Journal Information

Journal ID (publisher-id): chemical

Title: Journal of the Korean Chemical Society

Translated Title (ko): 대한화학회지

ISSN (print): 1017-2548

ISSN (electronic): 2234-8530

Publisher: Korean Chemical Society대한화학회

Article Information

Copyright statement: Copyright © 2021, Korean Chemical Society

Copyright: 2021

Date received: 12 January 2021

Date accepted: 14 January 2021

Publication date (print): 20 April 2021

Volume: 65

Issue: 2

Pages: s106-s108

Publisher ID: jkcs-65-s106

Synthesis, Antioxidant and Molecular Docking Studies of (−)-Catechin Derivatives

Deepak Kumar[†][‡]

Raj Kumar[§][#]

R. Ramajayam[]

Keun Woo Lee[§]

Dong-Soo Shin[†][*]

[†] Department of Chemistry, Changwon National University, Changwon, GN, 51140, S. Korea.

[‡] Department of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Shoolini University, Solan, H.P-173 229.

[§] Division of Applied Life Science (BK21 Plus), Systems and Synthetic Agrobiotech Center, Plant Molecular Biology and Biotechnology Research Center, Research Institute of Natural Science, Gyeongsang National University, Jinju, GN, 52828, Korea.

[#] Department of Biotechnology and Bioinformatics, Jaypee University of Information Technology, Waknaghat, Solan, Himachal Pradesh, 173234, India.

[] Pharmacy Department, DIT University, Dehradun, Uttrakhand, 248009, India.

Author notes:

Correspondence to: [*] E-mail: dsshin@changwon.ac.kr

Expand AllCollapse All

Characterization of the final compound (1a-1l)

(2S,3R)-2-(3,4-Dihydroxyphenyl)-3-(9-hydroxynonyl-oxy)chroman-5,7-diol (1a): Semi solid, Yield 83% (0.093g), [α]D25–52.4 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz): δ 6.88 (s, 1H), 6.84-6.74 (m, 2H), 5.96 (d, 2H, J = 3.28 Hz), 4.68 (d, 1H, J = 7.83 Hz), 3.73-3.68 (m, 1H), 3.58 (t, 2H, J = 6.56 Hz), 3.47-3.39 (m, 1H), 3.21-3.13 (m, 1H), 2.98(dd, 1H, J = 5.30, 16.16Hz), 2.57 (dd, 1H, J = 8.58, 16.16Hz), 1.58-1.49 (m, 2H), 1.43-1.03(m, 12H). 13C NMR (CD3OD, 100 MHz): δ 160.0, 159.8, 159.4, 148.3, 148.3, 135.1, 123.0, 118.7, 117.9, 103.7, 99.2, 98.6, 83.92, 79.5, 73.6, 66.2, 36.2, 33.4, 33.2, 33.0, 32.6, 29.4, 29.2. ESI-MS (m/z): 455 [M+Na]+.

(2S,3R)-2-(3,4-Dihydroxyphenyl)-3-(9-methoxy nonyl-oxy)chroman-5,7-diol (1b): Semi solid, Yield 83% (0.060 g), [α]D25 –59.9 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz): δ 6.82 (d, 1H, J = 1.76 Hz), 6.76-6.68 (m, 2H), 5.92 (d, 1H, J = 2.27Hz), 5.85 (d, 1H, J = 2.27 Hz), 4.62 (d, 1H, J = 7.32 Hz), 3.69-3.63 (m, 1H), 3.48-3.40 (m, 1H), 3.37 (t, 2H, J = 6.56 Hz), 3.31 (s, 3H), 3.21-3.15 (m, 1H), 2.86 (dd, 1H, J = 5.33, 15.91 Hz), 2.50(dd, 1H, J = 1.80, 16.16 Hz), 1.58-1.49 (m, 2H), 1.42-1.10 (m, 12H).13C NMR (CD3OD, 100 MHz) δ 157.8, 157.5, 157.0, 146.1, 146.1, 132.6, 119.9, 116.1, 115.2, 100.8, 96.4, 95.6, 81.2, 77.1, 74.0, 70.7,58.6, 30.8, 30.6, 30.5, 30.4, 30.3, 27.1, 27.0, 26.2. ESI-MS (m/z): 469 [M+Na]+.

(2S,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychroman-3-yl-oxy)nonylacetate (1c): Semi solid, Yield 82% (0.055 g), [α]D25 –46.9 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz): δ 6.82 (d, 1H, J = 1.76 Hz), 6.77-6.68 (m, 2H), 5.92 (d, 1H, J = 2.27Hz), 5.85 (d, 1H, J = 2.27 Hz), 4.62 (d, 1H, J = 7.32 Hz), 4.04 (t, 2H, J = 6.56 Hz), 3.70-3.63 (m, 1H), 3.49-3.38 (m, 1H), 3.23-3.14 (m, 1H), 2.87 (dd, 1H, J = 5.30, 16.16 Hz), 2.51 (dd, 1H, J = 7.83, 15.91Hz), 2.01 (s, 3H), 1.65-1.55 (m, 2H), 1.43-1.10 (m, 12H). 13C NMR (CD3OD, 100 MHz): δ 173.2, 157.8, 157.6, 156.9, 146.1, 132.6, 119.9, 116.0, 115.3, 100.8, 96.4, 95.6, 81.3, 77.2, 70.6, 65.8, 30.8, 30.5, 30.4, 30.2, 29.7, 27.2, 26.9, 26.2, 20.8. ESI-MS (m/z): 475 [M+H]+.

(2S,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychroman-3-yl)oxy)nonyl benzoate (1d): Semi solid, Yield 84% (0.061 g), [α]D25 –24.4 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz): δ 7.93-7.83 (m, 2H), 7.51-7.46 (m, 1H), 7.39-7.34 (m, 2H), 6.72 (d, 1H, J = 1.76 Hz), 6.66-6.58 (m, 2H), 5.83 (d, 1H, J = 2.27 Hz), 5.75 (d, 1H, J = 2.27 Hz),4.51 (d, 1H, J = 7.57 Hz), 4.21 (t, 2H, J = 6.56 Hz), 3.59-3.51 (m, 1H), 3.38-3.30 (m, 1H), 3.11-3.04 (m, 1H), 2.76 (dd, 1H, J = 5.30, 16.16 Hz), 2.40 (dd, 1H, J = 8.08, 16.16 Hz), 1.72-1.62 (m, 2H), 1.38-0.98 (m, 12H). 13C NMR (CD3OD, 100 MHz): δ 168.2, 157.9, 157.5, 157.0, 146.1, 134.1, 132.5, 131.7, 119.9, 116.0, 115.2, 100.7, 96.4, 95.6, 81.2, 77.1, 70.7, 66.3, 30.8, 30.4, 30.2, 30.2, 29.7, 27.1, 26.9, 26.2. ESI-MS (m/z): 560 [M+Na]+.

(2S,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychroman-3-yl-oxy nonyl oxy)-1-morpholinoethanone (1e): Semi solid, Yield 75% (0.046 g), [α]D25 –27.5 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz): δ 6.85 (d, 1H, J = 2.02 Hz), 6.79-6.70 (m, 2H), 5.96 (d, 1H, J = 2.27 Hz), 5.90 (d, 1H, J = 2.27 Hz), 4.65 (d, 1H, J = 7.57 Hz), 4.15 (s, 2H), 3.74-3.64 (m, 5H), 3.61-3.56 (m, 2H), 3.53-3.41 (m, 5H), 3.23-3.16 (m, 1H), 2.91 (dd, 1H, J = 5.30, 16.16 Hz), 2.54 (dd, 1H, J = 8.08, 16.16 Hz), 1.65-1.55 (m, 2H), 1.36-1.08 (m, 12H). 13C NMR (CD3OD, 100 MHz): δ 170.0, 157.3, 157.1, 156.5, 145.7, 132.1, 119.6, 115.7, 114.9, 100.5, 96.2, 80.9, 76.7, 76.7, 72.4, 70.5, 67.5, 61.3, 46.4, 43.3, 30.4, 30.2, 30.0, 29.9, 26.7, 26.6, 26.0, 20.9. ESI-MS (m/z): 582 [M+Na]+.

(2S,3R)-2-(3,4-Dihydroxyphenyl)-5,7dihydroxychroman-3-yl) oxy-nonyl-oxy-1-(4-phenylpiperazin-1(-yl)ethanone (1f): Semi solid, Yield 79%, (0.046 g), [α]D25 –26.4 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz): δ 7.25-7.20 (m, 2H), 6.98-6.93 (m, 2H), 6.88-6.83 (m, 1H) 6.70 (t, 3H, J = 2.01 Hz), 5.96 (d, 1H, J = 2.27 Hz), 5.85 (d, 1H, J = 2.27 Hz), 4.62 (d, 1H, J = 2.02 Hz), 4.20 (s, 2H), 3.74-3.69 (m, 1H), 3.67-3.61 (m, 2H), 3.61-3.55 (m, 1H), 3.54-3.39 (m, 4H), 3.22-3.10 (m, 3H), 2.85 (dd, 1H, J = 2.52, 16.16 Hz), 2.65-2.58 (m, 2H), 2.50 (dd, 1H, J = 8.58, 16.16 Hz), 1.67-1.55 (m, 2H), 1.42-1.09 (m, 12H).13C NMR (CD3OD, 100 MHz) δ 168.0, 158.7, 157.8, 149.0, 131.7, 129.2, 129.5, 128.5, 120.6, 120.5, 116.6, 115.1, 114.2, 102.5, 94.5, 93.7, 80.1, 75.5, 70.8, 70.2, 70.1, 49.8, 45.1, 29.8, 29.7, 29.6, 29.5, 26.1, 25.9.ESI-MS (m/z): 635 [M+H]+.

(2S,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxychroman-3-yl)oxy)nonyl)oxy)-1-(4-(4-fluorophenyl)piperazin-1-yl)ethanone (1g): Semi solid, Yield 77% (0.046 g), [α]D25 –25.5 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz): δ 6.89-6.88 (m, 2H), 6.87-6.86 (m, 2H), 6.72 (d, 1H, J = 2.02 Hz), 6.66-6.68 (m, 2H), 5.92 (d, 1H, J = 2.27 Hz), 5.82 (d, 1H, J = 2.27 Hz), 4.61 (d, 1H, J = 7.57 Hz), 4.20 (s, 2H), 3.74-3.69 (m, 1H), 3.67-3.61 (m, 2H), 3.61-3.55 (m, 1H), 3.54-3.39 (m, 4H), 3.22-3.10 (m, 3H), 2.85 (dd, 1H, J = 2.52, 16.16 Hz), 2.65-2.58 (m, 2H), 2.50 (dd, 1H, J = 8.58, 16.16 Hz), 1.67-1.55 (m, 2H), 1.42-1.09 (m, 12H).13C NMR (CD3OD, 100 MHz) δ 168.9, 158.7, 157.9, 154.0, 152.6, 152.0, 148.2, 148.1, 148.1, 135.6, 134.9, 132.5, 130.5, 130.2, 125.6, 117.6, 116.3, 114.8, 102.6, 94.6, 78.7, 77.8, 75.8, 71.4, 59.4, 52.9, 52.1, 36.7, 36.4, 36.3, 34.6, 30.1, 25.1.ESI-MS (m/z): 653 [M+H]+.

(2S,3R)-2-(3,4-Dihydroxyphenyl)-5,7dihydroxychroman-3yl-oxy nonyl oxy)-1-(4-(2-fluorophenyl piperazin-1 yl) propan-1-one (1h): Semi solid, Yield 77% (0.054 g), [α]D25 –22.4 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz) δ 7.26-7.20 (m, 2H), 7.00-6.93 (m, 1H), 6.87-6.82 (m, 1H), 6.81 (d, 1H, J = 2.02 Hz), 6.76-6.67 (m, 2H), 5.92 (d, 1H, J = 2.27 Hz), 5.84 (d, 1H, J = 2.27 Hz), 4.61 (d, 1H, J = 7.32 Hz), 3.77-3.68 (m, 6H), 3.67-3.61 (m, 2H), 3.50-3.38 (m, 3H), 3.20-3.09 (m, 4H), 2.86 (dd, 1H, J = 5.30, 16.16 Hz), 2.69 (t, 2H, J = 6.06 Hz), 2.49 (dd, 1H, J = 5.30, 16.16 Hz), 1.57-1.49 (m,2H) 1.38-1.08 (m, 12H).13C NMR (CD3OD, 100 MHz) δ 168.9, 158.7, 157.9, 154.0, 152.6, 152.0, 148.2, 148.1, 148.1, 135.6, 134.9, 132.5, 130.5, 130.2, 125.6, 117.6, 116.3, 114.8, 102.6, 94.6, 78.7, 77.8, 75.8, 71.4, 59.4, 52.9, 52.1, 36.7, 36.4, 36.3, 34.6, 30.1, 25.1.

(2S,3R)-2-(3,4-Dihydroxyphenyl)-5,7dihydroxychroman-3yl-nonyl-oxy-1-(2-trifluoromethyl phenyl)piperazin1-yl)propanone (1i): Semi solid, Yield 83% (0.093 g), [α]D25 –14.9 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz): δ 7.45-7.36 (m, 1H), 7.23-7.16 (m, 2H), 7.13-7.07 (m, 1H), 6.81 (d, 1H, J = 2.02 Hz), 6.76-6.67 (m, 2H), 5.92 (d, 1H, J = 2.27 Hz), 5.84 (d, 1H, J = 2.27 Hz), 5.85 (d, 1H, J = 2.27 Hz), 4.61 (d, 1H, J = 7.32 Hz),, 3.79-3.61 (m, 7H), 3.49-3.39 (m, 3H), 3.28-3.12 (m, 5H), 2.86 (dd, 1H, J = 5.30, 16.16 Hz), 2.69 (t, 2H, J = 6.06 Hz), 2.48 (dd, 1H, J = 7.83, 16.16 Hz), 1.58-1.48(m,2H) 1.39-1.02 (m, 12H).13C NMR (CD3OD, 100 MHz) δ 171.0, 157.8, 157.5, 152.6, 146.2, 145.4, 131.4, 130.9, 127.8, 126.6, 123.9, 121.9, 120.6, 117.1, 116.4, 116.0, 112.0, 109.4, 104.7, 95.5, 79.5, 79.2, 78.9, 72.3, 69.2, 59.0, 50.1, 45.3, 34.4, 30.7, 30.5, 30.3, 30.2, 27.2, 26.9, 26.2. ESI-MS (m/z): 740 [M+Na]+.

(2S,3R)-3-9-(3-Chloro-5-(trifluoromethyl)pyridin-2-yl)oxy)nonyl-oxy)-2-(3,4-dihydroxyphenyl)-chroman-5,7-diol (1j): Semi solid, Yield 80% (0.085 g), [α]D25 –29.9 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz): δ 8.25-8.23 (m, 1H), 7.94-7.92 (m, 1H), 6.73 (d, 1H, J = 2.27 Hz), 6.66-6.58 (m, 2 H), 5.83 (d, 1H, J = 2.27 Hz), 5.75 (d, 1H, J = 2.27 Hz), 4.52 (d, 1H, J = 7.32 Hz), 4.33 (d, 2H, J = 7.32 Hz), 3.60-3.51 (m, 1H) 3.37-3.28 (m, 1H), 3.12-3.03 (m, 1H), 2.77 (dd, 1H, J = 5.30, 16.16 Hz), 2.40 (dd, 1H, J = 8.08, 16.16 Hz), 1.75-1.65 (m,2H) 1.46-0.99 (m, 12H). 13C NMR (CD3OD, 100 MHz): δ 162.8, 157.8, 157.5, 156.9, 146.1, 146.1, 143.7, 136.4, 132.5, 126.1, 123.4, 121.8, 119.9, 116.0, 115.2, 100.7, 96.4, 81.2, 77.1, 70.7, 69.2, 30.8, 30.7, 30.5, 30.2, 29.7, 27.2, 26.3, 20.9. ESI-MS (m/z): 634 [M+Na]+.

(2S,3R)-3-(9-(5-Aminopyridin-2-yl)oxy-nonyl-oxy)-2-(3,4dihydroxyphenyl) chroman-5,7-diol (1k): Semi solid, Yield 73% (0.085 g), [α]D25 –44.4 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz) δ 8.30-8.28 (m, 1H), 7.96 (dd, 1H, J = 2.27 ,9.09 Hz), 6.72 (d, 1H, J = 2.02 Hz), 6.66-6.58 (m, 3H), 5.82 (d, 1H, J = 2.27 Hz), 5.74(d, 1H, J = 7.33 Hz), 4.54 (d, 1H, J = 7.32 Hz ), 4.36 (t 1H, J = 6.56 Hz) 3.60-3.53 (m, 1H), 3.46-3.41 (m, 1H) 3.39-3.32 (m, 1H), 3.12-3.05 (m, 1H), 2.76 (dd, 1H, J =5.05, 15.95 Hz), 2.40 (dd, 1H, J =7.83, 15.91 Hz), 1.76-1.16 (m, 2H), 1.48-0.97 (m, 12H).13C NMR (CD3OD, 100 MHz) δ 157.7, 156.9, 155.9, 154.0, 145.9, 143.0, 137.0, 131.9, 131.9, 126.8, 120.8, 119.5, 115.0, 111.1, 101.7, 95.8, 81.0, 79.8, 70.6, 69.8, 30.8, 30.7, 30.5, 30.1, 29.6, 27.2, 26.2, 20.7. ESI-MS (m/z): 547 [M+Na]+.

(2S,3R)-5-(Benzyloxy)-2-(3,4-dihydroxyphenyl)-7 hydroxy chroman-3-yl)oxy)nonyl 3-phenylpropanoate (1l): Semi solid, Yield 46% (0.080 g), [α]D25 –20.9 (c 1.0, MeOH). 1H NMR (CD3OD, 400 MHz) δ 7.30-7.12 (m, 5H), 6.82 (d, 1H, J = 2.02 Hz), 6.76-6.67 (m, 2H), 5.92 (d, 1H, J = 2.27 Hz), 5.84 (d, 1H, J = 2.27 Hz), 4.61 (d, 1H, J = 7.57 Hz), 4.03 (t, 2H, J = 6.31 Hz), 3.69-3.62 (m, 1H), 3.41 (t, 2H, J = 6.31), 2.9 (m, 3H), 2.60 (m, 2H), 2.50 (dd, 1H, J = 8.08, 16.16 Hz), 1.60-1.48 (m, 2H) 1.42-1.06 (m, 12H).13C NMR (CD3OD, 100 MHz) δ 175.3, 157.8, 157.6, 146.2, 146.1, 141.9, 129.4, 129.3, 127.2, 119.9, 116.0, 115.2, 107.6, 96.4, 95.6, 81.3, 73.8, 71.9, 65.7, 36.8, 32.0, 30.7, 30.5, 30.4, 29.7, 27.1, 26.9, 26.2, 23.7. ESI-MS (m/z): 587 [M+Na]+.