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11-carbonyl-20-ethyoxyl Jiyuan oridonin and 14-OH esterified series derivatives and application thereof

A technology of Rubescensin A and ethoxylate, which is applied in the field of Rubescensin A compounds in Jiyuan, achieving good development prospects

Active Publication Date: 2022-07-05
ZHENGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • 11-carbonyl-20-ethyoxyl Jiyuan oridonin and 14-OH esterified series derivatives and application thereof
  • 11-carbonyl-20-ethyoxyl Jiyuan oridonin and 14-OH esterified series derivatives and application thereof
  • 11-carbonyl-20-ethyoxyl Jiyuan oridonin and 14-OH esterified series derivatives and application thereof

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Embodiment 1

[0023]

[0024] Weigh 400 mg of 20-ethoxy jiyuan oridonin A to make it completely dissolved in dichloromethane, add 676 mg of Dess Martin oxidant under ice bath conditions, quench with saturated sodium thiosulfate solution after the reaction, extract and dry Column chromatography gave a white solid in 70%-75% yield. 1 H NMR (400MHz, DMSO-d 6 )δ6.00(s, 1H), 5.63(d, J=1.2Hz, 1H), 5.56(d, J=2.8Hz, 1H), 4.98(s, 1H), 4.72(d, J=2.9Hz, 1H), 4.21–4.18 (m, 1H), 3.82–3.77 (m, 1H), 3.41–3.36 (m, 1H), 2.97 (ddd, J=5.2, 2.4, 1.2Hz, 1H), 2.75 (dd, J=18.6, 5.1Hz, 1H), 2.46 (dt, J=14.7, 2.3Hz, 1H), 2.38 (dd, J=18.4, 2.3Hz, 1H), 2.03 (dt, J=13.4, 2.3Hz, 1H) ), 1.74(s, 1H), 1.63(dt, J=13.9, 5.1Hz, 1H), 1.52–1.43(m, 1H), 1.40(s, 1H), 1.39–1.37(m, 2H), 1.35( d, J=5.5Hz, 1H), 1.09(t, J=7.0Hz, 4H), 0.89(s, 3H), 0.81(s, 3H). 13 C NMR (101MHz, DMSO-d 6 )δ204.30,202.90,148.43,120.64,97.48,71.89,65.17,61.80,57.41,57.01,47.47,46.53,42.67,41.22,33.88,31.94,30.10,23.50,10.61,18.12

Embodiment 2

[0026]

[0027] Weigh 200 mg of JOA11 and dissolve it in 10 mL of dichloromethane, add 118 mg of 4-chloromethylbenzoic acid under ice bath conditions, and then add catalyst 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) 133 mg and 4-dimethylaminopyridine (DMAP) 8 mg. After the reaction, the product was extracted and dried, concentrated, and purified by column chromatography to obtain a white solid product with a yield of 83%. 1 H NMR (400MHz, DMSO-d 6 )δ7.89-7.85(m,2H),7.61-7.58(m,2H),6.31-6.29(m,1H),6.16(d,J=1.5Hz,1H),5.78(s,1H),5.02 (s, 1H), 4.83 (s, 2H), 4.20–4.16 (m, 1H), 3.84 (dq, J=9.4, 7.1 Hz, 1H), 3.44–3.39 (m, 1H), 2.93 (dd, J =18.7,5.2Hz,1H),2.60–2.53(m,1H),2.49(d,J=8.9Hz,1H),2.11(s,1H),2.01(dq,J=14.1,2.6Hz,1H) ,1.69(dt,J=14.0,5.1Hz,1H),1.60–1.52(m,1H),1.48(dd,J=11.7,5.3Hz,1H),1.42(s,2H),1.39(s,1H) ),1.35–1.22(m,1H),1.19(t,J=7.0Hz,3H),1.15–1.08(m,1H),0.87(s,3H),0.81(s,3H). 13 C NMR (101MHz, DMSO-d 6 )δ202.85,201.10,164.19,146.24,143.34,1...

Embodiment 3

[0029]

[0030]Substitute 140 mg of 5-chloro-2-nitrobenzoic acid for 4-chloromethylbenzoic acid, and other operations are the same as in Example 2, to obtain a white solid product with a yield of 53%. 1 H NMR (400MHz, DMSO-d 6 )δ8.14(d,J=8.7Hz,1H),7.92(dd,J=8.7,2.3Hz,1H),7.87(d,J=2.3Hz,1H),6.36(s,1H),6.13( d, J=1.4Hz, 1H), 5.81(s, 1H), 5.05(s, 1H), 4.11-4.08(m, 1H), 3.95-3.89(m, 1H), 3.50-3.44(m, 1H) ,3.44–3.41(m,1H),2.93(dd,J=18.7,5.1Hz,1H),2.59(dd,J=18.5,2.4Hz,1H),2.48–2.39(m,1H),2.08(s , 1H), 2.02–1.96 (m, 1H), 1.66 (dt, J=14.1, 5.1Hz, 1H), 1.55 (ddd, J=13.9, 9.5, 7.4Hz, 1H), 1.49–1.44 (m, 1H) ), 1.44–1.40(m, 2H), 1.39(s, 1H), 1.19(t, J=7.0Hz, 3H), 1.15–1.08(m, 1H), 0.88(s, 3H), 0.80(s, 3H). 13 C NMR (101MHz, DMSO-d 6 )δ202.55,200.54,162.75,145.86,145.60,138.64,132.65,129.16,127.93,126.36,122.76,97.46,78.41,64.90,62.00,57.44,55.81,46.48,42.86,39.79,38.25,33.86,31.84,29.89,23.17 ,20.52,18.08,14.73.

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Abstract

The invention relates to the field of natural products and medicinal chemistry, and discloses 11-carbonyl-20-ethyoxyl Jiuyuan oridonin, 14-OH esterified series derivatives of the 11-carbonyl-20-ethyoxyl Jiuyuan oridonin and application of the 11-carbonyl-20 The preparation method comprises the following steps: by taking 20-ethyoxyl Jimayuan oridonin as a raw material, oxidizing the 20-ethyoxyl Jimayuan oridonin with a Dess Martin reagent to obtain a target compound 11-carbonyl-20-ethyoxyl Jimayuan oridonin, and esterifying the target compound 11-carbonyl-20-ethyoxyl Jimayuan oridonin with organic acid on the premise of not destroying an active center to obtain a series of derivatives. The compound has anti-tumor activity and good stability, can be used for preparing anti-cancer drugs, and is applied to clinical treatment of esophageal cancer, pancreatic cancer, lung cancer, cervical cancer, colon cancer, breast cancer, prostatic cancer and the like. The compound has the following general formula.

Description

technical field [0001] The invention relates to the field of natural products and medicinal chemistry, in particular to Jiyuan Rubescensin A compounds: 11-carbonyl-20-ethoxy Jiyuan Rubescensine A 14-OH esterification series derivatives, a synthesis method and application thereof . Background technique [0002] Rubescensica, a plant of the Lamiaceae family, is bitter, sweet, and slightly cold in nature. It has the effect of clearing away heat and detoxifying, promoting blood circulation and relieving pain. The research on the chemical constituents of Rubescens mainly involves diterpenoids, volatile oils, flavonoids and organic acids, etc. Among them, Rubescens A is the main anticancer active ingredient in Rubescens, a colorless prismatic crystalline powder. Almost insoluble in water, slightly soluble in organic solvents such as ether, methanol and ethanol. Rubescensine A can inhibit the growth of various tumor cells in vitro, including gastric cancer, esophageal cancer, na...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10C07D493/08A61K31/352A61P35/00
CPCC07D493/10C07D493/08A61P35/00C07B2200/07Y02P20/55
Inventor 可钰赵梦圆贾小苹王妮张怡欣刘玥刘宏民徐霞
Owner ZHENGZHOU UNIV