Green chemistry approach to the synthesis of 3-substituted-quinazolin-4(3H)-ones and 2-methyl-3-substituted-quinazolin-4(3H)-ones and biological evaluation

Figures & data

Figure 1. The quinazolinone structures core ( 12).

Figure 2. Some marketed anticancer drugs with quinazoline moiety.

Figure 3. Synthetic path for synthesis of desired derivatives.

Figure 4. A proposed mechanism for synthesis of 3-substituted quinazolin-4(3H)-ones.

Figure 5. A proposed mechanism for benzoxazinone synthesis.

Figure 6. A plausible mechanism of 2-methyl-3-substituted-quinazolin-4(3H)-ones formation.

Table 1. Calculated IC₅₀ values [μM] for two affected cancer cell lines and two non-cancerous cell lines as control for synthesized compounds.

Comp.	BJ	MDCK-1	CaCo-2	Hut-78
1	>100	>100	59.3 ± 10.6	51.4 ± 5.1
2	>100	>100	>100	48.3 ± 15.9
3	>100	>100	>100	70.0 ± 25.8
4	>100	>100	>100	>100
5	>100	>100	>100	72.2 ± 17.4
6	>100	>100	>100	100
7	>100	>100	>100	>100
8	>100	>100	>100	70.9 ± 23.1
9	>100	>100	>100	100
10	>100	>100	>100	>100

Note: Bold values are used to differentiate those instances where the substance had an inhibitory effect.

Tiwary, B.K.; Pradhan, K.; Nanda, A.K.; Chakraborty, R. J. Chem. Biol. Therap. 2015, 1, 1–7.

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