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Yield: 88%. M.P.: 11-115\u00b0C. IR (KBr) \u03bdmax (cm-1): 1760 (ester, C=O). 1H NMR (DMSO-d6) \u03b4 (ppm): \u03b4 1.29 (t, H, CH of ester), \u03b4 4.10 (q, 2H, CH2 of ester), \u03b4 4.82 (s, 2H, OCH2), \u03b4 6.91-7.66 (m, 7H, Ar-H)"},{"key":"#cr-split#-10.1016\/j.bmcl.2020.127743_b0170.2","unstructured":"H, 6.09%. b: Ethyl(2-methyl-quinolin-8-yloxy)acetate. Yield: 82%. M.P.: 116-118\u00b0C. IR (KBr) \u03bdmax (cm-1): 1750 (ester, C=O). 1H NMR (DMSO-d6) \u03b4 (ppm): \u03b4 1.27 (t, H, CH of ester), 2.24 (s, H, Ar-CH), \u03b4 4.10 (q, 2H, CH2 of ester), \u03b4 4.82 (s, 2H, OCH2), \u03b4 6.95-7.64 (m, 5H, Ar-H)"},{"key":"#cr-split#-10.1016\/j.bmcl.2020.127743_b0170.3","unstructured":"N, 5.96%. d: Ethyl(naphthalen-1-yloxy)acetate. Yield: 80%. M.P.: 125-12\u00b0C. IR (KBr) \u03bdmax (cm-1): 1740 (ester, C=O).1H NMR (DMSO-d6) \u03b4 (ppm): \u03b4 1.28 (t, H, CH of ester), \u03b4 4.12 (q, 2H, CH2 of ester), \u03b4 4.72 (s, 2H, OCH2), \u03b4 6.81-7.56 (m, 7H, Ar-H)"},{"key":"#cr-split#-10.1016\/j.bmcl.2020.127743_b0170.4","unstructured":"H, 7.19%. i: Ethyl(pyridin--yloxy)acetate. Yield: 88%. M.P.: 129-15\u00b0C. IR (KBr) \u03bdmax (cm-1): 1725 (ester, C=O). 1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 1.28 (t, H, CH of ester), \u03b4 4.10 (q, 2H, CH2 of ester), \u03b4 4.85 (s, 2H, OCH2), \u03b4 7.5-8.55 (m, 4H, Ar-H). LC-MS m\/z182 (M+1). Anal. Cal. for C9H11NO (181): C, 59.66"},{"key":"#cr-split#-10.1016\/j.bmcl.2020.127743_b0170.5","unstructured":"N, 7.69%. j: Ethyl(4-methyl-phenoxy)acetate. Yield: 88%. M.P.: 10-15\u00b0C. IR (KBr) \u03bdmax (cm-1): 1750 (ester, C=O).1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 1.29 (t, H, CH of ester), 2.2 (s, H, Ar-CH), \u03b4 4.12 (q, 2H, CH2 of ester), \u03b4 4.89 (s, 2H, OCH2), \u03b4 6.62-6.95 (m, 4H, Ar-H). LC-MS m\/z 195 (M+1). Anal. Cal. for C11H14O (194): C, 68.02"},{"key":"#cr-split#-10.1016\/j.bmcl.2020.127743_b0170.6","unstructured":"a: Ethyl(naphthalen-2-yloxy)acetate. Yield: 88%. M.P.: 11-115\u00b0C. IR (KBr) \u03bdmax (cm-1): 1760 (ester, C=O). 1H NMR (DMSO-d6) \u03b4 (ppm): \u03b4 1.29 (t, H, CH of ester), \u03b4 4.10 (q, 2H, CH2 of ester), \u03b4 4.82 (s, 2H, OCH2), \u03b4 6.91-7.66 (m, 7H, Ar-H); LCMS m\/z 21 (M+1). Anal. Cal. for: C14H14O"},{"key":"#cr-split#-10.1016\/j.bmcl.2020.127743_b0170.7","unstructured":"(20) C, 7.0; H, 6.1. Found: C, 72.94; H, 6.09%. b: Ethyl(2-methyl-quinolin-8-yloxy)acetate. Yield: 82%. M.P.: 116-118\u00b0C. IR (KBr) \u03bdmax (cm-1): 1750 (ester, C=O). 1H NMR (DMSO-d6) \u03b4 (ppm): \u03b4 1.27 (t, H, CH of ester), 2.24 (s, H, Ar-CH), \u03b4 4.10 (q, 2H, CH2 of ester), \u03b4 4.82 (s, 2H, OCH2), \u03b4 6.95-7.64 (m, 5H, Ar-H); LCMS m\/z 246 (M+1). Anal. Cal. for: C14H15NO (245): C, 68.56; H, 6.16; N, 5.71; Found: C, 68.50; H, 6.10; N, 5.69%. c: Ethyl(quinolin-8-yloxy)acetate. Yield: 81%. M.P.: 120-122\u00b0C. IR (KBr) \u03bdmax (cm-1): 170 (ester, C=O). 1H NMR (DMSO-d6) \u03b4 (ppm): \u03b4 1.1 (t, H, CH of ester), \u03b4 4.10 (q, 2H, CH2 of ester), \u03b4 4.82 (s, 2H, OCH2), \u03b4 6.81-7.69 (m, 6H, Ar-H); LCMS m\/z 22 (M+1). Anal. Cal. for: C1H1NO (21): C, 67.52; H, 5.67; N, 6.06; Found: C, 67.49; H, 5.59; N, 5.96%. d: Ethyl(naphthalen-1-yloxy)acetate. Yield: 80%. M.P.: 125-12\u00b0C. IR (KBr) \u03bdmax (cm-1): 1740 (ester, C=O).1H NMR (DMSO-d6) \u03b4 (ppm): \u03b4 1.28 (t, H, CH of ester), \u03b4 4.12 (q, 2H, CH2 of ester), \u03b4 4.72 (s, 2H, OCH2), \u03b4 6.81-7.56 (m, 7H, Ar-H); LCMS m\/z 21 (M+1). Anal. Cal. for: C14H14O (20): C, 7.0; H, 6.1; Found: C, 72.98; H, 6.09%. e: Ethyl 2-(2,4-dimethylphenoxy)acetate. Yield: 78%. M.P.: 15-17\u00b0C. IR (KBr) \u03bdmax (cm-1): 170 (ester, C=O).1H NMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 1.27 (t, H, CH of ester), 2.28 (s, 6H, Ar-CH), \u03b4 4.10 (q, 2H, CH2 of ester), \u03b4 4.85 (s, 2H, OCH2), \u03b4 6.51-7.21 (m, H, Ar-H). LC-MS m\/z 209 (M+1). Anal. Cal. for C12H16O (208): C, 69.21; H, 7.74.Found: C, 69.14; H, 7.6%. f: Ethyl(4-bromo-phenoxy)acetate. Yield: 79%. M.P.: 125-10\u00b0C. IR (KBr) \u03bdmax (cm-1): 175 (ester, C=O).1H NMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 1.0 (t, H, CH of ester), \u03b4 4.10 (q, 2H, CH2 of ester), \u03b4 4.90 (s, 2H, OCH2), \u03b4 6.65-7.9 (m, 4H, Ar-H). LC-MS m\/z 259 (M+), 261 (M+2). Anal. Cal. for C10H11BrO (259): C, 46.6; H, 4.28. Found: C, 46.29; H, 4.20%. g: Ethyl(4-chloro-phenoxy)acetate. Yield: 80%. M.P.: 118-125\u00b0C. IR (KBr) \u03bdmax (cm-1): 170 (ester, C=O).1H NMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 1.24 (t, H, CH of ester), \u03b4 4.12 (q, 2H, CH2 of ester), \u03b4 4.95 (s, 2H, OCH2), \u03b4 6.75-7.20 (m, 4H, Ar-H). LC-MS m\/z 214 (M+), 216 (M+2). Anal. Cal. for C10H11ClO (214): C, 55.96; H, 5.17; Found: C, 55.85; H, 5.10%. h: Ethyl(2-methyl-phenoxy)acetate. Yield: 78%. M.P.: 125-129\u00b0C. IR (KBr) \u03bdmax (cm-1): 170 (ester, C=O). 1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 1.26 (t, H, CH of ester), \u03b42. (s, H, Ar-CH), \u03b4 4.20 (q, 2H, CH2 of ester), \u03b4 4.95 (s, 2H, OCH2), \u03b4 6.65-6.92 (m, 4H, Ar-H). LC-MS m\/z195 (M+1). Anal. Cal. for C11H14O (194): C, 68.02; H, 7.27; Found: C, 67.98; H, 7.19%. i: Ethyl(pyridin--yloxy)acetate. Yield: 88%. M.P.: 129-15\u00b0C. IR (KBr) \u03bdmax (cm-1): 1725 (ester, C=O). 1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 1.28 (t, H, CH of ester), \u03b4 4.10 (q, 2H, CH2 of ester), \u03b4 4.85 (s, 2H, OCH2), \u03b4 7.5-8.55 (m, 4H, Ar-H). LC-MS m\/z182 (M+1). Anal. Cal. for C9H11NO (181): C, 59.66; H, 6.12; N, 7.7; Found: C, 59.55; H, 6.09; N, 7.69%. j: Ethyl(4-methyl-phenoxy)acetate. Yield: 88%. M.P.: 10-15\u00b0C. IR (KBr) \u03bdmax (cm-1): 1750 (ester, C=O).1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 1.29 (t, H, CH of ester), 2.2 (s, H, Ar-CH), \u03b4 4.12 (q, 2H, CH2 of ester), \u03b4 4.89 (s, 2H, OCH2), \u03b4 6.62-6.95 (m, 4H, Ar-H). LC-MS m\/z 195 (M+1). Anal. Cal. for C11H14O (194): C, 68.02; H, 7.27; Found: C, 67.98; H, 7.20%."},{"key":"10.1016\/j.bmcl.2020.127743_b0175","unstructured":"a: (Naphthalen-2-yloxy)-acetic acid hydrazide. Yield: 9%. M.P.: 143-14\u00b0C. IR (KBr) \u03bdmax (cm-1): 320-326 (NH), 332-3430 (NH2). 1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 4.13 (s, 2H, NH2), \u03b4 4.82 (s, 2H, OCH2), \u03b4 7.10-7.72 (m, 7H, Ar-H), \u03b4 9.39 (s, 1H, NH). LC-MS m\/z 217 (M+1). Anal. Cal. for C12H12N2O2 (216): C, 66.6; H, .9; N, 12.96. Found: C, 66.49; H, .43; N, 12.89%. b: (2-Methyl-quinolin-8-yloxy)-acetic acid hydrazide. Yield: 92%. M.P.: 149-11\u00b0C. IR (KBr) \u03bdmax (cm-1): 3260-328 (NH), 3320-3420 (NH2).1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 2.24 (s, 3H, Ar-CH3), \u03b4 4.10 (s, 2H, NH2), \u03b4 4.72 (s, 2H, OCH2), \u03b4 7.20-7.62 (m, H, Ar-H), \u03b4 9.40 (s, 1H, NH). LC-MS m\/z 232 (M+1). Anal. Cal. for C12H13N3O2 (231): C, 62.33; H, .67; N, 18.17. Found: C, 62.26; H, .3; N, 18.09%. c: (Quinolin-8-yloxy)-acetic acid hydrazide. Yield: 89%. M.P.: 1-16\u00b0C. IR (KBr) \u03bdmax (cm-1): 326-327 (NH), 333-3410 (NH2).1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 4.12 (s, 2H, NH2), \u03b4 4.79 (s, 2H, OCH2), \u03b4 6.71-7.2 (m, 6H, Ar-H), \u03b4 9.29 (s, 1H, NH). LC-MS m\/z 218 (M+1). Anal. Cal. for C11H11N3O2 (217): C, C, 60.82; H, .10; N, 19.34. Found: C, 60.7; H, .08; N, 19.29%. d: (Naphthalen-1-yloxy)-acetic acid hydrazide. Yield: 90%. M.P.: 12-14\u00b0C. IR (KBr) \u03bdmax (cm-1): 32-327 (NH), 33-3430 (NH2).1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 4.22 (s, 2H, NH2), \u03b4 4.89 (s, 2H, OCH2), \u03b4 6.92-7.7 (m, 7H, Ar-H), \u03b4 9.21 (s, 1H, NH). LC-MS m\/z 217 (M+1). Anal. Cal. for C12H12N2O2 (216): C, 66.6; H, .9; N, 12.96. Found: C, 66.61; H, .39; N, 12.88%. e : (2,4-Dimethyl-phenoxy)-acetic acid hydrazide. Yield: 88%. M.P.: 148-14\u00b0C. IR (KBr) \u03bdmax (cm-1): 3240-3260 (NH), 33-342 (NH2). 1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 2.31 (s, 6H, Ar-CH3), \u03b4 4.20 (s, 2H, NH2), \u03b4 4.82 (s, 2H, OCH2), \u03b4 6.2-7.10 (m, 3H, Ar-H), \u03b4 9.18 (s, 1H, NH). LC-MS m\/z 19 (M+1). Anal. Cal. for C10H14N2O2 (194): C, 61.84; H, 7.27; N, 14.42; Found: C, 61.84; H, 7.27; N, 14.42%. f: (4-Bromo-phenoxy)-acetic acid hydrazide. Yield: 88%. M.P.: 1-19\u00b0C. IR (KBr) \u03bdmax (cm-1): 320-326 (NH), 330-3430 (NH2). 1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 4.20 (s, 2H, NH2), \u03b4 4.81 (s, 2H, OCH2), \u03b4 6.6-7.68 (m, 4H, Ar-H), \u03b4 9.10 (s, 1H, NH). LC-MS m\/z 244 (M+), 246 (M+2). Anal. Cal. for C8H9BrN2O2 (244): C, 39.21; H, 3.70N, 11.43; Found: C, 39.19; H, 3.6; N, 11.39%. g: (4-Chloro-phenoxy)-acetic acid hydrazide. Yield: 86%. M.P.: 14-149\u00b0C. IR (KBr) \u03bdmax (cm-1): 3240-3260(NH), 3360-3420 (NH2).1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 4.18 (s, 2H, NH2), \u03b4 4.79 (s, 2H, OCH2), \u03b4 6.74-7.20 (m, 4H, Ar-H), \u03b4 9.20 (s, 1H, NH). LC-MS m\/z 200 (M+), 202 (M+2). Anal. Cal. for C8H9ClN2O2 (200): C, 47.89; H, 4.2; N, 13.96; Found: C, 47.86; H, 4.49; Cl, N, 13.90%. h: (2-Methyl-phenoxy)-acetic acid hydrazide. Yield: 8%. M.P.: 143-14 0C. IR (KBr) \u03bdmax (cm-1): 320-326 (NH), 332-3430 (NH2). 1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 2.31 (s, 3H, Ar-CH3), \u03b4 4.20 (s, 2H, NH2), \u03b4 4.79 (s, 2H, OCH2), \u03b4 6.6-7.20 (m, 4H, Ar-H), \u03b4 9.19 (s, 1H, NH). LC-MS m\/z 181 (M+1). Anal. Cal. for C9H12N2O2 (180): C, 9.99; H, 6.71; N, 1.; Found: C, 9.92; H, 6.68; N, 1.2%. i: (Pyridin-3-yloxy)-acetic acid hydrazide. Yield: 82%. M.P.: 143-14\u00b0C. IR (KBr) \u03bdmax (cm-1): 320-326 (NH), 332-3430 (NH2).1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 4.19 (s, 2H, NH2), \u03b4 4.76 (s, 2H, OCH2), \u03b4 7.36-8.0 (m, 4H, Ar-H), \u03b4 9.20 (s, 1H, NH). LC-MS m\/z 168 (M+1). Anal. Cal. for C7H9N3O2 (167): C, 0.29; H, .43; N, 2.14; Found: C, 0.2; H, .40; N, 2.09%. j: (4-Methyl-phenoxy)-acetic acid hydrazide. Yield: 80%. M.P.: 14-10\u00b0C. IR (KBr) \u03bdmax (cm-1): 3240-3260 (NH), 3320-3430 (NH2). 1HNMR (400 MHz) (CDCl3) \u03b4 (ppm): \u03b4 2.30 (s, 3H, Ar-CH3), \u03b4 4.21 (s, 2H, NH2), \u03b4 4.80 (s, 2H, OCH2), \u03b4 6.62-6.9 (m, 4H, Ar-H), \u03b4 9.20 (s, 1H, NH). LC-MS m\/z 181(M+1). Anal. Cal. for C9H12N2O2 (180): C, 9.99; H, 6.71; N, 1.; Found: C, 9.91; H, 6.69; N, 1.49%."},{"key":"10.1016\/j.bmcl.2020.127743_b0180","unstructured":"a: N(Naphthalen-2-yloxy)acetate-N'-[3-(3,4-dihydroxy-phenyl)-acryloyl]-hydrazide. Yield: 98%. M.P.: 142-144\u00b0C. IR (KBr) \u03bdmax (cm-1): 1640 (amide, C=O), 3540 (Ar-OH), 3250-3265(NH). 1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 4.0 (s, 2H, OCH2), \u03b4 6.3 (d, 1H, CH=CH-CONH), \u03b4 6.38-.85 (m, 10H, Ar-H), .23 (d, 1H, Ar-CH=CH), \u03b4 9.29 (s, 2H, NH), \u03b4 10.11 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 13.2, 169.3, 158.6, 149.4, 146.6, 143.2, 13., 131.2, 130.5, 129.8, 128., 12.5, 126.4, 124., 122.3, 120.1, 119.8, 118.0, 115.3, 10.2, 4.0. LC-MS m\/z 39 (M+1). Anal. Cal. for C21H18N2O5 (38): C, 66.66; H, 4.9; N, .40. Found: C, 66.53; H, 4.2; N, .38%. b: N(2-Methyl-quinolin-8-yloxy)acetate-N'-[3-(3,4-dihydroxy-phenyl)-acryloyl]-hydrazide. Yield: 96%. M.P.: 164-166\u00b0C. IR (KBr) \u03bdmax (cm-1): 1650 (amide, C=O), 3510 (Ar-OH), 3250-320(NH). 1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 2.31 (s, 3H, Ar-CH3),\u03b4 4.1 (s, 2H, OCH2), \u03b4 6.30 (d, 1H, CH=CH-CONH), \u03b4 6.32-.82 (m, 8H, Ar-H), .20 (d, 1H, Ar-CH=CH), \u03b4 9.21 (s, 2H, NH), \u03b4 10.10 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 15.6, 168.2, 159.8, 156.2, 148., 145.2, 142., 140., 13.5, 130.3, 12.8, 126.1, 124., 121.6, 120.8, 119.3, 118.4, 115.4, 108., 80.4, 25.3. LC-MS m\/z 394 (M+1). Anal. Cal. for C21H19N3O5 (393): C, 64.12; H, 4.8; N, 10.68. Found: C, 64.05; H, 4.81; N, 10.62%. c: N(Quinolin-8-yloxy)acetate-N'-[3-(3,4-dihydroxy-phenyl)-acryloyl]-hydrazide.Yield: 95%. M.P.: 138-140\u00b0C. IR (KBr) \u03bdmax (cm-1): 160 (amide, C=O), 3550 (Ar-OH), 3255-3265(NH).1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 4.69 (s, 2H, OCH2), \u03b4 6.29 (d, 1H, CH=CH-CONH), \u03b4 6.35-.92 (m, 9H, Ar-H), .23 (d, 1H, Ar-CH=CH), \u03b4 9.21 (s, 2H, NH), \u03b4 10.10 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 12.3, 166.2, 15.5, 148.1, 14.4, 144., 142.6, 139.4, 13.2, 135.3, 129.8, 12.5, 122., 121.4, 120.8, 118., 116.0, 115.5, 105.6, .9. LC-MS m\/z 380 (M+1). Anal. Cal. for C20H1N3O5 (39): C, 63.32; H, 4.52; N, 11.08. Found: C, 63.2; H, 4.45; N, 11.03%. d: N(Naphthalen-1-yloxy)acetate- N'-[3-(3,4-dihydroxy-phenyl)-acryloyl]-hydrazide. Yield: 94%. M.P.: 149-151\u00b0C. IR (KBr) \u03bdmax (cm-1): 1630 (amide, C=O), 3590 (Ar-OH), 3250-3260(NH).1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 4.2 (s, 2H, OCH2), \u03b4 6.25-.8 (m, 10H, Ar-H), \u03b4 6.35 (d, 1H, CH=CH-CONH), .21 (d, 1H, Ar-CH=CH), \u03b4 9.2(s, 2H, NH), \u03b4 10.09 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 11.8, 168.5, 156.4, 14., 144.2, 143.6, 135.5, 129., 128.4, 12.3, 126.2, 125.5, 124.0, 122.9, 121.2, 120., 119.3, 118.2, 115.3, 104.6, 4.. LC-MSm\/z 39 (M+1). Anal. Cal. for C21H18N2O5 (38): C, 66.66; H, 4.9; N, .40. Found: C, 66.51; H, 4.61; N, .33%. e: N(2,4-Dimethyl-phenoxy)-acetic acid N'-[3-(3,4-dihydroxy-phenyl)-acryloyl]-hydrazide. Yield: 92%. M.P.: 139-14\u00b0C. IR (KBr) \u03bdmax (cm-1): 160 (amide, C=O), 3610 (Ar-OH), 3250-3260(NH). 1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 2.31 (s, 6H, Ar-CH3), \u03b4 4.68 (s, 2H, OCH2), \u03b4 6.55-.10 (m,6H, Ar-H), \u03b4 6.81 (d, 1H, CH=CH-CONH), .50 (d, 1H, Ar-CH=CH), \u03b4 9.19 (s, 2H, NH), \u03b4 10.11 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 12.3, 16.3, 160.2, 148.4, 145.3, 142.6, 133., 130.9, 129., 128.8, 124.3, 121., 120., 118.0, 115.3, 114.0, 8.8, 24., 18.. LC-MS m\/z 35 (M+1). Anal. Cal. for C19H20N2O5 (356): C, 64.04; H, 5.66; N, .86; Found: C, 63.93; H, 5.59; N, .80%. f: N(4-Bromo-phenoxy)acetate-N'-[3-(3,4-dihydroxy-phenyl)-acryloyl]-hydrazide. Yield: 91%. M.P.: 145-15\u00b0C. IR (KBr) \u03bdmax (cm-1): 1630 (amide, C=O), 3620 (Ar-OH), 3240-3250(NH).1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 4.80 (s, 2H, OCH2), \u03b4 6.56-.40 (m, H, Ar-H), \u03b4 6.9 (d, 1H, CH=CH-CONH), .51 (d, 1H, Ar-CH=CH), \u03b4 9.20(s, 2H, NH), \u03b4 10.10 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 11.5, 166.8, 163., 150., 149.2, 144., 13.8, 135., 129., 123.5, 119.3, 118.9, 11.3, 115., 8.3. LC-MS m\/z 406 (M+), 408 (M+2). Anal. Cal. for C1H15BrN2O5 (406): C, 50.14; H, 3.1; N, 6.88; Found: C, 50.09; H, 3.69; N, 6.9%. g: N(4-Chloro-phenoxy)acetate-N'-[3-(3,4-dihydroxy-phenyl)-acryloyl]-hydrazide. Yield: 91%. M.P.: 129-132\u00b0C. IR (KBr) \u03bdmax (cm-1): 160 (amide, C=O), 3220 (Ar-OH), 3240-3255(NH). 1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 4.0 (s, 2H, OCH2), \u03b4 6.3 (d, 1H, CH=CH-CONH), \u03b4 6.38-.85 (m, H, Ar-H), .23 (d, 1H, Ar-CH=CH), \u03b4 9.25 (s, 2H, NH), \u03b4 10.12 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 15.4, 165.9, 160.1, 144.4, 143., 141.6, 129.9, 128.9, 126.1, 120.2, 119.8, 11.0, 115.5, 114.8, 6.. LC-MS m\/z 362 (M+), 364 (M+2). Anal. Cal. for C1H15ClN2O5 (362): C, 56.29; H, 4.1; N, .2. Found: C, 56.21; H, 4.09; N, .65%. h: N(2-Methyl-phenoxy)acetate-N'-[3-(3, 4-dihydroxy-phenyl)-acryloyl]-hydrazide. Yield: 90%. M.P.: 159-165\u00b0C. IR (KBr) \u03bdmax (cm-1): 1630 (amide, C=O), 3560 (Ar-OH), 3250-320(NH). 1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 2.30 (s, 3H, Ar-CH3), \u03b4 4.68 (s, 2H, OCH2), \u03b4 6.25-.9 (m, H, Ar-H), \u03b4 6.85 (d, 1H, CH=CH-CONH), .54 (d, 1H, Ar-CH=CH), \u03b4 9.22(s, 2H, NH), \u03b4 10.09 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 12., 16.3, 163.4, 14.3, 143.2, 134., 130.3, 12.5, 125., 123.3, 121.4, 120., 119., 118.3, 115.5, 113.6, 8.3, 1.3. LC-MS m\/z 343 (M+1). Anal. Cal. for C18H18N2O5 (342): C, 63.15; H, 5.30; N, 8.18; Found: C, 63.10; H, 5.2; N, 8.10%. i: N(Pyridin-3-yloxy)acetate-N'-[3-(3,4-dihydroxy-phenyl)-acryloyl]-hydrazide. Yield: 89%. M.P.: 142-144\u00b0C. IR (KBr) \u03bdmax (cm-1): 160 (amide, C=O), 3220 (Ar-OH), 3245-3250(NH). 1HNMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 4.81 (s, 2H, OCH2), \u03b4 6.55-8.50 (m, H, Ar-H), \u03b4 6.5 (d, 1H, CH=CH-CONH), .21 (d, 1H, Ar-CH=CH), \u03b4 9.20 (s, 2H, NH), \u03b4 10.08 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 13., 168.3, 159.5, 148.2, 14.1, 144.1, 142., 140.3, 131., 123.2, 121.5, 120., 118.4, 11.8, 114., 6.6. LC-MS m\/z 330 (M+1). Anal. Cal. for C16H15N3O5 (329): C, 58.36; H, 4.59; N, 12.6; Found: C, 58.29; H, 4.50; N, 12.69%. j: N(4-Methyl-phenoxy)acetate-N'-[3-(3,4-dihydroxy-phenyl)-acryloyl]-hydrazide. Yield: 88%. M.P.: 142-144\u00b0C. IR (KBr) \u03bdmax (cm-1): 1650 (amide, C=O), 3562 (Ar-OH), 3245-3262(NH). 1H NMR (400 MHz) (DMSO-d6) \u03b4 (ppm): \u03b4 2.32 (s, 3H, Ar-CH3), \u03b4 4.83 (s, 2H, OCH2), \u03b4 6.58-.60 (m, H, Ar-H), \u03b4 6.9 (d, 1H, CH=CH-CONH), .51 (d, 1H, Ar-CH=CH), \u03b4 9.21(s, 2H, NH), \u03b4 10.0 (s, 2H, OH). 13C NMR (DMSO-d6) \u03b4: 11.5, 16.8, 160., 148.3, 144., 142.6, 135.4, 131., 12.2, 121., 119.9, 118., 115.4, 112.3, 80., 23.5. LC-MS m\/z 343 (M+1). Anal. Cal. for C18H18N2O5 (342): C, 63.15; H, 5.30; N, 8.18; Found: C, 63.10; H, 5.28; N, 8.10%."},{"key":"10.1016\/j.bmcl.2020.127743_b0185","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1016\/0041-008X(79)90153-4","volume":"50","author":"Cioli","year":"1979","journal-title":"Toxicol Appl Pharmacol"}],"container-title":["Bioorganic & Medicinal Chemistry Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X20308544?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0960894X20308544?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T07:37:29Z","timestamp":1760773049000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0960894X20308544"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,2]]},"references-count":43,"alternative-id":["S0960894X20308544"],"URL":"https:\/\/doi.org\/10.1016\/j.bmcl.2020.127743","relation":{},"ISSN":["0960-894X"],"issn-type":[{"value":"0960-894X","type":"print"}],"subject":[],"published":{"date-parts":[[2021,2]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Molecular docking and synthesis of caffeic acid analogous and its anti-inflammatory, analgesic and ulcerogenic studies","name":"articletitle","label":"Article Title"},{"value":"Bioorganic & Medicinal Chemistry Letters","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bmcl.2020.127743","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2020 Elsevier Ltd. All rights reserved.","name":"copyright","label":"Copyright"}],"article-number":"127743"}}