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Novel heptacyclic compound and synthesis, activity evaluation and application thereof
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A technology of cyclic compounds and drugs, applied in the field of its preparation, can solve problems such as reducing
Active Publication Date: 2017-04-26
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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However, the effective dose of β-carboline, for example, the effective dose of 3S-3-carboxy-1,2,3,4-tetrahydro-β-carboline is as high as 5 μmol / kg, which still needs to be reduced.
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Embodiment 1
[0019] Example 1 Preparation of 3S-3-carboxy-1,2,3,4-tetrahydro-β-carboline
[0020] To 5.0g (24.5mmol) L-Trp, 25ml H 2 SO 4 Add 8ml formaldehyde (36-38%) to the compound of (1M) and 80ml water. The reaction compound was stirred at room temperature for 2 h, adjusted to pH 7 with concentrated ammonia water, placed at 0°C for 12 h, and the resulting precipitate was filtered out. After recrystallization from acetone, 3.97 g (75%) of the title compound were obtained as colorless crystals. Mp:280-282℃; ESI / MS:217[M+H] + ;IR(KBr):3450,3200,3000,2950,2850,1700,1601,1452,1070,900cm -1 ; 1 HNMR (BHSC-500, DMSO-d6): δ10.99(s, 1H), 9.89(s, 1H), 7.30(t, J=7.5Hz, 1H), 7.22(t, J=8.0Hz, 1H) ,7.01(d,J=8.0Hz,1H),6.81(d,J=7.5Hz,1H),4.01(t,J=4.8Hz,1H),3.75(dd,J=10.5Hz,J=5.0Hz , 1H), 3.64 (dd, J=10.5Hz, J=2.4Hz, 1H), 2.91 (d, J=10.5Hz, 2H), 2.86 (s, 1H).
Embodiment 2
[0021] Embodiment 2 prepares THPDTPI
[0022] Add 0.3mL N -Methylmorpholine to adjust the pH to 9. The reaction mixture was stirred at room temperature for 12 h, TLC (CH 2 Cl 2 / CH 3 OH, 15 / 1) indicated the reaction was complete. The reaction mixture was concentrated under reduced pressure at 45 °C, and the residue was repeatedly triturated with water and acetone, and then purified by silica gelcolumn chromatography (CH 2 Cl 2 / CH 3 OH, 30 / 1), yielding 535 mg (90%) of the title compound as a colorless powder. FT-MS 397.1586[M+H] + . 1 H NMR (800MHz, CDCl 3 ): δ=7.930(s, 2H), 7.448(d, J=8.0Hz, 2H), 7.360(d, J=8.0Hz, 2H), 7.204(t, J=8.0Hz, 2H), 7.124(t ,J=8.0Hz,2H),5.737(d,J=16.0Hz,2H),4.468(dd,J=12.0Hz,J=4.0Hz,2H),4.264(d,J=16.0Hz,2H), 3.535(dd, J=14.4Hz, J=2.4Hz, 2H), 2.927(t, J=13.6Hz, 2H). 13 C NMR (200MHz, CDCl 3 ): δ=169.98, 165.05, 136.71, 136.46, 130.31, 128.40, 126.75, 121.72, 121.60, 119.22, 118.24, 118.15, 111.63, 107.11, 106.01, 57.06, 56.46, 28.06.
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Abstract
The invention discloses a novel heptacyclic compound (2'S,5'S)-tetrahydropyrazine [1',2':1,6] and bis{2,3,4,9-tetrahydro-1H-pyridine [3,4-b] indole}-1',4'-diketone (THPDTPI for short), a preparation method thereof, and antithrombosis action, anti-inflammatory action, anti-tumor action, free radical scavenging action and P-selectin expression inhibition action thereof. Therefore, the invention discloses application of the THPDTPI in preparing a medicament which takes the P-selectin as a target and simultaneously inhibits thrombosis, inflammation and tumor. Because thrombosis and inflammation are the most popular complications in patients with tumor, the THPDTPI not only can treat tumor, but also can prevent patients with tumor from complicating thrombosis and inflammation. The THPDTPI disclosed by the invention has favorable clinical application prospects.
Description
[0001] field of invention [0002] The present invention relates to a novel seven-ring compound (2'S,5'S)-tetrahydropyrazine[1',2':1,6]bis{2,3,4,9-tetrahydro-1H-pyridine[3,4- b] Indole}-1',4'-diketone (abbreviated THPDTPI), relating to its preparation method, relating to its antithrombotic effect, relating to its anti-inflammatory effect, relating to its anti-tumor effect, and further relating to it Free radical scavenging and inhibition of P-selectin expression. Therefore, the present invention relates to the application of THPDTPI in the preparation of drugs targeting P-selectin for inhibiting thrombus, inflammation and tumors. Since thrombus and inflammation are the most common complications of tumor patients, THPDTPI of the present invention can not only treat tumors, but also prevent tumor patients from concurrent thrombosis and inflammation. The THPDTPI of the present invention has a good clinical application prospect. The invention belongs to the field of biomedicine. ...
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