Isopropyl alcohol bridged sulfonazole type compound as well as preparation method and application thereof

An isopropanol bridged, sulfonylazole technology, applied in the direction of organic chemistry, resistance to vector-borne diseases, antibacterial drugs, etc., to achieve the effect of short synthesis route, simple preparation of raw materials, and resolution of drug resistance

Inactive Publication Date: 2018-11-23
SOUTHWEST UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, drug resistance and drug side effects caused by the abuse of antibacterial drugs are still the main factors limiting their clinical application

Method used

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  • Isopropyl alcohol bridged sulfonazole type compound as well as preparation method and application thereof
  • Isopropyl alcohol bridged sulfonazole type compound as well as preparation method and application thereof
  • Isopropyl alcohol bridged sulfonazole type compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of Intermediate III

[0043]

[0044] Add sodium p-acetamidobenzenesulfonate (4.73g, 21.40mmol) and tetrabutylammonium iodide (0.01g, 0.03mmol) into a 150mL round-bottomed flask, with epichlorohydrin (30mL) as solvent, at 80°C The reaction was stirred, followed by TLC until the end of the reaction. The solvent was spin-dried under reduced pressure, and the residue was made of ethyl acetate as an extractant. The organic phase was collected and dried, and concentrated to obtain Intermediate III (2.03g), with a yield of 37.1%; white solid; melting point: 170-171 ℃; 1 H NMR (600MHz, DMSO-d 6 )δ10.38(s,1H,NH),7.83–7.79(m,4H,Ph-2,3,5,6-H),4.14(s,1H,SO 2 CH 2 ),4.08(s,1H,SO 2 CH 2 ),3.65–3.62(m,2H,CHOCH 2 ),3.58–3.55(m,1H,CHOCH 2 ),2.10(s,3H,CH 3) ppm; 13 C NMR (151MHz, DMSO-d 6 )δ 169.6, 144.4, 134.0, 129.7, 129.5, 119.0, 113.4, 66.3, 59.9, 49.0, 24.6ppm.

Embodiment 2

[0046] Preparation of compound I-1-1

[0047]

[0048] Add imidazole (0.14g, 2.04mmol) to a 150mL round bottom flask, use potassium carbonate as base (0.32g, 2.35mmol), acetonitrile as solvent, stir at 70°C for 30 minutes, cool to room temperature, add intermediate III (0.40 g, 1.57mmol) continued to heat up to 70°C for reaction, followed by TLC until the end of the reaction. After concentration, extraction, column chromatography separation, drying and other post-treatments, compound I-1-1 (0.42 g) was obtained, with a yield of 82.7%; white solid; melting point: 216-218°C; 1 HNMR (600MHz, DMSO-d 6 )δ10.35(s,1H,NH),7.72(d,J=8.8Hz,2H,Ph-2,6-H),7.65(d,J=8.8Hz,2H,Ph-3,5-H ),7.53(s,1H,Im-2-H),7.08(s,1H,Im-5-H),6.70(s,1H,Im-4-H),5.19(s,1H,OH), 4.54–4.50(m,1H,CHOH),3.99–3.95(m,1H,Im-CH 2 ), 3.76 (dd, J=15.1, 3.5Hz, 1H, Im-CH 2 ),3.59–3.52(m,2H,SO 2 CH 2 ),2.09(s,3H,COCH 3 ) ppm; 13 C NMR (150MHz, DMSO-d 6 )δ169.6, 144.4, 137.3, 133.0, 129.1, 128.6, 119.0, 118.2, 64.2, 56...

Embodiment 3

[0050] Preparation of Compound II-1-1

[0051]

[0052] Add compound I-1-1 (0.10g, 0.31mmol) and 5mL ethanol in a 50mL round-bottomed flask as a solvent, add dropwise a 40% hydrochloric acid solution (5mL), reflux at 90°C, follow up to the reaction by TLC Finish. After cooling to room temperature, the reaction mixture was diluted with distilled water (15 mL) and washed with saturated NaHCO 3 Solution neutralization. After filtration and precipitation, the desired compound II-1-1 (0.17g) was obtained with a yield of 95.3%; white solid; melting point was 243-245°C; 1 H NMR (600MHz, DMSO-d 6 )δ7.53(s,1H,Im-2-H),7.35(d,J=8.6Hz,2H,Ph-3,5-H),7.11(s,1H,Im-5-H),6.75 (s,1H,Im-4-H),6.57(d,J=8.6Hz,2H,Ph-2,6-H),6.15(s,2H,NH 2 ), 5.38 (s, 1H, OH), 4.46 (d, J=4.9Hz, 1H, CHOH), 3.76–3.72 (m, 1H, Im-CH 2 ), 3.64 (dd, J=14.9, 3.8Hz, 1H, Im-CH 2 ),3.60–3.47(m,2H,SO 2 CH 2 ) ppm; 13 C NMR (150MHz, DMSO-d 6 )δ154.2, 137.3, 129.8, 128.6, 118.3, 113.3, 64.2, 57.3, 54.9ppm.

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Abstract

The invention relates to an isopropyl alcohol bridged sulfonazole type compound as well as a preparation method and application thereof and belongs to the technical field of chemical synthesis. Structures of the isopropyl alcohol bridged sulfonazole type compound and medicinal salt thereof are shown as general formulas I to II; the compound has certain inhibition activity on the growth of Gram-positive bacteria, Gram-negative bacteria and fungi, and can be used for preparing antibacterial and/or anti-fungal medicines, so that more efficient and safe candidate medicines are provided for clinical anti-microbial treatment; the clinical treatment problems of increasingly serious drug resistance, stubborn disease-causing microorganisms, emerging harmful microorganisms and the like are easy to solve. The isopropyl alcohol bridged sulfonazole type compound has the advantages of simple preparation raw materials, cheap price and easiness for obtaining and short synthesis route, and has important meaning in application of infection resistance. The formulas are shown in the description.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to isopropanol-bridged sulfonylazole compounds and a preparation method and application thereof. Background technique [0002] With the frequent occurrence of antibiotic resistance, the number of human pathogenic bacteria caused by it has increased dramatically. Moreover, the high morbidity and mortality caused by bacterial infection have posed a serious threat to human health and survival. Therefore, it is extremely urgent to design and synthesize new antibacterial drugs against drug-resistant strains. As the first class of artificially synthesized antibacterial drugs, sulfa drugs have attracted great attention in the fields of biology and medicine for their further development. Among them, a large number of sulfonamide and sulfonamide drugs with various pharmacological activities have been widely used clinically, such as antiviral amprenavir and tipranavir...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C07D233/84C07D233/94C07D233/68C07D233/60A61P31/04A61P31/10
CPCA61P31/04A61P31/10C07D233/60C07D233/68C07D233/84C07D233/94C07D249/08Y02A50/30
Inventor 周成合曼纳保那·拉默汉·拉奥·亚达夫扈圆圆
Owner SOUTHWEST UNIVERSITY
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