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Preparation and application of a class of benzenesulfonyldihydropyrazole derivatives

A technology of benzenesulfonyldihydropyrazole and its derivatives, which is applied in the fields of medical preparations containing active ingredients, drug combinations, organic chemistry, etc., can solve the problems of large toxic and side effects, difficult synthesis, unstable structure, etc., and achieve The effect of low toxicity

Active Publication Date: 2021-12-17
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned drugs have problems such as large toxic and side effects, easy drug resistance, unstable structure, and difficult synthesis.

Method used

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  • Preparation and application of a class of benzenesulfonyldihydropyrazole derivatives
  • Preparation and application of a class of benzenesulfonyldihydropyrazole derivatives
  • Preparation and application of a class of benzenesulfonyldihydropyrazole derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of 3-phenyl-1-benzenesulfonyl-5-(3,4,5-trimethoxyphenyl)-4,5-dihydropyrazole (I-1)

[0020]

[0021] Under ice-bath conditions, add 3,4,5-trimethoxybenzaldehyde (5.0mmol) and acetophenone (5mmol) into absolute ethanol (20mL), and add 10% NaOH aqueous solution dropwise to the reaction solution while stirring (1mL), TLC tracking monitoring, complete reaction, the reaction solution was poured into saturated brine, a yellow solid precipitated, filtered and dried to obtain compound III-1. Under reflux conditions, compound III-1 (1 mmol) and 80% hydrazine hydrate (1 mL) were added to isopropanol (3 mL), and TLC was monitored. After complete reaction, the reaction solution was placed in cold hydrazine at -20°C and stirred until A white solid precipitated out, and compound IV-1 was obtained by suction filtration, which was quickly used for the next reaction. Under ice bath conditions, compound IV-1 (1 mmol), anhydrous potassium carbonate (1 mmol) and benzenesulf...

Embodiment 2

[0023] Preparation of 1-(4-chlorobenzenesulfonyl)-3-phenyl-5-(3,4,5-trimethoxyphenyl)-4.5-dihydropyrazole (I-2)

[0024]

[0025] The preparation method refers to Example 1. A white powder was obtained, yield: 77.1%, m.p.206-207°C. 1 H NMR (600MHz, DMSO) δ7.86 (d, J=8.7Hz, 2H), 7.74-7.66 (m, 4H), 7.51-7.42 (m, 3H), 6.69 (s, 2H), 4.94 (dd, J=11.0, 9.6Hz, 1H), 3.76(s, 6H), 3.72-3.65(m, 4H), 3.25(dd, J=17.7, 9.4Hz, 1H).MS(ESI): 487.97[M+H ] + ;Anal.Calcd.for C 24 h 23 ClN 2 o 5 S: C, 59.20; H, 4.76; N, 5.75. Found: C, 59.17; H, 4.78; N, 5.77.

Embodiment 3

[0027] Preparation of 3-phenyl-1-p-methylbenzenesulfonyl-5-(3,4,5-trimethoxyphenyl)-4,5-dihydropyrazole (I-3)

[0028]

[0029] The preparation method refers to Example 1. A white powder was obtained, yield: 77.2%, m.p.244-245°C. 1 H NMR (600MHz, DMSO) δ7.75 (d, J=8.3Hz, 2H), 7.69 (dd, J=8.0, 1.4Hz, 2H), 7.45 (ddd, J=24.6, 12.0, 6.9Hz, 5H) , 6.71(s, 2H), 4.92-4.82(m, 1H), 3.77(s, 6H), 3.67(s, 3H), 3.62(dd, J=17.7, 11.3Hz, 1H), 3.20(dd, J =17.7, 9.8Hz, 1H), 2.37(s, 3H).MS(ESI): 467.55[M+H] + ;Anal.Calcd.for C 25 h 26 N 2 o 5 S: C, 64.36; H, 5.62; N, 6.00. Found: C, 64.34; H, 5.60; N, 6.02.

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Abstract

The invention discloses a preparation method of a novel tubulin inhibitor benzenesulfonyl dihydropyrazole derivative and its application in antitumor. Has the structure shown in formula (I): wherein: R 1 Selected from: ‑H, ‑F, ‑Cl, ‑CH 3 ,-CF 3 ,-OCH 3 ,-OH,-NO 2 ; 2 Selected from: ‑H, ‑Cl, ‑F, ‑I, ‑CH 3 ,-CH 2 CH 3 ,-(CH 2 ) 2 CH 3 ,-CH(CH 3 ) 2 ,-OH,-NO 2 .

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method, activity evaluation and antitumor application of a class of benzenesulfonyl dihydropyrazole derivatives. Background technique [0002] Tumor is a common disease that seriously threatens human health, and malignant cell proliferation is its main feature. Chemotherapy, as a traditional tumor treatment method, can be divided into two categories according to different mechanisms of action: the first category is cell cycle non-specific inhibitory drugs, which can inhibit cells in different cell cycles, such as alkylating agents, hormones, etc.; The second category is cell cycle-specific inhibitory drugs, which mainly act on cells in the proliferating phase, and most of them target tubulin and microtubule-associated proteins, such as paclitaxel, colchicine, and vincristine. [0003] Microtubules are the main components of the cytoskeleton,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D231/06A61K31/415A61P35/00
Inventor 朱海亮夏林颖张萌李波燕张雅亮王保忠
Owner NANJING UNIV
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