Synthesis of 5-aryl-6-cinnamoyl-7-methyl-flavanones as novel antioxidants and antihyperlipidemics

Figures & data

Figure 1.  Hybridization of chalcone and flavanone to Cinamoyl flavanone.

Table 1.  Synthesis of 5-aryl-6-cinnamoyl-7-methyl-flavanone derivatives (25–48) by cyclization of different cinnamoyl chalcones.

Entry	Ring A	Ring B	Product	Time (h)	Isolated yield (%)	cLogP^a
1	Phenyl	4-chloro phenyl	25	40	94	8.15
2	Phenyl	Phenyl	26	40	92	6.92
3	Phenyl	4-fluoro phenyl	27	41	90	7.04
4	Phenyl	4-bromo phenyl	28	40	93	8.32
5	Phenyl	4-benzloxy phenyl	29	40	94	9.45
6	Phenyl	3-chloro phenyl	30	42	93	8.15
7	Phenyl	3,4-dimethoxy phenyl	31	41	92	6.51
8	Phenyl	1-naphthyl	32	40	90	9.29
9	Phenyl	2-naphthyl	33	41	94	9.29
10	4-bromo phenyl	Phenyl	34	42	89	7.62
11	4-bromo phenyl	4-bromo phenyl	35	43	90	9.02
12	4-bromo phenyl	4-fluoro phenyl	36	43	92	7.74
13	4-bromo phenyl	4-chloro phenyl	37	42	92	8.85
14	4-bromo phenyl	4-benzloxy phenyl	38	41	88	10.15
15	4-bromo phenyl	4-methoxy phenyl	39	40	91	7.41
16	4-Benzloxy phenyl	Phenyl	40	44	90	8.19
17	4-benzloxy phenyl	4-bromo phenyl	41	41	93	9.58
18	4-benzloxy phenyl	4-chloro phenyl	42	41	89	9.41
19	4-Benzloxy phenyl	4-benzloxy phenyl	43	42	92	10.72
20	4-Benzloxy phenyl	4-methoxy phenyl	44	41	91	7.98
21	4-benzloxy phenyl	3,4-dimethoxy phenyl	45	43	93	7.77
22	4-chloro phenyl	2-chloro phenyl	46	42	93	8.79
23	4-chloro phenyl	1-naphthyl	47	40	90	9.90
24	4-chloro phenyl	2-naphthyl	48	41	94	9.90

^acLogP was determined by OSIRIS Property Explorer Programme, available at htpp://www.organic-chemistry.org/prog/peo/.

Scheme 1.  Synthesis of 5-phenyl-6-cinnamoyl-7-methyl-flavanones (25–48).

Figure 2.  Structure of the compound no. 25.

Figure 3.  Showing the effect of compounds 25–48 at 200 µg/mL on superoxide ion (n mole formazone formed/min), hydroxyl radicals (n mole MDA formed/h) and lipid peroxidation in microsomes (n mole MDA formed/mg protein).

Figure 4.  Total cholesterol lowering activity of compounds 25–48 and the standard drug gemfibrozil.

Figure 5.  Phospholipid lowering activity of compounds 25–48 and the standard drug gemfibrozil.

Figure 6.  Triglyceride lowering activity of compounds 25–48 and the standard drug gemfibrozil.

Figure 7.  Protein lowering activity of compounds 25–48 and the standard drug gemfibrozil.