CN105585563B - 1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yls) propenyls and its application - Google Patents

1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yls) propenyls and its application Download PDF

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CN105585563B
CN105585563B CN201410573025.0A CN201410573025A CN105585563B CN 105585563 B CN105585563 B CN 105585563B CN 201410573025 A CN201410573025 A CN 201410573025A CN 105585563 B CN105585563 B CN 105585563B
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triazol
alcohol
propylene
yls
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CN105585563A (en
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胡艾希
李婉
杨子辉
丁娜
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Hunan University
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Abstract

The present invention relates to 1 alcohol of shown in chemical structural formula I or II 1 (5 base of benzofuran) 3 phenyl 2 (1,2,4 triazole, 1 base) 2 propylene or its salt：Wherein, R is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Alkyl；X1、X5It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Alkoxy, fluorine, chlorine, bromine or nitro；X3It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Alkoxy, fluorine, chlorine, bromine or nitro；X2、X4It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Alkyl or nitro；The application of 1 (5 base of benzofuran) 3 phenyl 2 (1,2,4 triazole, 1 base) 2 propylene, 1 alcohol or its salt in preparing anticancer drug.

Description

1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yls) propenyls and It is applied
Technical field
The present invention relates to a new class of compound and its preparation method and application, specifically 1- (benzofuran -5- bases) -3- Phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol and preparation method thereof is with it as the application for preparing anticancer drug.
Background technology
Overmeyer etc. [Mol.Cancer, 2011,10:69] with chalcone (1) for parent, structure of modification synthesis is carried out A series of chalcone analogs (2~4), compound 2 [Pharm.Biol., 2012,50 (12), 1551-1560] have certain Anti-human chronic myelocytic leukemia (K562) activity, compound 3 [Bioorg.＆Med.Chem., 2009,17,8168-8173] With anti-inflammatory, anti-oxidant and antibacterial activity, and it is substantially nontoxic to normal cell.Compound 4 [Mol.Cancer, 2011,10: 69] apoptosis of Malignant glioma cells can be caused.Chen Wen etc. [Org.Biomol.Chem., 2011,9,4250-4255] A series of coumaran imidazole salt compounds 5 have been synthesized, and have tested it to human breast cancer cell (MCF-7), people's lung The cytotoxicity of a variety of human tumor cells such as cancer cell (A549), wherein compound 5a are to human breast cancer cell (MCF-7) and people The IC of lung carcinoma cell (A549)50Respectively 7.95 μM and 12.35 μM.
Nagaraju etc. [Bioorg.Med.Chem.Lett., 2012,22,4314-4317] makees starting original by resorcinol Expect the benzofuranyl propylene ketones derivant 6~11 of synthesis, and tests it to Human Prostate Cancer Cells (PC-3), human lung cancer The inhibitory activity of a variety of cancer cells such as cell (NCI-H460), part of compounds is to prostate gland cancer cell (PC-3) and lung carcinoma cell (NCI-H460) there is preferable inhibitory activity.Tao Weifeng [Nankai University, Master's thesis, 2002] is described containing pyridyl group and triazole The synthesis of the propylene oxazolone (12), the third olefin conversion (13) class compound of base, compound 12 have certain bactericidal activity, compound 13 With plant growth regulation.
Chinese patent describes the preparation of 4- (benzofuran -5- bases) -2- benzyl imino thiazoles and its as antineoplastic The application [ZL 201010533786.5] of object, 4- (benzofuran -5- bases) -2- benzyls imino thiazoles and its as antineoplastic The application [ZL201010533786.5,2012.7.25 are authorized] of object and 2- (2,2- dimethyl -2,3- Dihydrobenzofuranes -5- Base) morpholine and the preparation method and application thereof [ZL201210106643.5,2014.7.23 are authorized].
Invention content
The object of the present invention is to provide 1- shown in chemical structural formula I or II (benzofuran -5- bases) -3- phenyl -2- (1, 2,4- triazol-1-yls) -2- propylene -1- alcohol or its salt：
Wherein, R is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl；X1、X5It is selected from：Hydrogen, deuterium, C1 ~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or branch alcoxyl Base, fluorine, chlorine, bromine or nitro；X3It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, hydroxyl, C1~C2 Alkoxy, C3~C4Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or nitro；X2、X4It is 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.
- 1- shown in formula I (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol is (Z) -1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol；- 1- (benzene shown in formula II And furans -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol be (E) -1- (benzofuran -5- bases) -3- Phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol.
The object of the present invention is to provide 1- shown in chemical structural formula III or IV (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol：
Wherein, X1、X5It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, hydroxyl, C1~C2Alcoxyl Base, C3~C4Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or nitro；X3It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Directly Alkyl group or branched alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or nitre Base；X2、X4It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl or nitro.
The object of the present invention is to provide 1- shown in chemical structural formula V or VI (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol：
Wherein, X1、X5It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, hydroxyl, C1~C2Alcoxyl Base, C3~C4Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or nitro；X3It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Directly Alkyl group or branched alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or nitre Base；X2、X4It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl or nitro.
The object of the present invention is to provide 1- shown in chemical structural formula VII or VIII (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol：
Wherein, X1、X5It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, hydroxyl, C1~C2Alcoxyl Base, C3~C4Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or nitro；X3It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Directly Alkyl group or branched alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or nitre Base；X2、X4It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl or nitro.
The present invention provides 1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- tri- shown in chemical structural formula I or II Azoles -1- bases) -2- propylene -1- alcohol preparation method, it is characterised in that it preparation reaction it is as follows：
Wherein, R is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl；X1、X5It is selected from：Hydrogen, deuterium, C1 ~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or branch alcoxyl Base, fluorine, chlorine, bromine or nitro；X3It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, hydroxyl, C1~C2 Alkoxy, C3~C4Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or nitro；X2、X4It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl or nitro；
The present invention provides 1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- tri- shown in chemical structural formula I~VIII Azoles -1- bases) -2- propylene -1- alcohol application in preparations of anti-tumor drugs.
The present invention has the following advantages that compared with prior art：The present invention provides 1- (benzofurans-shown in chemical formula I 5- yls) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol have anti-human cervical cancer cell (Hela), human breast carcinoma The activity of cell (MCF-7) and human lung carcinoma cell (A549).
Specific implementation mode
Following embodiment is intended to illustrate invention rather than limitation of the invention further.
Embodiment 1
(Z/E) -1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- aminomethyl phenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B1 and (E)-B1]
3.5mmol 1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -2- (1,2,4- triazoles) Catalytic amount piperidines is added dropwise in ethyl ketone (D1), 5.2mmol benzaldehydes and 30mL chloroforms, stirring, and flow back 6h.After reaction, reaction solution Through washing, saturated common salt washing, dry, precipitation, column chromatography for separation obtains product A1.
0.79mmol compounds A1,1.6mmol sodium borohydride is added in 100ml there-necked flasks, 20ml absolute ethyl alcohols, 40 DEG C anti- 15min is answered, precipitation is evaporated under reduced pressure, column chromatography for separation obtains product, yield 89.2%. (E)-B1:M.p.120~125 DEG C,1H NMR (400MHz, CDCl3)δ:1.49 (s, 6H, 2 × CH3), 2.28 (s, 3H, CH3), 2.98 (s, 2H, CH2), 3.80 (s, 3H, OCH3), 5.60 (s, 1H, CH), 6.65 (s, 1H, C6H24-H), 6.71 (d, J=8.0Hz, 2H, C6H43,5-H), 6.72 (s, 1H, C6H26-H), 6.84 (s, 1H, CCH), 7.01 (d, J=8.0Hz, 2H, C6H42,6-H), 7.61 (s, 1H, triazole ring 3-H), 8.08 (s, 1H, triazole ring 5-H)；(Z)-B1:M.p.69~71 DEG C,1H NMR (400MHz, CDCl3)δ:1.48 (s, 6H, 2 × CH3), 2.27 (s, 3H, CH3), 2.99 (s, 2H, CH2), 3.81 (s, 3H, OCH3), 5.12 (s, 1H, CH), 6.68 (s, 1H, C6H24-H), 6.72 (d, J=8.0Hz, 2H, C6H43,5-H), 6.82 (s, 1H, C6H26-H), 6.92 (d, J=8.0Hz, 2H, C6H42,6-H), 7.06 (s, 1H, CCH), 7.46 (s, 1H, triazole ring 3-H), 7.98 (s, 1H, triazole ring 5-H).
Embodiment 2
(Z/E) -1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2- methoxyphenyls) - The preparation of 2- (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B2 and (E)-B2]
Operation is the same as embodiment 1.React 0.5h, yield 86.7%.(E)-B2:M.p.141~144 DEG C,1H NMR (400MHz, CDCl3)δ:1.49 (s, 6H, 2 × CH3), 2.98 (s, 2H, CH2), 3.79 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 5.67 (s, 1H, CH), 6.58~6.74 (m, 2H, C6H24,6-H), 6.76~7.24 (m, 4H, C6H4), 7.03 (s, 1H, CCH), 7.65 (s, 1H, triazole ring 3-H), 8.03 (s, 1H, triazole ring 5-H)；(Z)-B2:M.p.154~157 DEG C,1H NMR (400MHz, CDCl3)δ:1.52 (s, 6H, 2 × CH3), 3.02 (s, 2H, CH2), 3.61 (s, 3H, OCH3), 3.71 (s, 3H, OCH3), 5.92 (s, 1H, CH), 6.68~6.74 (m, 2H, C6H2), 6.78~7.20 (m, 4H, C6H4), 7.13 (s, 1H, CCH), 7.95 (s, 1H, triazole ring 3-H), 8.15 (s, 1H, triazole ring 5-H).
Embodiment 3
(Z/E) -1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- fluorophenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B3 and (E)-B3]
Operation is the same as embodiment 1.React 0.5h, yield 85.0%.(E)-B3:Liquid,1H NMR (400MHz, CDCl3)δ: 1.28 (s, 6H, 2 × CH3), 2.89 (s, 2H, CH2), 3.71 (s, 3H, OCH3), 5.22 (s, 1H, CH), 6.34 (s, 1H, C6H24- H), 6.55 (s, 1H, C6H26-H), 6.88~7.00 (m, 4H, C6H4), 7.40 (s, 1H, CCH), 7.55 (s, 1H, triazole ring 3- H), 7.61 (s, 1H, triazole ring 5-H)；(Z)-B3:M.p.75~78 DEG C,1H NMR (400MHz, CDCl3)δ:1.33 (s, 6H, 2 ×CH3), 2.90 (s, 2H, CH2), 3.96 (s, 3H, OCH3), 5.24 (s, 1H, CH), 6.35 (s, 1H, C6H24-H), 6.56 (s, 1H, C6H26-H), 7.35~7.40 (m, 4H, C6H4), 7.52 (s, 1H, CCH), 7.55 (s, 1H, triazole ring 3-H), 7.61 (s, 1H, triazole ring 5-H).
Embodiment 4
(Z/E) -1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2- chlorphenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B4 and (E)-B4]
Operation is the same as embodiment 1.React 0.5h, yield 87.1%.(E)-B4:M.p.83~84 DEG C,1H NMR (400MHz, CDCl3)δ:1.46 (s, 6H, 2 × CH3), 2.94 (s, 2H, CH2), 3.78 (s, 3H, OCH3), 5.96 (s, 1H, CH), 6.67~ 6.80 (m, 2H, C6H24,6-H), 7.32 (m, 4H, C6H4), 7.07 (s, 1H, CCH), 8.01 (s, 1H, triazole ring 3-H), 8.49 (s, 1H, triazole ring 5-H)；(Z)-B4:M.p.69~72 DEG C,1H NMR (400MHz, CDCl3)δ:1.49 (s, 6H, 2 × CH3), 2.98 (s, 2H, CH2), 3.84 (s, 3H, OCH3), 5.83 (s, 1H, CH), 6.68~6.74 (m, 2H, C6H2, 7.32 4,6-H)~ 7.51 (m, 4H, C6H4), 7.40 (s, 1H, CCH), 8.00 (s, 1H, triazole ring 3-H), 8.24 (s, 1H, triazole ring 5-H).
Embodiment 5
(Z/E) -1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- chlorphenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B5 and (E)-B5]
Operation is the same as embodiment 1.React 0.5h, yield 76.7%.(E)-B5:M.p.78~81 DEG C,1H NMR (400MHz, CDCl3)δ:1.48 (s, 6H, 2 × CH3), 2.97 (s, 2H, CH2), 3.78 (s, 3H, OCH3), 5.08 (br, 1H, OH), 5.57 (s, 1H, CH), 6.62 (s, 1H, C6H24-H), 6.85 (s, 1H, C6H26-H), 6.85 (d, J=8.0Hz, 2H, C6H43,5-H), 7.17 (d, J=8.0Hz, 2H, C6H42,6-H), 7.58 (s, 1H, CCH), 8.01 (s, 1H, triazole ring 3-H), 8.20 (s, 1H, three Azoles ring 5-H)；(Z)-B5:M.p.82~84 DEG C,1H NMR (400MHz, CDCl3)δ:1.50 (s, 6H, 2 × CH3), 3.00 (s, 2H, CH2), 3.81 (s, 3H, OCH3), 4.42 (br, 1H, OH), 5.03~5.04 (m, 1H, CH), 6.53 (s, 1H, C6H24-H), 6.63 (s, 1H, C6H26-H), 6.83 (d, J=8.0Hz, 2H, C6H43,5-H), 7.16 (d, J=8.0Hz, 2H, C6H42,6-H), 7.26 (s, 1H, CCH), 7.70 (s, 1H, triazole ring 3-H), 8.02 (s, 1H, triazole ring 5-H).
Embodiment 6
(Z/E) -1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2,4 dichloro benzene base) - The preparation of 2- (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B6 and (E)-B6]
Operation is the same as embodiment 1.React 0.5h, yield 76.7%.(E)-B6:M.p.72~75 DEG C,1H NMR (400MHz, CDCl3)δ:1.49 (s, 6H, 2 × CH3), 2.98 (s, 2H, CH2), 3.83 (s, 3H, OCH3), 5.68 (s, 1H, CH), 6.62~ 6.71 (m, 2H, C6H24,6-H), 6.75~7.42 (m, 3H, C6H3), 7.52 (s, 1H, CCH), 8.00 (s, 1H, triazole ring 3- H), 8.43 (s, 1H, triazole ring 5-H)；(Z)-B6:M.p.84~87 DEG C,1H NMR (400MHz, CDCl3)δ:1.47 (s, 6H, 2 ×CH3), 2.95 (s, 2H, CH2), 3.77 (s, 3H, OCH3), 5.84 (s, 1H, CH), 6.56~6.68 (m, 2H, C6H24,6-H), 7.15~7.77 (m, 3H, C6H3), 7.80 (s, 1H, CCH), 8.58 (s, 1H, triazole ring 3-H), 8.99 (s, 1H, triazole ring 5- H)。
Embodiment 7
(Z/E) -1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (3- nitrobenzophenones) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B7 and (E)-B7]
Operation is the same as embodiment 1.React 0.5h, yield 84.9%.(E)-B7:Liquid,1H NMR (400MHz, CDCl3)δ: 1.35 (s, 6H, 2 × CH3), 2.50 (s, 2H, CH2), 3.64 (s, 3H, OCH3), 5.76 (s, 1H, CH), 6.00 (br, 1H, OH), 6.50 (s, 1H, C6H24-H), 6.61 (s, 1H, C6H26-H), 7.46~7.80 (m, 4H, C6H4), 7.96 (s, 1H, CCH), 8.02 (s, 1H, triazole ring 3-H), 8.48 (s, 1H, triazole ring 5-H)；(Z)-B7:M.p.91~94 DEG C,1H NMR (400MHz, CDCl3) δ:1.39 (s, 6H, 2 × CH3), 2.96 (s, 2H, CH2), 3.70 (s, 3H, OCH3), 4.82 (s, 1H, CH), 5.62 (br, 1H, OH), 6.67 (s, 1H, C6H24-H), 6.77 (s, 1H, C6H26-H), 7.45~7.90 (m, 4H, C6H4), 7.86 (s, 1H, CCH), 8.31 (s, 1H, triazole ring 3-H).
Embodiment 8
(Z/E) -1- (7- ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- aminomethyl phenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B8 and (E)-B8]
Operation is the same as embodiment 1.React 0.5h, yield 80.0%.(E)-B8:M.p.57~60 DEG C,1H NMR (400MHz, CDCl3)δ:1.41 (t, J=8.0Hz, 3H, CH3), 1.50 (s, 6H, 2 × CH3), 2.24 (s, 3H, CH3), 2.98 (s, 2H, CH2), 4.05 (q, J=8.0Hz, 2H, CH2), 4.38~4.40 (m, 1H, OH), 5.09~5.10 (m, 1H, CH), 6.68~ 6.70 (m, 2H, C6H2), 6.72 (d, J=8.0Hz, 2H, C6H42,6-H), 6.96 (d, J=8.0Hz, 2H, C6H43,5-H), 7.45 (s, 1H, triazole ring 3-H), 7.94 (s, 1H, triazole ring 5-H)；(Z)-B8:M.p.59~62 DEG C,1H NMR (400MHz, CDCl3)δ:1.37 (t, J=8.0Hz, 3H, CH3), 1.47 (s, 6H, 2 × CH3), 2.40 (s, 3H, CH3), 2.93 (s, 2H, CH2), 4.03 (q, J=8.0Hz, 2H, CH2), 5.90 (s, 1H, OH), 6.12 (s, 1H, CH), 6.62~6.64 (m, 2H, C6H2), 7.09~7.30 (m, 4H, C6H4), 7.96 (s, 1H, triazole ring 3-H), 8.37 (s, 1H, triazole ring 5-H).
Embodiment 9
(Z/E) -1- (7- ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2- methoxyphenyls) - The preparation of 2- (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B9 and (E)-B9]
Operation is the same as embodiment 1.React 0.5h, yield 66.7%.(E)-B9:M.p.163~165 DEG C,1H NMR (400MHz, CDCl3)δ:1.37 (t, J=7.2Hz, 3H, CH3), 1.47 (s, 6H, 2 × CH3), 2.94 (s, 2H, CH2), 3.89 (s, 3H, CH3), 4.12 (q, J=7.2Hz, 2H, CH2), 6.01 (s, 1H, CH), 6.69 (s, 1H, C6H24-H), 6.74 (s, 1H, C6H26-H), 6.95~7.02 (m, 4H, C6H4), 7.31 (s, 1H, C=CH), 7.97 (s, 1H, triazole ring 3-H), 8.44 (s, 1H, triazole ring 5-H)；(Z)-B9:M.p.165~168 DEG C,1H NMR (400MHz, CDCl3)δ:1.37 (t, J=7.2Hz, 3H, CH3), 1.48 (s, 6H, 2 × CH3), 2.97 (s, 2H, CH2), 3.95 (s, 3H, CH3), 4.09 (q, J=7.2Hz, 2H, CH2), 5.67 (s, 1H, CH), 6.58~6.79 (m, 2H, C6H2), 6.95~7.02 (m, 4H, C6H4), 7.39 (s, 1H, C=CH), 7.60 (s, 1H, triazole ring 3-H), 8.02 (s, 1H, triazole ring 5-H).
Embodiment 10
(Z/E) -1- (7- ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- fluorophenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B10 and (E)-B10]
Operation is the same as embodiment 1.React 0.5h, yield 60.0%.(E)-B10:M.p.48~51 DEG C,1H NMR (400MHz, CDCl3)δ:1.38 (t, J=7.2Hz, 3H, CH3), 1.48 (s, 6H, 2 × CH3), 2.95 (s, 2H, CH2), 4.04 (q, J= 7.2Hz, 2H, CH2), 6.06 (s, 1H, CH), 6.66 (s, 1H, C6H2, 4-H), 6.73 (s, 1H, C6H26-H), 7.09~7.41 (m, 4H, C6H4), 7.38 (s, 1H, C=CH), 7.98 (s, 1H, triazole ring 3-H), 8.43 (s, 1H, triazole ring 5-H)；(Z)- B10:M.p.40~43 DEG C,1H NMR (400MHz, CDCl3)δ:1.40 (t, J=7.2Hz, 3H, CH3), 1.48 (s, 6H, 2 × CH3), 2.97 (s, 2H, CH2), 4.07 (q, J=7.2Hz, 2H, CH2), 6.59 (s, 1H, CH), 6.65 (s, 1H, C6H24-H), 6.72 (s, 1H, C6H26-H), 7.09~7.41 (m, 4H, C6H4), 7.24 (s, 1H, C=CH), 7.63 (s, 1H, triazole ring 3- H), 8.04 (s, 1H, triazole ring 5-H)
Embodiment 11
(E) -1- (7- ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2,4 dichloro benzene base) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(E)-B11]
Operation is the same as embodiment 1.React 0.5h, yield 87.5%.(E)-B11:M.p.63~65 DEG C,1H NMR (400MHz, CDCl3)δ:1.24~1.25 (m, 3H, CH3), 1.42 (s, 6H, 2 × CH3), 2.94 (s, 2H, CH2), 3.14~3.31 (m, 2H, CH2), 4.03 (q, J=7.6Hz, 2H, CH2), 5.96 (s, 1H, CH), 6.71~7.03 (m, 2H, C6H2), 7.30~7.45 (m, 4H, C6H4), 7.52 (s, 1H, C=CH), 8.08 (s, 1H, triazole ring 3-H), 8.24 (s, 1H, triazole ring 5-H).
Embodiment 12
(Z/E) -1- (7- ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- bromophenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B12 and (E)-B12]
Operation is the same as embodiment 1.React 0.5h, yield 72.7%.(E)-B12:M.p.65~69 DEG C,1H NMR (400MHz, CDCl3)δ:1.39 (t, J=8.0Hz, 3H, CH3), 1.49 (s, 6H, 2 × CH3), 2.97 (s, 2H, CH2), 4.05 (q, J= 8.0Hz, 2H, CH2), 5.58 (s, 1H, OH), 6.05 (s, 1H, CH), 6.64~6.69 (m, 2H, C6H2), 6.70~6.84 (m, 2H, C6H43,5-H), 7.35 (d, J=8.0Hz, 2H, C6H42,6-H), 7.54~7.56 (m, 1H, CCH), 7.60 (s, 1H, three Azoles ring 3-H), 8.09 (s, 1H, triazole ring 5-H)；(Z)-B12:M.p.81~85 DEG C,1H NMR (400MHz, CDCl3)δ:1.41 (t, J=8.0Hz, 3H, CH3), 1.50 (s, 6H, 2 × CH3), 2.99 (s, 2H, CH2), 4.08 (q, J=8.0Hz, 2H, CH2), 4.43 (s, 1H, OH), 5.11 (s, 1H, CH), 6.67~6.71 (m, 2H, C6H2), 6.71~6.72 (m, 2H, C6H43,5-H), 7.28 (d, J=8.0Hz, 2H, C6H42,6-H), 7.52~7.55 (m, 1H, CCH), 7.70 (s, 1H, triazole ring 3-H), 8.00 (s, 1H, triazole ring 5-H).
Embodiment 13
(Z/E) -1- (7- ethyoxyl -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- nitrobenzophenones) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B13 and (E)-B13]
Operation is the same as embodiment 1.0.5h is reacted, receives 73.3%.(E)-B13:M.p.127~130 DEG C,1H NMR (400MHz, CDCl3)δ:1.41 (t, J=8.0Hz, 3H, CH3), 1.49 (s, 6H, 2 × CH3), 2.98 (s, 2H, CH2), 4.05 (q, J= 8.0Hz, 2H, CH2), 5.63 (s, 1H, CH), 6.64 (s, 1H, C6H24-H), 6.72 (s, 1H, C6H26-H), 7.02 (d, J= 8.0Hz, 2H, C6H42,6-H), 7.44~7.60 (m, 2H, C6H43,5-H), 7.67 (s, 1H, CCH), 8.07 (s, 1H, triazole rings 3-H), 8.11 (s, 1H, triazole ring 5-H)；(Z)-B13:M.p.55~58 DEG C,1H NMR (400MHz, CDCl3)δ:1.40~ 1.44 (m, 3H, CH3), 1.50 (s, 6H, 2 × CH3), 2.99 (s, 2H, CH2), 4.10~4.14 (m, 2H, CH2), 4.63 (s, 1H, OH), 5.15 (s, 1H, CH), 6.69~6.73 (m, 2H, C6H2), 7.00~7.34 (m, 4H, C6H4), 7.52~7.54 (m, 1H, CCH), 8.03~8.07 (m, 2H, triazole rings 3,5-H).
Embodiment 14
(Z+E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- aminomethyl phenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [B14]
Operation is the same as embodiment 1.React 0.5h, yield 63.6%.B14:M.p.55~58 DEG C,1H NMR (400MHz, CDCl3)δ:0.92~0.95 (m, 3H, CH3), 1.36 (s, 6H, 2 × CH3), 1.61~1.67 (m, 2H, CH2), 2.92 (s, 2H, CH2), 3.80~3.86 (m, 2H, CH2), 4.70~4.75 (m, 1H, OH), 5.88~5.90 (m, 1H, CH), 6.48 (s, 1H, C6H24-H), 6.59 (s, 1H, C6H26-H), 6.85 (d, J=8.0Hz, 2H, C6H42,6-H), 6.95 (d, J=8.0Hz, 2H, C6H43,5-H), 7.26~7.27 (m, 1H, C=CH), 7.83 (s, 1H, triazole ring 3-H), 7.93 (s, 1H, triazole ring 5-H).
Embodiment 15
(Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2- methoxyphenyls) - The preparation of 2- (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B15 and (E)-B15]
Operation is the same as embodiment 1.React 0.5h, yield 81.8%.(E)-B15:M.p.152~155 DEG C,1H NMR (400MHz, CDCl3)δ:1.00 (t, J=7.2Hz, 3H, CH3), 1.48 (s, 6H, 2 × CH3), 1.79~1.82 (m, 2H, CH2), 2.96 (s, 2H, CH2), 3.79 (s, 3H, OCH3), 3.94~3.99 (t, J=7.2Hz, 2H, CH2), 4.58 (s, 1H, OH), 5.66 (s, 1H, CH), 6.58~6.75 (m, 2H, C6H2), 6.79~7.03 (m, 4H, C6H4), 7.23 (s, 1H, C= CH), 7.71 (s, 1H, triazole ring 3-H), 8.04 (s, 1H, triazole ring 5-H)；(Z)-B15:M.p.92~95 DEG C,1H NMR (400MHz, CDCl3)δ:1.01 (t, J=7.6Hz, 3H, CH3), 1.51 (s, 6H, 2 × CH3), 1.80~1.83 (m, 2H, CH2), 3.01 (s, 2H, CH2), 3.16~3.22 (d, J=7.2Hz, 2H, CH2), 3.27 (q, J=7.2Hz, 1H, CH), 3.27 (d, J=9.2Hz, 2H, CH2), 3.70 (s, 3H, CH3), 3.98 (t, J=7.2Hz, 2H, CH2), 4.78 (m, 1H, OH), 5.13 ~5.17 (m, 1H, CH), 6.69 (s, 2H, C6H2), 6.70~7.16 (m, 4H, C6H4), 7.52 (s, 1H, C=CH), 7.62 (s, 1H, triazole ring 3-H), 7.93 (s, 1H, triazole ring 5-H).
Embodiment 16
(Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- fluorophenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B16 and (E)-B16]
Operation is the same as embodiment 1.React 0.5h, yield 88.2%.(E)-B16:M.p.54~56 DEG C,1H NMR (400MHz, CDCl3)δ:0.96 (t, 3H, J=7.2Hz, CH3), 1.46 (s, 6H, 2 × CH3), 1.75~1.82 (m, 2H, CH2), 2.95 (s, 2H, CH2), 3.71~3.74 (m, 2H, CH2), 5.58 (s, 1H, OH), 6.11 (s, 1H, CH), 6.66~6.74 (m, 2H, C6H2), 6.82~7.40 (m, 4H, C6H4), 7.71 (s, 1H, CCH), 8.09 (s, 1H, triazole ring 3-H), 8.65 (s, 1H, triazoles Ring 5-H)；(Z)-B16:M.p.145~48 DEG C,1H NMR (400MHz, CDCl3)δ:1.02 (t, 3H, J=7.2Hz, CH3), 1.50 (s, 6H, 2 × CH3), 1.80~1.83 (m, 2H, CH2), 2.99 (s, 2H, CH2), 3.97~3.99 (m, 2H, CH2), 4.61 (s, 1H, OH), 4.93~4.95 (m, 1H, CH), 6.69~6.72 (m, 2H, C6H2), 6.86~7.35 (m, 4H, C6H4), 7.75 (s, 1H, CCH), 8.15 (s, 1H, triazole ring 3-H), 8.39 (s, 1H, triazole ring 5-H).
Embodiment 17
(Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2- chlorphenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B17 and (E)-B17]
Operation is the same as embodiment 1.React 0.5h, yield 75.0%.(E)-B17:M.p.56~59 DEG C,1H NMR (400MHz, CDCl3)δ:0.98 (t, J=7.2Hz, 3H, CH3), 1.46 (s, 6H, 2 × CH3), 1.74~1.78 (m, 2H, CH2), 2.93 (s, 2H, CH2), 3.92 (t, J=7.2Hz, 2H, CH2), 5.92 (s, 1H, OH), 6.67 (s, 2H, C6H2), 7.00~7.47 (m, 4H, C6H4), 7.49 (s, 1H, C=CH), 8.02 (s, 1H, triazole ring 3-H), 8.52 (s, 1H, triazole ring 5-H)；(Z)-B17: M.p.146~148 DEG C,1H NMR (400MHz, CDCl3)δ:1.02 (t, J=7.2Hz, 3H, CH3), 1.51 (s, 6H, 2 × CH3), 1.80~1.85 (m, 2H, CH2), 2.99 (s, 2H, CH2), 3.99 (t, J=7.2Hz, 2H, CH2), 4.82~4.83 (m, 1H, OH), 5.19 (s, 1H, CH), 6.74~6.77 (m, 2H, C6H2), 7.00~7.35 (m, 4H, C6H4), 7.52 (s, 1H, C= CH), 8.13 (s, 1H, triazole ring 3-H), 8.29 (s, 1H, triazole ring 5-H).
Embodiment 18
(Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- chlorphenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B18 and (E)-B18]
Operation is the same as embodiment 1.React 0.5h, yield 71.4%.(E)-B18:M.p.40~43 DEG C,1H NMR (400MHz, CDCl3)δ:1.01 (t, 3H, J=7.2Hz, CH3), 1.50 (s, 6H, 2 × CH3), 1.78~1.82 (m, 2H, CH2), 2.99 (s, 2H, CH2), 3.92~3.97 (m, 2H, CH2), 5.11~5.12 (m, 1H, CH), 6.70~6.72 (m, 2H, C6H24,6-H), 6.81 (d, J=8.0Hz, 2H, C6H42,6-H), 7.14 (d, J=8.0Hz, 2H, C6H43,5-H), 7.20 (s, 1H, CCH), 8.04~8.25 (m, 2H, triazole rings)；(Z)-B18:M.p.56~58 DEG C,1H NMR (400MHz, CDCl3)δ:1.10 (t, 3H, J =7.2Hz, CH3), 1.49 (s, 6H, 2 × CH3), 1.78~1.84 (m, 2H, CH2), 2.99 (s, 2H, CH2), 3.93~4.00 (m, 2H, OCH2), 4.34~4.37 (m, 1H, OH), 5.09~5.10 (m, 1H, CH), 6.65~6.70 (m, 2H, C6H24,6- H), 6.72 (d, J=8.2Hz, 2H, C6H42,6-H), 7.12 (d, J=8.2Hz, 2H, C6H43,5-H), 7.45 (s, 1H, CCH), 7.97~8.10 (m, 2H, triazole rings).
Embodiment 19
(Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2,4- chlorphenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B19 and (E)-B19]
Operation is the same as embodiment 1.Reaction 0.5h, yield 91.7%, m.p.65~69 DEG C, 1.01 (t, J=6.8Hz, 3H, CH3), 1.49 (s, 6H, 2 × CH3), 1.81 (m, 2H, CH2), 2.96 (s, 2H, CH2), 3.95~3.97 (m, 2H, CH2), 4.71 (br, 1H, OH), 5.01 (m, 1H, CH), 5.18 (s, 1H, C=CH), 6.58~6.73 (m, 2H, C6H24-H), 7.18 (s, 1H, C6H26-H), 7.28~7.50 (m, 3H, C6H3), 8.07 (s, 1H, triazole ring 3-H), 8.46 (s, 1H, triazole ring 5-H).
Embodiment 20
(Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- bromophenyls) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B20 and (E)-B20]
Operation is the same as embodiment 1.React 0.5h, yield 66.7%.(E)-B20:M.p.135~137 DEG C,1H NMR (400MHz, CDCl3)δ:0.99 (t, J=7.2Hz, 3H, CH3), 1.49 (s, 6H, 2 × CH3), 1.74~1.78 (m, 2H, CH2), 2.95~2.97 (m, 2H, CH2), 3.93 (t, J=7.2Hz, 2H, CH2), 5.59 (s, 1H, OH), 6.12 (s, 1H, CH), 6.66 (s, 1H, C6H24-H), 6.70~6.73 (m, 2H, C6H43,5-H), 6.83 (s, 1H, C6H26-H), 7.36~7.37 (m, 2H, C6H42,6-H), 7.75 (s, 1H, C=CH), 8.12 (s, 1H, triazole ring 3-H), 8.78 (s, 1H, triazole ring 5-H)；(Z)- B20:M.p.55~58 DEG C,1H NMR (400MHz, CDCl3)δ:0.97 (t, J=7.2Hz, 3H, CH3), 1.51 (s, 6H, 2 × CH3), 1.77~1.80 (m, 2H, CH2), 2.97 (s, 2H, CH2), 3.94 (t, J=7.2Hz, 2H, CH2), 5.60 (s, 1H, OH), 6.18 (s, 1H, CH), 6.67~6.70 (m, 2H, C6H2), 6.78~6.83 (m, 2H, C6H42,6-H), 7.31~7.35 (m, 2H, C6H43,5-H), 7.56 (s, 1H, C=CH), 8.01 (s, 1H, triazole ring 3-H), 8.05 (s, 1H, triazole ring 5-H).
Embodiment 21
(Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2- nitrobenzophenones) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B21 and (E)-B21]
Operation is the same as embodiment 1.React 0.5h, yield 65.2%.(E)-B21:M.p.123~126 DEG C,1H NMR (400MHz, CDCl3)δ:0.98 (t, J=7.2Hz, 3H, CH3), 1.44 (s, 6H, 2 × CH3), 1.72~1.76 (m, 2H, CH2), 2.90 (s, 2H, CH2), 3.87 (t, J=7.2Hz, 2H, CH2), 5.18 (s, 1H, OH), 5.75 (s, 1H, CH), 6.58~ 6.59 (m, 2H, C6H2), 7.54~8.06 (m, 4H, C6H4), 8.06 (s, 1H, CCH), 8.24~8.26 (m, 1H, triazole ring 3- H), 8.64 (s, 1H, triazole ring 5-H)；(Z)-B21:M.p.56~58 DEG C,1H NMR (400MHz, CDCl3)δ:1.02 (t, J= 7.2Hz, 3H, CH3), 1.48 (s, 6H, 2 × CH3), 1.80~1.82 (m, 2H, CH2), 2.97 (s, 2H, CH2), 4.02 (m, 2H, CH2), 5.00 (s, 1H, OH), 5.20 (m, 1H, CH), 5.75 (s, 1H, C=CH), 6.68~6.70 (m, 1H, C6H24-H), 6.80 (m, 1H, C6H26-H), 7.43~7.93 (m, 4H, C6H4), 7.98 (s, 1H, triazole ring 3-H), 8.11~8.13 (m, 1H, Triazole ring 5-H).
Embodiment 22
(Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (3- nitrobenzophenones) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B22 and (E)-B22]
Operation is the same as embodiment 1.React 0.5h, yield 84.6%.(E)-B22:M.p.95~98 DEG C,1H NMR (400MHz, CDCl3)δ:1.02 (t, J=7.2Hz, 3H, CH3), 1.50 (s, 6H, 2 × CH3), 1.78~1.83 (m, 2H, CH2), 2.98 (s, 2H, CH2), 3.49 (t, J=7.2Hz, 2H, CH2), 4.69 (s, 1H, OH), 5.12~5.13 (m, 1H, CH), 6.70 (s, 2H, C6H2), 7.20~8.02 (m, 4H, C6H4), 7.91 (s, 1H, C=CH), 8.10 (s, 1H, triazole ring 3-H), 8.30 (s, 1H, three Azoles ring 5-H)；(Z)-B22:M.p.115~118 DEG C,1H NMR (400MHz, DMSO-d6)δ:0.96 (t, J=7.2Hz, 3H, CH3), 1.39 (s, 6H, 2 × CH3), 1.68~1.70 (m, 2H, CH2), 2.96 (s, 2H, CH2), 3.86~3.88 (m, 2H, CH2), 4.80 (s, 1H, CH), 4.81~4.83 (m, 1H, OH), 5.59 (m, 1H, C=CH), 6.69 (s, 1H, C6H24-H), 6.76 (s, 1H, C6H26-H), 7.43~7.84 (m, 4H, C6H4), 7.95 (s, 1H, triazole ring 3-H), 8.30 (s, 1H, triazole rings 5-H)。
Embodiment 23
(Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- nitrobenzophenones) -2- The preparation of (1,2,4- triazol-1-yls) -2- propylene -1- alcohol [(Z)-B23 and (E)-B23]
Operation is the same as embodiment 1.React 0.5h, yield 92.3%.(E)-B23:M.p.134~137 DEG C,1H NMR (400MHz, CDCl3)δ:0.88 (t, 3H, J=7.2Hz, CH3), 1.42 (s, 6H, 2 × CH3), 1.77~1.80 (m, 2H, CH2), 2.96~2.97 (m, 2H, CH2), 3.94 (t, J=7.2Hz, 2H, CH2), 5.63 (s, 1H, OH), 6.06 (s, 1H, CH), 6.65 (s, 1H, C6H24-H), 6.71~6.74 (m, 1H, C6H26-H), 7.01 (s, 1H, C=CH), 7.43~8.09 (m, 4H, C6H4), 8.11 (s, 1H, triazole ring 3-H), 8.28 (s, 1H, triazole ring 5-H)；(Z)-B23:M.p.99~101 DEG C,1H NMR (400MHz, CDCl3)δ:1.02 (t, 3H, J=7.2Hz, CH3), 1.25 (s, 6H, 2 × CH3), 1.81~1.82 (m, 2H, CH2), 2.96 (s, 2H, CH2), 3.97 (t, J=7.2Hz, 2H, CH2), 4.71 (s, 1H, OH), 5.14 (s, 1H, CH), 6.70 (s, 2H, C6H2), 7.11~8.04 (m, 4H, C6H4), 8.04~8.06 (m, 2H, triazole rings).
Embodiment 24
1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol active anticancers measure
1. antitumor activity principle
Mtt assay biological activity test is also known as MTT colorimetric methods, is a kind of method of detection cell survival and growth.MTT is analyzed Method is with living cells metabolin reducing agent tetrazolium bromide [3- (4,5- dimethyl -2- thiazoles) -2,5- diphenyl bromination tetrazoles；3- (4, 5-dimethylthiazol-2-yl) -2,5-diphenyltetrazolium bromide, MTT] based on.MTT is a kind of It can receive the dyestuff of hydrogen atom.The MTT of yellow can be converted in the cell with the relevant dehydrogenases of NADP in living cells mitochondria At the first a ceremonial jade-ladle, used in libation (formazon) of insoluble bluish violet, and dead cell is then without this function.After dissolving formazon with DMSO, one OD value is measured with microplate reader under standing wave length, can both quantify the survival rate for measuring cell.It is observed according to the variation of OD value Inhibiting effect of the sample to tumour cell.
2. antitumor activity is tested
Sample：1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol or its salt：
Wherein, R is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl；X1、X5It is selected from：Hydrogen, deuterium, C1 ~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, hydroxyl, C1~C2Alkoxy, C3~C4Unbranched alkoxy or branch alcoxyl Base, fluorine, chlorine, bromine or nitro；X3It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl, hydroxyl, C1~C2 Alkoxy, C3~C4Unbranched alkoxy or branched alkoxy, fluorine, chlorine, bromine or nitro；X2、X4It is selected from：Hydrogen, deuterium, C1~C2Alkyl, C3~C4Straight chained alkyl or branched alkyl or nitro.
Cell line：Cervical cancer tumer line Hela, lung adenocarcinoma cell system MCF-7 and breast cancer cell line MCF-7 (Central South University Xiang Ya medical colleges cell bank provides).
Reagent：(U.S.'s hero's life technology is public for tetrazolium bromide (MTT), RPMI 1640 culture mediums, newborn bovine serum, antibiotic Department)；Pancreatin (AMRESCO companies of the U.S.)；96 well culture plates (hero Life Technologies, Inc. of the U.S.)；Dimethyl sulfoxide (DMSO) (the U.S. Sigma companies).
Instrument：HFsafe-1500 types superclean bench, HF151UV types CO2(Shanghai power Shen scientific instrument are limited for incubator Company)；XSP-15C types inverted microscope (the rectangular optical instrument Co., Ltd in Shanghai)；Multiskan MK3 types microplate reader is (beautiful Thermo companies of state)；Ultra-pure water preparing instrument (Milli-Q companies of the U.S.).
Experimental implementation：Test of the sample for cancer cell.In experimentation, 5 concentration gradients are arranged in per sample (p.s.) (1.000 μm of ol/mL, 0.300 μm of ol/mL, 0.100 μm of ol/mL, 0.030 μm of ol/mL and 0.010 μm of ol/mL), each concentration Four parallel samples, every group of experiment is 3 times parallel, and is drawn a conclusion by blank group control.Microplate reader detects each hole OD values, detection Wavelength 570nm.
3. antitumor activity evaluation
1) cell inhibitory rate calculates：
2)IC50Value calculates
Sample solution concentration logarithm and cell inhibitory rate linear regression calculate sample using software SPSS and press down to the half of cell Concentration IC processed50Value.1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol is to cancer cell IC50It is shown in Table 1~2.
Table 1 (Z) -1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol is thin to cancer The IC of born of the same parents50
Table 2 (E) -1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol is thin to cancer The IC of born of the same parents50
1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- aminomethyl phenyls) -2- (1,2, 4- triazol-1-yls) -2- propylene -1- alcohol is to the IC of human cervical carcinoma cell (Hela) and human lung carcinoma cell (A549)50Respectively 44.0 With 93.2 μm of ol/L.
Test result shows (Z/E) -1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- third Alkene -1- alcohol or its salt respectively have human cervical carcinoma cell (Hela), human lung carcinoma cell (A549) and human breast cancer cell (MCF-7) Good inhibitory activity can be used as the application for preparing anticarcinogen.

Claims (3)

1- shown in chemical structural formula I or II 1. (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yls) -2- third Alkene -1- alcohol or its salt：
Wherein, 1- shown in I or II (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yl) -2- propylene -1- alcohol It is selected from：1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (4- fluorophenyls) -2- (1,2,4- tri- Azoles -1- bases) -2- propylene -1- alcohol, 1- (7- methoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- bases) -3- (2,4- bis- Chlorphenyl) -2- (1,2,4- triazol-1-yls) -2- propylene -1- alcohol, 1- (7- propoxyl group -2,2- dimethyl -2,3- dihydrobenzo furans Mutter -5- bases) -3- (2,4- chlorphenyls) -2- (1,2,4- triazol-1-yls) -2- propylene -1- alcohol or 1- (7- propoxyl group -2,2- diformazans Base -2,3- Dihydrobenzofuranes -5- bases) -3- (4- nitrobenzophenones) -2- (1,2,4- triazol-1-yls) -2- propylene -1- alcohol；Its salt It is selected from：Hydrochloride, hydrobromate, sulfate, nitrate, phosphate, mesylate, benzene sulfonate, tosilate, apple Hydrochlorate, lactate, succinate or butene dioic acid salt.
2. 1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yls) -2- propylene -1- alcohol described in claim 1 Preparation method, it is characterised in that it preparation reaction it is as follows：
The definition of formula I and II is as described in claim 1.
3. 1- (benzofuran -5- bases) -3- phenyl -2- (1,2,4- triazol-1-yls) -2- propylene -1- alcohol described in claim 1 Or application of its salt in preparing anti-human cervical cancer cell or human lung carcinoma cell drug.
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