1,2-diketone naphthalene compound as well as preparation method and application thereof

A technology of diketone naphthalene and compounds, which is applied in the field of drug synthesis, can solve the problems of less research on CRAC channel blockers, blockade, low activity and selectivity of compounds, and achieve strong anti-inflammatory, mild reaction conditions, and easy-to-obtain raw materials Effect

Active Publication Date: 2014-12-24
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although it has been found that CRAC channels can be used as targets for the treatment of inflammatory responses and autoimmune diseases, clinical drugs that selectively block CRAC channels have not yet been obtained, and even the research on CRAC channel blockers is relatively sm

Method used

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  • 1,2-diketone naphthalene compound as well as preparation method and application thereof
  • 1,2-diketone naphthalene compound as well as preparation method and application thereof
  • 1,2-diketone naphthalene compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1: Preparation of 4-((4-chlorophenyl)amino)-1,2-diketonenaphthalene (CR-3)

[0065] Sodium 1,2-naphthoquinone-4-sulfonate (52 mg, 0.2 mmol) and K 2 CO 3 (43 mg, 0.2 mmol) was dissolved in 50 mL of water, stirred until the solution was clear, and then p-chloroaniline (51 mg, 0.4 mmol) was dissolved in 5 mL of absolute ethanol, and then slowly added to the above aqueous solution, the solution rapidly changed to red and produces a red precipitate. After 1 h of reaction, filter, wash the filter residue with distilled water, and dry under vacuum at room temperature to obtain 46.6 mg of red powder with a reaction yield of 83.2%, m.p: 243-265°C. 1 H-NMR (300MHz, CDCl 3 ): δ=8.33(d, J=7.8Hz, 1H), 8.07(dd, J=7.5Hz, J=1.2Hz, 1H), 7.89(t, J=7.8Hz, 1H), 8.07(dt, J =7.8Hz, J=0.9Hz, 1H), 7.55(d, J=11.4Hz, 2H), 7.24(br.s, 2H), 5.94(br.s, 1H); ESI-HRMS: m / z calcd for C 16 h 10 ClNO 2 [(M+H) + ], 284.0478; found, 284.0546.

Embodiment 2

[0066] Example 2: Preparation of 4-((4-sulfonic acid phenyl)amino)-1,2-diketone naphthalene (CR-7)

[0067] React with 1,2-naphthoquinone-4-sodium sulfonate (52 mg, 0.2 mmol) and p-aminobenzenesulfonic acid (70 mg, 0.4 mmol) as raw materials, and the preparation method is the same as in Example 1 to obtain 45 mg of red powder , the yield was 68.1%. m.p.: 189-208°C. 1 H-NMR (300 MHz, CDCl 3 ):δ=11.67(brs,1H),8.02(dt,J=6.9Hz,J=0.9Hz,2H),7.96(d,J=1.5Hz,1H),7.94(t,J=1.2Hz,1H ),7.87~7.78(m,4H),6.18(s,1H);ESI-HRMS:m / z calcd for C 16 h 11 NO 5 S[(M-H) - ], 328.0280; found, 328.0318.

Embodiment 3

[0068] Embodiment 3: Preparation of 4-((naphthalene-2-amino)-1,2-diketonenaphthalene (CR-8)

[0069] 1,2-naphthoquinone-4-sodium sulfonate (52 mg, 0.2 mmol) and 2-naphthylamine (58 mg, 0.4 mmol) were used as raw materials for the reaction, and the preparation method was the same as in Example 1 to obtain 48.2 mg of red powder, Yield 82.6%, m.p: 285-292°C. 1 H-NMR (300MHz, CDCl 3 ):δ=8.41(d,J=7.8Hz,1H),8.10~8.06(m,3H),8.00~7.93(m,2H),7.90~7.88(m,1H),7.80~7.75(m,1H ),7.59~7.53(m,2H),7.52(br.s,1H),6.20(br.s,1H);ESI-HRMS:m / z calcd for C 20 h 13 NO 2 [(M+H) + ], 300.1025; found, 300.0989.

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Abstract

The invention discloses a 1,2-diketone naphthalene compound which has a general structural formula (I) described in the specification, wherein Ar represents benzene ring, naphthalene ring, quinoline ring or isoquinoline ring, naphthalene diimide ring or coumarin ring; amino acid is directly connected with the Ar; when a substituent group exists on the Ar, R is an electron-withdrawing, electron-donating or neutral group. The invention further discloses a preparation method of the compound and application of the compound to preparation of inflammation-resistant and immunocompetence-resistant drugs. The compound is relatively good in inflammation and immunological competence resistance, is a CRAC (Ca<2+> release activated Ca<2+>) blocker with a novel structure, and can be used as a lead compound of the inflammation-resistant and immunocompetence-resistant drugs. According to the preparation method, the reaction condition is mild, raw materials are cheap and easily available, and the operation and the post-treatment process are simple.

Description

technical field [0001] The invention relates to a 1,2-diketone naphthalene compound and its preparation method and application, belonging to the technical field of drug synthesis. Background technique [0002] Calcium ions (Ca 2+ ) is the most abundant cation in the human body. An adult’s body contains about 1 kg of calcium. Most of the calcium in the human body exists in bones and teeth in the form of phosphate, and a small part exists in body fluids and cartilage tissues. In cells, calcium is mainly stored in intracellular calcium pools (mitochondrion, endoplasmic reticulum or sarcoplasmic reticulum). extracellular Ca 2+ The concentration is about 10 -3 M, the concentration of intracellular calcium ions is about 10 -7 -10 -8 M. The difference between the two is more than 10,000 times. Although present in small amounts at the cellular level, calcium is critical to maintaining many metabolic activities within the cell. Calcium channel maintains intracellular and int...

Claims

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Application Information

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IPC IPC(8): C07C225/22C07C221/00C07C303/22C07C309/46C07C309/47C07D217/02C07D221/14C07D311/10A61K31/472A61K31/473A61K31/352A61K31/136A61K31/145A61P29/00A61P37/02
Inventor 李敏勇周育斌杜吕佩
Owner SHANDONG UNIV
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