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2-indolone compound with anti-inflammatory activity, preparation method and medicinal application thereof

A compound, indolinone technology, applied in the field of new 2-indolinone compounds and their preparation, can solve the problems of bronchial asthma and spasm, aggravate the development of inflammation, increase the generation of LTs, etc., and achieve the effect of good analgesic activity

Inactive Publication Date: 2011-02-16
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, they also inhibit the production of PGs that have protective effects on the gastrointestinal tract, kidneys, and cardiovascular system, and also compensatoryly increase the production of LTs, aggravating the development of inflammation
Clinically, some patients have adverse reactions such as bronchial asthma and spasm after taking traditional NSAIDs, which is usually due to the compensatory increase of LTs

Method used

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  • 2-indolone compound with anti-inflammatory activity, preparation method and medicinal application thereof
  • 2-indolone compound with anti-inflammatory activity, preparation method and medicinal application thereof
  • 2-indolone compound with anti-inflammatory activity, preparation method and medicinal application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0100] Preparation of E-3-{[4-(sulfamoyl)phenyl]methylene}-2-indolinone (101)

[0101]

[0102] Add p-sulfamoylbenzaldehyde (2mmol), 2-indolinone (2mmol), molten sodium acetate (7mmol) and 5mL glacial acetic acid into the reaction flask, heat to reflux, and track the reaction by TLC until the raw material spots disappear. Cool to room temperature, filter with suction, wash with water, dry, and recrystallize from ethyl acetate to obtain orange-yellow crystals, yield 45%, mp 230-232°C. IR (KBr, cm -1 ): 3357 (NH 2 ), 3263 (NH 2 ), 1687 (C=O), 1334 (SO 2 ), 1163 (SO 2 ). 1 H NMR (300MHz, DMSO-d 6 )δ: 6.84-6.90 (m, 2H, ArH), 7.24 (t, 1H, J = 7.2Hz, ArH), 7.43 (d, 1H, J = 7.2Hz, ArH), 7.47 (s, 2H, NH 2 ), 7.64(s, 1H, =CH), 7.87(d, 2H, J=8.1Hz, ArH), 7.94(d, 2H, J=8.1Hz, ArH), 10.67(s, 1H, NH).ESI -MS (m / z): 299[M-H] - .Anal.(C 15 h 12 N 2 o 3 S, C%, H%, N%): 55.99, 4.03, 9.33; Found: 56.13, 4.08, 9.24.

Embodiment 2

[0104] Preparation of E-3-{[4-(sulfamoyl)phenyl]methylene}-5-fluoro-2-indolinone (102)

[0105]

[0106] Referring to the preparation method of 101, by reacting p-sulfamoylbenzaldehyde and 5-fluoro-2-indolinone, recrystallized from ethyl acetate, an orange-yellow powdery solid was obtained, yield 62.9%, mp 196~198°C. IR (KBr, cm -1 ): 3353 (NH 2 ), 3242 (NH 2 ), 1695 (C=O), 1317 (SO 2 ), 1157 (SO 2 ). 1 H NMR (300MHz, DMSO-d 6 )δ: 6.88(s, 1H, ArH), 7.10-7.13(m, 2H, ArH), 7.47(s, 2H, NH 2 ), 7.72(s, 1H, =CH), 7.88(d, 2H, J=8.4Hz, ArH), 7.96(d, 2H, J=8.4Hz, ArH), 10.69(s, 1H, NH).ESI - MS (m / z): 317 [M-H] - .Anal.(C 15 h 11 FN 2 o 3 S, C%, H%, N%): 56.60, 3.48, 8.80; Found: 56.36, 3.35, 8.95.

Embodiment 3

[0108] Preparation of E-3-{[4-(sulfamoyl)phenyl]methylene}-5-chloro-2-indolinone (103)

[0109]

[0110] Referring to the preparation method of 101, react p-sulfamoylbenzaldehyde and 5-chloro-2-indolinone, and recrystallize from ethyl acetate to obtain an orange-red solid with a yield of 46.3%, mp 216-218°C. IR (KBr, cm -1 ): 3342 (NH 2 ), 3249 (NH 2 ), 1718 (C=O), 1301 (SO 2 ), 1157 (SO 2 ). 1 H NMR (300MHz, DMSO-d 6 )δ: 6.91(d, 1H, J=8.1Hz, ArH), 7.31(d, 1H, J=8.1Hz, ArH), 7.34(s, 1H, ArH), 7.52(s, 2H, NH 2 ), 7.73(s, 1H, =CH), 7.89(d, 2H, J=8.1Hz, ArH), 7.97(d, 2H, J=8.1Hz, ArH), 10.82(s, 1H, NH).ESI -MS (m / z): 333[M-H] - .Anal.(C 15 h11 ClN 2 o 3 S, C%, H%, N%): 53.82, 3.31, 8.37; Found: 54.11, 3.24, 8.28.

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Abstract

The invention relates to the medicament field, in particular to a new 2-indolone compound and a preparation method thereof. The invention also discloses a medicinal composition containing the compound and application thereof in treating inflammatory diseases such as rheumatic arthritis, rheumatoid arthritis, osteoarthritis and the like and treating other diseases or symptoms by inhibiting activities of cyclooxygenase (COX) and 5-lipoxygenase (5-LOX).

Description

technical field [0001] The invention relates to the field of medicines, in particular to a new class of 2-indolinone compounds and a preparation method thereof. The invention also discloses a pharmaceutical composition containing the compound and its therapeutic effect on rheumatoid arthritis, rheumatoid arthritis, osteoarthritis and other inflammatory diseases and by inhibiting cyclooxygenase (COX) and 5-lipid oxidation Enzyme (5-LOX) activity to treat other diseases or conditions. Background technique [0002] Inflammation is a basic pathological process in which the body responds mainly to defense responses to the damage of inflammatory factors. Inflammatory mediators refer to chemically active substances that are produced and released by local tissues or plasma under the action of inflammatory factors and participate in or cause inflammatory reactions. Prostaglandins (PGs) and leukotrienes (LTs) are the products of arachidonic acid (AA) through the cyclooxygenase (COX)...

Claims

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Application Information

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IPC IPC(8): A61P35/00C07D209/34A61P29/00A61P19/02A61P19/04A61P11/00A61P11/02A61P11/06A61P7/02A61P17/06A61P17/00A61P37/08A61K31/404
Inventor 赖宜生黄文星季晖张奕华虞兴刘文清马琳李月珍
Owner CHINA PHARM UNIV
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