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Locoagralan alcohol hydroxyl derivative as well as preparation method and application thereof

A technology of rocimilanol hydroxyl and derivatives, applied in organic chemistry methods, drug combinations, organic chemistry, etc., can solve problems such as side effects, effective dose and toxic dose side effects, difficulty in accepting chemotherapy, etc.

Pending Publication Date: 2022-06-24
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing chemotherapeutic drugs are one of the commonly used methods for non-surgical treatment of cancer or tumors. There are problems such as the effective dose and the toxic dose are very close, and toxic and side effects. Among them, the most obvious reactions are the impaired digestive function and the inhibition of bone marrow hematopoietic function, which often make cancer Or tumor patients are difficult to accept chemotherapy or cannot adhere to complete the entire course of treatment due to severe reactions
In addition, radiotherapy and chemotherapy are not selective, have severe side effects on normal tissues, and can induce drug resistance in cancer cells

Method used

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  • Locoagralan alcohol hydroxyl derivative as well as preparation method and application thereof
  • Locoagralan alcohol hydroxyl derivative as well as preparation method and application thereof
  • Locoagralan alcohol hydroxyl derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the preparation method of target compound 10a, comprises the following steps:

[0050] (1) Synthesis of compound 3

[0051]

[0052]Weigh 20g apigenin (compound 1, 0.0740mol) into a 500ml round-bottomed flask, add 51g anhydrous potassium carbonate (5.0eq) and 250ml acetone as a solvent to the flask, and slowly add 24.5 ml dimethyl sulfate under stirring (3.5eq), put the system into an oil bath and heated to reflux for 72h at 70°C. The reaction was followed by TLC. After the reaction was completed, it was cooled to room temperature and adjusted to pH=11 with ammonia water. The precipitate was removed by filtration, the filtrate was washed with a saturated saline solution, dried with anhydrous sodium sulfate, part of the solvent was spin-dried, silica gel was added to mix the sample, and purified using a flash silica gel column (chloroform:acetone=8:2) to obtain a pale yellow solid compound 2 ( 12g), 52.3% yield.

[0053] Weigh 700mg of compound 2 (2.2...

Embodiment 2

[0075] Example 2: Preparation of target compound 10b

[0076] The procedure was the same as that in Example 1, except that the benzoic acid was replaced by p-fluorobenzoic acid to prepare the target compound 10b in a yield of 58.9%.

[0077] 1-(p-Fluorobenzoyl-2-hydroxyacetyl)-rocmilanol (10b). White solid; mp 159-160°C; 1 H NMR (400MHz, CDCl 3 )δ:8.03–7.96(2H,m),7.16–7.05(9H,m),6.64(2H,d,J=9.0Hz),6.13(1H,d,J=1.9Hz),6.04(1H,d ,J=1.9Hz),5.94(1H,d,J=4.0 Hz),4.69(1H,d,J=16.0Hz),4.60(1H,d,J=16.0Hz),4.00(1H,dd,J =13.9, 6.1 Hz), 3.82 (3H, s), 3.81 (3H, s), 3.68 (3H, s), 2.88 (1H, td, J=13.9, 5.3 Hz), 2.35 (1H, ddd, J= 13.8, 6.1, 1.3Hz), 2.10 (1H, s); 13 C NMR (100MHz, CDCl 3 )δ: 166.5, 164.7, 163.7, 160.7, 158.6, 157.9, 138.2, 132.5, 132.4, 128.7, 128.7, 128.0, 128.0, 127.8, 127.8, 127.0, 126.3, 125.4, 115.6, 106.5, 112.6, 115.2 , 91.9, 88.2, 80.2, 60.9, 55.5, 55.5, 55.4, 55.0, 53.7, 35.5, 35.5; ESIMS m / z 637.3[M+Na] + ;HRESIMS m / z 649.1646[M+Cl] - (Calcd.forC 35 H 31 O 9...

Embodiment 3

[0078] Example 3: Preparation of target compound 10c

[0079] The steps were the same as those in Example 1, except that the benzoic acid was replaced with p-methoxybenzoic acid to prepare the target compound 10c with a yield of 55.9%.

[0080] 1-(p-Methoxybenzoyl-2-hydroxyacetyl)-rocmilanol (10c). White solid; mp 71-72°C; 1 H NMR (400MHz, CDCl 3 )δ: 7.94(2H,d,J=8.6Hz),7.14–7.06(7H,m), 6.90(2H,d,J=8.6Hz),6.64(2H,d,J=8.6Hz),6.15( 1H,d,J=1.9Hz),6.05(1H,d,J=1.9Hz),5.94(1H,dd,J=5.1,1.4Hz),4.67(1H,d,J=16.0Hz),4.57( 1H,d,J=16.0Hz), 4.01(1H,dd,J=13.7,6.1Hz), 3.87(3H,s), 3.82(3H,s), 3.80(3H,s), 3.68(3H,s) ), 2.87(1H,td,J=13.5,5.3Hz),2.36(1H,ddd,13.8,6.4,1.7Hz),2.12(1H,s); 13 C NMR (100MHz, CDCl 3 )δ: 166.8,165.4,163.7,163.6,160.7,158.6, 157.9,138.3,131.9,128.7,128.7,128.0,128.0,127.8,127.8,127.0,127.0,126.3, 121.5,106.2.6, , 91.8, 88.3, ​​80.1, 60.7, 55.5, 55.5, 55.5, 55.4, 55.0, 53.7, 35.5, 35.5; ESIMS m / z 649.3[M+Na] + ;HRESIMS m / z 661.1845[M +Cl] - (Calcd.for C 36 H 34 O ...

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Abstract

The invention discloses a roxagralan alcohol hydroxyl derivative and a preparation method and application thereof, the roxagralan alcohol hydroxyl derivative has the following structural formula (I), in the structural formula (I), R is benzoic acid group, p-fluorobenzoic acid group, p-methoxybenzoic acid group, p-bromobenzoic acid group, 4, 5-dimethoxy-2-nitro-benzoic acid group, p-nitro cinnamic acid group, 2-furancarboxylic acid group, 2-picolinic acid group, 6-chloronicotinic acid group, 4, 5-dimethoxy-2-nitro-benzoic acid group, 4, 5-dimethoxy-2-nitro-benzoic acid group, 4-nitrocinnamic acid group, 2-furancarboxylic acid group, 2-picolinic acid group, 6-chloronicotinic acid The compound is prepared from a butyric acid group, a decanoic acid group, a dimethylamino group, a diethylamino group, a dibutylamino group, a dioctylamino group, a phenylamino group, a 3, 4-dimethoxyphenylamino group, a 1-pyrrolidinyl group, a 1-imidazolyl group, a 1-pyrazolyl group, a 1-morpholinyl group, a 1-piperidyl group or a 4-methylpiperazine-1-group. The compound disclosed by the invention has nanomole-level anti-colorectal cancer activity, anti-leukemia activity and anti-breast cancer activity.

Description

technical field [0001] The invention belongs to the technical field of medicines, and specifically relates to a roquemilanol hydroxy derivative, also relates to a preparation method of the roquemilanol hydroxy derivative, and the application of the roquemilanol hydroxy derivative in the preparation of antitumor drugs. Background technique [0002] Cancer or tumor is a common and frequently-occurring disease that seriously threatens human health, and currently the mortality rate has risen to the first place according to the statistics of the World Health Organization. There are three main methods of treatment for cancer or tumor: surgery, radiation and chemotherapy. However, the current clinical treatment is still largely dominated by chemotherapy. Existing chemotherapeutic drugs are one of the common methods for non-surgical treatment of cancer or tumors, and there are problems such as the close effective dose and toxic dose, and toxic and side effects. Or tumor patients a...

Claims

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Application Information

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IPC IPC(8): C07D307/93C07D405/12A61P35/00A61P35/02
CPCC07D307/93C07D405/12A61P35/00A61P35/02C07B2200/07
Inventor 苑春茂郝小江李亚男邱洁李艳梅杨珏胡占兴顾玮黄烈军
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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