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Antitumor compound and its preparation method and use

A technology of anti-tumor drugs and compounds, applied in the field of medicine, can solve the problems that prostate cancer cannot be cured, and cannot improve treatment results or survival rates

Active Publication Date: 2019-09-20
袁牧
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, metastatic prostate cancer is not curable and androgen ablation therapy becomes standard therapy
None of the conventional cancer treatments for prostate cancer have been very successful, although various chemotherapeutic drugs alone or in combination with radiation therapy are used to treat patients with advanced disease
Other studies have shown that once tumor cells become hormone-resistant, standard cytotoxic agents do little to improve treatment outcomes or survival in hormone-insensitive prostate cancer, although they do provide some pain relief for patients

Method used

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  • Antitumor compound and its preparation method and use
  • Antitumor compound and its preparation method and use
  • Antitumor compound and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the preparation of compound 5

[0068]

[0069] Add 100mg (0.22mmol) intermediate 4, 46.8mg (0.26mmol) 1-(4-fluorophenyl) piperazine, 182mg (1.32mmol) potassium carbonate, 15mL acetonitrile in a 25mL round bottom flask, and react at 86°C 16h, TLC showed that the starting material was completely reacted. The reaction was stopped, filtered and concentrated. The crude product was purified by silica gel column chromatography, eluent: V (ethyl acetate): V (petroleum ether) = 1:3, to obtain 91.7 mg of white solid, yield: 61%. M.p.:165-166℃; MS(ESI,m / z):459.1[M+1] + ; 1 H NMR (500MHz, CDCl 3 )δin ppm: 8.01(d, J=8.7Hz, 1H), 7.35(d, J=8.0Hz, 2H), 7.26(d, J=3.6Hz, 2H), 7.00–6.94(m, 2H), 6.90 (d, J=4.3Hz, 2H), 6.88(dd, J=4.7, 1.9Hz, 1H), 6.78(d, J=2.3Hz, 1H), 5.08(s, 2H), 3.16(t, J= 4.9Hz, 4H), 2.92(t, J=6.0Hz, 2H), 2.87(dd, J=9.7, 6.5Hz, 2H), 2.71(t, J=4.9Hz, 4H), 2.68(dd, J= 9.8, 6.6Hz, 2H), 2.61(t, J=6.5Hz, 2H), 2.11(t, J=6.4Hz, 2H); 13 C NMR (126MHz, C...

Embodiment 2

[0070] Embodiment 2: the preparation of compound 6

[0071]

[0072] The reaction of intermediate 4 with 1-(4-chlorophenyl)piperazine, the synthesis process is the same as that of Example 1. 79.3 mg of white solid, yield: 76%. M.p.:169-170℃; MS(ESI,m / z):475.1[M+1] + ; 1 H NMR (500MHz, CDCl 3 )δin ppm: 8.02(d, J=8.7Hz, 1H), 7.36(d, J=8.0Hz, 2H), 7.27(d, J=2.6Hz, 2H), 7.22(d, J=2.1Hz, 1H ), 7.21 (d, J=2.1Hz, 1H), 6.90 (dd, J=8.7, 2.5Hz, 1H), 6.86 (d, J=2.1Hz, 1H), 6.85 (d, J=2.1Hz, 1H ), 6.79(d, J=2.4Hz, 1H), 5.09(s, 2H), 3.22(t, J=4.9Hz, 4H), 2.93(t, J=6.1Hz, 2H), 2.88(dd, J =9.6, 6.5Hz, 2H), 2.73–2.67(m, 6H), 2.62(t, J=6.5Hz, 2H), 2.12(t, J=6.4Hz, 2H); 13 C NMR (126MHz, CDCl 3 )δin ppm:197.18,162.73,158.12,156.24,149.87,146.95,140.26,134.07,129.69,129.06,128.97,127.77,126.52,124.62,117.27,113.67,113.60,77.04,76.78,69.93,60.23,53.05,49.12, 38.91, 33.24, 30.17, 23.37, 77.29, 77.24.

Embodiment 3

[0073] Embodiment 3: the preparation of compound 7

[0074]

[0075] The reaction of intermediate 4 with 1-(2-chlorophenyl)piperazine is the same as in Example 1. 45.9 mg of white solid was obtained, yield: 44%. M.p.:171-172℃; MS(ESI,m / z):475.1[M+1] + ; 1 H NMR (500MHz, CDCl 3 )δin ppm: 8.04(d, J=8.7Hz, 1H), 7.39(d, J=1.5Hz, 1H), 7.38(d, J=1.6Hz, 1H), 7.29(d, J=6.6Hz, 3H ), 7.25(td, J=8.0, 1.5Hz, 1H), 7.09(dd, J=8.1, 1.4Hz, 1H), 7.00(td, J=7.7, 1.5Hz, 1H), 6.92(dd, J= 8.7, 2.5Hz, 1H), 6.81(d, J=2.4Hz, 1H), 5.11(s, 2H), 3.16(s, 2H), 2.94(t, J=6.1Hz, 2H), 2.91(dd, J=9.9, 6.5Hz, 2H), 2.78(s, 4H), 2.73(dd, J=9.9, 6.5Hz, 4H), 2.63(t, J=6.5Hz, 2H), 2.14(t, J=6.4 Hz, 2H). 13 C NMR (126MHz, CDCl 3 )δin ppm:197.18,162.75,149.22,146.95,140.40,134.01,130.66,129.69,129.07,128.80,127.77,127.62,126.52,123.74,120.40,113.68,113.59,77.29,77.04,76.78,69.95,60.35,53.36, 51.16, 38.92, 33.288, 30.17, 23.37, 77.24.

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PUM

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Abstract

The invention provides an antitumor compound as well as a preparation method and application thereof. The invention provides a compound of a general formula (I) shown in the description. Compared with a reference compound Naftopidil, the representative compound of the general formula (I) of the invention has equal and even higher in-vitro antitumor cell activity; meanwhile, the selectively is higher compared with the reference compound.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a novel antitumor compound and its preparation method and application. [0002] technical background [0003] Prostate cancer (PCa) is a very common disease in men, and ranks second among the lethal cancers in men, and its morbidity and mortality are second only to lung cancer. The incidence of PCa in European and American countries is much higher than that in China, Japan and other East Asian countries, and now the incidence of prostate cancer in my country is also showing an increasing trend, and prostate cancer has become a global problem. [0004] Clinically, localized disease can be cured by surgery or radiation therapy to remove or destroy cancer cells. However, metastatic prostate cancer is not curable and androgen ablation therapy has become the standard therapy. Despite the use of various chemotherapeutic drugs alone or in combination with radiation therapy ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/092A61K31/495A61P35/00
Inventor 袁牧陈洪叶碧波杨宗琳
Owner 袁牧