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An oxygen-bridged bicyclo-[2.2.1]-heptene compound containing a boronic acid derivative group, its synthesis method and application
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A technology of compounds and groups, applied in the field of medicine
Active Publication Date: 2019-11-08
WUHAN UNIV
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However, since this type of compound contains sulfonamide groups and polyaromatic ring conjugated structures, the solubility needs to be optimized urgently; at the same time, there is room for further optimization of its ability to bind to estrogen receptors
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[0116] Weigh 3-(4-hydroxyphenyl)-4-(4-boronate phenyl)-furan 9 compound (150mg, 414.4mmol) and N-(4-chloro)-N-methylethylenesulfonamide 32 (94mg, 414.4mmol) was placed in a 50mL two-necked bottle, mixed with tetrahydrofuran as a solvent, reacted at 90°C for 10 hours, and directly spin-dried for column chromatography purification, the mobile phase was petroleumether:ethyl acetate=4:1, After purification, 96 mg of compound 40 was obtained as a pale yellow solid, with a yield of about 39.3%. 1 H NMR (400MHz, DMSO-d 6 )δ7.62–7.10(m,10H),6.73(dd,J=16,8Hz,2H),5.44(m,2H),3.76–3.18(m,7H),1.88(s,1H),1.30( s,12H). 13 CNMR (100MHz, DMSO-d 6 )δ158.33,144.45,141.43,140.73,137.01,136.36,135.16,131.70,130.51,129.50,128.49,127.00,126.63,122.83,122.19,116.08,84.22,82.63,73.98,60.45,60.05,25.42,25.04.HRMS(ESI )calcd for C 32 h 36 BNO 7 S[M+H] ...
[0118] Compound 41 was prepared as in Example 1, and the product was a yellow solid with a yield of about 37.4%. 1 H NMR (400MHz, DMSO-d 6 )δ7.68–7.17(m,11H),6.81–6.64(m,2H),5.43(m,2H),3.76–3.46(m,3H),1.98(t,J=12Hz,1H),1.29( s,12H),1.10(d,J=20.7Hz,3H). 13 C NMR (100MHz, DMSO-d 6 )δ158.33,146.40,144.45,141.13,140.45,139.21,136.75,136.15,135.17,134.38,129.83,129.62,128.08,127.64,127.06,126.52,122.93,122.18,116.10,84.34,82.54,73.98,61.36,46.09,26.81 , 25.43, 25.12, 14.70. HRMS (ESI) calcd for C 32 h 36 BNO 6 S[M+Na] + ,596.2249; found 596.2247.
[0120] Compound 42 was prepared as in Example 1, and the product was a yellow solid with a yield of about 41.4%. 1 H NMR (400MHz, DMSO-d 6 )δ7.70–7.01(m,10H),6.80–6.61(m,2H),5.57–5.28(m,2H),3.82–3.49(m,6H),1.97(dd,J=12,6Hz,1H ),1.29(s,12H).HRMS(ESI)calcd for C 32 h 35 BClNO 6 S[M+Na] + ,630.1859; found 630.1863.
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Abstract
The invention discloses an oxo-bridge bicyclo-[2.2.1]-heptene compound containing a boric acid derived group as well as a synthesis method and application thereof. A target compound disclosed by the invention is prepared from 3-(4-hydroxylphenyl)-4-(4-boratephenyl)-furan and an ethylene sulfonamide derivative through Diels-Alder reaction and subsequent hydrolysis reaction. The oxo-bridge bicyclo-[2.2.1]-heptene compound has the advantages of relatively high reaction total yield, mild conditions and high speed. An in-vivo experiment proves that compared with an existing breast-cancer-resistingmedicine 4-hydroxytamoxifen (4-OHT), the novel oxo-bridge bicyclo-[2.2.1]-heptene compound containing the boric acid derived group has a higher inhibition effect on proliferation of hormone-dependingbreast cancer MCF-7 cells.
Description
technical field [0001] The invention belongs to the technical field of medicine, and relates to a class of oxygen-bridged bicyclo-[2.2.1]-heptene compounds containing boronic acid derivative groups, their synthesis method and application. Background technique [0002] Breast cancer is the most common malignant tumor in women, statistics show that on average about 1 in 8 women may suffer from breast cancer. Female breast cancer patients account for about 30% of all female cancer patients. About 2 / 3 of breast cancers are related to estrogen and estrogen receptors in the human body. Estrogen binds to estrogen receptors to form a ligand-receptor complex. Under the action of coactivators, the DNAbinding domain on estrogen receptors can bind to DNA to form subsequent transcription and translation processes, thereby regulating the growth and differentiation of mammary glands . Selective estrogen receptor downregulators (selective estrogen receptor downregulators, SERDs) are a n...
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