CN104387373B - 1-(7-propoxy benzofuran-5-group)-3-(2-methoxyl phenyl)-2-(1,2,4-triazole-1- group)acrylketone - Google Patents

1-(7-propoxy benzofuran-5-group)-3-(2-methoxyl phenyl)-2-(1,2,4-triazole-1- group)acrylketone Download PDF

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CN104387373B
CN104387373B CN201410581454.2A CN201410581454A CN104387373B CN 104387373 B CN104387373 B CN 104387373B CN 201410581454 A CN201410581454 A CN 201410581454A CN 104387373 B CN104387373 B CN 104387373B
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propylene
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CN104387373A (en
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胡艾希
杨子辉
李婉
闫忠忠
叶姣
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Hunan University
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
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Abstract

The invention relates to 1-(7-propoxy-2,2-dimethyl-2,3-dihydro benzofuran-5-group)-3-(2-methoxyl phenyl)-2-(1,2,4-triazole-1-group)-2-propylene-1-ketone of which the chemical formulas (Z)-I and (E)-II are shown in the description, as well as a salt, namely (Z)-1-(7-propoxy-2,2-dimethyl-2,3-dihydro benzofuran-5-group)-3-(2-methoxyl phenyl)-2-(1,2,4-triazole-1-group)-2-propylene-1-ketone of which the molecular structure is shown in the attached drawing. The single crystal belongs to a triclinic system, and the space group is P1. The invention further discloses application of the 1-(7-propoxy-2,2-dimethyl-2,3-dihydro benzofuran-5-group)-3-(2-methoxyl phenyl)-2-(1,2,4-triazole-1-group)-2-propylene-1-ketone or the salt thereof in preparing anti-cancer drugs.

Description

1- (7- propoxyl group benzofuran -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- Triazol-1-yl) propenone
Technical field
The present invention relates to new compound and its preparation method and application, specifically (Z) -1- (7- propoxyl group -2,2- diformazan Base -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone and Its preparation method and mono-crystalline structures.
Background technology
Chinese patent [CN102010405B, 2012.7.25 authorize] describes 4- (benzofuran -5- base) -2- benzyl imido The preparation of base thiazole and its application as antitumor drug, Chinese patent [CN 102786515B, 2014.7.23 authorize] is retouched State the preparation method of 2- (2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) morpholine and its answered as preparing antidepressants With.
It is contemplated that synthesis (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- Methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone, and determine its crystal structure.
Content of the invention
Object of the present invention is to provide chemical structural formula (Z)-I and 1- (7- propoxyl group -2, the 2- bis- shown in (E)-I Methyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone Or its salt：
Its salt is selected from：Hydrochlorate, hydrobromate, sulfate, nitrate, phosphate, mesylate, benzene sulfonate, to first Benzene sulfonate, malate, lactate, succinate or butene dioic acid salt.
Object of the present invention is to provide 1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) - The preparation method of 3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone is it is characterised in that its preparation Reaction is as follows：
(E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- is obtained by column chromatography for separation (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone [(E)-I] and (Z) -1- (7- propoxyl group -2,2- bis- Methyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone [(Z)-Ⅰ].
Object of the present invention is to provide (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- Base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystal, it belongs to anorthic system, empty Between group beCell parameter is：β=75.854 (3)°；Z=2,Dc=1.285Mg/m3, F (000)=460, μ=0.09mm-1, 3434 considerable measuring points [I ＞ 2 σ (I)], considerable measuring point refine final discrepancy factor R1=0.0410, wR2=0.0890, (Δ/σ)max=0.019, S= 0.97,
Object of the present invention is to provide (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- Base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystal, in molecular structure atom compile Number as follows：
Object of the present invention is to provide (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- Base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystal preparation method, its feature exists In (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2, 4- triazol-1-yl) -2- propylene -1- ketone dissolves in methanol, ethanol or acetone, the solution room temperature obtaining place slow volatilize, 5～7 (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- is separated out after it (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystal.
Object of the present invention is to provide (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- Base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone or its salt has active anticancer.
Brief description
Fig. 1 is (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone crystal molecular structure.
Fig. 2 is (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone crystal crystal accumulation figure.
Specific embodiment
Following examples are intended to illustrate rather than limitation of the invention further.
Embodiment 1
1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1, 2,4- triazol-1-yls) -2- propylene -1- ketone preparation
(1) 1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -2- (1,2,4- triazole) ethyl ketone Preparation
The bromo- 1- of 0.14mol 2- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) ethyl ketone, 0.16mol 1,2,4- triazole, 4.0mmol PEG600,0.54mol potassium carbonate and 100mL ethyl acetate, flow back 1.5h.Reaction Liquid sucking filtration obtains brown liquid, under condition of ice bath, Deca 0.15mol nitric acid, and obtain white precipitate, sucking filtration, 500mL ethyl acetate is molten Solution, Deca 30%NaOH, adjust pH7, stir to solution clarification, point liquid, take organic faciess, vacuum distillation, obtain 1- (7- propoxyl group- 2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -2- (1,2,4- triazole) ethyl ketone, yield 85.3%, m.p.147～149 DEG C,1H NMR (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).
(2) (Z/E) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone preparation
3.5mmol 1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -2- (1,2,4- triazole) Ethyl ketone, 5.2mmol Benzaldehyde,2-methoxy and 30mL chloroform, stirring, addition piperidines, flow back 5h.Reaction is finished, and reactant liquor is through water Wash, saturated common salt is washed, be dried, precipitation, column chromatography for separation obtains (E) -1- (7- propoxyl group -2,2- dimethyl -2,3- dihydrobenzo Furan -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone [(E)-I] and (Z) -1- (7- Propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazole -1- Base) -2- propylene -1- ketone [(Z)-I], yield 59.5%.(E)-Ⅰ:M.p.192～193 DEG C,1H NMR (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, OCH2), 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 ring 3-H), 8.34 (s, 1H, triazole ring 5-H)；(Z)-Ⅰ: M.p.58～60 DEG C,1H NMR (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, OCH2), 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 2
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- The preparation of (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystal
0.5g (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone, with ethanol dissolving, the solution room temperature placement obtaining is slow to volatilize, 5～ After 7 days separate out (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) - 2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystal.
Embodiment 3
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- The preparation of (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystalline
0.5g (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone, with methanol dissolving, the solution room temperature placement obtaining is slow to volatilize, 5～ After 6 days separate out (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) - 2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystal.
Embodiment 4
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- The preparation of (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystalline
0.5g (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone, with acetone solution, the solution room temperature placement obtaining is slow to volatilize, 5～ After 6 days separate out (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) - 2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystal.
Embodiment 5
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- The preparation of (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystalline
0.5g (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone, is dissolved with ethanol-acetone, the solution room temperature obtaining is placed and slowly waved Send out, after 5～6 days, separate out (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyl group Phenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone monocrystal.
Embodiment 6
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone crystal structure
(1) X-ray structure measures
Choose 0.36 × 0.24 × 0.21mm3Monocrystalline, on BRUKER SMART APEX 1000CCD diffractometer collect Diffraction data, Mo K alpha ray (λ=0.071073nm) using graphite monochromator monochromatization, under 150 (2) K withSweep The mode of retouching collects diffraction data.With Bruker SAINTPLUS program by data convert, carry out with SADABS program simultaneously Empirical absorption correction.Application SHELXS-97 and SHELXL-97 program [Sheldrick, G.M.SHELXS97and SHELXL97, University ofGermany, 1997] direct method parsing and refined structure.All of non-hydrogen atom adopts Complete matrix least square method carries out structure refinement.All non-hydrogen atoms all do anisotropy refine.Theoretical hydrogenation, hydrogen atom respectively to Same sex thermal parameter correction.Crystal data and structural parameters list table 1 in.
Table 1 (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) crystal data of -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone and structural parameters
(2) (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone mono-crystalline structures
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- The non-hydrogen atom coordinate of (1,2,4- triazol-1-yl) -2- propylene -1- ketone and thermal parameter are listed in table 2, and part bond distance and bond angle are listed in Table 3 and table 4.
Table 2 (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone crystal atomic coordinates (× 104) and thermal parameter
x y z U(eq)
C(1) 4155(2) 5288(2) 3769(1) 18(1)
C(2) 4697(2) 6579(2) 3297(1) 20(1)
C(3) 4098(2) 7718(2) 3781(1) 22(1)
C(4) 2986(2) 7570(2) 4757(1) 23(1)
C(5) 2458(2) 6305(2) 5249(1) 23(1)
C(6) 3034(2) 5180(2) 4755(1) 21(1)
C(7) 4873(2) 4141(2) 3238(1) 19(1)
C(8) 4517(2) 2842(2) 3371(1) 18(1)
C(9) 5567(2) 1798(2) 2884(1) 18(1)
C(10) 1041(2) 1839(2) 4613(2) 31(1)
C(11) 3011(2) 1360(2) 5026(1) 23(1)
C(12) 6709(2) 2182(2) 1838(1) 17(1)
C(13) 6453(2) 3117(2) 918(1) 18(1)
C(14) 7544(2) 3356(2) -60(1) 18(1)
C(15) 8872(2) 2708(2) -105(1) 18(1)
C(16) 9162(2) 1770(2) 801(1) 17(1)
C(17) 8049(2) 1495(2) 1767(1) 17(1)
C(18) 7601(2) 4198(2) -1213(1) 23(1)
C(19) 9224(2) 4189(2) -1788(1) 21(1)
C(20) 9905(2) 5458(2) -1671(2) 26(1)
C(21) 9591(2) 3878(2) -3003(1) 25(1)
C(22) 6541(2) 7887(2) 1939(2) 33(1)
C(23) 10831(2) 228(2) 1549(1) 23(1)
C(24) 12415(2) -143(2) 1210(2) 27(1)
C(25) 13367(2) 1012(2) 1194(2) 35(1)
N(1) 3205(1) 2310(1) 4091(1) 18(1)
N(2) 1914(1) 2628(2) 3806(1) 26(1)
N(3) 1652(1) 1041(2) 5390(1) 28(1)
O(1) 5491(1) 634(1) 3383(1) 22(1)
O(2) 9857(1) 3046(1) -1104(1) 22(1)
O(3) 10523(1) 1229(1) 644(1) 21(1)
O(4) 5817(1) 6632(1) 2352(1) 29(1)
Table 3 (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone crystal bond distance
Table 4 (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone crystal bond angle [°]
Chemical bond Bond angle [°] Chemical bond Bond angle [°]
C(6)-C(1)-C(2) 118.09(14) C(14)-C(18)-H(18A) 111.2
C(4)-C(3)-H(3) 120.3 C(14)-C(18)-H(18B) 111.2
C(8)-C(7)-C(1) 131.95(14) H(18A)-C(18)-H(18B) 109.1
C(8)-C(7)-H(7) 114.0 O(2)-C(19)-C(21) 105.92(13)
C(1)-C(7)-H(7) 114.0 C(21)-C(19)-C(20) 113.02(13)
C(7)-C(8)-N(1) 123.96(14) O(2)-C(19)-C(18) 104.89(11)
C(7)-C(8)-C(9) 121.35(13) C(21)-C(19)-C(18) 114.45(13)
N(1)-C(8)-C(9) 114.25(13) H(22B)-C(22)-H(22C) 109.5
O(1)-C(9)-C(12) 120.95(14) O(3)-C(23)-C(24) 106.99(13)
O(1)-C(9)-C(8) 118.82(14) O(3)-C(23)-H(23A) 110.3
C(12)-C(9)-C(8) 120.19(13) C(23)-C(24)-C(25) 112.83(14)
N(2)-C(10)-N(3) 116.03(14) H(24A)-C(24)-H(24B) 107.8
N(2)-C(10)-H(10) 122.0 C(24)-C(25)-H(25A) 109.5
C(13)-C(12)-C(9) 121.94(13) C(11)-N(1)-N(2) 109.24(12)
C(17)-C(12)-C(9) 117.20(13) C(11)-N(1)-C(8) 128.93(13)
C(13)-C(14)-C(18) 132.33(13) N(2)-N(1)-C(8) 121.42(12)
O(2)-C(15)-C(14) 114.36(14) C(10)-N(2)-N(1) 101.63(13)
O(3)-C(16)-C(17) 126.65(14) C(11)-N(3)-C(10) 102.12(14)
O(3)-C(16)-C(15) 116.16(13) C(16)-O(3)-C(23) 117.04(12)
C(14)-C(18)-C(19) 102.77(12) C(2)-O(4)-C(22) 118.03(13)
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- The molecular structure of (1,2,4- triazol-1-yl) -2- propylene -1- ketone crystal is as shown in Figure 1；Structure cell accumulation graph is as shown in Figure 2.
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone crystal belongs to anorthic system, and space group isCell parameter is： β=75.854 (3) °；Z=2, Dc=1.285Mg/m3, F (000)=460, μ=0.09mm-1, 3434 considerable measuring points [I ＞ 2 σ (I)], considerable measuring point refine is Whole discrepancy factor R1=0.0410, wR2=0.0890, (Δ/σ)max=0.019, S=0.97,
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) - In 2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone crystal structure, intermolecular is to act on by π-π maintaining the steady of crystal structure Fixed.
Embodiment 7
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone active anticancer measures
1. anti-tumor activity principle
Mtt assay biological activity test, also known as MTT colorimetry, is a kind of method of detection cell survival and growth.MTT analyzes Method is with living cells metabolite reducing agent tetrazolium bromide [3- (4,5- dimethyl -2- thiazole) -2,5- diphenyl bromination tetrazole；3- (4, 5-dimethylthiazol-2-yl) -2,5-diphenyltetrazolium bromide, MTT] based on.MTT is a kind of The dyestuff of hydrogen atom can be accepted.In living cells mitochondria, the MTT of yellow can be converted by the dehydrogenase in the cell related to NADP Become insoluble hepatic first a ceremonial jade-ladle, used in libation (formazon), and dead cell then no this function.After DMSO dissolving formazon, one Optical density value is measured with microplate reader, both Crestor measured the survival rate of cell under standing wave length.Change according to optical density value is observed The inhibitory action to tumor cell for the sample.
2. anti-tumor activity experiment
Sample：(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxybenzene Base) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone.
Cell line：Cervical cancer tumer line Hela, human lung carcinoma cell (A549) and breast cancer cell line MCF-7 (Central South University Hunan refined medical college cell bank provides).
Reagent：(U.S.'s hero's life technology is public for tetrazolium bromide (MTT), RPMI RPMI-1640, new-born calf serum, antibiotic Department)；Pancreatin (AMRESCO company of the U.S.)；96 well culture plates (hero Life Technologies, Inc. of the U.S.)；Dimethyl sulfoxide (the U.S. Sigma company).
Instrument：HFsafe-1500 type superclean bench, HF151UV type CO2(Shanghai power Shen scientific instrument are limited for incubator Company)；XSP-15C type inverted microscope (Shanghai rectangular optical instrument company limited)；Multiskan MK3 type microplate reader is (beautiful Thermo company of state)；Ultra-pure water preparing instrument (Milli-Q company of the U.S.).
Experimental implementation：Sample is for the test of cancerous cell.In experimentation, per sample (p.s.) arranges 5 Concentraton gradient (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, test parallel 3 times for every group, and are reached a conclusion by blank group comparison.Microplate reader detects each hole OD value, detection Wavelength 570nm.
3. antitumor activity evaluation
1) cell inhibitory rate calculates：
2)IC50Value calculates
Sample solution concentration logarithm value and cell inhibitory rate linear regression, calculate sample using software SPSS and the half of cell are pressed down Concentration IC processed50Value.
(Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone is to human cervical carcinoma (Hela) cell, human lung cancer (A549) cell and human breast carcinoma (MCF-7) IC of cell50It is respectively 0.0671 μm of ol/mL, 0.0100 μm of ol/mL and 0.0352 μm of ol/mL.
Active anticancer test result shows (Z) -1- (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- Base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone or its salt is to human cervical carcinoma cell (Hela), human lung carcinoma cell (A549) and human breast cancer cell (MCF-7) have good inhibitory activity, can be used as preparing anticarcinogen Application.

Claims (2)

1. (Z) -1- shown in chemical structural formula (Z)-I (7- propoxyl group -2,2- dimethyl -2,3- Dihydrobenzofuranes -5- base) - The monocrystal of 3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone：
It is characterized in that it belongs to anorthic system, space group isCell parameter is： β=75.854 (3) °；Z=2,Dc=1.285Mg/m3, F (000)=460, μ=0.09mm-1, 3434 considerable measuring points [I ＞ 2 σ (I)], considerable measuring point refine final discrepancy factor R1=0.0410, wR2= 0.0890, (Δ/σ)max=0.019, S=0.97,
2. the preparation method of the monocrystal described in claim 1 it is characterised in that (Z) -1- (7- propoxyl group -2,2- dimethyl -2, 3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone dissolves in first In alcohol, ethanol or acetone, the solution room temperature obtaining places slow volatilization, separates out (Z) -1- (7- propoxyl group -2,2- bis- after 5～7 days Methyl -2,3- Dihydrobenzofuranes -5- base) -3- (2- methoxyphenyl) -2- (1,2,4- triazol-1-yl) -2- propylene -1- ketone Monocrystal.
CN201410581454.2A 2014-10-27 2014-10-27 1-(7-propoxy benzofuran-5-group)-3-(2-methoxyl phenyl)-2-(1,2,4-triazole-1- group)acrylketone Expired - Fee Related CN104387373B (en)

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008040057A1 (en) * 2006-10-04 2008-04-10 Bionomics Limited Novel benzofuran potassium channel blockers and uses thereof
CN101492426A (en) * 2009-03-11 2009-07-29 湖南大学 Thiazole schiff base containing nitryl, preparation and uses thereof
CN101845026A (en) * 2009-12-30 2010-09-29 湖南大学 5-(4-chlorophenylmethyl)-4-tertiary butyl thiazole derivatives and preparation method and application thereof
CN102010405A (en) * 2010-11-08 2011-04-13 湖南大学 4-(benzofuran-5-yl)-2-benzal aminothiazole and application of 4-(benzofuran-5-base)-2-benzal aminothiazole as antineoplastic agent
CN102675303A (en) * 2011-10-19 2012-09-19 湖南大学 4-alkyl-2-arylamino-5-(1,2,4-triazole-1-group) thiazole and application thereof to preparation of medicaments for resisting cancer
CN103145700A (en) * 2013-04-01 2013-06-12 湖南大学 2-(2-benzyl hydrazono)-4-(benzofuran-5-yl) thiazole and preparation method and application thereof
CN103570643A (en) * 2012-12-03 2014-02-12 湖南大学 N-[4-tertbutyl-5-(2-nitroethyl)thiazole-2-yl]benzamide, preparation method and application

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105585562B (en) * 2014-10-24 2018-09-21 湖南大学 1- (benzofuran -5- bases) -3- aryl -2- (triazol-1-yl) propenone and its application as anticarcinogen

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008040057A1 (en) * 2006-10-04 2008-04-10 Bionomics Limited Novel benzofuran potassium channel blockers and uses thereof
CN101492426A (en) * 2009-03-11 2009-07-29 湖南大学 Thiazole schiff base containing nitryl, preparation and uses thereof
CN101845026A (en) * 2009-12-30 2010-09-29 湖南大学 5-(4-chlorophenylmethyl)-4-tertiary butyl thiazole derivatives and preparation method and application thereof
CN102010405A (en) * 2010-11-08 2011-04-13 湖南大学 4-(benzofuran-5-yl)-2-benzal aminothiazole and application of 4-(benzofuran-5-base)-2-benzal aminothiazole as antineoplastic agent
CN102675303A (en) * 2011-10-19 2012-09-19 湖南大学 4-alkyl-2-arylamino-5-(1,2,4-triazole-1-group) thiazole and application thereof to preparation of medicaments for resisting cancer
CN103570643A (en) * 2012-12-03 2014-02-12 湖南大学 N-[4-tertbutyl-5-(2-nitroethyl)thiazole-2-yl]benzamide, preparation method and application
CN103145700A (en) * 2013-04-01 2013-06-12 湖南大学 2-(2-benzyl hydrazono)-4-(benzofuran-5-yl) thiazole and preparation method and application thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
5-苄基-4-叔丁基-2-芳氨基噻唑氢溴酸盐的合成、表征及抗肿瘤活性;彭俊梅，等;《高等学校化学学报》;20130731;第34卷(第7期);第1646-1652页 *

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