CN103864742A - Preparation and anti-tumor application of novel naringenin derivatives - Google Patents

Preparation and anti-tumor application of novel naringenin derivatives Download PDF

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CN103864742A
CN103864742A CN201210537184.6A CN201210537184A CN103864742A CN 103864742 A CN103864742 A CN 103864742A CN 201210537184 A CN201210537184 A CN 201210537184A CN 103864742 A CN103864742 A CN 103864742A
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naringenin
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boric acid
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trimethylammonium
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郁彭
褚杰
付晓丽
全德武
郭娜
吕蕾
温少鹏
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Tianjin University of Science and Technology
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
    • C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
    • C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
    • C07D311/32—2,3-Dihydro derivatives, e.g. flavanones
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Abstract

The present invention relates to preparation and an anti-tumor application of a class of novel naringenin derivatives. According to the present invention, naringenin is adopted as a raw material, and electrophilic substitution, heck and other reactions are performed to obtain a series of the derivatives.

Description

The derivative preparation of novel naringenin of one class and antitumor application
Technical field
The present invention relates to preparation method and the active research of the naringenin derivative of new replacement.
Technical background
Naringenin is the glucoside unit of naringin, belongs to flavanone kind composition, has antibacterial, anti-inflammatory, anticancer, spasmolysis and choleretic effect, and clinical application is infected in treatment bacterium, calm, anticancer class.
Naringenin is naringinglucoside unit, belong to flavanone kind composition, there is antibacterial, anti-inflammatory, removing free radical, anti-oxidant, cough-relieving apophlegmatic, reducing blood-fat, anticancer antitumor, spasmolysis and cholagogic, prevention and treatment hepatopathy, anti-platelet clotting, anti- congee sample arteriosclerosisdeng effect, can be widely used in the field such as medicine, food.
Take naringenin as raw material, obtain first having a series of naringenin derivatives of potential source biomolecule activity by reactions such as replacement, demethylation, Heck herein.
Invention summary
First, the invention provides formula (I) compound
Figure BSA00000822603400011
Formula (I)
Wherein R1 represents any of following blocking group.
R1 is preferably: Benzyl Chloride, acetic anhydride, methyl iodide, iodoethane, chloromethyl ether
R2 is preferably: hydroxyl, Benzyl Chloride, ethanoyl, methyl, ethyl, chloromethyl ether
R3 is preferably: iodine, phenylo boric acid, to methylphenylboronic acid, to fluorobenzoic boric acid, to chlorobenzene boric acid, to bromobenzene boric acid, to iodobenzene boric acid, to methoxyphenylboronic acid, to ethylbenzene boric acid, to cyanophenylboronic acid, isopropyl benzene boric acid, to methoxycarbonyl phenylo boric acid, to trifluoromethyl phenylo boric acid
R4 is preferably: iodine, phenylo boric acid, to methylphenylboronic acid, to fluorobenzoic boric acid, to chlorobenzene boric acid, to bromobenzene boric acid, to iodobenzene boric acid, to methoxyphenylboronic acid, to ethylbenzene boric acid, to cyanophenylboronic acid, isopropyl benzene boric acid, to methoxycarbonyl phenylo boric acid, to trifluoromethyl phenylo boric acid
Specilization compound of the present invention comprises
1) 5,7,4 '-tribenzyl naringenin
2) 5,7,4 '-triacetyl naringenin
3) 5,7,4 '-trimethylammonium naringenin
4) 5,7,4 '-triethyl naringenin
5) 5,7,4 '-tri-methyl ether naringenins
6) 7,4 '-dibenzyl naringenin
7) 7,4 '-diacetyl naringenin
8) 7,4 '-dimethyl naringenin
9) 7,4 '-diethyl naringenin
10) 7,4 '-methyl ether base naringenin
11) 5,7,4 '-tribenzyl-8-iodine naringenin
12) 5,7,4 '-triacetyl-8-iodine naringenin
13) 5,7,4 '-trimethylammonium-8-iodine naringenin
14) 5,7,4 '-triethyl-8-iodine naringenin
15) 5,7,4 '-tri-methyl ethers-8-iodine naringenin
16) 7,4 '-dibenzyl-6-iodine naringenin
17) 7,4 '-diacetyl-6-iodine naringenin
18) 7,4 '-dimethyl-6-iodine naringenin
19) 7,4 '-diethyl-6-iodine naringenin
20) 5,7,4 '-trimethylammonium-8-phenyl naringenin
21) 5,7,4 '-trimethylammonium-8-p-methylphenyl naringenin
22) 5,7,4 '-trimethylammonium-8-is to fluorophenyl naringenin
23) 5,7,4 '-trimethylammonium-8-rubigan naringenin
24) 5,7,4 '-trimethylammonium-8-is to bromophenyl naringenin
25) 5,7,4 '-trimethylammonium-8-is to iodophenyl naringenin
26) 5,7,4 '-trimethylammonium-8-p-methoxyphenyl naringenin
27) 5,7,4 '-trimethylammonium-8-is to ethylphenyl naringenin
28) 5,7,4 '-trimethylammonium-8-is to cyano-phenyl naringenin
29) 5,7,4 '-trimethylammonium-8-p-isopropyl phenyl naringenin quinoline
30) 5,7,4 '-trimethylammonium-8-p-isopropyl naringenin
31) 5,7,4 '-trimethylammonium-8-(to methoxycarbonyl) phenyl naringenin
32) 5,7,4 '-trimethylammonium-8-phenyl naringenin
33) 8-p-methylphenyl naringenin
34) 8-is to fluorophenyl naringenin
35) 8-rubigan naringenin
36) 8-is to bromophenyl naringenin
37) 8-is to iodophenyl naringenin
38) 8-p-methoxyphenyl naringenin
39) 8-is to ethylphenyl naringenin
40) 8-is to cyano-phenyl naringenin
41) 8-p-isopropyl phenyl naringenin quinoline
42) 8-p-isopropyl naringenin
43) 8-(to methoxycarbonyl) phenyl naringenin
Detailed Description Of The Invention
The synthetic route of formula (I)
Figure BSA00000822603400031
Illustrate 1
5,7,4 '-trimethylammonium naringenin
Step: naringenin 1g and salt of wormwood 2.7g (6eq) are dissolved in to 10mL DMF, stir after 20 minutes, drip methyl iodide 1.24mL (6eq), drip and finish, stirring at normal temperature reaction, TLC detects, and treats raw material complete reaction, drips dilute hydrochloric acid, dichloromethane extraction, sherwood oil: ethyl acetate: methylene dichloride=1: cross silicagel column, obtain product 1.1g, productive rate 90% at 1: 1
1HNMR(400MHz，CDCl3)：d＝2.78(dd，J＝3.2Hz，1H)，3.09(dd，J＝12.8Hz，1H)，3.80(s，3H)，3.83(s，3H)，?6.05(d，J＝8.8Hz，2H)，6.95(d，J＝8.4Hz，2H)，7.38(d，J＝8.4Hz)，12.02(s，1H).13CNMR(400MHz，CDCl3)：d＝43.2，55.3，55.6，79.0，94.2，95.1，103.1，114.2，127.7，130.4，160.0，162.9，164.1，167.9，196.0
MS(ESI)m/zfound：299.06[M-H] -.Calcd?for?C 17H 16O s：300.1020
Illustrate 2.
5,7,4 '-trimethylammonium-8-iodine naringenin
Step: mountain compound 10.2g and NIS 29mg (1.2eq) are dissolved in to 5mL DMF, 60 degree stirring reactions, TLC detects, treat raw material complete reaction, add solution of potassium carbonate cancellation, dichloromethane extraction, sherwood oil: ethyl acetate=1: 1 crosses silicagel column, obtain product 0.28g, productive rate 78%
1HNMR(400MHz，CDCl3)：d＝2.90-3.05(m，2H)，3.82(s，3H)，3.95(s，3H)，3.96(s，3H)，5.50(dd，J＝11.6Hz，3.2Hz，1H)，6.14(s，1H)，6.94(d，J＝8.4Hz，2H)，7.44(d，J＝8.4Hz，2H).13CNMR(400MHz，CDCl3)：d＝44.8，55.3，56.3，56.5，66.3，78.7，89.1，106.7，114.0，127.3，130.5，159.6，162.4，163.1，164.2，189.1
MS(ESI)m/z?found：441.00[M+H] +.Calcd?for?C 18H 17IO 5：440.01.
Illustrate 3.
7,4 '-dimethyl naringenin
Step: naringenin 0.3g and sodium carbonate 0.26g (2.2eq) are dissolved in to 5mL DMF, stir after 20 minutes, drip methyl iodide 0.16mL (2.4eq), drip and finish, stirring at normal temperature reaction, TLC detects, and treats raw material complete reaction, drips dilute hydrochloric acid, dichloromethane extraction, sherwood oil: ethyl acetate=5: 1 crosses silicagel column, obtains product 0.2g, productive rate 60%
1HNMR(400MHz，CDCl3)：d＝2.78(dd，J＝3.2Hz，1H)，3.09(dd，J＝12.8Hz，1H)，3.80(s，3H)，3.83(s，3H)，6.05(d，J＝8.8Hz，2H)，6.95(d，J＝8.4Hz，2H)，7.38(d，J＝8.4Hz)，12.02(s，1H).13CNMR(400MHz，CDCl3)：d＝43.2，55.3，55.6，79.0，94.2，95.1，103.1，114.2，127.7，130.4，160.0，162.9，164.1，167.9，196.0
MS(ESI)m/zfound：299.06[M-H] -.Calcd?for?C 17H 16O 5：300.10
Illustrate 4
7,4 '-dimethyl-6-iodine naringenin
Step: compound (1) 0.3g is dissolved in to 3mL DMF, add NIS 0.21g (1.2eq), stirring at normal temperature reaction, TLC detects, treat raw material complete reaction, add solution of potassium carbonate, dichloromethane extraction, sherwood oil: ethyl acetate=3: 1 crosses silicagel column obtains product (2) 0.35g productive rate 86%.
1HNMR(400MHz，CDCl3)：d＝2.83(dd，J＝17.2Hz，3.2Hz，1H)，3.14(dd，J＝17.2Hz，13.2Hz，1H)，3.83(s，3H)，3.90(s，3H)，5.39(dd，J＝13.2Hz，2.8Hz，1H)，6.13(s，1H)，6.96(d，J＝8.8Hz，2H)，7.38(d，J＝8.8Hz，1H)，12.84(s，1H).
13CNMR(400MHz，CDCl3)：d＝42.5，55.3，56.7，66.0，79.3，91.9，103.3，114.3，127.7，129.9，160.2，162.4，163.8，165.7，195.5.MS(ESI)m/z?found：426.80[M+H] +.Calcd?for?C 17H 15IO 5：426.00
Illustrate 5.
5,7,4 '-triethyl naringenin
Step: naringenin 1g and salt of wormwood 2.7g (6eq) are dissolved in to 10mL DMF, stir after 20 minutes, drip iodoethane 1.6mL (6eq), drip and finish, stirring at normal temperature reaction, TLC detects, and treats raw material complete reaction, drips dilute hydrochloric acid, dichloromethane extraction, sherwood oil: ethyl acetate: methylene dichloride=1: cross silicagel column, obtain product 1.2g, productive rate 82% at 1: 1
Illustrate 6.
5,7,4 '-triethyl-8-iodine naringenin
Step: compound (1) 0.3g is dissolved in to 3mL DMF, add NIS 0.21g (1.2eq), be heated to 50 degree stirring reactions, TLC detects, treat raw material complete reaction, add solution of potassium carbonate, dichloromethane extraction, methylene dichloride: methyl alcohol=10: 1 crosses silicagel column obtains product (2) 0.32g productive rate 82%.
Illustrate 7.
7,4 '-diethyl naringenin
Step: naringenin 1g and salt of wormwood 2.0g (4.5eq) are dissolved in to 10mL DMF, stir after 20 minutes, drip iodoethane 1.2mL (4.5eq), drip and finish, stirring at normal temperature reaction, TLC detects, and treats raw material complete reaction, drips dilute hydrochloric acid, dichloromethane extraction, sherwood oil: ethyl acetate=3: 1 crosses silicagel column, obtains product 0.75g, productive rate 56%
Illustrate 8
7,4 '-diethyl-6-iodine naringenin
Step: compound (1) 0.3g is dissolved in to 3mL DMF, add NIS 0.2g (1.2eq), stirring at normal temperature reaction, TLC detects, treat raw material complete reaction, add solution of potassium carbonate, dichloromethane extraction, sherwood oil: ethyl acetate=3: 1 crosses silicagel column obtains product (2) 0.3g productive rate 78%.
Illustrate 9.
5,7,4 '-tribenzyl naringenin
Step: by naringenin 1g, be dissolved in HMPA, add benzyl chlorine 4.2g, salt of wormwood 2.8g, triethyl benzyl ammonia chloride 0.2g, room temperature reaction 35h, adds water treatment, crosses the product 2.3g of silicagel column, productive rate 90%
Illustrate 10.
5,7,4 '-tribenzyl-8-iodine naringenin
Step: compound (1) 0.3g is dissolved in to 3mL DMF, add NIS 0.1g (1.2eq), be heated to 60 degree stirring reactions, TLC detects, treat raw material complete reaction, add solution of potassium carbonate, dichloromethane extraction, methylene dichloride: methyl alcohol=10: 1 crosses silicagel column obtains product (2) 0.24g productive rate 70%.
Illustrate 11.
7,4 '-dibenzyl naringenin
Step: naringenin 1g and salt of wormwood 2.7g (6eq) are dissolved in to 10mL DMF, stir after 20 minutes, drip benzyl chlorine 3.4g (8eq), drip and finish, 40 degree stirring reactions, TLC detects, and treats raw material complete reaction, drips dilute hydrochloric acid, dichloromethane extraction, sherwood oil: ethyl acetate=8: 1 crosses silicagel column, obtains product 1.3g, productive rate 60%
Illustrate 12
7,4 '-dibenzyl-6-iodine naringenin
Step: compound (1) 0.3g is dissolved in to 3mL DMF, add NIS 0.15g (1.2eq), stirring at normal temperature reaction, TLC detects, treat raw material complete reaction, add solution of potassium carbonate, dichloromethane extraction, sherwood oil: ethyl acetate=7: 1 crosses silicagel column obtains product (2) 0.28g productive rate 78%.
Accompanying drawing explanation:
Fig. 1 is 7,4 '-dimethyl naringenin 1h-NMR
Fig. 2 is 7,4 '-dimethyl-8-iodine naringenin 1h-NMR
Fig. 3 is 5,7,4 '-trimethylammonium naringenin 1h-NMR
Fig. 4 is 5,7,4 '-trimethylammonium-8-iodine shaddock 1h-NMR.

Claims (7)

1. naringenin analog derivative, is characterized in that: the general structure of derivative is as follows:
Wherein R1 represents any of following blocking group.
R1 is preferably: Benzyl Chloride, acetic anhydride, methyl iodide, iodoethane, chloromethyl ether
R2 is preferably: hydroxyl, Benzyl Chloride, ethanoyl, methyl, ethyl, chloromethyl ether
R3 is preferably: iodine, phenylo boric acid, to methylphenylboronic acid, to fluorobenzoic boric acid, to chlorobenzene boric acid, to bromobenzene boric acid, to iodobenzene boric acid, to methoxyphenylboronic acid, to ethylbenzene boric acid, to cyanophenylboronic acid, isopropyl benzene boric acid, to methoxycarbonyl phenylo boric acid, to trifluoromethyl phenylo boric acid
R4 is preferably: iodine, phenylo boric acid, to methylphenylboronic acid, to fluorobenzoic boric acid, to chlorobenzene boric acid, to bromobenzene boric acid, to iodobenzene boric acid, to methoxyphenylboronic acid, to ethylbenzene boric acid, to cyanophenylboronic acid, isopropyl benzene boric acid, to methoxycarbonyl phenylo boric acid, to trifluoromethyl phenylo boric acid.
2. naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-tribenzyl-8-iodine naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-triacetyl-8-iodine naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-trimethylammonium-8-iodine naringenin 15, naringenin derivative according to claim 1, it is characterized in that: described derivative is 5,74 '-triethyl-8-iodine naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-tri-methyl ethers-8-iodine naringenin.
3. naringenin derivative according to claim 1, is characterized in that: described derivative is 7,4 '-dibenzyl-6-iodine naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 7,4 '-diacetyl-6-iodine naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 7,4 '-dimethyl-6-iodine naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 7,4 '-diethyl-6-iodine naringenin.
4. naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-trimethylammonium-8-phenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-trimethylammonium-8-p-methylphenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7, and 4 '-trimethylammonium-8-is to fluorophenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-trimethylammonium-8-rubigan naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7, and 4 '-trimethylammonium-8-is to bromophenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7, and 4 '-trimethylammonium-8-is to iodophenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-trimethylammonium-8-p-methoxyphenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7, and 4 '-trimethylammonium-8-is to ethylphenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7, and 4 '-trimethylammonium-8-is to cyano-phenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-trimethylammonium-8-p-isopropyl phenyl naringenin quinoline
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-trimethylammonium-8-p-isopropyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-trimethylammonium-8-(to methoxycarbonyl) phenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 5,7,4 '-trimethylammonium-8-phenyl naringenin.
5. naringenin derivative according to claim 1, is characterized in that: described derivative is 8-p-methylphenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is that 8-is to fluorophenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 8-rubigan naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is that 8-is to bromophenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is that 8-is to iodophenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 8-p-methoxyphenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is that 8-is to ethylphenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is that 8-is to cyano-phenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 8-p-isopropyl phenyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 8-p-isopropyl naringenin
Naringenin derivative according to claim 1, is characterized in that: described derivative is 8-(to methoxycarbonyl) phenyl naringenin.
6. the preparation method of the intermediate of naringenin analog derivative
Become route as follows:
Figure FSA00000822603300031
R1 is preferably: Benzyl Chloride, acetic anhydride, methyl iodide, iodoethane, chloromethyl ether
R2 is preferably: hydroxyl, Benzyl Chloride, ethanoyl, methyl, ethyl, chloromethyl ether
R3 is preferably: iodine, phenylo boric acid, to methylphenylboronic acid, to fluorobenzoic boric acid, to chlorobenzene boric acid, to bromobenzene boric acid, to iodobenzene boric acid, to methoxyphenylboronic acid, to ethylbenzene boric acid, to cyanophenylboronic acid, isopropyl benzene boric acid, to methoxycarbonyl phenylo boric acid, to trifluoromethyl phenylo boric acid.
7. such compound medicine activity: this compounds has that cardiovascular systems is safeguarded, antibacterial and antiviral, antitumor, anti-oxidant, anti-inflammatory, the multiple biological activity such as ease pain, protect the liver.
CN201210537184.6A 2012-12-13 2012-12-13 Preparation and anti-tumor application of novel naringenin derivatives Pending CN103864742A (en)

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CN114349730A (en) * 2021-11-30 2022-04-15 宁波大学 Naringenin derivative and application thereof

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CN104387360A (en) * 2014-11-21 2015-03-04 段煜 Naringenin fatty acid ester and preparation method thereof as well as pharmaceutical composition with naringenin fatty acid ester as active component and application of pharmaceutical composition
CN105732562A (en) * 2014-12-31 2016-07-06 三星显示有限公司 Compound, organic light-emitting device comprising the compound, and panel dislay device comprising the organic light-emitting device
CN105732562B (en) * 2014-12-31 2021-06-01 三星显示有限公司 Compound, organic light emitting device including the same, and flat panel display device including the same
CN107118192A (en) * 2017-06-25 2017-09-01 石家庄学院 Derivative of dihydromyricetin containing halogen and its preparation method and application
CN107118192B (en) * 2017-06-25 2019-11-15 石家庄学院 Derivative of dihydromyricetin containing halogen and its preparation method and application
PL422925A1 (en) * 2017-09-21 2019-03-25 Uniwersytet Przyrodniczy we Wrocławiu 5,7,4'-tripropoxynaringenin and method for obtaining 5,7,4'-tripropoxynaringenin
PL422923A1 (en) * 2017-09-21 2019-03-25 Uniwersytet Przyrodniczy we Wrocławiu 7-isopropoxy-naringenin and 7,4'-diisopropoxy-naringenin and method for simultaneously obtaining 7-isopropoxy-naringenin and 7,4'-diisopropoxy-naringenin
CN111892567A (en) * 2020-07-22 2020-11-06 河南中医药大学 Flavanone compound extracted from lindera reflexa hemsl and preparation method and application thereof
CN111892567B (en) * 2020-07-22 2024-01-26 河南中医药大学 Dihydroflavonoid compound extracted from lindera reflexa hemsl, and preparation method and application thereof
CN114349730A (en) * 2021-11-30 2022-04-15 宁波大学 Naringenin derivative and application thereof
CN114349730B (en) * 2021-11-30 2023-10-31 宁波大学 Naringenin derivative and application thereof

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Application publication date: 20140618