nerve.

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Antagonists of slow reacting substance of anaphylaxis. Synthesis of a series of chromone-2-carboxylic acids

Cited by 55 publications

References 1 publication

Synthesis of Functionalised Chromonyl‐pyrimidines and Their Potential as Antimycobacterial Agents

Synthesis of Functionalised Chromonyl‐pyrimidines and Their Potential as Antimycobacterial Agents

Chromone and chromanone derivatives as strand transfer inhibitors of HIV-1 integrase

Histamine-Induced Increase in Isometric Tension of Smooth Muscle Is Mediated by Local Vagus Nerve in Human Bronchus

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