Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of synthetic method of mycoleptodiscin A

A synthetic method and technology of sesquiterpene, which is applied in the field of synthesis of marine natural product mycoleptodiscinA, can solve the problems of long reaction route, harsh reaction conditions, unsuitability for industrial production, etc., and achieve high overall yield, few reaction steps, and simple operation Effect

Active Publication Date: 2020-01-14
威海创惠环保科技有限公司
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the above methods have disadvantages such as long reaction routes and harsh reaction conditions, and are not suitable for industrial production.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of mycoleptodiscin A
  • A kind of synthetic method of mycoleptodiscin A

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of sesquiterpene indole 4

[0027] Dissolve 3.09 g (2, 15.0 mmol) of enone sesquiterpene and 2.2 g (3, 15.0 mmol) of 7-methoxyindole in 100 ml of 1,2-dichloroethane, add trifluoromethanesulfonic acid 0.63 g (1.5 mmol) of tin was stirred and reacted at room temperature for 3 hours, and the reaction was detected by TLC. Add 100 ml of water, wash the reaction liquid, extract the aqueous phase with dichloromethane (30 mL x 2), wash the combined organic phase with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain 5.09 g of a white solid. The yield was 96%.

[0028] H NMR spectrum data: 1 H-NMR ((400 MHz, CDCl 3 ): δ = 8.14 (br, s, 1 H), 7.20(d, J = 7.9 Hz, 1 H), 7.04 (d, J = 7.7 Hz, 1 H), 7.00 (s, 1 H), 6.63 ( d, J =7.6 Hz, 1 H), 3.94 (s, 3 H), 3.19 (dd, J = 13.9, 10.1 Hz, 1 H), 2.68 (d, J =14.1 Hz, 1 H), 2.49 (d , J = 9.7 Hz, 1 H), 2.38 (dd, J = 12.8, 2.4 Hz, 1 H), 2.21 (td...

Embodiment 2

[0030] Embodiment 2: the synthesis of sesquiterpene indolol 5

[0031] Take 4.24 g of sesquiterpene indole (4, 12.0 mmol) and dissolve it in 100 ml of anhydrous tetrahydrofuran. Repeat argon filling and exhausting three times to exhaust the air. The temperature was lowered to -10 °C, and 11.25 ml (1.6 M, 18 mmol) of methyllithium was slowly added dropwise, and the reaction was stirred at this temperature for 2 hours, and the reaction was detected by TLC. Add 50 ml of saturated sodium carbonate solution to the reaction system, extract with ether (50 mL x 3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain 4.16 g of white solid , the yield is 94%.

[0032] H NMR spectrum data: 1 H-NMR ((400 MHz, CDCl3 ): δ = 8.29 (br, s, 1 H), 7.33(d, J = 7.9 Hz, 1 H), 7.07 (d, J = 7.8 Hz, 1 H), 6.94 (s, 1 H), 6.67 ( d, J =7.6 Hz, 1 H), 3.97 (s, 3 H), 2.97 (dd, J = 16.7, 5.7 Hz, 1 H), ...

Embodiment 3

[0034] Example 3: Synthesis of N-phenylsulfonyl protected sesquiterpene indole 6

[0035] Dissolve 3.69 g (5, 10.0 mmol) of sesquiterpene indole in 100 ml of toluene, cool down to 0 °C, add 0.68 g (2 mmol) of tetrabutylammonium bisulfate, 50 wt% sodium hydroxide in sequence 100 ml of aqueous solution, slowly dropwise added 1.54 ml (12 mmol) of phenylsulfonyl chloride. The temperature was raised to room temperature, and the stirring reaction was continued for 2 hours, and TLC detected that the reaction was complete. Add 50 ml of water to the reaction system, separate the layers, extract the aqueous phase with dichloromethane (50 mL x 3), combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain 4.89 g of light yellow foamy solid, yield 96%.

[0036] H NMR spectrum data: 1 H-NMR ((400 MHz, CDCl 3 ): δ = 7.80 (d, J = 8.1 Hz, 1H), 7.57 (s, 1 H), 7.52 (m, 1 H), 7.44 (t, J = 7.5 Hz...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a synthetic method for marine natural product mycoleptodiscin A, and belongs to the field of chemical synthesis. The method comprises the following steps: ketene sesquiterpene2 and 7-methoxyindole 3 are used as starting raw materials, the ketone sesquiterpene 2 and the 7-methoxyindole 3 are subjected to coupling to form sesquiterpene indole 4, the sesquiterpene indole 4 is methylated to form sesquiterpene indolol 5, the sesquiterpene indolol 5 reacts with an electron-withdrawing protecting group, protection is performed on -NH to form N-EWG protected sesquiterpene indole 6, the N-EWG protected sesquiterpene indole 6 is subjected to a cyclization reaction to form pentacyclic sesquiterpene indole 7, the pentacyclic sesquiterpene indole 7 is subjected to removal of N-EWG protection to form -NH pentacyclic sesquiterpene indole 8, the -NH pentacyclic sesquiterpene indole 8 is subjected to demethylation to form -NH pentacyclic sesquiterpene indoxyl 9, and finally the -NH pentacyclic sesquiterpene indoxyl 9 is subjected to an oxidation reaction to form the final natural product mycoleptodiscin A. The method provided by the invention has the characteristics of having few reaction steps, simple operation and good product selectivity and being suitable for industrialized production.

Description

technical field [0001] The invention relates to a synthesis method of marine natural product mycoleptodiscin A. Background technique [0002] The marine natural product mycoleptodiscin A was first isolated and extracted from the endophytic fungus Mycoleptodiscus sp. in 2013 (Ortega H E, Graupner P R, Asai Y, et al. Journal of natural products, 2013, 76(4): 741-744.). as attached figure 1 As shown, the natural product mycoleptodiscin B with a hydroxyl group at the C-4 position has various biological activities such as anticancer and antibacterial (Ortega H E, Graupner P R, AsaiY, et al. Journal of natural products, 2013, 76(4): 741- 744; Dissanayake R K, Ratnaweera P B, Williams D E, et al. Journal of Applied Pharmaceutical Science Vol, 2016, 6(01): 001-006.). In order to better study the biological activity of mycoleptodiscin A and provide a material basis for the subsequent pharmacological research of this natural product, an efficient and concise synthesis method of myco...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07J71/00
CPCC07J71/0042Y02P20/55
Inventor 吴彦超王洪双李惠静
Owner 威海创惠环保科技有限公司
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com