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Sesterterpene AsperterpinolB derivatives sourced from marine microorganisms, synthetic method and anti-inflammatory application

A technology of sesquiterpene and derivatives, which is applied in the field of medicinal chemistry and can solve problems such as adverse reactions

Active Publication Date: 2018-07-20
SOUTH CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This non-steroidal approach to treatment is widespread, but has the disadvantage of a wide range of adverse effects

Method used

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  • Sesterterpene AsperterpinolB derivatives sourced from marine microorganisms, synthetic method and anti-inflammatory application
  • Sesterterpene AsperterpinolB derivatives sourced from marine microorganisms, synthetic method and anti-inflammatory application
  • Sesterterpene AsperterpinolB derivatives sourced from marine microorganisms, synthetic method and anti-inflammatory application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] AsB-1:(2aS,6aS,6bS,12S,12aS,13R,13aS,Z)-2a,5,5,9,12,13a-hexamethyl-2,2a,3,4,5,6,6a, Synthesis of 6b,7,8,12,12a,13,13a-tetradecahydro-1H-cyclopenta[4,5]cycloocta[1,2-a]naphthalen-13-ol

[0030]

[0031] Experimental steps:

[0032]Weigh AsB (38.7mg, 0.103mmol, 1eq) in a 50ml round bottom flask, add 2ml of dichloromethane to dissolve, add boron trifluoride ether (mass fraction 46.5%-49.5%) dropwise into 1ml syringe (50ul, 0.135mmol , 1.3eq) in the solution, stirring at room temperature for half an hour, adding triethylamine to stop the reaction after half an hour, adjusting the pH to neutral, adding 15ml of saturated saline and dichloromethane (3×20ml) for extraction, and separating the organic phase, dried by adding anhydrous magnesium sulfate, and distilled under reduced pressure to obtain a crude product. Column chromatography in petroleum ether ethyl acetate system (V:V=1:10) gave 38.5 mg of a white solid with a yield of 95%.

[0033] White solid, yield 95%, m.p....

Embodiment 2

[0036] AsB-S 1 :(2aS,6aS,6bS,11R,12R,12aS,13R,13aS,Z)-13-hydroxy-2a,5,5,9,12,13a-hexamethyl-2,2a,3,4,5,6 ,6a,6b,7,8,10,11,12,12a,13,13a-hexadecahydro-1H-cyclopenta [4,5]cycloocta[1,2-a]naphthalen-11-yl acetate synthesis

[0037]

[0038] Experimental steps:

[0039] Weigh AsB (42.3mg, 0.11mmol, 1eq) in a 50ml two-necked round-bottom flask, add 2ml of anhydrous pyridine to dissolve, add anhydride (1.1mmol, 10eq), put it in an oil bath at 90°C to condense and reflux for reaction, and follow the reaction by TLC until The response is complete. Cool to room temperature and add 2M HCl solution to stop the reaction, adjust the pH of the solution to 2, stir for 15 minutes, add saturated brine 15ml and EA (3×15ml) to extract the organic phase, dry over anhydrous magnesium sulfate, and distill under reduced pressure to obtain the crude product, petroleum A pure white solid was obtained by column chromatography of ether ethyl acetate system (V:V=1:2).

[0040] White solid, yield 6...

Embodiment 3

[0043] AsB-S 2 :(2aS,6aS,6bS,11R,12R,12aS,13R,13aS,Z)-13-hydroxy-2a,5,5,9,12,13a-h examethyl-2,2a,3,4,5, Synthesis of 6,6a,6b,7,8,10,11,12,12a,13,13a-hexadecahydro-1H-cyclopenta[4,5]cycloocta[1,2-a]naphthalen-11-yl butyrate

[0044]

[0045] Experimental procedure: with embodiment 2

[0046] White solid, yield 72.04%, m.p.51.7-54.7℃. 1 H NMR (500MHz, CDCl 3 )δ4.75 (d, J = 6.5Hz, 1H), 4.57 (d, J = 10.7Hz, 1H), 3.01 (d, J = 1.8Hz, 1H), 2.78 (dd, J = 17.8, 6.5Hz, 1H), 2.62(t, J=14.8Hz, 1H), 2.22(ddd, J=18.3, 14.3, 7.0Hz, 4H), 1.73–1.65(m, 3H), 1.64(d, J=0.5Hz, 1H ),1.63(s,3H),1.62–1.49(m,2H),1.43–1.36(m,2H),1.35–1.24(m,6H),1.19–1.09(m,3H),1.08(s,3H ),0.97–0.92(m, 3H),0.91(s,3H),0.88(d,J=6.8Hz,6H),0.77(s,3H).

[0047] HRMS(ESI)for[M+Na] + :calcd for C 29 h 48 o 3 Na: 467.34957. Found: 467.3492.

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Abstract

The invention discloses sesterterpene AsperterpinolB derivatives sourced from marine microorganisms, a synthetic method and an anti-inflammatory application. In terms of the chemical structure, the derivatives comprise ester derivatives shown as structural formula I in the description, amide derivatives shown as structural formula II in the description, five-membered ring dehydrated derivatives shown as structural formula III in the description, eight-membered ring dehydrated amide derivatives shown as structural formula IV in the description or pharmaceutically acceptable salts, stereoisomersor prodrug molecules, wherein R0 is X substituted C1-C10 alkane, olefin, alkyne, cycloalkane or phenyl, and X is H, Cl, Br, F, I, CN, NO2, CF3, OH, OCH3, COOH or COOCH3; R1 and R2 are X substituted C1-C10 alkane, olefin, alkyne, cycloalkane, N / O / S heterocyclic ring or phenyl, and X is H, Cl, Br, F, I, CN, NO2, CF3, OH, OCH3, COOH or COOCH3. A series of compounds with good anti-inflammatory activity are obtained by modifying the AsperterpinolB structure, and novel anti-inflammatory drugs are provided for clinic treatment selection.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to the preparation of sesquiterpene Asperterpinol B derivatives derived from marine microorganisms and the application of the derivatives in anti-inflammatory drugs. Background technique [0002] Inflammation, the basic defense mechanism of immunity, is an adaptive response to noxious stimuli, infection, or tissue damage. However, inflammation itself may cause tissue damage and lead to many diseases or cancers (R. Medzhitov et al., 2008; R. Medzhitov et al., 2010). Thus, control of the inflammatory response is generally believed to be beneficial (e.g., in preventing infection), but can become detrimental if dysregulated (e.g., septic-causing). [0003] Inflammation is closely related to nitric oxide. Nitric oxide (NO) is an important intracellular and intercellular highly active signaling molecule, which plays an important role in regulating the immune system in cardiovascular, ...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61P29/00
CPCC07J63/00
Inventor 龙玉华李婷妹佘志刚刘红菊范炜隆温世彤颜樟元郭惠娴
Owner SOUTH CHINA NORMAL UNIVERSITY
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