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Tanshinol derivative and preparation method and medical application thereof

A Danshensu derivative and pharmaceutical technology, applied in the field of Danshensu derivatives and its preparation, can solve the problems of irritation, intestinal mucosal damage, and DSS cycle time not being improved, and achieve easy synthesis, reasonable design, and significant protective effect Effect

Pending Publication Date: 2021-05-25
深圳市高盈医药科技开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the above preparations have improved the oral bioavailability of DSS to a certain extent, the circulation time of DSS in the body has not been improved, and some absorption enhancers may cause damage and irritation to the intestinal mucosa

Method used

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  • Tanshinol derivative and preparation method and medical application thereof
  • Tanshinol derivative and preparation method and medical application thereof
  • Tanshinol derivative and preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] The synthesis of embodiment 1 compound DA-01

[0073]

[0074] The specific synthesis is as follows:

[0075]Danshensu sodium (200mg, 0.909mmol) and 8ml of anhydrous N,N-dimethylformamide (DMF) were added into a 25ml single-necked round bottom flask and stirred at room temperature. 1-Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) (260 mg, 1.36 mmol), 1-hydroxybenzotriazole (HOBT) ( 184mg, 1.36mmol), N,N-diisopropylethylamine (DIPEA) (470mg, 3.636mmol), activated at room temperature for 1 hour. Finally, L-dimethylglutamic acid dimethyl hydrochloride (230 mg, 1.09 mmol) was added to the reaction system and stirred at room temperature for reaction. After 18 hours, the reaction was completed and the reaction was stopped. Add 10ml of water to the reaction system, adjust the pH to 5 with 1M dilute hydrochloric acid, extract 3 times with ethyl acetate (50ml×3), combine the organic phases and wash with saturated NaCl. Anhydrous Na for organic phase 2 S...

Embodiment 2

[0079] The synthesis of embodiment 2 compound DA-02

[0080]

[0081] The same operation was carried out in Example 1, only the L-glutamic acid methyl ester hydrochloride used in the example was changed to L-norleucine methyl ester hydrochloride to obtain a white solid powder with a yield of 73.5%.

[0082] DA-02 corresponds to the compound of formula I, where X represents NH, A1 represents norleucine, and A2 represents methyl.

[0083] 1 H NMR data are as follows: 1 H NMR (CDCl 3 ,300MHz)δ:0.87(t,3H,J=6.2Hz),1.25(s,2H),1.28(s,2H),1.67(s,1H),1.79(s,1H),2.82(s,1H ),2.97-3.05(m,1H),3.72(s,1H),4.25(s,1H),4.54(d,J=4.4Hz),5.30(s,1H),6.60(s,1H),6.76 (s,1H),7.16(d,1H,J=6.1Hz);

[0084] 13 The C NMR data are as follows: 13 C NMR (CDCl 3 ,75MHz) δ: 13.80, 22.21, 27.44, 31.81, 39.87, 52.13, 52.60, 72.73, 115.41, 116.42, 121.85, 128.40, 143.49, 144.02, 173.14.

Embodiment 3

[0085] The synthesis of embodiment 3 compound DA-03

[0086]

[0087] The same operation was carried out in Example 1, only the L-glutamic acid methyl ester hydrochloride used in the example was changed to L-tert-leucine methyl ester hydrochloride to obtain a white solid powder with a yield of 65.9%.

[0088] DA-03 corresponds to the compound of formula I, where X represents NH, A1 represents tert-leucine, and A2 represents methyl.

[0089] 1 H NMR data are as follows: . 1 H NMR (CDCl 3 ,300MHz)δ:0.96(s,9H),2.78-2.85(m,1H),2.97-3.03(m,1H),3.71(s,3H),4.26(dd,1H,J=4.0,7.3Hz) ,4.24(d,1H,J=9.3Hz),6.59(d,1H,J=7.8Hz),6,70(s,1H),6.77(d,1H,J=8.1Hz),7.19(d, 1H,J=9.2Hz);

[0090] 13 The C NMR data are as follows: 13 C NMR (CD 3 OD, 75MHz) δ: 25.40, 34.11, 39.58, 51.05, 59.86, 72.41, 114, 64, 116.43, 120.68, 128.48, 143.51, 144.50, 170.93, 174.55.

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Abstract

The invention discloses a tanshinol derivative as well as a preparation method and medical application thereof. The tanshinol derivative has a structure as shown in a formula I. The tanshinol derivative can be applied to drugs for preventing, processing, treating and / or relieving cardiovascular and cerebrovascular diseases and orthopedic diseases of patients, and a new therapeutic drug is provided for preventing and treating the cardiovascular and cerebrovascular diseases and orthopedic diseases.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and medicine, and in particular relates to an amino acid-containing danshensu derivative, a preparation method thereof and a medical application thereof. Background technique [0002] The traditional Chinese medicine Salvia (Salvia miltiorrhiza Bunge) has the functions of dispelling blood stasis and relieving pain, promoting blood circulation and promoting menstrual flow, clearing the heart and eliminating troubles, and is widely used in the treatment of angina pectoris, myocardial infarction, stroke and other cardiovascular and cerebrovascular diseases. Hardening, improving blood circulation, anti-platelet adhesion and aggregation, scavenging oxygen free radicals in the body, improving hypoxia resistance, improving coronary blood supply and protecting heart and brain cell damage, etc., is one of the most commonly used Chinese herbal medicines for the treatment of coronary heart disease...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/34C07C233/47C07C323/59C07C231/02C07C231/14C07C237/12C07C319/20A61K31/225A61K31/223A61P9/12A61P9/10A61P9/06A61P9/04A61P9/00A61P19/02A61P19/08A61P19/10A61P29/00
CPCC07C235/34C07C233/47C07C323/59C07C237/12A61P9/12A61P9/10A61P9/06A61P9/04A61P9/00A61P19/02A61P19/08A61P19/10A61P29/00Y02P20/55
Inventor 张川王庭芳熊礼燕
Owner 深圳市高盈医药科技开发有限公司
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