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Fluconazole analog derived from imidazobenzothiazole and its preparation method and application

A benzothiazole and imidazo technology, which is applied to the preparation field of the compound, can solve the problems such as the ineffective treatment effect of non-albicans Candida, and achieve the effects of solving drug resistance, simple preparation method and easy-to-obtain raw materials

Active Publication Date: 2020-08-18
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fluconazole has the advantages of strong antibacterial ability, low hepatotoxicity, good oral absorption, high bioavailability, and wide tissue distribution. Clinically, the treatment effect of non-albicans such as Aspergillus is not obvious, so further research on fluconazole is highly valued

Method used

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  • Fluconazole analog derived from imidazobenzothiazole and its preparation method and application
  • Fluconazole analog derived from imidazobenzothiazole and its preparation method and application
  • Fluconazole analog derived from imidazobenzothiazole and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1, the preparation of compound I-1

[0037]

[0038] In a 50mL round bottom flask, add intermediate II (0.348g, 1mmol), NaHCO 3 (0.126g, 1.5mmol) and epoxide III (0.237g, 1mmol), using ethanol (10mL) as a solvent, stirring the reaction at 70°C until the end of the reaction (TLC tracking reaction), cooling, acidifying, and distilling the solvent under reduced pressure, After extraction, separation by column chromatography, and drying, compound I-10.216 g was obtained, with a yield of 37%.

[0039] Compound I-1: white solid; 173–174°C; 1 H NMR (600MHz, CDCl 3 )δ:8.24(s,1H,Tri 3-H),8.00(d,1H,J=5.5Hz,Ar-H),7.81(s,1H,Tri 5-H),7.69–7.64(m,3H ,Ar-H),7.54–7.51(m,1H,Ar-H),7.45(t,2H,CH 2 ),7.42–7.35(m,2H,Ar-H),7.31(t,1H,J=6Hz,Ar-H),6.82–6.65(m,2H,Ar-H),5.22(br,1H,J =6Hz, Ar-H), 4.58–4.46(m, 2H, Tri-CH 2 ), 3.98(s,2H), 2.87(d,1H, J=6.5Hz, Pip-CH 2 ),2.69(d,1H,J=6.5Hz,OH),2.50(br,4H,Piperzine-H),2.30(br,4H,Piperzine-H)ppm.

Embodiment 2

[0040] Embodiment 2, the preparation of compound 1-2

[0041]

[0042] In a 50mL round bottom flask, add intermediate II (0.393g, 1mmol), NaHCO 3(0.126g, 1.5mmol) and epoxide III (0.237g, 1mmol), using ethanol (10mL) as a solvent, stirring the reaction at 70°C until the end of the reaction (TLC tracking reaction), cooling, acidifying, and distilling the solvent under reduced pressure, After extraction, separation by column chromatography and drying, 0.208 g of compound I-2 was obtained, with a yield of 33%.

[0043] Compound I-2: white solid; 165–166°C; 1 H NMR (600MHz, CDCl 3 )δ: 8.24(s,1H,Tri 3-H),7.81(s,1H,Tri 5-H),7.75(d,1H,J=6.0Hz,Ar-H),7.67(d,2H,J =6.0Hz, Ar-H), 7.46(t, 2H, J=5.5Hz, Ar-H), 7.45–7.37(m, 2H, Ar-H), 7.22(d, 1H, J=6.0Hz, Ar -H),7.02(d,1H,J=6.0Hz,Ar-H),6.82–6.65(m,2H,Ar-H),5.22(br,1H,OH),4.58–4.46(m,2H, Tri-CH 2 ), 4.22(s, 2H), 4.09(q, 2H, J=6.5Hz, OCH 2 CH 3 ), 2.88 (d, 1H, J=6.5Hz, Pip-CH 2 ), 2.72 (d, 1H, J=6.5Hz, Pip-CH 2 ),2.54(br,4H,Piperzi...

Embodiment 3

[0044] Embodiment 3, the preparation of compound 1-3

[0045]

[0046] In a 50mL round bottom flask, add intermediate II (0.348g, 1mmol), NaHCO 3 (0.126g, 1.5mmol) and epoxide III (0.287g, 1mmol), using ethanol (10mL) as a solvent, stirring the reaction at 70°C until the end of the reaction (TLC tracking reaction), cooling, acidifying, and distilling the solvent under reduced pressure, After extraction, separation by column chromatography and drying, 0.191 g of compound I-3 was obtained, with a yield of 30%.

[0047] Compound I-3: white solid; melting point: 73–74°C; 1 H NMR (600MHz, CDCl 3 )δ:8.05–7.85(m,2H,Ar-H),7.80–7.71(m,4H,Ar-H),7.58–7.31(m,8H,Ar-H),6.85–6.67(m,2H, Ar-H), 5.22(br,1H,OH), 4.12(s,2H), 4.58–4.46(m,2H,Tri-CH 2 ), 2.87 (d, 1H, J=6.5Hz, Pip-CH 2 ),2.70(d,1H,J=6.5Hz,Pip-CH 2 ),2.50(br,4H,Piperzine-H),2.31(br,4H,Piperzine-H)ppm.

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Abstract

The invention discloses imidazobenzothiazole-derived fluconazole analogues described in formula I. The invention also discloses a preparation method of such kind of compounds and has the advantages of being short in synthetic route, high in the degree of raw material commercialization, low in cost, easy to obtain and simple in method. The imidazobenzothiazole-derived fluconazole analogues have certain inhibition activities to a part of gram positive bacteria, gram negative bacteria and fungi, and are capable of being used in preparing potential anti-bacterial and / or anti-fungal drug molecules. The R1, R2, R3, R4, R5, R6, X1, X2, X3 and Im in the universal molecular formula are defined in the claims.(The formula is shown in the description.).

Description

technical field [0001] The invention belongs to the field of chemistry, relates to a new class of organic compound, and also relates to the preparation method and medical application of the compound. Background technique [0002] Fluconazole is the drug of choice for the treatment of systemic fungal infections, and it is also the first-line drug in the field of antifungals. Fluconazole has the advantages of strong antibacterial ability, low hepatotoxicity, good oral absorption, high bioavailability, and wide tissue distribution. Clinically, the treatment effect of non-albicans such as Aspergillus is not obvious, so further research on fluconazole has attracted much attention. In recent years, research on fluconazole has mainly focused on the following three aspects: a) prodrug research to improve bioavailability and further improve curative effect; It is expected to obtain derivatives that can efficiently bind to the active site of fungal lanosterol 14α-demethylase; c) des...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04A61K31/496A61P31/04A61P31/10
CPCC07D513/04Y02A50/30Y02P20/55
Inventor 周成合马迪丽·丝维塔·卡维斯瓦瑞彭莘媚段俊蓉
Owner SOUTHWEST UNIV
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