7-(trimethoxyphenyl)-pyrrolo[2,3-d]pyrimidine and application thereof

A technology of trimethoxyphenyl and trifluoromethoxyphenyl, which is applied in the field of pyrrolopyrimidine compounds and can solve the problems of easy drug resistance and large toxic and side effects

Active Publication Date: 2019-12-13
SOUTHERN MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main problems that exist are: 1. large toxicity and side effects; 2. easy to produce drug resistance (multidrug resistance / MDR); and vinca alkaloid binding sites, for example, they can be administered orally due to their better water solubility; moreover, they are less prone to multidrug resistance

Method used

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  • 7-(trimethoxyphenyl)-pyrrolo[2,3-d]pyrimidine and application thereof
  • 7-(trimethoxyphenyl)-pyrrolo[2,3-d]pyrimidine and application thereof
  • 7-(trimethoxyphenyl)-pyrrolo[2,3-d]pyrimidine and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Embodiment 1 (synthetic compound 1)

[0063] Synthesis of Step 1 Compound II

[0064]

[0065] Dissolve 1.0 g of 3,4,5-trimethoxyacetophenone (compound I) in 15 mL of ethanol, then add 5.0 g of N,N-dimethylformamide dimethyl acetal to the above solution, and heat Reflux, TLC monitoring. After the reaction was completed, the reaction solution was spin-dried, extracted with ethyl acetate-water, the ethyl acetate layer was dried over anhydrous sodium sulfate, the solution was concentrated, and 1.0 g of solid was obtained by column chromatography of dichloromethane-methanol 100:3. Yield 79.2%.

[0066] The obtained compound II is identified by nuclear magnetic resonance spectrum and mass spectrometry, and the identification results are:

[0067] 1 H NMR (400MHz, CDCl 3 )δ7.80(d, J=12.3Hz, 1H), 7.16(s, 2H), 5.63(d, J=12.3Hz, 1H), 3.92(s, 6H), 3.89(s, 3H), 3.05( ss,6H).ESI-MS m / z:265.1[M+H] + 266.1.

[0068] Synthesis of Step 2 Compound III

[0069]

[0070] 1....

Embodiment 2

[0078] Embodiment 2 (synthetic compound 2)

[0079] The synthesis method of Compound 2 uses 3,4,5-trimethoxyacetophenone and 5-(1-methylindole)phenylboronic acid as raw materials, and the method is the same as in Example 1.

[0080]

[0081] Compound 2 was prepared in the same manner as in Example 1 except that the corresponding raw materials were used, and the yield was 75.3%.

[0082] The obtained compound is identified by nuclear magnetic resonance spectrum and mass spectrometry, and the identification results are:

[0083] 1 H NMR (400MHz, Chloroform-d) δ8.43(s, 1H), 8.31(s, 1H), 7.94(d, J=8.5Hz, 1H), 7.59(s, 2H), 7.36(d, J= 11.5Hz,1H),7.11(s,1H),7.06(s,1H),6.85(s,1H),6.56(s,1H),4.01(s,3H),3.99(s,3H),3.77( s,3H).HRMS:calcd for C 24 h 22 N 4 o 3 [M+H] + 415.1770,found 415.1783.

Embodiment 3

[0084] Embodiment 3 (synthetic compound 3)

[0085] The synthesis method of compound 3 uses 3,4,5-trimethoxyacetophenone and p-methoxyphenylboronic acid as raw materials, and the method is the same as in Example 1.

[0086]

[0087] Compound 3 was prepared in the same manner as in Example 1 except that the corresponding raw materials were used, and the yield was 74.4%.

[0088] The obtained compound is identified by nuclear magnetic resonance spectrum and mass spectrometry, and the identification results are:

[0089] 1 H NMR (400MHz, DMSO-d 6 )δ8.57(d, J=3.8Hz, 1H), 8.00(d, J=7.9Hz, 2H), 7.68(s, 2H), 7.33(s, 1H), 7.24(s, 1H), 7.06( d,J=8.4Hz,2H),3.92(s,7H),3.82(d,J=4.7Hz,7H).HRMS:calcd for C 22 h 21 N 3 o 4 [M+H] + 392.1610, found 392.1622.

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Abstract

The invention relates to 7-(trimethoxyphenyl)-pyrrolo[2,3-d]pyrimidine. The chemical structure of the compound is shown in a following formula (a), wherein R<1> is selected from 3-indolyl, 4-methylphenyl, phenyl, 4-methoxyphenyl, 4-trifluoromethoxyphenyl, 4-fluorophenyl, 5-(1-methylindazolyl), 6-indolyl, 3-methylphenyl, 3,4-dimethylphenyl, 5-(1-methylindolyl), 3-(1-methylindolyl), 6-(1-methylindolyl), 4-N,N-dimethylphenyl, 4-(1-methylpyrazolyl), 4-vinylphenyl, 3-(1-hydroxymethylindolyl), 3-fluoro-4-methoxyphenyl, 3-amino-4-methoxyphenyl, 3-(1-Boc indolyl) and 4-hydroxymethylphenyl. The 7-(trimethoxyphenyl)-pyrrolo[2,3-d]pyrimidine disclosed by the invention can inhibit tumor cell proliferation and tubulin aggregation and can enable a cell cycle to be stay in a G2/M period, so that a noveltubulin inhibitor is provided for inhibiting tumor cell proliferation.

Description

technical field [0001] The invention relates to organic compounds, in particular to pyrrolopyrimidine compounds, which can inhibit tumor proliferation and can be used for treating tumors. Background technique [0002] Malignant tumor is the most serious type of disease that endangers human health. Its incidence rate is second only to cardiovascular and cerebrovascular diseases, and it is the second largest "killer" of human health. the first place. Therefore, finding and developing new drugs for treating tumors is a major issue at present. Since microtubules play a key role in the proliferation and division of tumor cells, tubulin is an ideal target for antitumor drugs. [0003] Microtubules play important roles in various cellular processes, including spindle formation, cell shape maintenance and intracellular transport. The function of microtubules in cell mitosis makes them attractive targets for anticancer drugs. Microtubule-targeting agents disrupt microtubule format...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P35/00
CPCA61P35/00C07D487/04
Inventor 陈建军李刚邓欣任益昌李玲
Owner SOUTHERN MEDICAL UNIVERSITY
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