SINTESIS DAN AKTIVITAS ANTIKANKER SENYAWA C-4-ALILOKSI-3-METOKSIFENILKALIKS[4]RESORSINARENA

Indonesian Journal of Pure and Applied Chemistry Pub Date : 2021-04-30 DOI:10.26418/indonesian.v3i1.46505

Endah Sayekti, Jumina Jumina, Dwi Siswanta, M. Mustofa

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引用次数: 1

Abstract

The aims of this study was to synthesize of C-4-alyloxy-3-methoxyphenylcalix[4]resorcinarene (3). The syntheses was conducted by condensation reaction of resorcinol with 4-allyloxy-3-methoxybenzaldehyde (2) in ethanol with hydrochloric acid as a catalyst. The (2) compound was synthesized by the reaction of the 4-hydroxy-3-methoxybenzaldehyde (vanillin) (1) via allylation reaction using an allylbromide with the sodium metal as a catalyst in ethanol. A (3) compound was orange solid. m.p. of 176–177 °C (dec.). Yield (78%). FTIR (KBr, ν; cm-1): 3441 (-OH); 3086 and 3008 (Csp2-H); 2939 (Csp3-H ); 1612 (C=C aliphatic); 1512 (C=C aromatic); 1427 (>CH- methine); 1234, 1211, 1080 and 1018 (C-O-C asymmetric); 925 (C=CH2 terminal). 1H-NMR (DMSO-d6; 500 MHz) δ (ppm): 8,50 (8H, s, OH); 6.43 (4H, s, ArC-H); 6,36-6,38 (4H, d, J=10 Hz); 6.32 (4H, s, ArC-H); 6.26-6.28 (4H, d, J=10 Hz); 6.13 (4H, s, ArC-H); 6.00-6.05 (4H, m, =C-H); 5.38-5.40 (4H, d, J=10 Hz); 5.31 (4H, s, >C-H methine); 5.16-5.18 (4H, d, J=10 Hz); 4.34-4.36 (8H, d, J=10 Hz); 3.29 (12H, s, -OCH3). 13C-NMR (DMSO-d6; 500 MHz) dC (ppm): 33 (4 x CH methine); 55 (4 x CH3); 69 (4 x CH2-); 101 (4 x ArC-H); 112 (4 x ArC-H); 113 (4 x ArC-H); 116 (4 x =CH allyl terminal); 120 (4 x ArC-H); 122 (8x ArC-); 132 (4 x ArC-H); 134 (4 x =CH allyl); 137 (4 x ArC-); 145 (4 x ArC-O); 148 (4 x ArC-O); 152 (8 x ArC-OH). MS (ESI) m/z: 1137.5 (M+). Anticancer evaluation was performed on (3) compound by MTT (3-(4,5-dimethyltiazole-2-yl)-2,5-diphenyltetrazolium bromide) method showed that (3) compound has a cytotoxic activity against HeLa and T47D cells which IC50 value respectively are 13,58 and 65,26 µg/mL.

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合成和抗癌活性化合物c -4- alilok- 3-方法论[4]度假村

本研究的目的是合成c -4-烯丙氧基-3-甲氧基苯基杯[4]间苯二酚(3)。间苯二酚与4-烯丙氧基-3-甲氧基苯甲醛(2)在乙醇中以盐酸为催化剂缩合反应合成。以烯丙基溴为催化剂，在乙醇中以金属钠为催化剂，由4-羟基-3-甲氧基苯甲醛(香兰素)(1)经烯丙基化反应合成(2)化合物。A(3)化合物为橙色固体。温度为176-177°C(12月)。收益率(78%)。FTIR (KBr， ν;cm-1): 3441 (-OH);3086和3008 (Csp2-H);2939 (Csp3-H);1612 (C=C脂族);1512 (C=C芳);1427 (>CH-甲基);1234、1211、1080和1018 (C-O-C不对称);925 (C=CH2端子)。1 h - nmr (DMSO-d6;δ (ppm): 8,50 (8H, s, OH);6.43 (4H, s, ArC-H);6,36-6,38 (4H, d, J=10 Hz);6.32 (4H, s, ArC-H);6.26-6.28 (4H, d, J=10 Hz);6.13 (4H, s, ArC-H);6.00-6.05 (4H, m， =C-H);5.38-5.40 (4H, d, J=10 Hz);5.31 (4H, s， >C-H甲基);5.16-5.18 (4H, d, J=10 Hz);4.34-4.36 (8H, d, J=10 Hz);3.29 (12H, s， -OCH3)。色谱仪(DMSO-d6;500 MHz) dC (ppm): 33 (4 ×甲烷);55 (4 × CH3);69 (4 × CH2-);101 (4 × ArC-H);112 (4 × ArC-H);113 (4 × ArC-H);116 (4 x =CH烯丙基端);120 (4 × ArC-H);122 (8x ArC-);132 (4 × ArC-H);134 (4 x =CH烯丙基);137 (4 × ArC-);145 (4 × ArC-O);148(4倍ArC-O);152 (8 × ArC-OH)。MS (ESI) m/z: 1137.5 (m +)。采用MTT(3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四唑)法对化合物进行抗癌评价，结果表明化合物对HeLa和T47D细胞具有细胞毒活性，IC50值分别为13、58和65、26µg/mL。

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Indonesian Journal of Pure and Applied Chemistry

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