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Four-membered ring-containing hetero-diterpenoid compound, preparation method and application thereof, and pharmaceutical composition

A technology of compounds and diterpenoids, applied in the preparation of organic compounds, drug combinations, compounds of Group 4/14 elements of the periodic table, etc.

Pending Publication Date: 2021-05-18
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in the prior art, there is no good channel for obtaining these heteroditerpenoids, and neither the extraction technology from natural products nor the artificial synthesis technology needs to be further developed.

Method used

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  • Four-membered ring-containing hetero-diterpenoid compound, preparation method and application thereof, and pharmaceutical composition
  • Four-membered ring-containing hetero-diterpenoid compound, preparation method and application thereof, and pharmaceutical composition
  • Four-membered ring-containing hetero-diterpenoid compound, preparation method and application thereof, and pharmaceutical composition

Examples

Experimental program
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preparation example Construction

[0044] The embodiment of the present invention also provides a preparation method of the above-mentioned four-membered ring-containing heteroditerpenoid compound, which includes:

[0045] Compound I is oxidized and then deprotected to obtain heteroditerpene compound A;

[0046] The heteroditerpene compound A is esterified or etherified to obtain the heteroditerpene compound B; wherein, the structural formula of the compound I is

[0047] In the formula, PG is a hydroxyl protecting group selected from TBDPS, TMS, TES, TBDMS or TIPS.

[0048] The oxidation of compound I is achieved by an oxidizing agent, for example, sodium chlorite can be used as an oxidizing agent. The oxidizing agent can oxidize the aldehyde group in the compound I to a carboxyl group, and then remove the protecting group on the hydroxyl group to obtain the heteroditerpene compound A. The quality of the oxidant is 0.1-1 times that of the compound I, and the oxidation of the aldehyde group is relatively su...

Embodiment 1

[0069] This embodiment provides a kind of preparation method of compound IV-a, and its reaction formula is as follows:

[0070]

[0071] Its specific preparation steps include:

[0072] Dissolve raw material V-a (0.01~100g) and raw material VI-a in (1~100mL) 1,2-dichloroethane or dichloromethane, add (0.01~10mL) organic base, at -40~25℃ Add Tf dropwise 2 O (0.01-20mL) in 1,2-dichloroethane or dichloromethane solution, react at -20-25°C for 1-48 hours, spot plate to detect the disappearance of raw materials, add inorganic alkali aqueous solution or water 1-200mL, Stir at room temperature or under heating for 1 to 10 hours. The new product is no longer increased by spot plate detection. Extract with an equal volume of organic solvent for 2 to 6 times, combine the filtrate, concentrate the sample on a rotary evaporator, and obtain a white solid by various purification methods. It was identified as compound IV-a by mass spectrometry, one-dimensional and two-dimensional nuclea...

Embodiment 2

[0077] This embodiment provides a kind of preparation method of compound IV-a, and its reaction formula is as follows:

[0078]

[0079] Its specific preparation steps include:

[0080] Dissolve raw material V-b (0.01~100g) and raw material VI-b in (1~100mL) 1,2-dichloroethane or dichloromethane, add (0.01~10mL) organic base, at -40~25℃ Add Tf dropwise 2 O (0.01-20mL) in 1,2-dichloroethane or dichloromethane solution, react at -20-25°C for 1-48 hours, spot plate to detect the disappearance of raw materials, add inorganic alkali aqueous solution or water 1-200mL, Stir at room temperature or under heating for 1 to 10 hours. The new product is no longer increased by spot plate detection. Extract with an equal volume of organic solvent for 2 to 6 times, combine the filtrate, concentrate the sample on a rotary evaporator, and obtain a white solid by various purification methods. It was identified as compound IV-b by mass spectrometry, one-dimensional and two-dimensional nuclea...

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Abstract

The invention discloses a four-membered ring-containing hetero-diterpenoid compound, and relates to the technical field of medicines and a preparation method and application thereof, the hetero-diterpenoid compound is novel in structure, has an inhibition effect on T and B lymphocyte proliferation, has selectivity on the inhibition effect on T cells, and can be widely applied to preparation of immunosuppressive medicines. The preparation method of the hetero-diterpenoid compound is easy to operate and mild in condition, and the hetero-diterpenoid compound can be rapidly and efficiently obtained. The invention also discloses a pharmaceutical composition which comprises the hetero-diterpenoid compound and pharmaceutically acceptable auxiliary materials. The compound has good immunosuppressive activity and can be used as an immunosuppressive agent.

Description

technical field [0001] The invention relates to the technical field of medicines, in particular to a heteroditerpene compound containing a four-membered ring, its preparation method and application, and a pharmaceutical composition. Background technique [0002] The plants of the genus Fragrantia are one of the important medicinal plant resources in our country. Among them, Dongling grass has been included in the Chinese Pharmacopoeia. At the same time, many plants of this genus are widely used as herbal medicines in our country for clearing away heat and detoxification, anti-inflammatory and antibacterial , anti-tumor and so on. Plants of this genus are rich in diterpene compounds with various structures, which have activities in antitumor, antibacterial and immunosuppressive aspects, such as oridonin A, eelin B and kachagenin B have significant antitumor activity . Isodonscoparius [Isodonscoparius C.Y.Wu et H.W.Li(Dunn) Kudo] belongs to the genus Isodonscoparius of the f...

Claims

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Application Information

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IPC IPC(8): C07C69/757C07C67/313C07C67/317C07F7/18A61K31/216A61P37/06
CPCC07C67/313C07C67/317C07C69/757C07F7/1892A61P37/06C07C2603/08Y02P20/55
Inventor 普诺·白玛丹增颜秉超周敏杜雪李昂孙汉董
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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