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Sesquiterpene lactone compound and uses of derivative thereof in preparation of drugs

A technology for preparing drugs and compounds, which is applied in the field of inhibiting cancer stem cells, treating cancer drugs, and preparing and treating rheumatoid arthritis

Active Publication Date: 2013-12-04
ACCENDATECH LUOYANG CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There is no report about the formula (I) compound or its pharmaceutical composition being used for the treatment of cancer by inhibiting cancer stem cells

Method used

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  • Sesquiterpene lactone compound and uses of derivative thereof in preparation of drugs
  • Sesquiterpene lactone compound and uses of derivative thereof in preparation of drugs
  • Sesquiterpene lactone compound and uses of derivative thereof in preparation of drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the preparation method of compound 1-50

[0029] Preparation of compound 1:

[0030] Parthenolide (50 mg, 0.2 mmol) was dissolved in 2.5 mL of dichloromethane, and p-toluenesulfonic acid (5 mg, 0.026 mmol) was added. The reaction system was left at room temperature and stirred overnight. Transfer the reaction solution to NaHCO 3 (10mL) in a saturated solution, collect the organic phase, extract the aqueous phase with a small amount of dichloromethane, combine the organic phases, and wash with Na 2 SO 4 After drying and filtering, the organic solvent was distilled under reduced pressure with a rotary evaporator, and purified on a silica gel column to obtain compound 1 (45 mg, yield 90%). 1 H NMR (CDCl 3 , 400MHz) δ6.20(d, J=3.2Hz, 1H) 5.49(d, J=3.2Hz, 1H) 3.81(t, J=10.4Hz, 1H), 2.70(d, J=10.4Hz, 1H) , 2.65-2.62(m, 2H), 2.40-2.34(m, 1H), 2.07-2.26(m, 4H), 1.73-1.86(m, 2H), 1.68(s, 3H), 1.36-1.28(m, 4H); 13 C NMR (CDCl 3, 100MHz) δ169.8, 138.7, 131.7...

Embodiment 2

[0171] Example 2: Anti-rheumatoid arthritis activity test of compound 1-50

[0172] In the field of rheumatoid arthritis drugs, there are many literatures reporting the effects of drug ingredients on the secretion of TNF-α, PGE2 and IL-1β by synoviocytes, and the data of animal experiments are used to investigate the effect of drug treatment of RA. These documents include: [1] Ju Dahong, Jia Hongwei, Wu Hao, etc., Effects of Lugua Polypeptide Injection on C II-induced Immune Arthritis Rat Serum TNF-α, IL-6 and C II Antibody Activity, Chinese Traditional Medicine Foundation Medical Journal, 2003, 9(11):17. [2] He Jinhua, Liang Qinghua, Zhang Huasheng, etc., Effect of Bizhongxiao Decoction on Plasma TNF-α in Rats with Experimental Arthritis, Journal of Hunan Medical University, 2002, 27(5): 524. [3] Huang Qingchun , Zhang Shengpeng, Xu Qiuying, Effects of Compound Salvia Miltiorrhiza on Type II Collagen-Induced Synoviocyte Secretion and Tumor Necrosis Factor in Rat Model, Moder...

Embodiment 3

[0187] Example 3: Activity test of compounds inhibiting cancer stem cells

[0188] Take fresh or frozen (acute myeloid leukemia (AML, marked as CD34 + / CD38 + ), chronic myeloid leukemia (CML, Ph+ / CD34+ / CXCR4+), chronic lymphocytic leukemia (CLL, CD133+ / CD19- / CD38-), skin cancer (CD34+), breast cancer (CD44+ / CD24- / ESA+), ovarian cancer (CD44+ / CD117+), brain tumor (CD133+), prostate cancer (CD44+ / CD24-), head and neck squamous cell carcinoma (CD44+), laryngeal cancer (CD 133+), pancreatic cancer (ESA+ / CD44+ / CD24+), retinoblastoma (ABCG2 / ALDH1), childhood hepatoblastoma (CD34+ / THY1+ / c-kit+), liver cancer (CD133+), malignant melanoma (CD133+), colorectal cancer (EpCAM high / CD44+), colon adenocarcinoma (CD44 high ), glioma (ABCG-2 / BCRP1), digestive tract tumor (ABCG-2 / BCRP1), nasopharyngeal carcinoma (ABCG2), brain glioma (Dlk-1 / Pref-1), gastric cancer (CD45+), Clinical specimens of patients with lung adenocarcinoma (Sca-1 / CD45- / Pecam- / CD34+) and lung cancer (CD133+CD34+CD44+...

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PUM

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Abstract

The invention relates to a sesquiterpene lactone compound and uses of a derivative thereof in preparation of drugs, belongs to the technical field of the drugs, specially relates to the uses of a formula (I) compound in preparation of the drugs, and particularly relates to the uses of a formula (I) compound in preparation of the drugs for treatment of rheumatoid arthritis and treatment of cancer through inhibition of cancer stem cells.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to sesquiterpene lactone compounds, which are used as active ingredients or pharmaceutical compositions in the preparation of medicines, especially in the preparation and treatment of rheumatoid arthritis, by inhibiting cancer Use of stem cells in medicine for the treatment of cancer. Background technique [0002] Rheumatoid arthritis (RA) is a chronic, inflammatory, systemic autoimmune disease. Tumors are a great threat to human health. There are about 2 million cancer patients in my country, and 1.6 million new cases occur every year. For example, this is not a small group. Rheumatoid arthritis is a progressive systemic autoimmune disease with polyarticular inflammation as the main manifestation. The main manifestations are synovial inflammatory hyperplasia, mononuclear cell infiltration and neovascularization. form. At present, there is no cure and preventive measur...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/365A61K31/4192A61K31/4025A61K31/4525A61K31/496A61K31/5377A61P29/00A61P19/02A61P35/00A61P35/02C07D307/93C07D405/12C07D493/10C07D405/06C07D401/06
Inventor 陈悦张泉龙菁马维维翟佳黛杨修东范洪霞丁亚辉王良韩滨马小彦张浩亮邱传将
Owner ACCENDATECH LUOYANG CO LTD
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