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Naringenin derivative and application thereof

A derivative, the technology of naringenin, which is applied in the field of naringenin derivatives, can solve the problems that no one has disclosed the structure of naringenin derivatives, achieve good application prospects, reduce the pain of chemotherapy, and reduce the effect of pain

Pending Publication Date: 2022-04-15
NINGBO UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, no one has disclosed the structure of naringenin derivatives and its application in analgesia.

Method used

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  • Naringenin derivative and application thereof
  • Naringenin derivative and application thereof
  • Naringenin derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Compound Y1 preparation of

[0021] Dissolve naringenin (100 mg, 0.37 mmol, 1.0 eq.) in 1 mL DMF, add K 2 CO 3 (153 mg, 1.11 mmol, 3 eq.) was stirred at room temperature for 15 min, and MeI (131 mg, 0.93 mmol, 2.5 eq.) was added and stirred overnight at room temperature, and the reaction was monitored by TLC and LCMS. filter, flash (reverse) (H 2 O / 0.05%FA) / MeCN:25%-65%, 20min) to obtain 1.5 mg of yellow solid, yield 1.4%. Compound structure data characterization: 1 H NMR (500 MHz, DMSO-d6)δ 12.15 (d, J = 8.8 Hz, 1H), 9.55 (s, 1H), 7.22 -7.30 (m, 2H), 6.70 – 6.79(m, 2H), 6.15 ( d, J = 11.0 Hz, 1H), 5.40 (dt, J = 12.3, 2.3 Hz, 1H), 3.62 –3.79 (m, 4H), 2.62 – 2.76 (m, 1H), 1.83 (d, J = 10.0 Hz , 3H). MS (ESI): C 17 h 16 o 5 , Calcd for [M+H] + 301.1071; Found: 301.1.

Embodiment 2

[0022] Example 2: Compound Y2 (naringenin trimethyl ether) preparation of

[0023] Dissolve naringenin (100 mg, 0.37 mmol, 1.0 eq.) in 1 mL DMF, add K 2 CO 3 (153 mg, 1.11 mmol, 3 eq.) was stirred at room temperature for 15 min, and MeI (131 mg, 0.93 mmol, 2.5 eq.) was added and stirred overnight at room temperature, and the reaction was monitored by TLC and LCMS. filter, flash (reverse) (H 2 O / 0.05%FA) / MeCN:25%-65%, 20min) to obtain 13.7 mg of yellow oil, with a yield of 11.8%. Compound structure data characterization: 1 H NMR (500 MHz, DMSO-d6) δ 7.40 – 7.47 (m, 2H), 6.93 – 7.00 (m, 2H), 6.17 – 6.23 (m, 2H), 5.46(dd, J = 12.7, 2.9 Hz, 1H ), 3.75 – 3.84 (m, 9H), 3.01 – 3.11 (m, 1H), 2.56 –2.63 (m, 1H). MS (ESI): C 18 h 18 o 5 , Calcd for [M+H] + 315.1227; Found: 315.1.

Embodiment 3

[0024] Example 3: Compound Y3 (4',7-Dimethylnaringenin) preparation of

[0025] Dissolve naringenin (100 mg, 0.37 mmol, 1.0 eq.) in 1 mL DMF, add K 2 CO 3 (153 mg, 1.11 mmol, 3 eq.) was stirred at room temperature for 15 min, and MeI (131 mg, 0.93 mmol, 2.5 eq.) was added and stirred overnight at room temperature, and the reaction was monitored by TLC and LCMS. filter, flash (reverse) (H 2 O / 0.05%FA) / MeCN:25%-65%, 20min) to obtain 3.8mg of 3 yellow solids, yield 3.4%. Compound structure data characterization: 1H NMR (500 MHz, DMSO-d6)δ 12.04 (s, 1H), 7.35 – 7.42 (m, 2H), 6.88 – 6.95 (m, 2H), 6.03 (dd, J =15.2, 2.3 Hz, 2H), 5.49 (dd, J = 12.7, 3.0 Hz, 1H), 3.71 (d, J = 8.2 Hz, 6H), 3.22 – 3.29 (m, 1H), 2.66 – 2.73 (m, 1H). MS (ESI): C 17 h 16 o 5 , Calcd for [M+H] + 301.1071; Found: 301.1.

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PUM

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Abstract

The naringenin derivative is characterized in that the naringenin derivative is a compound with a structural formula shown in a formula I. R1, R2 and R3 are H, CH3, CH2F, CHF2, CF3, straight-chain alkane with the carbon atom number of 1-5, ester group, silyl ether, trifluoroalkane or polyfluoroalkane with the carbon atom number of 1-5, and straight-chain terminal alkyne alkane with the carbon atom number of 1-6, n is equal to 1, 2, 3, 4 or 5, m is equal to 1, 2, 3, 4, 5 or 6, and n is equal to 1, 2, 3, 4, 5 or 6. The naringenin derivative can be used for preparing drugs for treating chemotherapy pain, inhibitors for activating spinal glial cells induced by chemotherapy pain and drugs for relieving inflammatory pain and neuropathic pain, and has the advantage of remarkable analgesic effect.

Description

technical field [0001] The invention relates to a naringenin derivative and its application. Background technique [0002] In clinical anti-tumor therapy, one of the common side effects of chemotherapy drugs (such as paclitaxel (PTX) and platinum drugs) is chemotherapy-induced peripheral neuropathy (Chemotherapy-induced peripheral neuropathy, CIPN) accompanied by neuropathic pain and neuroinflammation , Seriously affecting the quality of life of cancer patients, clinically there is also a lack of effective drugs and therapies. It has been reported in the literature that peripheral neuropathic pain caused by PTX affects 68% of patients in the first month after chemotherapy, and about 30% of patients still have pain symptoms 6 months after chemotherapy. [0003] Naringenin (Naringenin, Nar) belongs to dihydroflavonoids, mainly found in Rutaceae grapefruit, tomato, grape and citrus fruits. Studies have shown that naringenin has anti-inflammatory, antioxidant, anti-tumor and a...

Claims

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Application Information

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IPC IPC(8): C07D311/32A61P29/00
Inventor 陈晓薇倪锋陈晴歌徐霖斌卢祺晨闫杰洪邦赵增祥田丰耿祎
Owner NINGBO UNIV