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Journal ArticleDOI

Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde

01 Nov 2008-Journal of Heterocyclic Chemistry (Wiley)-Vol. 45, Iss: 6, pp 1529-1547
TL;DR: The chemistry and application of the title aldehyde and some simple derivatives thereof are reviewed in this paper, where the authors propose a simple derivative of the aldehydes, which they call simple aldeheeds.
About: This article is published in Journal of Heterocyclic Chemistry.The article was published on 2008-11-01. It has received 42 citations till now. The article focuses on the topics: Benzopyran.
Citations
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Journal ArticleDOI
TL;DR: Under mild acidic conditions, the tricyclic benzopyrones rearrange to provide highly substituted and electron-poor chromone-fused dienes in good yields.

11 citations

Journal ArticleDOI
TL;DR: Pyridoxal undergoes oxa-Michael initiated ring closure with 2-(trifluoromethyl)chromones giving 11a,13-dihydro-6 H-1-benzopyrano[3′,2′:6,7]oxepino[3,4- c ]pyridin-6-ones and 6 H,11a H -1-bensopyranos[3'',2'':5,6]pyrano [2,3]-pyride[2,

9 citations

Journal ArticleDOI
TL;DR: In this paper, the reaction of 6-methylchromone-3-carbonitrile (1) with malonitrile dimer gave the unexpected (3-cyano-9-methyl-5-oxo-1,5-dihydro-2H-chromeno[4,3- b ]pyridin-2-ylidene) propanedinitrile.

9 citations

Journal ArticleDOI
TL;DR: In this paper, 3-acyl-chromones with heterocyclic ketene aminals (HKAs) were used as selective phosphatase inhibitors, and the product distribution depends on the type of acyl group located at the 3-position of the chromone and on the size of the heterocycyclic moiety of the HKAs.

9 citations

References
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Journal ArticleDOI
TL;DR: A highly efficient, mild, and simple protocol is presented for the oxidation of aldehydes to carboxylic acids utilizing Oxone as the sole oxidant.

412 citations

Journal ArticleDOI
TL;DR: Quantitative structure-activity relationship (QSAR) analysis showed that, besides the essential pharmacophore (-NHCONHOH), hydrophobicity, molecular size/polarizability, and the presence of an oxygen-containing group at the ortho position (I) were important determinants for the antitumor activities.
Abstract: Thirty Schiff bases of hydroxysemicarbazide (Ar−CHNNHCONHOH) have been synthesized and tested against L1210 murine leukemia cells. The IC50 values were found to be in a range from 2.7 × 10-6 to 9.4 × 10-4 M. A total of 17 out of the 30 compounds had higher inhibitory activities than hydroxyurea (an anticancer drug currently used for the treatment of melanoma, leukemia, and ovarian cancer) against L1210 cells. Six compounds with IC50 values in micromolar range were 11- to 30-fold more potent than hydroxyurea (IC50 = 8.2 × 10-5 M). The partition coefficient (log P) and ionization constants (pKa) of a model compound [1-(3-trifluoromethylbenzylidene)-4-hydroxysemicarbazide, 1] were measured by the shake-flask method, and the measured log P was used to derive Hansch−Fujita π constant of −CHNNHCONHOH. On the basis of the newly derived π and those of other moieties, the partition coefficients (SlogP) of the other 29 compounds were calculated by the summation of π values. Quantitative structure−activity relations...

257 citations

Journal ArticleDOI
TL;DR: By the application of the Vilsmeier-Haack reaction to various o-hydroxyacetophenone derivatives, 4-oxo-4H-1-benzopyran-3-carboxaldehydes were synthesized in one step as discussed by the authors.

175 citations

Journal ArticleDOI
TL;DR: In this paper, the condensation reaction of 4-oxo-(4H)-1-benzopyran-3-carbaldehydes and of aromatic aldehydes with 3-methyl-1-phenylpyrazolin-5-4H-one were carried out in an ionic liquid, ethylammonium nitrate, at room temperature in shorter times with higher yields of 78−92 and 70−75%, respectively, than found using conventional procedures.

114 citations

Journal ArticleDOI
TL;DR: The compounds displayed promising anticancer activity under these test systems and shall serve as useful 'leads' for further design.

88 citations