Chemistry and application of 4-oxo-4H-1-benzopyran-3-carboxaldehyde
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.
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TL;DR: In this paper, a review describes the synthetic procedures for the preparation of arylideneacetophenones, aryylidenecycloalkanones, 2-arylidene-1-indanones and 2-ylidene -1-tetralones.
Abstract: This review describes the synthetic procedures for the preparation of arylideneacetophenones, arylidenecycloalkanones, 2-arylidene-1-indanones, 2-arylidene-1-tetralones, 2-arylidene-1-benzosuberones, aurones, 1-thioaurones, 3-arylidene-4-chromanones, 3-arylidene-1-thio-4-chromanones, 3-arylideneflavanones, 3-arylidene-1-thioflavanones, arylideneanilines, arylidenemalononitriles, diethylarylidenemalonates, ethylarylidenecyanoacetates, arylidenecyanoacetamides, 5-arylidene derivatives of barbituric and thiobarbituric acids, arylidene derivatives of Meldrum’s acid and arylidene derivatives of dimedone. Also, it demonstrates the reactivity of these arylidene derivatives in heterocyclic synthesis with emphasis on the most recent findings. Some of these are the α,β-enones, viz. aurones and 3-arylidene-4-chromanones belong to the natural products. The others are synthetic substances which are convenient and important intermediates for the synthesis of a variety of useful and novel heterocyclic systems.
12 citations
Cites background from "Chemistry and application of 4-oxo-..."
...Current literature showed that there has been an increasing trend towards the synthesis of heterocycles containing these two ring systems [172]....
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12 citations
TL;DR: In this article, the synthesis of 2-pyridone derivatives from different substituted amines and various 3-(E)-methyl 3-(4-oxo-4H-chromen-3-yl)acrylate derivatives was proposed and described.
11 citations
TL;DR: The three-component reaction involving chromone-3-carbaldehyde, 4-hydroxycoumarin and cyclohexyl isocyanide produces furocarbaldehyde derivatives as mentioned in this paper.
Abstract: The three-component reaction involving chromone-3-carbaldehyde, 4-hydroxycoumarin and cyclohexyl isocyanide produces furocoumarin and biscoumarin derivatives. Formation of the latter compound seems...
11 citations
References
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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
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
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
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
TL;DR: The compounds displayed promising anticancer activity under these test systems and shall serve as useful 'leads' for further design.
88 citations