Indolo[ 3 , 2 ‑ a ] Carbazole Derivatives and Their Applications

A technology of carbazole derivatives and derivatives, which is applied in the fields of drug combination, organic chemistry, anti-tumor drugs, etc., can solve the problems of little research on medicinal chemistry and activity, limited natural sources, and few synthetic methods.

Active Publication Date: 2017-12-22
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Indolo[ 3 , 2 - a ] carbazole alkaloids are relatively new natural products, which were not discovered from marine sponges until 2002. They have a wide range of biological activities, esp

Method used

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  • Indolo[ 3 , 2 ‑ a ] Carbazole Derivatives and Their Applications
  • Indolo[ 3 , 2 ‑ a ] Carbazole Derivatives and Their Applications
  • Indolo[ 3 , 2 ‑ a ] Carbazole Derivatives and Their Applications

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0041] Preparation of starting material F

[0042] Figure 1 shows the technical route for the preparation of compound F. Specific method: Weigh compound A (4.03 mmol) and dissolve it in 10 mL ultra-dry tetrahydrofuran, add triethylamine (4.8 mmol, 1.2 eq), then add tert-butyl hypochlorite (4.83 mmol, 1.2 eq ), after reacting for 40 min, compound B ( 8.06 mmol, 2.0 eq ) and boron trifluoride were added sequentially . Diethyl ether (16.09 mmol, 4.0 eq ), raised to room temperature and reacted for 5 h, slowly added saturated aqueous sodium bicarbonate solution to adjust pH = 7, extracted with ethyl acetate (3 × 10 mL), combined organic layers, dried over anhydrous magnesium sulfate, Filtration, concentration under reduced pressure to obtain a crude product, and separation and purification by column chromatography to obtain compound C; compound C (0.97 mmol) was dissolved in a mixed solvent of methanol / dichloromethane (v / v = 1:1), and 80 % hydrazine hydrate (3.88mmol, 4.0 eq), r...

Embodiment 1

[0044] Preparation of C1:

[0045]

[0046] The technical route for preparing C1 is:

[0047]

[0048] The specific operation method is: dissolve 0.2 mmol compound F in dry DMF, add 0.25 mmol HOBt·H 2 O and 0.38 mmol EDCI, stirred at room temperature for 20 min, then added 0.5 mmol Et 3 N and 0.25 mmol compound G, stirred overnight at room temperature. Add 20 mL of saturated Na to the reaction system 2 CO 3 , extracted twice with ethyl acetate (2 × 10 mL), combined the organic phases, washed with water, anhydrous Na 2 SO 4 Drying, filtering, taking the filtrate and concentrating under reduced pressure to obtain a crude product, and then purifying by column chromatography to obtain 59.3 mg of a white solid with a yield of 80%;

[0049] The NMR data of C 1 are shown in Table 2.

Embodiment 2

[0051] Preparation of C3:

[0052]

[0053] The technical route for preparing C3 is:

[0054]

[0055] The specific operation method is: dissolve 0.2 mmol compound F in dry DMF, add 0.25 mmol HOBt·H 2 O and 0.38 mmol EDCI, stirred at room temperature for 20 min, then added 0.5 mmol Et 3 N and 0.25 mmol compound H, stirred at room temperature overnight. Add 20 mL of saturated Na to the reaction system 2 CO 3 , extracted twice with ethyl acetate (2 × 10 mL), combined the organic phases, washed with water, and anhydrous Na 2 SO 4 After drying and filtering, the filtrate was concentrated under reduced pressure to obtain a crude product, which was then purified by column chromatography to obtain 57.8 mg of a yellow solid with a yield of 73%;

[0056] The NMR data of C 3 are shown in Table 2.

[0057] Preparation of raw material M

[0058] Figure 2 shows the technical route for the preparation of raw material M. The specific operation method: weigh compound I (4.03 mm...

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Abstract

The invention relates to the field of medicinal chemistry, in particular to application of an indolo[3,2-a]carbazole derivative with the general formula shown in a formula I in preparation of a drug for resisting tumors, and definitions of all substituent groups are shown in the description.The indolo[3,2-a]carbazole derivative has good activity in human erythrocyte leukemic (HEL) cells, leukemia cells K562-1, human melanoma cells WM9-1, breast cancer cells MDA-MB231, human lymphoblast TK6 and prostate cancer cells PC-3 and has a good research and development prospect.(Please see the formula I in the description.).

Description

technical field [0001] The present invention relates to the field of chemical medicines, specifically using tryptophan methyl ester as a starting material to synthesize a series of indolo[3,2-a]carbazole derivatives and derivative salts and their use in the preparation of antitumor application in medicine. Background technique [0002] Tumors have always been a major threat to human life, and the struggle between humans and tumors has continued. The most effective method is drug therapy, and many drugs for treating tumors have low efficiency and high toxicity, so development and research Drugs with anti-tumor activity and low toxicity have always been an important direction in the field of medicine. Researchers in related fields have been working hard to find a class of effective and low-toxic compounds to solve this big problem for humans. [0003] Indolo[ 3 , 2 - a ] carbazole alkaloids are relatively new natural products, which were not discovered from marine sponges unt...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61P35/00
CPCC07D487/04
Inventor 刘晟本大卫·雅科夫肖潇徐梅杨超梁丽娜范田运韩飞刘唐婧君郝小江
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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