Unlock instant, AI-driven research and patent intelligence for your innovation.

A 7-position chalcone derivative of benzoborazole and its preparation and application

A technology of chalcone derivatives and benzoborazole, which is applied in the field of chalcone derivatives at the 7-position of benzoborazole and its preparation and application, can solve the problems of less research in the field of anti-tumor, and achieve simple and efficient synthesis. Low cost, good suppression effect

Active Publication Date: 2020-08-25
SHANGHAI JIAOTONG UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although benzoborazole compounds are widely used in antifungal, antibacterial, antiparasitic, antiviral and anti-inflammatory fields (Chem.Rev.2015,115,5224-5247.; Sci.China Chem.2013,56 ,1372-1381.), but there are few related studies in the field of anti-tumor

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A 7-position chalcone derivative of benzoborazole and its preparation and application
  • A 7-position chalcone derivative of benzoborazole and its preparation and application
  • A 7-position chalcone derivative of benzoborazole and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (E)-1-phenyl-3-(1-hydroxy-1,3-dihydro-benzo[c][1,2]borazol-7-yl)-2-propenone (1)

[0026]

[0027] Acetophenone (223 mg, 1.85 mmol) and sodium hydroxide (245 mg, 6.15 mmol) were added to a mixed solvent of ethanol (8 mL) and water (2 mL). After stirring at room temperature for 10 minutes, compound 1-hydroxy-7-formyl-1,3-dihydro-benzo[c][1,2]borazole (200 mg, 1.23 mmol) was added and stirred overnight at room temperature. The pH value of the reaction solution was adjusted to 3 with 1M hydrochloric acid and then filtered. The filter cake was purified by silica gel column chromatography (dichloromethane / methanol=250 / 1), and the obtained product was further slurried with n-hexane / ethyl acetate=3 / 1 to obtain compound 1 (90.0 mg, 27.6%). 1 H NMR (400MHz, DMSO-d 6 ): δ9.38(s,1H),8.22(d,J=16.0Hz,1H),8.15(d,J=7.8Hz,2H),8.10(d,J=16.0Hz,1H),8.04(d ,J=7.6Hz,1H),7.69(t,J=7.6Hz,1H),7.58(t,J=7.8Hz,3H).7.47(d,J=7.6Hz,1H),5.04(s,2H ) ppm; 13 C NMR (100MHz, DMSO-d 6 ):δ189.4,154...

Embodiment 2

[0029] (E)-1-(naphthalen-1-yl)-3-(1-hydroxy-1,3-dihydro-benzo[c][1,2]borazol-7-yl)-2-propenone (2)

[0030]

[0031] Synthetic method is similar to embodiment 1, and difference is:

[0032] (1) Soluble in an aqueous solution of methanol, wherein the volume ratio of methanol to water is 0.5:1;

[0033] (2) NaOH:

[0034] (3) The reaction time was 72 hours. After the reaction, the pH was adjusted to 1 with hydrochloric acid, and the compound 2 (72.5 mg, 62.3%) was finally obtained by beating. 1 H NMR (400MHz, DMSO-d 6 ):δ9.23(s,1H),8.36-8.34(m,1H),8.16(d,J=8.2Hz,1H),8.12(d,J=16.0Hz,1H),8.06-8.03(m, 1H), 8.01(dd, J=7.2, 1.0Hz, 1H), 7.96(d, J=7.6Hz, 1H), 7.75(d, J=16.0Hz, 1H), 7.67-7.60(m, 3H), 7.56(t, J=7.6Hz, 1H), 7.47(d, J=7.6Hz, 1H), 5.03(s, 2H)ppm; 13 C NMR (100MHz, DMSO-d 6 ):δ154.6,143.6,137.6,136.2,133.3,131.7,131.1,129.8,128.4,127.8,127.5,127.4,126.3,125.3,125.1,124.7,123.2,69.6ppm; HRMS(ESI):[M+H] + C 20 h 16 BO 3 calcd 315.1192, found 315.1196; mp: 1...

Embodiment 3

[0036] (E)-1-(furan-2-yl)-3-(1-hydroxy-1,3-dihydro-benzo[c][1,2]borazol-7-yl)-2-propenone (3)

[0037]

[0038] Synthetic method is similar to embodiment 1, and difference is:

[0039] (1) Soluble in an aqueous solution of methanol, wherein the volume ratio of ethanol to water is 10:1;

[0040] (2) NaOH:

[0041] (3) The reaction time was 0.5 h. After the reaction, the pH was adjusted to 6.9 with hydrochloric acid, and the compound 3 (43.0 mg, 45.7%) was finally obtained by beating. 1H NMR (400MHz, DMSO-d 6 ): δ9.36(s, 1H), 8.21(d, J=16.0Hz, 1H), 8.07(d, J=1.6Hz, 1H), 8.01(d, J=7.6Hz, 1H), 7.86(d ,J=16.0Hz,1H),7.78(d,J=3.6Hz,1H),7.57(t,J=7.6Hz,1H),7.47(d,J=7.6Hz,1H),6.80(dd,J =3.6,1.6Hz,1H),5.04(s,2H)ppm; 13 CNMR (100MHz, DMSO-d 6 ):δ176.8,154.5,152.9,148.2,141.3,137.6,131.0,125.1,123.0,122.9,119.2,112.5,69.6ppm; HRMS(ESI):[M+H] + C 14 h 12 BO 4 calcd 255.0829, found 255.0833; mp: 126-129°C; HPLC: purity 99.3%, retention time 15.3min.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to 7-benzoxaborole chalcone derivatives and a preparation method and application thereof. A molecular formula of the derivatives is as follows. Synthesis of the derivatives comprises the steps of: adding the following compounds and sodium hydroxide or potassium hydroxide, performing even stirring, adding the following matter, performing stirring for a reaction, regulating thepH value to be acidic by using hydrochloric acid, carrying out filtration, and purifying the obtained filter cake by using silica gel column chromatography so as to obtain the derivatives. The derivatives have strong activity for inhibiting proliferation of tumor cell lines, and therefore the kind of compounds can be used as a new type of anti-tumor drugs.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to a benzoborazole 7-chalcone derivative and its preparation and application. Background technique [0002] In the past ten years, the application of benzoborazole compounds in the field of medicinal chemistry has been rapidly developed, and it is expected to become a new class of anti-infective drugs. At present, the antifungal drug 5-fluorobenzoborole (tavaborole) was approved by the US Food and Drug Administration (FDA) in 2014 for the treatment of onychomycosis; in addition, the phosphodiesterase-4 inhibitor crisaborole In 2016, it was approved by the US Food and Drug Administration (FDA) for the treatment of allergic dermatitis (http: / / www.fda.gov / ). [0003] Although benzoborazole compounds are widely used in antifungal, antibacterial, antiparasitic, antiviral and anti-inflammatory fields (Chem.Rev.2015,115,5224-5247.; Sci.China Chem.2013,56 ,1372-1381.), but the...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02A61P35/00
CPCC07F5/025
Inventor 周虎臣张煚杨斐林轶男朱明彦
Owner SHANGHAI JIAOTONG UNIV