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Application of resveratrol-group piperlongumine analogue in medicine

A technology based on peronamide and resveratrol, which is applied in the field of application of resveratrol-based peronamide analogs in the treatment of malignant tumors, and can solve the problem of unseen applications of resveratrol-based peronamide analogs And other issues

Active Publication Date: 2016-02-10
杭州世子合德生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] So far, there is no application of resveratrol-based perylene amide analogs in medicine

Method used

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  • Application of resveratrol-group piperlongumine analogue in medicine
  • Application of resveratrol-group piperlongumine analogue in medicine
  • Application of resveratrol-group piperlongumine analogue in medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Compound BLBB-1 preparation of

[0018] The synthetic route is as follows:

[0019]

[0020] For the synthetic route of intermediate 1, please refer to the reference (Shoujiao Pengetal, J. Med. Chem. 2015, 58, 5242? 5255).

[0021] For the synthetic route of intermediate 2, please refer to the reference (Liu Wenhu et al., Acta Pharmaceutica Sinica, 2014, 49(2):217-224).

[0022]

[0023] The synthetic route of intermediate 3 can be found in references (Hou Jian et al., China Journal of Pharmaceutical Industry, 2008, 39, 1, 1-8).

[0024] The synthetic route of compound BLBB-1 is shown in the literature (Hou Jian et al., China Journal of Pharmaceutical Industry, 2008, 39, 1, 1-8):

[0025]

[0026] Dissolve the intermediate 310mmol in 10ml DMF under ice bath, add NaOCH 3 10mmol and vigorously stirred, then dropwise into the intermediate 210mmol, room temperature for 10h. Then it was poured into ice water, extracted with ethyl acetate, washed wit...

Embodiment 2

[0030] Embodiment 2: compound BLBB-2 preparation of

[0031] The synthetic route is as compound BLBB-1.

[0032] 1 HNMR (400MHz, DMSO): δ9.50(s, 1H), 9.14(s, 1H), 7.92(d, J=15.6Hz, 1H), 7.34(d, J=15.6Hz, 1H), 6.94(d ,J=16.4Hz, 1H), 6.92-6.90(m, 3H), 6.82(d, J=16.4Hz, 1H), 6.52(d, J=2.0Hz, 2H), 6.21(t, J=2.4Hz , 1H), 6.01(t, J=9.6Hz, 1H), 4.00(t, J=6.4Hz, 2H), 3.88(s, 6H), 2.44(m, 2H).

[0033] MS-ESI (m / z): 421.15.

Embodiment 3

[0034] Embodiment 3: compound BLBB-3 preparation of

[0035] The synthetic route is as compound BLBB-1.

[0036] 1 HNMR (400MHz, DMSO): δ9.52(s, 1H), 9.12(s, 1H), 7.90(d, J=15.6Hz, 1H), 7.36(d, J=15.6Hz, 1H), 6.98(d ,J=16.4Hz,1H),6.94-6.92(m,3H),6.80(d,J=16.4Hz,1H),6.54(d,J=2.0Hz,2H),6.22(t,J=2.4Hz , 1H), 6.03(t, J=9.6Hz, 1H), 4.00(t, J=6.4Hz, 2H), 2.42(m, 2H).

[0037] MS-ESI (m / z): 397.11.

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Abstract

The invention provides application of a resveratrol group containing piperlongumine analogue in medicine. The structure of the resveratrol-group piperlongumine analogue is as shown in figure (I), and the analogue is obtained on the basis of a great amount of activity screening; the analogue is good in antineoplastic activity; therefore, a new choice is provided for the development and the application of antineoplastic drugs.

Description

technical field [0001] The present invention relates to the use of resveratrol-based perylene amide analogues in medicine, in particular to the application of resveratrol-based perylene amide analogues in the treatment of malignant tumors. Background technique [0002] Malignant tumor is a major disease that endangers human health, and it has become the first cause of death among Chinese residents. Chemotherapy is still the main means of treatment for many malignant tumors, but the resistance of tumor cells to chemotherapeutic drugs, including primary drug resistance and acquired drug resistance, has always been the primary problem that plagues and restricts the chemotherapy of malignant tumors in clinical practice. Therefore, it is urgent to find innovative drugs with high anticancer activity. In recent years, natural products and their derivatives have become an important source of innovative anticancer drugs. The development of class I new drugs through the structural m...

Claims

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Application Information

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IPC IPC(8): A61K31/4412C07D211/86A61P35/00
Inventor 金加明
Owner 杭州世子合德生物科技有限公司
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