W.-W. Ni et al.
Bioorganic&MedicinalChemistryxxx(xxxx)xxx–xxx
2.7.2.3. 2-(m-Methylphenoxy)acetohydroxamic
acid
(c3). White
MS (EI) m/z 185 (M+), 168, 95, 60; Anal. Calcd for C8H8FNO3: C 51.90;
powder, 56%, mp: 94–96 °C, 1H NMR (400 MHz, DMSO‑d6) δ (ppm):
2.28 (s, 3H, CH3); 4.43 (s, 2H, CH2); 6.74 (d, J = 7.8 Hz, 1H, 6-ArH);
6.77 (s, 1H, 2-ArH); 6.78 (d, J = 7.7 Hz, 1H, 4-ArH); 7.17 (t,
J = 8.1 Hz, 1H, 5-ArH); 8.97 (s, 1H, NH); 10.81 (s, 1H, OH); 13C
NMR (100 MHz, DMSO‑d6) δ (ppm): 27.25 (CH3); 65.03 (CH2); 111.26
(6-ArC); 120.52 (2-ArC); 126.70 (4-ArC); 127.88 (5-ArC); 130.17 (3-
ArC); 156.62 (1-ArC); 167.93 (C]O); MS (EI) m/z 181 (M+), 164, 91,
60; Anal. Calcd for C9H11NO3: C 59.66; H 6.12; N 7.73; found: C 59.63;
H 6.13; N 7.73.
H 4.36; F 10.26; N 7.56; found: C 51.93; H 4.36; F 10.24; N 7.55.
2.7.2.10. 2-(2-Fluorophenoxy)acetohydroxamic
acid
(c10). White
powder, 55%, mp: 127–128 °C, 1H NMR (400 MHz, DMSO‑d6) δ
(ppm): 4.54 (s, 2H, CH2); 6.92–7.02 (m, 1H, 6-ArH); 7.07–7.14 (m,
2H, 3,5-ArH); 7.19–7.26 (m, 1H, 4-ArH); 9.02 (s, 1H, NH); 10.84 (s, 1H,
OH); 13C NMR (100 MHz, DMSO‑d6) δ (ppm): 65.32 (CH2); 115.20 (d,
J = 8.9 Hz, 6-ArC); 117.24 (d, J = 27.3 Hz, 3-ArC); 123.55 (d,
J = 8.4 Hz, 4-ArC); 127.14 (5-ArC); 150.57 (d, J = 25.8 Hz, 1-ArC);
154.16 (d, J = 215.8 Hz, 2-ArC); 166.37 (C]O); MS (EI) m/z 185
(M+), 168, 95, 60; Anal. Calcd for C8H8FNO3: C 51.90; H 4.36; F 10.26;
N 7.56; found: C 51.87; H 4.36; F 10.28; N 7.57.
2.7.2.4. 2-(p-Methylphenoxy)acetohydroxamic acid (c4). White powder,
62%, mp: 134–136 °C, 1H NMR (400 MHz, DMSO‑d6) δ (ppm): 2.23 (s,
3H, CH3); 4.41 (s, 2H, CH2); 6.84 (d, J = 8.4 Hz, 2H, 2,6-ArH); 7.09 (d,
J = 8.3 Hz, 2H, 3,5-ArH); 9.89 (s, 2H, NH and OH); 13C NMR (100 MHz,
DMSO‑d6) δ (ppm): 20.55 (CH3); 66.41 (CH2); 114.93 (2C, 2,6-ArC);
130.22 (2C, 3,5-ArC); 130.29 (4-ArC); 156.17 (1-ArC); 164.83 (C]O);
MS (EI) m/z 181 (M+), 164, 91, 60; Anal. Calcd for C9H11NO3: C 59.66;
H 6.12; N 7.73; found: C 59.69; H 6.11; N 7.72.
2.7.2.11. 2-(4-Chlorophenoxy)acetohydroxamic
acid
(c11). White
powder, 62%, mp: 137–138 °C, 1H NMR (400 MHz, DMSO‑d6) δ
(ppm): 4.47 (s, 2H, CH2); 6.98 (d, J = 9.0 Hz, 2H, 2,6-ArH); 7.35 (d,
J = 8.9 Hz, 2H, 3,5-ArH); 9.01 (s, 1H, NH); 10.86 (s, 1H, OH); 13C NMR
(100 MHz, DMSO‑d6) δ (ppm): 66.50 (CH2), 116.90 (2C, 2,6-ArC),
125.32 (4-ArC), 129.66 (2C, 3,4-ArC), 157.10 (1-ArC), 164.47 (C]O);
MS (EI) m/z 203 (M+2)+, 201 (M+), 186, 184, 113, 111, 60; Anal.
Calcd for C8H8ClNO3: C 47.66; H 4.00; Cl 17.59; N 6.95; found: C 47.68;
H 4.00; Cl 17.58; N 6.95.
2.7.2.5. 2-(4-Methoxyphenoxy)acetohydroxamic
acid
(c5). White
powder, 52%, mp: 117–118 °C, 1H NMR (400 MHz, DMSO‑d6)
δ
(ppm): 3.70 (s, 3H, CH3); 4.39 (s, 2H, CH2); 6.86 (d, J = 9.4 Hz, 2H,
2,6-ArH); 6.90 (d, J = 9.3 Hz, 2H, 3,5-ArH); 9.15 (s, 1H, NH); 10.61 (s,
1H, OH); 13C NMR (100 MHz, DMSO‑d6) δ (ppm): 55.83 (CH3); 67.00
(CH2); 114.98 (2C, 2,6-ArC); 116.08 (2C, 3,5-ArC); 152.27 (4-ArC);
154.23 (1-ArC); 164.90 (C]O); MS (EI) m/z 197 (M+), 180, 166, 107,
60; Anal. Calcd for C9H11NO4: C 54.82; H 5.62; N 7.10; found: C 54.79;
H 5.63; N 7.11.
2.7.2.12. 2-(3-Chlorophenoxy)acetohydroxamic
acid
(c12). White
powder, 67%, mp: 132–134 °C, 1H NMR (400 MHz, DMSO‑d6) δ
(ppm): 4.51 (s, 2H, CH2); 6.94 (dt, J = 8.0 Hz, J = 1.7 Hz, 1H, 6-
ArH); 7.03 (dd, J = 8.5 Hz, J = 1.8 Hz, 1H, 4-ArH); 7.04 (d, J = 1.6 Hz,
1H, 2-ArH); 7.32 (t, J = 8.2 Hz, 1H, 5-ArH); 9.03 (s, 1H, NH); 10.84 (s,
1H, OH); 13C NMR (100 MHz, DMSO‑d6): 65.06 (CH2); 110.72 (6-ArC);
117.18 (2-ArC); 119.61 (4-ArC); 128.90 (5-ArC); 130.72 (3-ArC),
149.03 (1-ArC), 166.88 (C]O); MS (EI) m/z 203 (M+2)+, 201
(M+), 186, 184, 113, 111, 60; Anal. Calcd for C8H8ClNO3: C 47.66; H
4.00; Cl 17.59; N 6.95; found: C 47.63; H 4.00; Cl 17.60; N 6.96.
2.7.2.6. 2-(3,5-Dimethylphenoxy)acetohydroxamic acid (c6). White
powder, 53%, mp: 111–112 °C, 1H NMR (400 MHz, DMSO‑d6)
δ
(ppm): 2.23 (s, 6H, CH3); 4.40 (s, 2H, CH2); 6.57 (s, 2H, 2,6-ArH);
6.60 (s, 1H, 4-ArH); 8.96 (s, 1H, NH); 10.79 (s, 1H, OH); 13C NMR
(100 MHz, DMSO‑d6) δ (ppm): 21.52 (2C, CH3); 66.18 (CH2); 112.80
(2C, 2,6-ArC); 123.19 (4-ArC); 139.03 (2C, 3,5-ArC); 158.29 (1-ArC);
164.88 (C]O); MS (EI) m/z 195 (M+), 178, 105, 60; Anal. Calcd for
2.7.2.13. 2-(2-Chlorophenoxy)acetohydroxamic
acid
(c13). White
powder, 66%, mp: 133–134 °C, 1H NMR (400 MHz, DMSO‑d6) δ
(ppm): 4.55 (s, 2H, CH2); 6.99 (td, J = 7.7 Hz, J = 1.4 Hz, 1H, 4-
ArH); 7.07 (dd, J = 8.4 Hz, J = 1.4 Hz, 1H, 6-ArH); 7.30 (td,
J = 8.8 Hz, J = 1.6 Hz, 1H, 5-ArH); 7.44 (dd, J = 7.9 Hz, J = 1.6 Hz,
1H, 3-ArH); 9.10 (s, 1H, NH); 10.79 (s, 1H, OH); 13C NMR (100 MHz,
DMSO‑d6): 64.36 (CH2); 111.94 (6-ArC); 117.47 (4-ArC); 118.69 (2-
ArC); 128.62 (5-ArC); 129.77 (3-ArC), 154.14 (1-ArC), 166.92 (C]O);
MS (EI) m/z 203 (M+2)+, 201 (M+), 186, 184, 113, 111, 60; Anal.
Calcd for C8H8ClNO3: C 47.66; H 4.00; Cl 17.59; N 6.95; found: C 47.69;
H 4.00; Cl 17.57; N 6.94.
C
10H13NO3: C 61.53; H, 6.71; N 7.18; found: C 61.50; H, 6.72; N 7.19.
2.7.2.7. 2-(4-Bromophenoxy)acetohydroxamic acid (c7). White powder,
59%, mp: 146–147 °C, 1H NMR (400 MHz, DMSO‑d6) δ (ppm): 4.47 (s,
2H, CH2); 6.93 (d, J = 8.8 Hz, 2H, 2,6-ArH); 7.47 (d, J = 8.8 Hz, 2H,
3,5-ArH); 9.40 (s, 1H, NH); 10.35 (s, 1H, OH); 13C NMR (100 MHz,
DMSO‑d6) δ (ppm): 66.42 (CH2); 113.07 (4-ArC); 117.42 (2C, 2,6-ArC);
132.55 (2C, 3,5-ArC); 157.54 (1-ArC); 164.44 (C]O); MS (EI) m/z 247
,
(M+2)+ 245 (M+), 230, 228, 157, 155, 60; Anal. Calcd for
C8H8BrNO3: C 39.05; H 3.28; Br 32.47; N 5.69; found: C 39.02; H
3.28; Br 32.49; N 5.69.
2.7.2.14. 2-(2,3-Dichlorophenoxy)acetohydroxamic acid (c14). White
powder, 71%, mp: 166–168 °C, 1H NMR (400 MHz, DMSO‑d6) δ
(ppm): 4.61 (s, 2H, CH2); 7.06 (dd, J = 8.3 Hz, J = 1.3 Hz, 1H, 6-
ArH); 7.25 (dd, J = 8.2 Hz, J = 1.3 Hz, 1H, 4-ArH); 7.33 (t, J = 8.2 Hz,
1H, 5-ArH); 9.08 (s, 1H, NH); 10.84 (s, 1H, OH); 13C NMR (100 MHz,
DMSO‑d6): 65.41 (CH2); 111.36 (6-ArC); 122.25 (4-ArC); 123.80 (2-
ArC); 130.37 (5-ArC); 136.29 (3-ArC); 156.11 (1-ArC); 168.02 (C]O);
MS (EI) m/z 237 (M+2)+, 235 (M+), 220, 218, 147, 145, 60; Anal.
Calcd for C8H7Cl2NO3: C 40.71; H, 2.99; Cl 30.04; N 5.93; found: C
40.75; H, 2.99; Cl 30.02; N 5.92.
2.7.2.8. 2-(4-Fluorophenoxy)acetohydroxamic acid (c8). White powder,
64%, mp: 105–107 °C, 1H NMR (400 MHz, DMSO‑d6) δ (ppm): 4.45 (s,
2H, CH2); 6.97 (dd, J = 8.9 Hz, J = 4.6 Hz, 2H, 2,6-ArH); 7.14 (t,
J = 8.6 Hz, 2H), 3,5-ArH; 8.99 (s, 1H, NH); 10.84 (s, 1H, OH); 13C NMR
(100 MHz, DMSO‑d6) δ (ppm): 66.30 (CH2); 114.26 (d, J = 7.6 Hz, 2C,
2,6-ArC); 117.42 (d, J = 23.1 Hz, 2C, 3,5-ArC); 145.93 (1-ArC); 155.07
(d, J = 229.1 Hz, 4-ArC); 165.01 (C]O); MS (EI) m/z 185 (M+), 168,
95, 60; Anal. Calcd for C8H8FNO3: C 51.90; H 4.36; F 10.26; N 7.56;
found: C 51.94; H 4.36; F 10.25; N 7.55.
2.7.2.15. 2-(2,4-Dichlorophenoxy)acetohydroxamic acid (c15). White
powder, 74%, mp: 160–161 °C, 1H NMR (400 MHz, DMSO‑d6) δ
(ppm): 4.57 (s, 2H, CH2); 7.09 (d, J = 8.9 Hz, 1H, 6-ArH); 7.39 (dd,
J = 8.9 Hz, J = 2.6 Hz, 1H, 5-ArH); 7.60 (d, J = 1.1 Hz, 1H, 3-ArH);
9.07 (s, 1H, NH); 10.84 (s, 1H, OH); 13C NMR (100 MHz, DMSO‑d6):
64.34 (CH2); 117.76 (6-ArC); 121.97 (2-ArC); 128.99 (4-ArC); 129.61
(5-ArC); 131.63 (3-ArC); 152.38 (1-ArC); 166.64 (C]O); MS (EI) m/z
237 (M+2)+, 235 (M+), 220, 218, 147, 145, 60; Anal. Calcd for
2.7.2.9. 2-(3-Fluorophenoxy)acetohydroxamic acid (c9). White powder,
66%, mp: 123–125 °C, 1H NMR (400 MHz, DMSO‑d6) δ (ppm): 4.49 (s,
2H, CH2); 6.80–6.84 (m, 3H, 2,5,6-ArH); 7.30 (m, 1H, 4-ArH); 9.01 (s,
1H, NH); 10.86 (s, 1H, OH); 13C NMR (100 MHz, DMSO‑d6) δ (ppm):
64.68 (CH2); 104.03 (d, J = 27.5 Hz, 2-ArC); 110.81 (d, J = 25.9 Hz, 4-
ArC); 114.10 (6-ArC); 131.22 (d, J = 9.1 Hz, 5-ArC); 159.49 (d,
J = 232.4 Hz, 3-ArC); 163.13 (d, J = 8.7 Hz, 1-ArC); 167.02 (C]O);
3