3-Formylchromone derivatives

The 6-substituted 3-formylchromone derivatives (FC1-8) screened for their tumor-specific cytotoxic potentials are shown in Fig. 7. Their CC50 values for the four tumor cell fines and three normal cells are summarized in Table 3. Cytotoxic data for the related chromone derivatives (FC9-13),... 

Fig. 13 Structures of 3-formylchromone derivatives used in this study...

Fig. 14 The most stable conformation of each 3-formylchromone derivative used...

Table 7 CC50 and chemical descriptors for 3-formylchromone derivatives...

Fig. 15 Relationship between CC50 and each chemical descriptor of 3-formylchromone derivatives against HSG (A-1 to A-8) and HL-60 cells (B-1 to B-5)...

In conclusion, there was the best relationship between CC50 and descriptors in HSG cells. This cell line may provide the opportunity to search more active 3-formylchromone derivatives using QSAR with the concept of absolute hardness. 

Imino derivatives 61 were obtained directly from 3-formylchromone [36] 59 and creatinine [37] 60, with DM SO as solvent and boric acid as catalyst, and with micro-wave irradiation and classical heating (Tab. 8.4). The authors have also investigated the preparation of the 2-thioxo-5-imidazolidin-4-ones 63 from thiohydantoin 62 in... 

Treatment of 3-formylchromone (95) and 4-amino-3-phenyl-5-triazolinethione (96) with KOH and TBAHSO4 in benzene also gave a bicyclic derivative (97) (Equation (34)) <87SC1851>. 4-Amino-3-triazolinethione (98) reacts with the diketoacetylene (99) in a similar manner to give (100) (Equation (35)) <92CHE222>. 

This article is a summary of our recent extensive study of tumor specificity (TS) and the type of cell death induced by N-containing heterocycles such as 4-trifluoromethylimidazole [22] and phenoxazine derivatives [23], by O-containing heterocycles such as 3-formylchromone [24] and coumarin derivatives [25,26], and by other compounds such as vitamin K2 and prenyl-alcohols [27]. 

Fig. 7 Chemical structures and calculated logP values of 3-formylchromone and coumarin derivatives (FC1-16)...

The results show that all the 6-substituted 3-formylchromones, and the 6-nitro-substituted derivative FC5, exhibit a more potent cytotoxicity against tumor cell lines than the parent 3-formylchromone (FC1). However, there was no clear-cut correlation between the chemical structure of the com-... 

The third chapter, Quantitative Structure-Cytotoxicity Relationship of Bioactive Heterocycles by the Semi-empirical Molecular Orbital Method with the Concept of Absolute Hardness by Mariko Ishihara, Hiroshi Sakagami, Masami Kawase, and Noboru Motohashi, presents the relationship between the cytotoxicity (defined as 50% cytotoxic concentration) of heterocycles such as phenoxazine, 5-trifluoromethyloxazoles, O-heterocycles such as 3-formylchromone and coumarins, and vitamin K2 derivatives against some tumor cell lines and 15 chemical descriptors. The results suggest the importance of selecting the most appropriate descriptors for each cell type and compound. The review is of interest as it represents the relationship of the molecular structures with the cytotoxic activity of these heterocycles. 

The reactions of 3-formylchromones, e.g. (186), with various ort/io-substituted anilines (Y = S, O, or NH) provide a high-yielding route to the fused benzo-pyrano-compounds (187)." Various substituted 2,3-dihydro-l,4-benzox-azepin-5(4H )-one-7-acetic acid esters were prepared by the Schmidt reactions of chromanone derivatives." ... 

Under MWI, pyrimidine derivatives 658 and 3-formylchromone (659) were reacted to give pyrimido[l,2-a]pyrimidines 660 in >95% yields within 20min. Under conventional heating in ethanol for 4h, compounds 660 were obtained in 60-80% yields. Similarly, 658 were reacted with diethyl ethoxymethylenemalonate under MWI within 10 min to give 661 in yields exceeding 95%, compared to 40-60% produced after 8h reflux in ethanol (Scheme 128) (01T1785). 

Lazarenkow, A., Nawrot-Modranka, J., Brzezinska, E., Krajewska, U. and Rozalski, M. 2012. Synthesis, preliminary cytotoxicity evaluation of new 3-formylchromone hydrazones and phosphorohydrazone derivatives of coumarin and chromone. Med. Chem. Res. 21(8) 1861-1868. 

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