CN105585562A - 1-(benzofuran-5-yl)-3-aryl-2-(triazol-1-yl)-propenone and application thereof as anticancer drug - Google Patents

1-(benzofuran-5-yl)-3-aryl-2-(triazol-1-yl)-propenone and application thereof as anticancer drug Download PDF

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CN105585562A
CN105585562A CN201410572524.8A CN201410572524A CN105585562A CN 105585562 A CN105585562 A CN 105585562A CN 201410572524 A CN201410572524 A CN 201410572524A CN 105585562 A CN105585562 A CN 105585562A
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triazol
alkyl
triazole ring
propylene
ketone
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CN105585562B (en
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胡艾希
李婉
丁娜
杨子辉
向建南
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Hunan University
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Abstract

The invention relates to 1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propen-1-one or a salt thereof, and 1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propen-1-one or the salt thereof is represented by a chemical structure formula I or II. In the formula, R is selected from hydrogen, deuterium, C1-C2 alkyl, and C3-C4 alkyl; X1 and X5 are selected from hydrogen, deuterium, C1-C2 alkyl, C3-C4 alkyl, hydroxy, C1-C2 alkoxy, C3-C4 alkoxy, fluoro, chloro, bromo or nitro; X3 is selected from hydrogen, deuterium, C1-C2 alkyl, C3-C4 alkyl, hydroxy, C1-C2 alkoxy, C3-C4 alkoxy, fluoro, chloro, bromo or nitro; X2 and X4 are selected from hydrogen, deuterium, C1-C2 alkyl, C3-C4 alkyl or nitro. The invention also provides an application of 1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propen-1-one or the salt thereof in preparing anticancer drugs.

Description

1-(benzofuran-5-yl)-3-aryl-2-(triazol-1-yl) propenone and as the application of anticarcinogen
Technical field
The present invention relates to compound that a class is new and its preparation method and application, specifically (Z/E)-1-(benzofuran-5-yl)-3-Aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone and preparation method thereof with it as the application of preparing cancer therapy drug.
Background technology
ChenWen etc. [Org.Biomol.Chem., 2011,9,4250 – 4255] have synthesized coumaran imidazole saltsCompounds 1, and tested it to various human tumour cells such as human breast cancer cell (MCF-7), human lung carcinoma cells (A549)Cytotoxicity, the wherein IC of compound 1a to human breast cancer cell (MCF-7) and human lung carcinoma cell (A549)50Be respectively7.95 μ M and 12.35 μ M. Nagaraju etc. [Bioorg.Med.Chem.Lett., 2012,22,4314 – 4317] have describedOn the basis of compound 2, make the synthetic benzofuran propenone derivatives of initiation material 3 and 4 by 2,4-dihydroxyacetophenone,And tested its inhibition activity to multiple cancer cells such as Human Prostate Cancer Cells (PC-3), human lung carcinoma cells (NCI-H460),Part of compounds has to prostate gland cancer cell (PC-3) and lung carcinoma cell (NCI-H460) activity of inhibition. Tao Weifeng [Nankai University,Master's thesis, 2002] to describe containing the propenone (5) of pyridine radicals and triazolyl and synthesizing of propenyl (6), compound 5 hasCertain bactericidal activity, compound 6 has plant growth regulation.
Chinese patent has been described the preparation of 4-(benzofuran-5-yl)-2-benzyl imino thiazole and answering as antineoplastic thereofWith [ZL201010533786.5], 4-(benzofuran-5-yl)-2-benzyl imino thiazole and as the application of antineoplastic[ZL201010533786.5,2012.7.25 authorize] and 2-(2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl) morpholine andPreparation method and application [ZL201210106643.5,2014.7.23 authorizes].
The present invention is intended to utilize benzofuranol for raw material, and through etherificate, the multistep reactions such as acidylate are synthesized 1-(benzofuran-5-yl)-3-Aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone, and research and develop its antitumor activity.
Summary of the invention
The object of this invention is to provide the 1-shown in chemical structural formula I or II (benzofuran-5-yl)-3-aryl-2-(1,2,4-Triazol-1-yl)-2-propylene-1-ketone or its salt:
Wherein, R is selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl; X1、X5Be selected from: hydrogen,Deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl orBranched alkoxy, fluorine, chlorine, bromine or nitro; X3Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or side chainAlkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or branched alkoxy, fluorine, chlorine, bromine or nitro; X2、X4Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, or nitro; Its salt is selected from: hydrochloride,Hydrobromate, sulfate, nitrate, phosphate, mesylate, benzene sulfonate, tosilate, malate,Lactate, succinate or butene dioic acid salt; Shown in formula I-1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazole-1-yl)-2-propylene-1-ketone is (Z)-1-(2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-aryl-2-(1,2,4-triazole-1-yl)-2-propylene-1-ketone; Shown in formula II-1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-Ketone is (E)-1-(2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-Ketone.
The object of this invention is to provide the 1-shown in chemical structural formula III or IV (benzofuran-5-yl)-3-aryl-2-(1,2,4-Triazol-1-yl)-2-propylene-1-ketone:
Wherein, X1、X5Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or branched alkoxy, fluorine, chlorine, bromine or nitro; X3Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or side chain alcoxylBase, fluorine, chlorine, bromine or nitro; X2、X4Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl,Or nitro.
The object of this invention is to provide the 1-shown in chemical structural formula V or VI (benzofuran-5-yl)-3-aryl-2-(1,2,4-Triazol-1-yl)-2-propylene-1-ketone:
Wherein, X1、X5Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or branched alkoxy, fluorine, chlorine, bromine or nitro; X3Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or side chain alcoxylBase, fluorine, chlorine, bromine or nitro; X2、X4Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl,Or nitro.
The object of this invention is to provide the 1-shown in chemical structural formula VII or VIII (benzofuran-5-yl)-3-aryl-2-(1,2,4-Triazol-1-yl)-2-propylene-1-ketone:
Wherein, X1、X5Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or branched alkoxy, fluorine, chlorine, bromine or nitro; X3Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or side chain alcoxylBase, fluorine, chlorine, bromine or nitro; X2、X4Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl,Or nitro.
The invention provides (benzofuran-5-yl)-3-aryl-2-of the 1-shown in chemical structural formula I or II (1,2,4-triazol-1-yl)-The preparation method of 2-propylene-1-ketone, is characterized in that its preparation feedback is as follows:
Wherein, R is selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl; X1、X5Be selected from: hydrogen,Deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl orBranched alkoxy, fluorine, chlorine, bromine or nitro; X3Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or side chainAlkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or branched alkoxy, fluorine, chlorine, bromine or nitro; X2、X4Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, or nitro.
The invention provides (benzofuran-5-yl)-3-aryl-2-of the 1-shown in chemical structural formula I～VIII (1,2,4-triazol-1-yl)-2-Propylene-1-ketone is in the application of preparing in antineoplastic.
The present invention compared with prior art tool has the following advantages: the invention provides the 1-(benzofuran-5-shown in chemical formula I～VIIIBase)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone has anti-human cervical cancer cell (Hela), human breast cancer cellAnd the activity of human lung carcinoma cell (A549) (MCF-7).
Detailed description of the invention
Following examples are intended to illustrate the present invention instead of limitation of the invention further.
Embodiment 1
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-aryl-2-(1,2,4-triazole-1-Base) preparation of-2-propylene-1-ketone
The bromo-1-of 0.14mol2-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl) ethyl ketone (C1), 0.16mol1,2,4-triazole, 4mmolPEG600,0.54mol potash, 100mL ethyl acetate backflow 1.5h. Reactant liquor suction filtration obtainsBrown liquid, under condition of ice bath, drips 0.15mol nitric acid and obtains white precipitate, and suction filtration obtains white solid, adds 500mL secondAcetoacetic ester dissolves, and drips 30%NaOH and dissolves, and adjusts pH to 7, is stirred to solution clarification, and separatory, gets organic phase, subtractsPressure is distilled to obtain 31.2g white solid 1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-2-(1,2,4-Triazole) ethyl ketone (D1), yield 80.1%, 152～155 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ：1.57(s，6H，2×CH3)，3.11(s，2H，CCH2)，3.93(s，3H，OCH3)，5.64(s，2H，CH2)，7.45(s，1H，C6H2)，7.47(s，1H，C6H2), 8.04 (s, 1H, triazole ring 3-H), 8.39 (s, 1H, triazole ring 5-H).
3.5mmol1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-2-(1,2,4-triazole) ethyl ketone(D1), 5.2mmol benzaldehyde and 30mL chloroform, stir, add piperidines, backflow 6h. After reaction finishes, reactant liquorThrough washing, saturated common salt washing, dry, precipitation, column chromatography for separation obtains product (E)-A1 and (Z)-A1, yield 60.3%.(E)-A1: 175～177 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，3.08(s，2H，CH2)，3.90(s，3H，OCH3)，6.95(s，1H，C6H24-H)，6.97(s，1H，C6H26-H)，7.29～7.39(m，5H，C6H5), 7.51 (s, 1H, C=CH), 8.17 (s, 1H, triazole ring 3-H), 8.20 (s, 1H, triazole ring5-H); (Z)-A1: 62～64 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.48(s，6H，2×CH3)，2.93(s， 2H，CH2)，3.85(s，3H，OCH3)，7.22～7.26(m，2H，C6H24，6-H)，7.29～7.46(m，5H，C6H5), 7.55 (s, 1H, C=CH), 8.07 (s, 1H, triazole ring 3-H), 8.29 (s, 1H, triazole ring 5-H).
Embodiment 2
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-aminomethyl phenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 67.3%. (E)-A2: 158～159 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，2.34(s，3H，CH3)，3.07(s，2H，CH2)，3.89(s，3H，OCH3)，6.82(d，J＝8.0Hz，2H，C6H43，5-H)，7.10(d，J＝8.0Hz，2H，C6H42，6-H)，7.28(s，1H，C6H24-H)，7.37(s，1H，C6H26-H), 7.50 (s, 1H, C=CH), 8.14 (s, 1H, threeAzoles ring 3-H), 8.18 (s, 1H, triazole ring 5-H); (Z)-A2: 110～113 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.48(s，6H，2×CH3)，2.33(s，3H，CH3)，2.97(s，2H，CH2)，3.88(s，3H，OCH3)，7.02(d，J＝8.0Hz，2H，C6H43，5-H)，7.19(d，J＝8.0Hz，2H，C6H42，6-H)，7.40(s，1H，C6H24-H)，7.47(s，1H，C6H26-H), 7.48 (s, 1H, C=CH), 8.05 (s, 1H, triazole ring 3-H),8.26 (s, 1H, triazole ring 5-H).
Embodiment 3
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-hydroxy phenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 36.8%. (E)-A3: 194～196 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.55(s，6H，2×CH3)，2.96(s，2H，CH2)，3.82(s，3H，OCH3)，6.73(s，4H，C6H4)，7.28(s，1H，C6H2)，7.37(s，1H，C6H2), 7.53 (s, 1H, C=CH), 8.26 (s, 2H, threeAzoles ring); (Z)-A3: 180 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.57(s，6H，2×CH3)，3.09(s，2H，CH2)，3.90(s，3H，OCH3)，6.73(s，4H，C6H4)，7.28(s，1H，C6H2)，7.37(s，1H，C6H2), 7.53 (s, 1H, CCH), 8.29 (s, 2H, triazole ring).
Embodiment 4
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2-methoxyphenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 29.0%. (E)-A4: 126～128 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，3.08(s，2H，CH2)，3.80(s，3H，OCH3)，3.91(s，3H，OCH3)，6.62～6.82(m，2H，C6H2)，6.89～7.41(m，4H，C6H4)，7.80(s，1H，C＝CH)，8.15(s, 1H, triazole ring 3-H), 8.22 (s, 1H, triazole ring 5-H); (Z)-A4: 68～70 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.54(s，6H，2×CH3)，2.90(s，2H，CH2)，3.80(s，3H，OCH3)，3.93(s，3H，OCH3)，6.72～6.82(m，2H，C6H2)，6.89～7.41(m，4H，C6H4)，7.72(s，1H，C＝CH)，8.08(s, 1H, triazole ring 3-H), 8.12 (s, 1H, triazole ring 5-H).
Embodiment 5
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-fluorophenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 43.0%. (E)-A5: 155～156 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，3.11(s，2H，CH2)，3.96(s，3H，OCH3)，6.94(d，J＝8.0Hz，2H，C6H43，5-H)，7.18(d，J＝8.0Hz，2H，C6H42，6-H)，7.27(s，1H，C＝CH)，7.52(s，1H，C6H24-H)，7.65(s，1H，C6H26-H), 7.70 (s, 1H, triazole ring 3-H), 8.24 (s,1H, triazole ring 5-H); (Z)-A5: 124～126 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.55(s，6H，2×CH3)，3.06(s，2H，CH2)，3.91(s，3H，OCH3)，6.98(d，J＝8.0Hz，2H，C6H43，5-H)，7.20(d，J＝8.0Hz，2H，C6H42，6-H)，7.46(s，1H，C＝CH)，7.50(s，1H，C6H24-H)，7.96(s，1H，C6H26-H), 8.19 (s, 1H, triazole ring 3-H), 8.40 (s, 1H, triazole ring 5-H).
Embodiment 6
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2-chlorphenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 20.0%. (E)-A6: 65～68 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，3.09(s，2H，CH2)，3.92(s，3H，OCH3)，6.74～7.15(m，4H，C6H4)，7.39(s，1H，C6H24-H)，7.74(s，1H，C6H26-H)，7.75(s，1H，C＝CH)，8.08(s, 1H, triazole ring 3-H), 8.22 (s, 1H, triazole ring 5-H). (Z)-A6: liquid,1HNMR(400MHz，CDCl3)δ:1.47(s，6H，2×CH3)，2.93(s，2H，CH2)，3.84(s，3H，OCH3)，7.20～7.39(m，4H，C6H4)，7.41(s，1H，C＝CH)，7.65(s，1H，C6H24-H)，7.79(s，1H，C6H26-H)，8.11(s，1H, triazole ring 3-H), 8.36 (s, 1H, triazole ring 5-H).
Embodiment 7
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-chlorphenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 6h, yield 69.0%. (E)-A7: 131～134 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，3.07(s，2H，CH2)，3.89(s，3H，OCH3)，6.89(d，J＝8.0Hz，2H，C6H43，5-H)，7.28(d，J＝8.0Hz，2H，C6H42，6-H)，7.35(s，1H，C6H24-H)，7.45(s，1H，C6H26-H), 7.50 (s, 1H, CCH), 8.17～8.18 (m, 2H, triazole ring 3,5-H); (Z)-A7:85～88 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.50(s，6H，2×CH3)，2.95(s，2H，CH2)，3.87(s，3H，OCH3)，7.19(d，J＝8.0Hz，2H，C6H43，5-H)，7.25(d，J＝8.0Hz，2H，C6H42，6-H)，7.30(s，1H，C6H24-H)，7.35(s，1H，C6H26-H)，7.46(s，1H，CCH)，8.07 (s, 1H, triazole ring 3-H), 8.25 (s, 1H, triazole ring 5-H).
Embodiment 8
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 21.4%. (E)-A8: 187～189 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.57(s，6H，2×CH3)，3.08(s，2H，CH2)，3.91(s，3H，OCH3)，6.65(d，J＝8.4Hz，1H，C6H36-H)，7.10(dd，J＝8.4Hz，J＝2.0Hz，1H，C6H35-H)，7.41(s，1H，C6H24-H)，7.47(d，J＝2.0Hz，1H，C6H33-H)，7.56(s，1H，C6H26-H)，7.70(s，1H，C＝CH)，8.06(s，1H, triazole ring 3-H), 8.22 (s, 1H, triazole ring 5-H); (Z)-A8: 90～92 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.50(s，6H，2×CH3)，2.96(s，2H，CH2)，3.86(s，3H，OCH3)，6.75(d，J＝8.4 Hz，1H，C6H36-H)，7.02(dd，J＝8.4Hz，J＝2.0Hz，1H，C6H35-H)，7.36(d，J＝2.0Hz，1H，C6H33-H)，7.61(s，1H，C6H24-H)，7.78(s，1H，C6H26-H)，7.82(s，1H，C＝CH)，8.09 (s, 1H, triazole ring 3-H), 8.30 (s, 1H, triazole ring 5-H).
Embodiment 9
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-bromophenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 43.3%. (E)-A9: 157～160 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.57(s，6H，2×CH3)，3.09(s，2H，CH2)，3.90(s，3H，OCH3)，6.82(s，1H，C6H24-H)，6.82(s，1H，C6H26-H)，7.29～7.45(m，4H，C6H4)，7.47(s，1H，C＝CH)，8.25 (s, 1H, triazole ring 3-H), 8.30 (s, 1H, triazole ring 5-H); (Z)-A9: 70～73 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，2.95(s，2H，CH2)，3.88(s，3H，OCH3)，7.16(s，1H，C6H24-H)，7.18(s，1H，C6H26-H)，7.35～7.47(m，4H，C6H4)，7.49(s，1H，C=CH), 8.09 (s, 1H, triazole ring 3-H), 8.28 (s, 1H, triazole ring 5-H).
Embodiment 10
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2-nitrobenzophenone)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 7h, yield 21.7%. (E)-A10: 165～168 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，3.09(s，2H，CH2)，3.94(s，3H，OCH3)，7.18～7.81(m，4H，C6H4)，7.87(d，J＝1.2Hz，1H，C6H24-H)，8.13(d，J＝1.2Hz，1H，C6H26-H)，8.42 (s, 1H, C=CH), 10.17 (s, 1H, triazole ring 3-H), 10.42 (s, 1H, triazole ring 5-H); (Z)-A10:Liquid,1HNMR(400MHz，CDCl3)δ:1.57(s，6H，2×CH3)，3.07(s，2H，CH2)，3.90(s，3H，OCH3)，7.21～7.89(m，4H，C6H4)，7.78(s，1H，C6H24-H)，8.13(s，1H，C6H26-H)，10.21 (s, 1H, triazole ring 3-H), 10.80 (s, 1H, triazole ring 5-H).
Embodiment 11
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(3-nitrobenzophenone)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 43.8%. (E)-A11: 154～155 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，3.08(s，2H，CH2)，3.89(s，3H，OCH3)，7.21～7.47(m，4H，C6H4)，7.48～7.51(m，2H，C6H24，6-H)，7.96(s，1H，C＝CH)，8.17(s，1H，Triazole ring 3-H), 8.22 (s, 1H, triazole ring 5-H); (Z)-A11: 75～78 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.48(s，6H，2×CH3)，2.96(s，2H，CH2)，3.87(s，3H，OCH3)，7.35～7.45(m，4H，C6H4)，7.60～7.63(m，2H，C6H24,6-H), 8.10 (s, 1H, C=CH), 8.20 (s, 1H, triazolesRing 3-H), 8.27 (s, 1H, triazole ring 5-H).
Embodiment 12
(Z/E)-1-(7-methoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-nitrobenzophenone)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 8h, yield 22.6%. (E)-A12: 85～88 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.56(s，6H，2×CH3)，3.07(s，2H，CH2)，3.89(s，3H，OCH3)，7.17～7.34(m，4H，C6H4)，7.36(s，1H，C6H24-H)，7.48(s，1H，C6H26-H)，8.10(s，1H，C＝CH)，8.17(s, 1H, triazole ring 3-H), 8.20 (s, 1H, triazole ring 5-H); (Z)-A12: 78～80 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.50(s，6H，2×CH3)，2.96(s，2H，CH2)，3.89(s，3H，OCH3)，7.46～7.48(m，4H，C6H4)，7.63(s，1H，C6H24-H)，8.09(s，1H，C6H26-H)，8.12(s，1H，C＝CH)，8.15(s, 1H, triazole ring 3-H), 8.24 (s, 1H, triazole ring 5-H).
Embodiment 13
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-aminomethyl phenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-2-(1,2,4-triazole) ethyl ketone (D2)Press embodiment 1 method operation. Yield 86.0%, 169～171 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.46(t，J＝8.0Hz，3H，CH3)，1.57(s，6H，2×CH3)，3.10(s，2H，CH2)，4.18(q，J＝8.0Hz，2H，CH2)，5.6(s，2H，CH2)，7.27(s，1H，C6H24-H)，7.44(s，1H，C6H26-H)，8.01(s，1H, triazole ring 3-H), 8.26 (s, 1H, triazole ring 5-H).
Prepare A13 by embodiment 1, reaction 6h, yield 48.0%, (E)-A13: 154～156 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.44(t，J＝7.2Hz，3H，CH3)，1.55(s，6H，2×CH3)，3.06(s，2H，CH2)，4.13(q，J＝7.2Hz，2H，CH2)，6.65(s，1H，C6H24-H)，6.72(s，1H，C6H26-H)，7.28～7.37(m，5H，C6H5), 7.50 (s, 1H, C=CH), 8.15 (s, 1H, triazole ring 3-H), 8.18 (s, 1H,Triazole ring 5-H); (Z)-A13: 53～55 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.44(t，J＝7.2Hz，3H，CH3)，1.55(s，6H，2×CH3)，3.06(s，2H，CH2)，4.13(q，J＝7.2Hz，2H，CH2)，6.94(s，1H，C6H24-H)，6.96(s，1H，C6H26-H)，7.30～7.37(m，5H，C6H5)，7.50(s，1H, C=CH), 8.09 (s, 1H, triazole ring 3-H), 8.20 (s, 1H, triazole ring 5-H).
Embodiment 14
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-aminomethyl phenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 43.1%. (E)-A14: 115～118 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.47(t，J＝6.8Hz，3H，CH3)，1.57(s，6H，2×CH3)，2.35(s，3H，CH3)，3.08(s，2H，CH2)，4.14(q，J＝6.8Hz，2H，CH2)，6.85(d，J＝6.0Hz，2H，C6H43，5-H)，7.13(d，J＝6.0Hz，2H，C6H42，6-H)，7.30(s，1H，C6H24-H)，7.38(s，1H，C6H26-H), 7.56 (s, 1H, C=CH), 8.32 (s, 1H, triazole ring 3-H), 8.38 (s, 1H, triazole ring 5-H);(Z)-A14: 98～100 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.45(t，J＝6.8Hz，3H，CH3)， 1.56(s，6H，2×CH3)，2.35(s，3H，CH3)，3.07(s，2H，CH2)，4.14(q，J＝8.0Hz，2H，CH2)，6.82(d，J＝8.0Hz，2H，C6H43，5-H)，7.11(d，J＝6.0Hz，2H，C6H42，6-H)，7.29(s，1H，C6H24-H)，7.36(s，1H，C6H26-H), 7.52 (s, 1H, C=CH), 8.23 (s, 1H, triazolesRing 3-H), 8.24 (s, 1H, triazole ring 5-H).
Embodiment 15
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2-methoxyphenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 7h, yield 20.8%. (E)-A15: 50～53 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.40(t，J＝6.8Hz，3H，CH3)，1.47(s，6H，2×CH3)，3.07(s，2H，CH2)，3.80(s，3H，CH3)，4.13(q，J＝6.8Hz，2H，CH2)，6.78～6.91(m，2H，C6H24，6-H)，7.33～7.40(m，4H，C6H4), 7.80 (s, 1H, CCH), 8.08 (s, 1H, triazole ring 3-H), 8.21 (s, 1H, triazole ring5-H); (Z)-A15: 127～130 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.44(t，J＝6.8Hz，3H，CH3)，1.56(s，6H，2×CH3)，2.90(s，2H，CH2)，3.80(s，3H，CH3)，4.04(q，J＝6.8Hz，2H，CH2)，6.01～6.76(m，2H，C6H24，6-H)，7.14～7.20(m，4H，C6H4)，7.72(s，1H，CCH), 8.16 (s, 1H, triazole ring 3-H), 8.38 (s, 1H, triazole ring 5-H).
Embodiment 16
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-fluorophenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 53.3%. (E)-A16: 140～143 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.45(t，J＝6.8Hz，3H，CH3)，1.56(s，6H，2×CH3)，3.07(s，2H，CH2)，4.13(q，J＝6.8Hz，2H，CH2)，6.93～7.02(m，4H，C6H4)，7.28(s，1H，C6H24-H)，7.35(s，1H，C6H26-H), 7.49 (s, 1H, C=CH), 8.21 (s, 2H, triazole ring 3,5-H); (Z)-A16: molten54～58 DEG C of points,1HNMR(400MHz，CDCl3)δ:1.42(t，J＝6.8Hz，3H，CH3)，1.50(s，6H，2×CH3)，2.94(s，2H，CH2)，4.10(q，J＝6.8Hz，2H，CH2)，6.92～7.00(m，4H，C6H4)，7.29(s，1H，C6H24-H)，7.31(s，1H，C6H26-H)，7.44(s，1H，C＝CH)，8.14(s，1H，Triazole ring 3-H), 8.40 (s, 1H, triazole ring 5-H).
Embodiment 17
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2-chlorphenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 6.5h, yield 35.3%. (E)-A17: 148～150 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.40(t，J＝6.8Hz，3H，CH3)，1.47(s，6H，2×CH3)，2.92(s，2H，CH2)，4.08(q，J＝6.8Hz，2H，CH2)，7.00～7.18(m，2H，C6H24，6-H)，7.22～7.38(m，4H，C6H4), 7.77 (s, 1H, C=CH), 8.10 (s, 1H, triazole ring 3-H), 8.33 (s, 1H, triazole ring 5-H);(Z)-A17: 59～62 DEG C of fusing points,1HNMR(400MHz，DMSO-d6)δ：1.44(t，J＝6.1Hz，3H，CH3)，1.55(s，6H，2×CH3)，3.07(s，2H，CH2)，3.70(q，J＝7.0Hz，2H，CH2)，6.74(d，J＝7.8Hz，1H，C6H24-H)，7.11(d，J＝4.2Hz，1H，C6H26-H)，7.28～7.44(m，4H，C6H4)，7.65 (s, 1H, C=CH), 8.10 (s, 1H, triazole 3-H), 8.29 (s, 1H, triazole 5-H).
Embodiment 18
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-chlorphenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 4h, yield 38.9%. (E)-A18: 125～128 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.43(t，J＝6.8Hz，3H，CH3)，1.56(s，6H，2×CH3)，3.07(s，2H，CH2)，4.10(q，J＝6.8Hz，2H，CH2)，6.89(s，1H，C6H24-H)，6.90(s，1H，C6H26-H)，7.19～7.34(m，4H，C6H4), 7.85 (s, 1H, C=CH), 8.22 (s, 1H, triazole ring 3-H), 8.25 (s, 1H,Triazole ring 5-H); (Z)-A18: 50～52 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.43(t，J＝6.8Hz，3H，CH3)，1.50(s，6H，2×CH3)，2.94(s，2H，CH2)，4.10(q，J＝6.8Hz，2H，CH2)，7.22(s，2H，C6H24，6-H)，7.45(d，J＝8.0Hz，2H，C6H43，5-H)，7.54(d，J＝8.0Hz，2H，C6H42,6-H), 7.83 (s, 1H, C=CH), 8.11 (s, 1H, triazole ring 3-H), 8.31 (s, 1H, triazolesRing 5-H).
Embodiment 19
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 7h, yield 24.3%. (E)-A19: 126～129 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.25～1.28(m，3H，CH3)，1.33(s，6H，2×CH3)，2.92(s，2H，CH2)，4.08～4.10(m，2H，CH2)，7.11～7.12(m，2H，C6H24，6-H)，7.35～7.40(m，3H，C6H3)，7.52 (s, 1H, C=CH), 8.12 (s, 1H, triazole ring 3-H), 8.24 (s, 1H, triazole ring 5-H).
Embodiment 20
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-bromophenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 54.1%. (E)-A20: 153～156 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.43(t，J＝7.2Hz，3H，CH3)，1.56(s，6H，2×CH3)，3.07(s，2H，CH2)，4.12(q，J＝6.8Hz，2H，CH2)，6.80(s，1H，C6H24-H)，6.82(s，1H，C6H26-H)，7.28(s，1H，C＝CH)，7.35～7.46(m，4H，C6H4), 8.19～8.22 (m, 2H, triazole ring 3,5-H);(Z)-A20: 48～51 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.43(t，J＝7.2Hz，3H，CH3)，1.51(s，6H，2×CH3)，2.94(s，2H，CH2)，4.10(q，J＝6.8Hz，2H，CH2)，7.16(s，1H，C6H24-H)，7.18(s，1H，C6H26-H)，7.34～7.50(m，4H，C6H4)，7.49(s，1H，C＝CH)，8.10(s，1H, triazole ring 3-H), 8.30 (s, 1H, triazole ring 5-H).
Embodiment 21
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2-nitrobenzophenone)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 4h, yield 38.5%. (E)-A21: 100～103 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.41(t，J＝6.9Hz，3H，CH3)，1.56(s，6H，2×CH3)，3.08(s，2H，CH2)，4.15～4. 21(m，2H，CH2)，6.96(d，J＝6.3Hz，1H，C6H24-H)，7.12(s，1H，C6H26-H)，7.18(s，1H，C＝CH)，7.30(d，J＝7.6Hz，1H，C6H4)，7.53～7.41(m，3H，C6H4)，7.87(s，1H，Triazole ring 3-H), 8.10 (s, 1H, triazole ring 5-H); (Z)-A21: 58～60 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.47(t，J＝7.0Hz，3H，CH3)，1.56(s，6H，2×CH3)，3.08(s，2H，CH2)，4.16(t，J＝8.0Hz，2H，CH2)，6.75(d，J＝4.0Hz，1H，C6H24-H)，6.96～7.07(m，1H，C6H26-H)，7.12～7.49(m，4H，C6H4)，7.87(s，1H，C＝CH)，8.10(d，J＝8.0Hz，1H，C6H4)，8.45(d，J=8.0Hz, 1H, triazole ring 3-H), 8.46 (s, 1H, triazole ring 5-H).
Embodiment 22
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(3-nitrobenzophenone)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 32.5%. (E)-A22: 115～118 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.41(t，J＝7.0Hz，3H，CH3)，1.53(s，6H，2×CH3)，3.04(d，J＝5.2Hz，2H，CH2)，4.00～4.17(m，2H，CH2)，6.85(d，J＝8.4Hz，2H，C6H24-H)，7.19(s，1H，CH＝C)，7.32～7.44(m，4H，C6H4), 8.16 (s, 2H, triazole ring 3,5-H); (Z)-A22: 62～65 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.41(t，J＝7.0Hz，3H，CH3)，1.49(s，6H，2×CH3)，2.93(s，2H，CH2)，4.10(q，J＝7.1Hz，2H，CH2)，7.15～7.25(m，2H，C6H24，6-H)，7.34(s，1H，C6H42-H)，7.44～7.49(m，3H，C6H4), 8.07 (s, 1H, C=CH), 8.19 (s, 1H, triazole ring 3-H),8.25 (s, 1H, triazole ring 5-H).
Embodiment 23
(Z/E)-1-(7-ethyoxyl-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-nitrobenzophenone)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 34.7%. (E)-A23: 162～166 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.42(t，J＝7.0Hz，3H，CH3)，1.53(s，6H，2×CH3)，3.04(s，2H，CH2)，4.11(q，J＝7.0Hz，2H，CH2)，7.14(s，1H，C6H24-H)，7.16(s，1H，C6H26-H)，7.27(s，1H，C6H4)，7.33(s，1H，C6H4)，7.42(s，1H，C6H4)，8.11～8.17(m，2H，C6H4)，8.20(s，1H，Triazole ring 5-H); (Z)-A23: 63～66 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.47(t，J＝7.0Hz， 3H，CH3)，1.56(s，6H，2×CH3)，3.08(s，2H，CH2)，4.13(s，2H，CH2)，7.17(d，J＝8.8Hz，2H，C6H2)，7.30(s，1H，C6H4)，7.36(s，1H，C6H4)，7.46(d，J＝4.2Hz，1H，C6H4)，8.13～8.20(m，3H，C6H4, triazole ring 5-H), 8.24 (s, 1H, triazole ring 5-H).
Embodiment 24
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-phenyl-2-(1,2,4-triazole-1-Base) preparation of-2-propylene-1-ketone
The preparation of 1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-2-(1,2,4-triazole) ethyl ketone (D3)Press embodiment 1 method operation, yield 85.3%, 147～149 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.03(t，J＝8.0Hz，3H，CH3)，1.26(s，6H，2×CH3)，1.87～1.92(m，2H，CH2)，3.09(s，2H，CH2)，4.03～4.07(m，2H，CH2)，5.66(s，2H，CH2)，7.44(s，2H，C6H24-H)，7.51(s，2H，C6H26-H), 8.09 (s, 1H, triazole ring 3-H), 8.51 (s, 1H, triazole ring 5-H).
A24 is prepared by embodiment 1, reaction 6h, and yield 41.8%, 106～109 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.03(t，J＝8.0Hz，3H，CH3)，1.56(s，6H，2×CH3)，1.83～1.88(m，2H，CH2)，3.09(s，2H，CH2)，4.05(t，J＝8.0Hz，2H，CH2)，7.15～7.23(m，2H，C6H2)，7.45～7.62(m，5H，C6H5), 8.08 (s, 1H, CCH), 8.11 (s, 1H, triazole ring 3-H), 8.50 (s, 1H, triazole ring5-H)。
Embodiment 25
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-aminomethyl phenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 6h, yield 44.3%. A25: 116～118 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.04(t，3H，J＝7.2Hz，CH3)，1.58(s，6H，2×CH3)，1.83～1.88(m，2H，CH2)，3.11(s，2H，CH2)，4.08(t，J＝7.2Hz，2H，CH2)，6.61～7.07(m，2H，C6H2)，7.45～7.64(m，4H，C6H4), 7.70 (s, 1H, C=CH), 8.22 (s, 1H, triazole ring 3-H), 8.30 (s, 1H, triazole ring5-H)。
Embodiment 26
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2-methoxyphenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 59.5%. (E)-A26: 192～193 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.02(t，J＝7.2Hz，3H，CH3)，1.56(s，6H，2×CH3)，1.83～1.88(m，2H，CH2)，3.07(s，2H，CH2)，3.80(s，3H，OCH3)，4.04(t，J＝7.2Hz，2H，CH2)，6.63～6.81(m，2H，C6H2)，6.89～7.40(m，4H，C6H4), 7.82 (s, 1H, C=CH), 8.21 (s, 1H, triazole ring3-H), 8.34 (s, 1H, triazole ring 5-H); (Z)-A26: 58～60 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:0.99(t，J＝7.2Hz，3H，CH3)，1.47(s，6H，2×CH3)，1.78～1.82(m，2H，CH2)，2.89(s，2H，CH2)，3.81(s，3H，OCH3)，3.92(t，J＝7.2Hz，2H，CH2)，6.72～6.80(m，2H，C6H2)，6.91～7.44(m，4H，C6H4), 7.41 (s, 1H, C=CH), 8.11 (s, 1H, triazole ring 3-H), 8.42 (s, 1H,Triazole ring 5-H).
Embodiment 27
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-fluorophenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 7h, yield 52.9%. (E)-A27: 152～155 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.02(t，J＝7.2Hz，2H，CH3)，1.56(s，6H，2×CH3)，1.84～1.88(m，2H，CH2)，3.07(s，2H，CH2)，4.03(t，J＝7.2Hz，2H，CH2)，6.94～7.00(m，2H，C6H2)，7.02～7.36(m，4H，C6H4), 7.53 (s, 1H, C=CH), 8.31 (s, 1H, triazole ring 3-H), 8.41 (s, 1H,Triazole ring 5-H); (Z)-A27: 85～88 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.01(t，J＝7.6Hz，2H，CH3)，1.56(s，6H，2×CH3)，1.79～1.84(m，2H，CH2)，2.93(s，2H，CH2)，3.98(t，J＝7.2Hz，2H，CH2)，6.92～6.96(m，2H，C6H2)，7.30～7.44(m，4H，C6H4)，7.52(s，1H，C=CH), 8.10 (s, 1H, triazole ring 3-H), 8.30 (s, 1H, triazole ring 5-H).
Embodiment 28
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2-chlorphenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 7h, yield 30.0%. (E)-A28: 62～64 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.02(t，J＝7.2Hz，3H，CH3)，1.56(s，6H，2×CH3)，1.83～1.88(m，2H，CH2)，3.07(s，2H，CH2)，4.04(t，J＝7.2Hz，2H，CH2)，6.74～7.14(m，2H，C6H2)，7.30～7.46(m，4H，C6H4), 7.65 (s, 1H, CCH), 8.09 (s, 1H, triazole ring 3-H), 8.23 (s, 1H, triazole ring5-H); (Z)-A28: 142～144 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.00(t，J＝7.2Hz，3H，CH3)，1.47(s，6H，2×CH3)，1.77～1.83(m，2H，CH2)，2.92(s，2H，CH2)，3.95(t，J＝7.2Hz，2H，CH2)，7.03～7.15(m，2H，C6H2)，7.21～7.38(m，4H，C6H4)，7.79(s，1H，C＝CH)，8.12 (s, 1H, triazole ring 3-H), 8.37 (s, 1H, triazole ring 5-H).
Embodiment 29
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-chlorphenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 6h, yield 65.4%. (E)-A29: 155～158 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.01(t，J＝7.2Hz，2H，CH3)，1.54(s，6H，2×CH3)，1.78～1.86(m，2H，CH2)，3.05(s，2H，CH2)，4.01(t，J＝7.2Hz，2H，CH2)，6.89(d，J＝8.0Hz，2H，C6H43，5-H)，7.27(d，J＝8.0Hz，2H，C6H42，6-H)7.28(s，1H，C＝CH)，7.34(s，1H，C6H24-H)，7.44(s，1H，C6H26-H), 8.18 (s, 2H, triazole ring 3,5-H); (Z)-A29: fusing point 115～118℃，1HNMR(400MHz，CDCl3)δ:1.23(t，J＝7.2Hz，2H，CH3)，1.56(s，6H，2×CH3)，1.98～2.05(m，2H，CH2)，2.96(s，2H，CH2)，4.10(t，J＝7.2Hz，2H，CH2)，6.95(d，J＝8.0Hz，2H，C6H43，5-H)，7.27(d，J＝8.0Hz，2H，C6H42，6-H)，7.28(s，1H，CCH)，7.34(s，1H，C6H24-H)，7.47(s，1H，C6H26-H), 8.12 (s, 2H, triazole ring 3,5-H).
Embodiment 30
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 7h, yield 21.0%. (E)-A30: 122～126 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.02(t，3H，J＝7.2Hz，CH3)，1.55(s，6H，2×CH3)，1.83～1.88(m，2H，CH2)，3.07(s，2H，CH2)，4.04(t，J＝7.2Hz，2H，CH2)，6.65～6.70(m，1H，C6H2，4-H)，7.10～7.12(m，1H，C6H26-H)，7.36(d，J＝2.0Hz，1H，C6H35-H)，7.41(s，1H，C6H33-H)，7.47(d，J＝2.0Hz，1H，C6H36-H), 7.57 (s, 1H, C=CH), 8.09 (s, 1H, triazole ring 3-H), 8.28 (s, 1H,Triazole ring 5-H).
Embodiment 31
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-bromophenyl)-2-(1,2,4-Triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 6h, yield 55.5%. (E)-A31: 156～159 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.02(t，J＝7.2Hz，3H，CH3)，1.56(s，6H，2×CH3)，1.82～1.86(m，2H，CH2)，3.07(s，2H，CH2)，4.02(s，2H，CH2)，6.84(s，2H，C6H2)，7.25～7.46(m，4H，C6H4)，7.52 (s, 1H, C=CH), 8.26 (s, 2H, triazole ring 3,5-H); (Z)-A31: 80～84 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.01(t，J＝7.2Hz，3H，CH3)，1.50(s，6H，2×CH3)，1.79～1.82(m，2H，CH2)，2.93(s，2H，CH2)，3.98(t，J＝7.2Hz，2H，CH2)，6.79～6.81(m，1H，C6H24-H)，7.16(d，J＝8.2Hz，2H，C6H43，5-H)，7.33(s，1H，C6H26-H)，7.37(d，J＝8.2Hz，2H，C6H42,6-H), 7.50 (s, 1H, C=CH), 8.12 (s, 2H, triazole ring 3-H), 8.33 (s, 2H, triazolesRing 5-H).
Embodiment 32
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(2-nitrobenzophenone)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 6h, yield 38.9%. (E)-A32: 154～156 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:0.99(t，J＝7.2Hz，2H，CH3)，1.46(s，6H，2×CH3)，1.75～1.80(m，2H，CH2)，2.88(s，2H，CH2)，3.90(t，J＝7.2Hz，2H，CH2)，7.31(s，1H，C6H24-H)，7.34(s，1H，C6H26-H)，7.38～7.98(m，4H，C6H4)，8.01(s，1H，C＝CH)，8.14(s，1H，Triazole ring 3-H), 8.38 (s, 1H, triazole ring 5-H), (Z)-A32: 153～155 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.04(t，J＝7.2Hz，2H，CH3)，1.56(s，6H，2×CH3)，1.84-1.88(m，2H，CH2)，3.10(s，2H，CH2)，4.10(t，J＝7.2Hz，2H，CH2)，6.99～7.12(m，1H，C6H24-H)，7.47(s，1H，C6H26-H)，7.50～7.91(m，4H，C6H4), 7.91 (s, 1H, C=CH), 8.22～8.32 (m, 1H, threeAzoles ring 3-H), 8.44～8.50 (m, 1H, triazole ring 5-H).
Embodiment 33
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(3-nitrobenzophenone)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 6.5h, yield 29.1%. (E)-A33: 149～150 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.02(t，J＝7.2Hz，2H，CH3)，1.63(s，6H，2×CH3)，1.84～1.90(m，2H，CH2)，3.07(s，2H，CH2)，3.98(t，J＝7.2Hz，2H，CH2)，7.22～7.30(m，2H，C6H24，6-H)，7.31～7.48(m，4H，C6H4), 7.98 (s, 1H, CCH), 8.13 (s, 1H, triazole ring 3-H), 8.29(s, 1H, triazole ring 5-H); (Z)-A33: 123～125 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.02(t，J＝7.2Hz，2H，CH3)，1.48(s，6H，2×CH3)，1.82～1.86(m，2H，CH2)，2.93(s，2H，CH2)，3.98(t，J＝7.2Hz，2H，CH2)，7.30～7.42(m，2H，C6H24，6-H)，7.48～7.64(m，4H，C6H4)，8.00 (s, 1H, CCH), 8.17～8.29 (m, 2H, triazole ring 3,5-H).
Embodiment 34
(Z/E)-1-(7-propoxyl group-2,2-dimethyl-2,3-Dihydrobenzofuranes-5-yl)-3-(4-nitrobenzophenone)-2-(1,2,4-triazol-1-yl) preparation of-2-propylene-1-ketone
Operation, with embodiment 1, is reacted 5h, yield 36.5%. (E)-A34: 141～144 DEG C of fusing points,1HNMR(400MHz，CDCl3)δ:1.01(t，J＝7.2Hz，2H，CH3)，1.49(s，6H，2×CH3)，1.78～1.86(m，2H，CH2)，3.06(s，2H，CH2)，4.00(t，J＝7.2Hz，2H，CH2)，7.17(d，J＝8.0Hz，2H，C6H43，5-H)，7.30(d，J＝8.0Hz，2H，C6H42，6-H)，7.44(s，1H，C6H24-H)，7.48(s，1H，C6H26-H), 8.09 (s, 1H, CCH), 8.15 (s, 2H, triazole ring 3,5-H); (Z)-A34: fusing point 122～125℃，1HNMR(400MHz，CDCl3)δ:0.90(t，J＝7.2Hz，2H，CH3)，1.55(s，6H，2×CH3)，1.67～1.72(m，2H，CH2)，2.97(s，2H，CH2)，4.12(t，J＝7.2Hz，2H，CH2)，7.05(d，J＝8.0Hz，2H，C6H43，5-H)，7.30(d，J＝8.0Hz，2H，C6H42，6-H)，7.51(s，1H，C6H24-H)，7.61(s，1H，C6H26-H), 8.11 (s, 1H, C=CH), 8.21 (s, 2H, triazole ring 3,5-H).
Embodiment 35
1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone active anticancer is measured
1. antitumor activity principle
Mtt assay biological activity test claims again MTT colorimetric method, is a kind of method that detects cell survival and growth. MTTAnalytic approach is with living cells metabolin reducing agent tetrazolium bromide [3-(4,5-dimethyl-2-thiazole)-2,5-diphenyl bromination tetrazole;3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide, MTT] be basis. MTT is onePlant the dyestuff that can accept hydrogen atom. What in living cells mitochondria, the dehydrogenase relevant to NADP can be by yellow in cellMTT changes into insoluble hepatic first a ceremonial jade-ladle, used in libation (formazon), and dead cell is without this function. Dissolve with DMSOAfter formazon, under certain wavelength, measure OD value with ELIASA, both can quantitatively measure the survival rate of cell. According toThe inhibitory action of sample to tumour cell observed in the variation of OD value.
2. antitumor activity experiment
Sample: 1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone:
Wherein, R is selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl; X1、X5Be selected from: hydrogen,Deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl orBranched alkoxy, fluorine, chlorine, bromine or nitro; X3Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or side chainAlkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or branched alkoxy, fluorine, chlorine, bromine or nitro; X2、X4Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, or nitro.
Clone: cervical cancer tumer line Hela, lung adenocarcinoma cell line A549 and breast cancer cell line MCF-7 (Central South UniversityXiang Ya medical college cell bank provides).
Reagent: tetrazolium bromide (MTT), RPMI1640 nutrient solution, NBCS, antibiotic (U.S. hero life technologyCompany); Pancreatin (AMRESCO company of the U.S.); 96 well culture plates (hero Life Technologies, Inc. of the U.S.); Dimethyl sulfoxide (DMSO) (U.S.Sigma company of state).
Instrument: HFsafe-1500 type superclean bench, HF151UV type CO2(power Shen, Shanghai scientific instrument are limited for incubatorCompany); XSP-15C type inverted microscope (Shanghai rectangular optical instrument Co., Ltd); MultiskanMK3 type ELIASA (U.S.Thermo company of state); Ultra-pure water preparing instrument (Milli-Q company of the U.S.).
Experimental implementation: sample is for the test of cancer cell. In an experimentation, per sample (p.s.) arranges 5 concentration gradients(1.000 μ mol/mL, 0.300 μ mol/mL, 0.100 μ mol/mL, 0.030 μ mol/mL and 0.010 μ mol/mL), everyFour parallel samples of individual concentration, test parallel 3 times for every group, and reach a conclusion by the contrast of blank group. ELIASA detects eachHole OD value, detects wavelength 570nm.
3. antitumor activity evaluation
1) cell inhibitory rate calculates:
2)IC50Value is calculated
Sample solution concentration logarithm value and cell inhibitory rate linear regression, utilize software SPSS to calculate sample the half of cell suppressedConcentration IC50Value. (Z/E)-1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone is to cancer cellIC50In table 1～2.
The IC of table 1 (Z/E)-1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone50
The IC of table 2 (Z/E)-1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone50
Test result shows (Z/E)-(Z/E)-1-(benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone is respectively to human cervical carcinoma cell (Hela), human lung carcinoma cell (A549), and human breast cancer cell (MCF-7) has good pressing downSystem is active, can be used as the application of preparing anticarcinogen.

Claims (6)

1. (benzofuran-5-yl)-3-aryl-2-of the 1-shown in chemical structural formula I or II (1,2,4-triazol-1-yl)-2-propylene-1-ketone or its salt:
Wherein, R is selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl; X1、X5Be selected from: hydrogen,Deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl orBranched alkoxy, fluorine, chlorine, bromine or nitro; X3Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or side chainAlkyl, hydroxyl, C1～C2Alkoxyl, C3～C4Straight chain alkoxyl or branched alkoxy, fluorine, chlorine, bromine or nitro; X2、X4Be selected from: hydrogen, deuterium, C1～C2Alkyl, C3～C4Straight chained alkyl or branched alkyl, or nitro; Its salt is selected from: hydrochloride,Hydrobromate, sulfate, nitrate, phosphate, mesylate, benzene sulfonate, tosilate, malate,Lactate, succinate or butene dioic acid salt.
2. 1-claimed in claim 1 (benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone,It is characterized in that the compound shown in preferred chemical structural formula III or IV:
X in formula1～X5Definition as claimed in claim 1.
3. 1-claimed in claim 1 (benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone,It is characterized in that the compound shown in preferred chemical structural formula V or VI:
X in formula1～X5Definition as claimed in claim 1.
4. 1-claimed in claim 1 (benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketone,It is characterized in that the compound shown in preferred chemical structural formula VII or VIII:
X in formula1～X5Definition as claimed in claim 1.
5. 1-claimed in claim 1 (benzofuran-5-yl)-3-aryl-2-(1,2,4-triazol-1-yl)-2-propylene-1-ketonePreparation method, is characterized in that its preparation feedback formula is as follows:
R in formula, X1～X5Definition as claimed in claim 1.
6. (benzofuran-5-yl)-3-aryl-2-of the 1-described in any one (1,2,4-triazol-1-yl)-2-in claim 1～4Propylene-1-ketone or its salt are in the application of preparing in cancer therapy drug.
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CN104496973A (en) * 2015-01-23 2015-04-08 邵阳学院 Application of benzofuranol acrylketone derivative serving as insecticide

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