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Derivatives of pyrrolo[2,1-b]quinazoline natural products, preparation method and application thereof

A kind of technology of quinazolines and natural products, applied in the field of medicine

Inactive Publication Date: 2009-11-18
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

Therefore, there is no effective drug for the treatment of brain tissue damage caused by ischemia, so it is of great significance to find new and effective drugs for the treatment of cerebral ischemia.

Method used

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  • Derivatives of pyrrolo[2,1-b]quinazoline natural products, preparation method and application thereof
  • Derivatives of pyrrolo[2,1-b]quinazoline natural products, preparation method and application thereof
  • Derivatives of pyrrolo[2,1-b]quinazoline natural products, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: (S)-(-)-7-chloro-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline-1-carboxylic acid (A1)

[0050] Step A: Preparation of 2-(2-nitro-5-chlorobenzylamino)glutaric acid

[0051] L-glutamic acid (1.47g, 14mmol) was added to an aqueous solution of sodium hydroxide (2M, 25ml) at room temperature, and 5-chloro-2-nitrobenzaldehyde (2.6g, 14mmol) in ethanol was added dropwise with stirring solution (25ml), the mixture was stirred at room temperature for 60 minutes, cooled to 0°C in an ice-water bath, sodium borohydride (0.49g, 13mmol) was added to the reaction solution in batches, and the temperature was controlled not to exceed 5 °C, after the addition, the reaction solution was stirred at room temperature for 2 hours. Suction filtration, the resulting reaction solution was extracted with ether (70ml×3), the pH of the aqueous layer was adjusted to 3 with concentrated hydrochloric acid, and 1.9 g of white powdery solid was obtained by suction filtration, yield 42.32%, mp:...

Embodiment 2

[0058] Example 2: (S)-(-)-7-bromo-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline-1-carboxylic acid (A2)

[0059] The preparation method of the compound of Example 2 is the same as that of Example 1, except that 5-bromo-2-nitrobenzaldehyde is used instead of 5-chloro-2-nitrobenzaldehyde in the first step.

[0060] The total yield of three steps is 30.2%, mp: 274.0~277.7℃, ESI-MS: 295.0[M+1] + ; 1 H-NMR (CD 3 OD, 300MHz) δ: 2.25~2.29(1H, m, 3-Ha), 2.58~2.60(1H, m, 3-Hb), 2.97~3.04(2H, m, 2-H), 4.29~4.31(1H ,dd,J 1 =4.7HZ,J 2 =2.0HZ, 1-H), 4.72~4.75(1H, d, J=7.8Hz, 9-Ha), 4.94~4.97(1H, d, J=7.8Hz, 9-Hb), 6.91~6.92(1H , d, J=4.2Hz, 5-H), 7.42~7.42 (1H, d, J=0.7Hz, 8-H), 7.46~7.47 (1H, dd, J 1 =4.2HZ,J 2 =0.9HZ, 6-H).

Embodiment 3

[0061] Example 3: (R)-(+)-7-chloro-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline-1-carboxylic acid (A3)

[0062] The preparation method of the compound of Example 3 is the same as that of Example 1, except that D-glutamic acid is used instead of L-glutamic acid in the first step.

[0063] The total yield of three steps is 39.1%, mp: 276.4~279.7℃; 1 H-NMR (CD 3 OD, 300MHz) δ: 2.23~2.31(1H, m, 3-Ha), 2.55~2.62(1H, m, 3-Hb), 2.97~3.12(2H, m, 2-H), 4.28~4.32(1H ,dd,J 1 =9.3HZ,J 2 =4.1HZ, 1-H), 4.71~4.76(1H, d, J=15.7Hz, 9-Ha), 4.93~4.98(1H, d, J=15.7Hz, 9-Hb), 6.97~7.00(1H , d, J=8.5Hz, 5-H), 7.28 (1H, s, 8-H), 7.31~7.34 (1H, dd, J 1 =8.5HZ,J 2 =2.2HZ, 6-H).

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Abstract

The invention belongs to the technical field of medicaments, and relates to novel substituted derivatives of pyrrolo[2,1-b]quinazoline natural products, optical active bodies or racemic bodies and diastereoisomer mixtures thereof, a method for preparing compounds and application of the compounds in treating ischemic brain lesions, wherein the derivatives are shown in a general formula (I) and a general formula (II) and have anti-cerebral ischemia active effect,. The invention also relates to pharmaceutically acceptable salts of the compounds, medicinal compositions which take the compounds as active components, and pharmaceutical excipients and / or diluents of the compounds. Definitions of R1, R2, R3, R4, R5, R6 and X in the general formula (I) and the general formula (II) are shown in a discription.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to derivatives of pyrrolo[2,1-b]quinazoline natural products and their preparation methods and uses, in particular to novel pyrrolo[2,1-b]quinazolines Derivatives of natural products, their preparation methods and their application in the treatment of ischemic cerebrovascular diseases. Background technique [0002] Ischemic cerebrovascular disease (ischemic cerebrovascular disease) mainly refers to a group of diseases with corresponding mental symptoms caused by cerebral blood supply disorder. One of the reasons (Phillips, R.A. Progress in Cardiovascular Diseases., 2008, 50(4), 264). At present, with the aging of my country's population structure, the incidence of cerebrovascular disease has increased significantly, and it has become the second cause of death after malignant tumors. Ischemic cerebrovascular disease accounts for 70-80% of all cerebrovascular patients. The occurrenc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61K31/519A61P9/10
Inventor 程卯生马超田瑜刘经红沙宇王庆河
Owner SHENYANG PHARMA UNIVERSITY
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