Design, synthesis and biological potential of heterocyclic benzoxazole scaffolds as promising antimicrobial and anticancer agents

Kakkar, Saloni; Kumar, Sanjiv; Narasimhan, Balasubramanian; Lim, Siong Meng; Ramasamy, Kalavathy; Mani, Vasudevan; Shah, Syed Adnan Ali

doi:10.1186/s13065-018-0464-8

Table 2 Spectral data of synthesized compounds (1–20)

From: Design, synthesis and biological potential of heterocyclic benzoxazole scaffolds as promising antimicrobial and anticancer agents

Comp.	FT-IR (KBr cm⁻¹)									¹H NMR (δ, DMSO)	¹³C NMR (δ, DMSO)	MS: m/z
Comp.	C–H str. (Ar)	C=C str. (Ar)	N=CH str.	C–N str.	C–O–C str.	C–H str.	CONH str.	C–S str.	Other str.	¹H NMR (δ, DMSO)	¹³C NMR (δ, DMSO)	MS: m/z
1	3088	1477	1688	1262	1134	2834	1647	672	1350 NO₂ str.	7.63–8.57 (m, 8H, Ar–H), 7.33 (s, 1H, –CH of triazole), 4.76 (s, 2H, –N–CH₂), 7.95 (s, 1H, –NH)	164.9, 151.2, 147.9, 141.1, 139.4, 130.3, 125.7, 125.1, 124.4, 118.2, 113.3, 110.2, 52.3, 26.3	411
2	3133	1460	1685	1259	1194	2973	1649	687	1394 NO₂ str.	7.66–8.25 [m, 8H, Ar–H), 7.34 (s, 1H, –CH of triazole), 4.75 (s, 2H, –N–CH₂), 7.82 (s, 1H, –NH)]	165.2, 151.2, 144.4, 141.1, 124.6, 124.4, 118.3, 110.2, 52.3, 26.3	411
3	3138	1452	1662	1241	1178	2831	1618	674	–	6.88–7.59 (m, 8H, Ar–H), 4.26 (s, 2H, –CH₂S), 7.32 (s, 1H, –CH of triazole), 4.77 (s, 2H, –N–CH₂), 8.25 (s, 1H, –NH), 3.71 (s, 3H, –OCH₃)	164.1, 155.4, 151.1, 140.8, 131.4, 124.7, 124.5, 120.7, 118.2, 113.9, 110.2, 55.1, 52.2, 26.3	396
4	3072	1451	1697	1275	1177	2887	1647	671	1341 NO₂ str. 741 C–Cl str.	7.34–8.23 (m, 7H, Ar–H), 7.33 (s, 1H, –CH of triazole), 4.74 (s, 2H, –NCH₂), 8.21 (s, 1H, –NH)	165.7, 151.3, 143.5, 141.1, 124.6, 124.3, 123.7, 118.3, 110.2, 52.3, 26.3	445
5	3077	1499	1689	1277	1181	–	1653	676	743 C–Cl str.	7.35–7.66 (m, 6H, Ar–H), 7.34 (s, 1H, –CH of triazole), 4.73 (s, 2H, –N–CH₂), 8.09 (s, 1H, –NH)	165.3, 151.3, 141.1, 134.3, 130.6, 129.8, 124.9, 124.6, 124.3, 118.3, 110.2, 52.1, 26.3	469
6	3121	1499	1672	1272	1132	3067	1578	669	739 C–Cl str.	7.20–7.66 (m, 7H, Ar–H), 7.29 (s, 1H, –CH of triazole), 4.74 (s, 2H, –N–CH₂), 8.22 (s, 1H, –NH), 2.51 (s, 3H, –CH₃)	164.5, 151.2, 141.1, 136.9, 133.8, 130.3, 126.8, 124.6, 124.3, 118.3, 110.2, 51.9, 26.3	414
7	2986	1494	1674	1291	1185	2877	1601	742	622 C–Br str.	7.338–7.45 (m, 7H, Ar–H), 4.19 (s, 2H, –CH₂S), 7.332 (s, 1H, –CH of triazole), 4.76 (s, 2H, –N–CH₂), 8.24 (s, 1H, –NH), 2.51 (s, 3H, –CH₃)	164.3, 151.1, 141, 134.1, 132.8, 128.8, 124.6, 118.2, 110.2, 52.1, 17.4	459
8	3080	1449	1662	1237	1130	2965	1606	709	–	7.14–7.66 (m, 8H, Ar–H), 7.31 (s, 1H, –CH of triazole), 4.74 (s, 2H, –N–CH₂), 8.20 (s, 1H, –NH), 1.16 (s, 3H, –CH₃), 2.58 (s, 2H, –CH₂)	163.81, 151.3, 141.2, 136.1, 128.1, 124.6, 124.3, 118.3, 110.2, 52.2, 27.5, 15.5	394
9	3037	1486	1676	1293	1141	2993	1592	668	–	6.94–7.58 (m, 7H, Ar–H), 4.18 (s, 2H, –CH₂S), 7.31 (s, 1H, –CH of triazole), 4.77 (s, 2H, –NCH₂), 8.27 (s, 1H, –NH), 2.50 (s, 6H, (–CH₃)₂)	164.1, 151.1, 140.9, 134.6, 132.8, 131.4, 130.8, 126.5, 124.7, 124.4, 118.2, 110.2, 52.1, 26.3, 17.6	394
10	3121	1408	1675	1220	1137	2985	1641	675	743 C–Cl str.	7.15–7.58 (m, 8H, Ar–H), 7.34 (s, 1H, –CH of triazole), 4.74 (s, 2H, –NCH₂), 8.21 (s, 1H, –NH);	164.1, 151.3, 141.2, 125.6, 124.6, 124.3, 118.3, 110.2, 52.1, 26.4	400
11	3048	1491	1677	1289	1132	2879	1589	686	1235 C–F str.	7.19–7.65 (m, 8H, Ar–H), 7.31 (s, 1H, –CH of triazole), 4.75 (s, 2H, –NCH₂), 8.24 (s, 1H, –NH)	164.7, 151.3, 141.1, 134.1, 129.5, 124.6, 124.3, 118.3, 110.2, 52.1, 26.4	384
12	3018	1488	1682	1288	1178	2949	1597	753	738 C–Br str.	7.337–7.52 (m, 8H, Ar–H), 7.332 (s, 1H, –CH of triazole), 4.73 (s, 2H, –NCH₂), 8.20 (s, 1H, –NH)	164.3, 151.3, 141.2, 137.7, 131.7, 124.6, 118.3, 110.2, 52.2, 26.4	445
13	3315	1470	1677	1291	1130	2992	1588	689	744 C–Cl str.	7.33–7.58 (m, 7H, Ar–H), 7.34 (s, 1H, –CH of triazole), 4.74 (s, 2H, –N–CH₂), 8.21 (s, 1H, –NH)	164.7, 151.3, 141.2, 138.4, 131.1, 130.8, 124.6, 124.3, 120.4, 119.2, 110.2, 52.1, 26.4	435
14	3054	1495	1674	1286	1134	2880	1584	740	684 C–Br str.	7.14–7.60 (m, 8H, Ar–H), 7.31 (s, 1H, –CH of triazole), 4.73 (s, 2H, –NCH₂), 8.21 (s, 1H, –NH)	164.6, 151.3, 141.1, 132.7, 128.1, 126.8, 124.6, 124.3, 118.3, 110.2, 51.9, 26.3	445
15	3144	1496	1676	1261	1179	3001	1607	687	–	6.7–7.33 (m, 7H, Ar–H), 7.34 (s, 1H, –CH of triazole), 4.73 (s, 2H, –NCH₂), 8.18 (s, 1H, –NH), 2.50 (s, 6H, (–CH₃)₂)	163.9, 151.3, 141.1, 138.1, 137.8, 125.5, 124.6, 124.3, 118.3, 110.2, 52.2, 26.3, 21.1	394
16	3308	1475	1681	1226	1132	–	1619	743	676 C–Br str.	7.29–7.91 (m, 8H, Ar–H), 7.30 (s, 1H, –CH of triazole), 4.75 (s, 2H, –N–CH₂), 8.24 (s, 1H, –NH)	164.5, 151.3, 141.1, 139.8, 130.9, 126.3, 124.6, 124.3, 121.5, 118.3, 110.2, 52.2, 26.4	445
17	3016	1460	1671	1211	1133	2947	1585	737	–	7.02–7.34 (m, 7H, Ar–H), 7.14 (s, 1H, –CH of triazole), 4.72 (s, 2H, –N–CH₂), 8.18 (s, 1H, –NH), 2.50 (s, 6H, (–CH₃)₂)	164.3, 151.3, 141.2, 137.1, 130.9, 127.2, 125.5, 124.6, 124.3, 123.2, 118.3, 110.2, 51.9, 26.4, 13.9	394
18	3124	1454	1679	1293	1149	3057	1616	711	1207 C–F str.	7.16–7.67 (m, 8H, Ar–H), 7.29 (s, 1H, –CH of triazole), 4.73 (s, 2H, –N–CH₂), 8.20 (s, 1H, –NH)	164.7, 163.6, 151.3, 141.2, 125.6, 124.6, 124.4, 124.3, 123.6, 118.3, 115.4, 110.2, 51.9, 26.4	384
19	3310	1467	1678	1271	1130	3136	1595	680	742 C–Cl str.	7.14–7.66 (m, 8H, Ar–H), 7.33 (s, 1H, –CH of triazole), 4.73 (s, 2H, –NCH₂), 8.20 (s, 1H, –NH)	164.5, 151.3, 142.2, 141.2, 133.1, 130.6, 124.6, 124.3, 123.4, 118.3, 110.2, 52.1, 26.4	400
20	3126	1488	1670	1275	1148	3041	1589	671	739 C–Cl str.	7.31–7.59 (m, 8H, Ar–H), 7.33 (s, 1H, –CH of triazole), 4.73 (s, 2H, –NCH₂), 8.22 (s, 1H, –NH)	164.2, 151.3, 141.2, 137.3, 128.8, 124.6, 124.3, 118.3, 110.2, 52.2, 26.4	400

Str.: stretching, Ar: aromatic

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