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Andrographolide analogue and application of andrographolide analogue to treatment

A kind of technology of andrographolide, analog, applied in the field of new andrographolide analog

Active Publication Date: 2012-10-03
LIAONING LIFENG SCI & TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, searching all the literature on the structural modification of andrographolide, there is no 15 The introduction of substituents at the position to form new lactone analogs has antiviral and anticancer activity reported in the literature; 7 and C 15 The introduction of substituents to form new analogs and the literature reports on the antiviral and anticancer activities of the new analogs

Method used

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  • Andrographolide analogue and application of andrographolide analogue to treatment
  • Andrographolide analogue and application of andrographolide analogue to treatment
  • Andrographolide analogue and application of andrographolide analogue to treatment

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Experimental program
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Embodiment

[0032] Synthesis and preparation example (see 1-436 Table 1 for example chemical structure)

[0033] Andrographolide was purchased from China Huatai Biotechnology Co., Ltd., and the H NMR spectrum was determined by using 1 HNMR (600M Hz, DMSO-d 6 ).

[0034] General reaction A (hydroxyl esterification)

[0035] Andrographolide 3.00 grams (10mmol) and DMAP1.2 grams (10mmol), triethylamine 1.5 grams (15mmol) are mixed in the methylene chloride of 20 milliliters, add 4.8 grams (15mmol) of 4-O glucosyl benzoyl chloride respectively , stirring until the reaction is complete, the reaction solution is filtered and separated by silica gel column chromatography to obtain the target compound.

[0036] General reaction B (hydroxyl deprotection)

[0037] Acetylated protected andrographolide 4.30 g (10 mmol) was mixed with 20 ml of ethanol and 5 ml of water mixed solution, 1.50 g of potassium carbonate was added, the mixture was heated to reflux for 2 hours, the reaction solution was f...

Embodiment 23

[0044] Example 2.3, Preparation of 14,19-triacetyl andrographolide: 3.00 g (8.6 mmol) of andrographolide was dissolved in 20 ml of acetic anhydride, 2.0 g (0.3 mmol) of zinc chloride was added, and the mixture was reacted at 80° C. for 5 h. The reaction solution was extracted with ethyl acetate and separated by silica gel column chromatography to obtain the target product; IR (KBr, cm -1 ): 3436-3078, 1753, 1736, 1728, 1247, 1132, 1095, 1077; 1 HNMR (CDCl 3 ): δ6.89(t, 1H), 5.93(d, J=6Hz, 1H), 4.74(br, 2H), 4.56(m, 2H), 4.33(d, J=11.7Hz, 1H) 4.25(d , J=1.8Hz, 1H), 4.17(d, J=11.7Hz, 1H), 3.04(d, J=6.3Hz, 1H), 2.94(d, J=7.8Hz, 1H), 2.25(s, 3H ), 2.12(s, 3H), 2.08(s, 3H), 2.06(m, 1H), 2.04(m, 1H), 1.87(d, J=2.4Hz, 2H), 1.85(d, J=3.6Hz , 2H), 1.54(d, J=3.9Hz, 1H), 1.36(d, J=2Hz, 2H), 1.18(s, 3H), 1.08(s, 3H).

Embodiment 3

[0045]Example 3.7-((2-((4H-imidazol-2-yl)amino)-1-oxopropan-2-yl)amino)-12-(2-(pyridin-2-yl)amino)-14 Preparation of -deoxy-(E)-15-(4-(dimethylamino)benzylidene)-8,17-epoxyandrographolide: Reagent 7-((4H-imidazol-2-yl) Amino)-1-oxopropan-2-yl)amino-8-oxiranyl-12-(pyridin-2-yl)amino-14-deoxyandrographolide and 2-(4-(dimethylamino ) phenyl)-2-oxoacetic acid, using general reaction method C to obtain the target compound; 1 HNMR: δ7.65(s, 1H), 7.74(m, 2H), 7.58(d, J=9.0Hz, 2H), 7.04(m, 3H), 6.31(m, 1H), 6.06(d, J= 15.6Hz, 1H), 5.80(s, 1H), 5.02(s, 1H), 4.85(d, J=1.8Hz, 2H), 4.15(m, 1H), 3.85(m, 1H), 3.74(m, 1H), 3.33(m, 2H), 3.31(m, 1H), 2.98(s, 6H), 2.90(m, 1H), 2.63(d, J=3.0Hz, 1H), 2.16(d, J=10.2 Hz, 1H), 1.74(m, 3H), 1.58(m, 2H), 1.52(dd, J=3.6Hz, 4.2Hz, 1H), 1.49(m, 2H), 1.32(m, 2H), 1.28( s, 3H), 1.08 (s, 3H), 1.07 (m, 2H), 0.89 (s, 3H).

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Abstract

The invention discloses a novel andrographolide derivative and analogue as well as a preparation method of the novel andrographolide derivative and analogue and an application to the treatment, the prevention and the relief on human viruses and neoplastic diseases. The invention also relates to a medicine composition of the compound and an application as antivirus and anticancer disease medicine. Through chemical synthesis and preparation, semi-synthesis multi-series andrographolide analogues can be obtained.

Description

technical field [0001] The present invention relates to novel andrographolide analogues, which are very effective for treating, preventing and alleviating human virus and tumor diseases. The present invention also relates to the pharmaceutical composition of the compound and its application as an antiviral and anticancer drug. Background technique [0002] Andrographolide is the main active ingredient of Andrographis paniculata, which is the whole grass or leaves of Andrographis, a plant of the family Acanthaceae. Also known as spring lotus and autumn willow, yijianxi, elemi, bitter gall, golden herb, golden ear hook, Indian grass and bitter grass. It has the effects of clearing away heat and detoxification, reducing inflammation, reducing swelling and relieving pain. It is mainly used to treat bacillary dysentery, urinary tract infection, acute tonsillitis, enteritis, pharyngitis, pneumonia and influenza. It can be used externally to treat sores, furuncles, swollen toxins...

Claims

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Application Information

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IPC IPC(8): C07D307/58C07D405/14C07D407/06C07D307/60C07D405/12C07D405/06C07D405/10C07D471/04C07D473/18C07D487/04C07D487/18C07D519/00C07C243/32C07C241/04C07H15/26C07H15/203C07H17/02C07H17/04C07H1/00C07F9/655C07F9/6568A61K31/7064A61K31/5377A61K31/7048A61K31/437A61K31/506A61K31/527A61K31/4439A61K31/4184A61K31/444A61K31/4178A61K31/522A61K31/519A61K31/7056A61K31/665A61K31/496A61K31/365A61K31/16A61K31/4188A61K31/443A61P35/00A61P31/12
CPCA61K31/437C07D471/04A61K31/5377C07H15/203A61K31/4178C07D405/06C07D519/00C07D493/10A61K31/7048C07D487/18A61K31/522C07F9/65515A61K31/506C07D405/10C07H1/00C07D407/06C07H15/26C07D405/12C07H17/04C07D307/60A61K31/365C07D473/18A61K31/16A61K31/665A61K31/4439C07D405/14C07H17/02C07D307/58C07D487/04C07F9/65686A61K31/53A61K31/683A61K31/7034A61K31/704A61K45/06A61P31/12A61P35/00Y02A50/30A61K2300/00
Inventor 徐利锋
Owner LIAONING LIFENG SCI & TECH DEV
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