CN106749046A - The ketoxime ether derivative of 1,4 pentadiene 3 of one kind containing 4 (3H) quinazolinones and preparation method thereof - Google Patents
The ketoxime ether derivative of 1,4 pentadiene 3 of one kind containing 4 (3H) quinazolinones and preparation method thereof Download PDFInfo
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- CN106749046A CN106749046A CN201611119587.3A CN201611119587A CN106749046A CN 106749046 A CN106749046 A CN 106749046A CN 201611119587 A CN201611119587 A CN 201611119587A CN 106749046 A CN106749046 A CN 106749046A
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- NETOIUMQOSWOPE-COBSHVIPSA-N CC1C=CC=[I][C@@H]1C Chemical compound CC1C=CC=[I][C@@H]1C NETOIUMQOSWOPE-COBSHVIPSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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Abstract
The invention discloses Isosorbide-5-Nitrae pentadiene 3 ketoxime ether derivative of the one kind containing 4 (3H) quinazolinones, it is characterised in that：Its formula is as follows：Wherein, R1It is phenyl, substituted-phenyl or substitution aromatic heterocyclic；R2It is phenyl, substituted-phenyl or substitution aromatic heterocyclic；R3It is more than one hydrogen atom, the methoxyl group contained on 5,6,7 or 8 of 4 (3H) quinazolinones, nitro, methyl, trifluoromethyl or halogen atom.The compounds of this invention has treatment higher and protective effect to Cucumber Mosaic Virus (CMV) and tobacco mosaic virus disease (TMV), shows anti-phytoviral activity higher, can be used to prepare Antiphytoviral agricultural chemicals.
Description
Technical field
The present invention relates to chemical technology field, a kind of pentadiene ketoxime ether containing 4 (3H)-quinazolinones is related in particular to
The preparation method of analog derivative and its application in terms of Antiphytoviral.
Background technology
Every year, crops because infection plant's virus and caused by economic loss be up to 600,000,000,000 dollars, therefore, effectively control
Development with the treatment viroses of plant to whole agricultural has very important meaning.In numerous plant viruses, tobacco
The characteristics of leaf disease has the incidence of disease high and prevents and treats difficult, is listed in one of most destructive plant virus.However, so far
The plant antiviral agent of all commercializations is only 30~50% to the therapeutic activity of plant virus under 500 μ g/mL concentration,
Its histamine result is obviously unsatisfactory.Therefore, new, efficient and environment amenable plant antiviral agent how is developed to remain unchanged
It is a significant challenge of the pendulum in face of medicine initiative worker.
Natural products and its bionic pesticide have environmentally friendly, and action site is unique and the characteristics of high selectivity, preventing
Control plant disease aspect and play more and more important effect.Curcumin, as a kind of polyphenol compound in turmeric,
It is widely used as spices, food preservative, monosodium glutamate and dyestuff.Isosorbide-5-Nitrae-pentadiene ketone compounds, as a kind of important ginger
Flavin derivatives, the biology because of it with desinsection, antibacterial, Antiphytoviral, anticancer, anti-inflammatory and the more wide spectrum such as anti-oxidant
Activity, has been increasingly becoming one of the focus in medicament initiative field.Particularly, relevant report in recent years show Isosorbide-5-Nitrae-pentadiene-
3- ketone compounds possess extremely good anti-phytoviral activity.Therefore, based on such compound, its structure is carried out
Transformation, it is most likely that obtain the organic active molecule with excellent anti-phytoviral activity.
(the conjunction of Chou Qiujuan, Xue Wei, Lu Ping, Wang Zhenchao, Wei Xue the curcumin derivates of esters containing oxime of the beautiful grade of enemy autumn in 2011
Into and its antiviral activity [J] synthesis chemistry, 2011,19 (1):Method 36-40.) is spliced by oxime ester knot using bioactie agent
Structure is incorporated into single carbonyl curcumin derivative 1, in the skeleton of 5- substituted-phenyl-Isosorbide-5-Nitrae-pentadiene -3- ketone, synthesized it is a series of not
Symmetrical 1,5- disubstituted aryls-Isosorbide-5-Nitrae-pentadiene -3- ketoxime class ester curcumin derivates, and anti-cucumber mosaic virus has been carried out to it
The active testing of poison.Test result shows：In the drug concentration of 500 μ g/mL, synthesized target compound is to cucumber mosaic
Virus has certain inhibitory action, but is below its comparison medicament Ningnanmycin.
(Luo, the H. such as Luo in 2013；Liu,J.；Jin,L.；Hu,D.；Chen,Z.；Yang,S.；Wu,J.；Song,
B.Synthesis and antiviral bioactivity of novel(1E,4E)-1-aryl-5-(2-
(quinazolin-4-yloxy)phenyl)-1,4-pentadien-3-one derivatives[J].
Eur.J.Med.Chem.,2013,63:Quinazoline structure 662-669.) is incorporated into 1,5- diaryl -1,4- pentadiene -3- ketone
Skeleton in, synthesized a series of (1E, 4E) -1- aryl -5- (2- (4- oxoquinazolins) phenyl)-Isosorbide-5-Nitrae-pentadiene -3- ketone
Class compound, and the active testing of resisting tobacco mosaic virus and anti cucumber mosaic virus has been carried out to it.Test result shows：Should
Series compound has significantly protective effect to tobacco mosaic virus (TMV), wherein there is part of compounds in terms of protective effect to cigarette
The EC of showy flowers of herbaceous plants mosaic virus50Value is better than its comparison medicament Ningnanmycin.
(Ma, the J. such as Ma in 2014；Li,P.；Li,X.；Shi,Q.；Wan,Z.；Hu,D.；Jin,L.；Song,
B.Synthesis and Antiviral Bioactivity of Novel3-((2-((1E,4E)-3-oxo-5-
arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-quinazolinone Derivatives[J]
.J.Agric.Food Chem., 2014,62,8928-8934.) by 4 (3H)-quinazolinone structures be incorporated into 1,5- diaryl-
In the skeleton of Isosorbide-5-Nitrae-pentadiene -3- ketone, a series of pentadiene ketone compounds of Quinazolinone-containings are synthesized, and it have been carried out
The active testing of anti-TMV.Test result shows：When drug concentration is 500 μ g/mL, the compound synthesized by major part is to TMV
There is certain live body to suppress and healing effect.Wherein there is effect of the part of compounds in terms of live body treatment fabulous, its suppression
Rate is better than its comparison medicament Ningnanmycin.
(Chen, the M. such as Chen in 2015；Hu,D.；Li,X.；Yang,S.；Zhang,W.；Li,P.；Song,
B.Antiviral activity and interaction mechanisms study of novel
glucopyranoside derivatives[J].Bioorg.Med.Chem.Lett.,2015,25:3840-3844.) in order to
New and effective and low toxicity the anti-plant virus agent of initiative, based on curcumin, principle is spliced using active group, will naturally be lived
Property composition pyranoside is introduced into pentadienone structure, has synthesized a series of pentadiene ketone compounds containing pyranoside, and
Using half leaf withered spot method, with virazole as comparison medicament, the passivation activity of the anti-TMV of target compound is tested.Test result
Show：Synthesized compound has certain passivation activity to TMV, wherein have the passivation effect of part of compounds preferably, its
EC50Value is superior to its comparison medicament virazole.Preliminary study mechanism shows：Such compound mainly by with TMV shell eggs
White independence is combined and makes its passivation inactivation.
(Han, the Y. such as Han in 2015；Ding,Y.；Xie,D.；Hu,D.；Li,P.；Li,X.；Xue,W.；Jin,L.；
Song,B.Design,synthesis and antiviral activity of novel rutin derivatives
containing 1,4-pentadien-3-one moiety[J].Eur.J.Med.Chem.,2015,92:732-737.) will
Isolated rutin is incorporated into the skeleton of 1,5- diaryl-Isosorbide-5-Nitrae-pentadiene -3- ketone in stalwart wormwood artemisia, has synthesized a series of molecules
In the novel rutin class compound containing Isosorbide-5-Nitrae-pentadiene -3- ketone structures, and it has been carried out anti-TMV and anti-CMV activity survey
Examination.Test result shows：When drug concentration is 500 μ g/mL, the compound of major part synthesis has certain anti-TMV and resists
The activity of CMV.Wherein there is the therapeutic activity of anti-CMV of part of compounds preferably, its EC50Value is mould better than its comparison medicament Ningnan
Element.
(Long, the C. such as Long in 2015；Li,P.；Chen,M.；Dong,L.；Hu,D.；Song,B.Synthesis,
anti-tobacco mosaic virus and curcumber mosaic virus activity,and3D-QSAR
study of novel 1,4-pentadien-3-one derivatives containing4-thioquinazoline
moiety[J].Eur.J.Med.Chem.,2015,102:Thio quinazoline 639-647.) is incorporated into 1,5- diaryl -1,4-
In the skeleton of pentadiene -3- ketone, synthesize a series of pentadiene ketone compounds containing the substitution of quinazoline thioether in molecules, and
The active testing of anti-TMV and anti-CMV has been carried out to it.Test result shows：When drug concentration is 500 μ g/mL, the change of synthesis
Compound has the activity of certain anti-TMV and anti-CMV.Which part compound is to TMV and CMV in terms for the treatment of and protective effect
With excellent inhibitory activity, its EC50Value is better than comparison medicament Ningnanmycin.
(Gan, the X. such as Gan in 2016；Hu,D.；Li,P.；Wu,J.；Chen,X.；Xue,W.；Song,B.Design,
synthesis,antiviral activity and three-dimentional quantitative structure-
activity relationship study of novel 1,4-pentadien-3-one derivatives
containing 1,3,4-oxadiazole moiety[J].Pest Manag.Sci.,2016,72:534-543.) by 1,3,
4- oxadiazole structures are incorporated into the skeleton of 1,5- diaryl-Isosorbide-5-Nitrae-pentadiene -3- ketone, to have been synthesized and contain 1 in a series of molecules,
The pentadiene ketone compounds of 3,4- oxadiazole thio ethoxies, and anti-TMV active testings have been carried out to it.Test result table
It is bright：When drug concentration is 500 μ g/mL, the compound of synthesis has the activity of preferable anti-TMV.Which part compound exists
Anti- TMV protection activities aspect has excellent activity, its EC50Value is much better than its comparison medicament virazole.
Quianzolinones, as the important heterocycle compound of a class, because it is structure is in polytropy and has
More the bioactivity of broad-spectrum high efficacy and turn into the focus in medicament initiative field.Recent studies indicate that：Such compound
There is relatively broad prospect in terms of Antiphytoviral.
(Gao, the X. such as Gao in 2007；Cai,X.；Yan,K.；Song,B.；Gao,L.；Chen,Z.Synthesis and
antiviral bioactivities of2-phenyl-3-(substituted-benzalamino)-4(3H)-
quinazolinone derivatives[J].Molecules,2007,12:2621-2642.) design has synthesized and a series of has contained 4
The Schiff class compound of (3H)-quinazolinone structure, and the active testing of anti-TMV has been carried out to it.Test result shows：
When drug concentration is 500 μ g/mL, the compound synthesized by major part has certain live body inhibitory action to TMV.
(Ma, the J. such as Ma in 2014；Li,P.；Li,X.；Shi,Q.；Wan,Z.；Hu,D.；Jin,L.；Song,
B.Synthesis and Antiviral Bioactivity of Novel3-((2-((1E,4E)-3-oxo-5-
arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-quinazolinone Derivatives[J]
.J.Agric.Food Chem., 2014,62,8928-8934.) by 4 (3H)-quinazolinone structures be incorporated into 1,5- diaryl-
In the skeleton of Isosorbide-5-Nitrae-pentadiene -3- ketone, a series of pentadiene ketone compounds of Quinazolinone-containings are synthesized, and it have been carried out
The active testing of anti-TMV.Test result shows：When drug concentration is 500 μ g/mL, the compound synthesized by major part is to TMV
There is certain live body to suppress and healing effect.Effect of the which part compound in terms of live body treatment is fabulous, its inhibiting rate
Better than its comparison medicament Ningnanmycin.
(Chen, the M. such as Chen in 2016；Li,P.；Hu,D.；Zeng,S.；Li,T.；Jin,L.；Xue,W.；Song,
B.Synthesis,antiviral activity,3D-QSAR,and interaction mechanisms study of
novel malonate derivatives containing quinazolin-4(3H)-4-one moitey[J]
.Bioorg.Med.Chem.Lett.,2016,26:168-173.) 4 (3H)-quinazolinone structures are effectively tied with malonate
Close, design has synthesized a series of quianzolinones containing malonate in molecules, and the activity of anti-CMV has been carried out to it
Test.Test result shows：When drug concentration is 500 μ g/mL, the compound synthesized by major part has certain to CMV
Live body inhibitory action.Effect of the which part compound in terms of live body treatment is fabulous, and its inhibiting rate is peaceful better than its comparison medicament
Southern mycin.
In sum, Isosorbide-5-Nitrae-pentadiene -3- ketone compounds and 4 (3H)-quianzolinones are in Antiphytoviral
Aspect has certain researching value, but the compound with antiviral activity currently formulated out is not also being protected and controlled
Treat two aspects of activity and exceed Ningnanmycin simultaneously, while also there are no on the Isosorbide-5-Nitrae-penta two containing 4 (3H)-quinazolinones
Report in terms of the synthesis of alkene -3- ketoxime ether compounds and anti-phytoviral activity.
The content of the invention
The technical problem to be solved in the present invention is：Pentadiene ketoxime ether containing 4 (3H)-quinazolinones in a kind of structure is provided
Class compound and preparation method thereof, effect is prevented and treated to solve antiviral activity compound in the prior art in terms of plant virus is prevented and treated
The not good technical problem of fruit.
The technical scheme is that：Isosorbide-5-Nitrae-pentadiene -3- ketoxime ether derivative of the one kind containing 4 (3H)-quinazolinones,
Its formula is as follows：
Wherein, R1It is phenyl, substituted-phenyl or substitution aromatic heterocyclic；R2It is phenyl, substituted-phenyl or substitution virtue
Heterocyclic radical；R3It is that the more than one hydrogen contained on 5,6,7 or 8 of 4 (3H)-quinazolinones is former
Son, methoxyl group, nitro, methyl, trifluoromethyl or halogen atom.
Described substituted-phenyl be it is o-, m- on phenyl ring, pair or foregoing two upper contain more than one methoxyl group, nitro, first
Base, trifluoromethyl or halogen atom；Described substitution aromatic heterocyclic is furyl, pyridine radicals, thienyl, pyrrole radicals, thiazolyl, 2-
Chloropyridine base or 2- diuril oxazolyls.
The preparation method of Isosorbide-5-Nitrae-pentadiene -3- ketoxime ether derivative of the one kind containing 4 (3H)-quinazolinones, with containing substitution
3- (chloromethyl) quinazoline -4 (3H) ketone and 1- (4- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- the pentadienes -3- of base
Ketoxime or 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketoximes are that raw material is prepared containing 4 (3H)-quinolines
1,4- pentadiene -3- ketoxime ether the derivatives of oxazoline ketone:
Described 1- (4- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketoximes or 1- (2- (substitutions
Benzyloxy) phenyl) preparation method of -5- substituted aryl -1,4- pentadiene -3- ketoximes is：(1) with acetone, salicylide or 4- hydroxyls
Benzaldehyde is raw material, prepare in the basic conditions 2- (hydroxy phenyl) -3- butene-2s -one or 4- (hydroxy phenyl) -3- butylene -
2- ketone:
(2) it is with substituted aroma aldehyde, 2- (hydroxy phenyl)-3- butene-2s -one or 4- (hydroxy phenyl)-3- butene-2 -one
Raw material, prepares 1- substituted aryls -5- (4- hydroxy phenyls)-Isosorbide-5-Nitrae-pentadiene -3- ketone or 1- substituted aryls -5- in the basic conditions
(2- hydroxy phenyls) -1,4- pentadiene -3- ketone：
(3) with replace benzyl chloride, 1- substituted aryls -5- (4- hydroxy phenyls) -1,4- pentadiene -3- ketone or 1- substituted aryls -
5- (2- hydroxy phenyls) -1,4- pentadiene -3- ketone is that raw material prepares 1- (4- (substituted benzyloxy) phenyl) -5- substituted aryl -1,
4- pentadiene -3- ketone or 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone：
(4) with hydroxylamine hydrochloride, 1- (4- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone or 1-
(2- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone is that raw material prepares 1- (4- (substituted benzyloxy) benzene
Base) -5- substituted aryl -1,4- pentadiene -3- ketoximes or 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryls -1,4- penta 2
Alkene -3- ketoximes：
The preparation method of described 3- (chloromethyl) quinazoline -4 (3H) ketone containing substitution base is：(1) with containing substitution base
(3H) ketone of quinazoline -4 and formaldehyde are that raw material prepares 3- (hydroxymethyl) quinazoline -4 (3H) ketone containing substitution base：
(2) prepared containing substitution base as raw material with (3H) ketone of 3- hydroxymethyls quinazoline -4 and thionyl chloride containing substitution base
3- (chloromethyl) quinazoline -4 (3H) ketone：
Beneficial effects of the present invention：4 (3H)-quinazolinone structures with excellent activity are introduced pentadienone by the present invention
In the structure of oxime ether, design has synthesized a series of pentadienone oximido ether compound containing 4 (3H)-quinazolinones in structures,
And the synthesized 1,4- pentadiene -3- ketoxime ether compounds containing 4 (3H)-quinazolinones are applied to Antiphytoviral aspect
Research, find such compound than currently having compound (cucumber mosaic virus and Tobacco mosaic in terms of Antiphytoviral
Virus) possess more prominent activity, which part compound is in terms for the treatment of and protection activity to the suppression of tobacco mosaic virus (TMV)
System activity exceedes its comparison medicament Ningnanmycin, with certain application value.
Specific embodiment
Total embodiment：
(1) 2- (hydroxy phenyl) -3- is prepared as raw material, in the basic conditions with acetone, salicylide or 4- hydroxy benzaldehydes
Butene-2 -one or 4- (hydroxy phenyl)-3- butene-2 -one:
(2) it is with substituted aroma aldehyde, 2- (hydroxy phenyl)-3- butene-2s -one or 4- (hydroxy phenyl)-3- butene-2 -one
Raw material, prepares 1- substituted aryls -5- (4- hydroxy phenyls)-Isosorbide-5-Nitrae-pentadiene -3- ketone or 1- substituted aryls -5- in the basic conditions
(2- hydroxy phenyls) -1,4- pentadiene -3- ketone：
(3) with replace benzyl chloride, 1- substituted aryls -5- (4- hydroxy phenyls) -1,4- pentadiene -3- ketone or 1- substituted aryls -
5- (2- hydroxy phenyls) -1,4- pentadiene -3- ketone is that raw material prepares 1- (4- (substituted benzyloxy) phenyl) -5- substituted aryl -1,
4- pentadiene -3- ketone or 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone：
(4) with hydroxylamine hydrochloride, 1- (4- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone or 1-
(2- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone is that raw material prepares 1- (4- (substituted benzyloxy) benzene
Base) -5- substituted aryl -1,4- pentadiene -3- ketoximes or 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryls -1,4- penta 2
Alkene -3- ketoximes：
(5) 3- (hydroxymethyl) quinoline containing substitution base is prepared as raw material with (3H) ketone of quinazoline -4 and formaldehyde containing substitution base
Oxazoline -4 (3H) ketone；
(6) prepared containing substitution base as raw material with (3H) ketone of 3- hydroxymethyls quinazoline -4 and thionyl chloride containing substitution base
3- (chloromethyl) quinazoline -4 (3H) ketone：
(7) taken with 3- (chloromethyl) quinazoline -4 (3H) ketone and 1- (4- (substituted benzyloxy) phenyl) -5- containing substitution base
For aryl -1,4- pentadiene -3- ketoximes or 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketoximes
For raw material prepares the 1,4- pentadiene -3- ketoxime ether derivatives containing 4 (3H)-quinazolinones：
Specific embodiment is listed in the way of list below, be see the table below：
Embodiment 1
(3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- penta 2
(compound number is I for the synthesis of alkene -3- ketoxime ethers1), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
4- hydroxy benzaldehydes (6.1g, 50mmol) are added in the acetone of 60mL, after stir about 15min, this is anti-for ice bath
After answering system about 30min, to the NaOH solution of 5% that about 100mL is added in system, after ice bath room after completion of dropping, is removed, often
Warm stir about 24h.After question response terminates, system is transferred in the beaker of 500mL and appropriate frozen water is added, then with 5%
After dilute hydrochloric acid solution regulation system pH is about 5~6, there are a large amount of yellow solids to separate out, solid is extracted out, finally use ethanol/water body
System's recrystallization, obtains final product 5.30g yellow solids (Theoretical Mass 8.10g), yield 65%.
(2) synthesis of 1- (2- pyridine radicals) -5- (4- hydroxy phenyls) -1,4- pentadiene -3- ketone：
By 4- (hydroxy phenyl) -3- butene-2s -one (4.0g, 24.7mmol), pyridine-2-formaldehyde (2.86mL,
29.6mmol) it is added in the there-necked flask of 250mL with 50mL ethanol, after stir about 30min, to 5% of 60mL in system
NaOH solution, after after completion of dropping, removing ice bath room, stirring at normal temperature about 24h.After question response terminates, system is transferred to 500mL
Beaker in and add appropriate frozen water, after being then about 5~6 with 5% dilute hydrochloric acid solution regulation system pH, have a large amount of yellow consolidate
Body is separated out, and solid is extracted out, obtains final product 4.96g yellow solids (theoretical yield 6.20g), yield 80%.
(3) synthesis of 1- (4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
1- (2- pyridine radicals) -5- (4- hydroxy phenyls) -1,4- pentadienes -3- is sequentially added in the there-necked flask of 100mL
Ketone (2.50g, 9.95mmol), a methyl benzyl chloride (1.71g, 11.94mmol), potassium carbonate (2.06g, 14.92mmol), KI
(0.83g, 4.97mmol) and acetone (60mL), it is to be mixed it is uniform after be heated to reflux, reaction terminates after about 3~4h, removes molten, post layer
Analysis, obtains 1.25g yellow solids (theoretical yield 3.21g), yield 39%.
(4) synthesis of 1- (4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
1- (4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- penta 2 is sequentially added in the there-necked flask of 100mL
Alkene -3- ketone (3.00g, 8.44mmol), hydroxylamine hydrochloride (1.76g, 25.32mmol), pyridine (25mL) and ethanol (50mL), normal temperature
There is white solid to separate out after stir about 24h, in system, this solid is extracted out, ethanol rinse, obtain final product white solid 1.87g (theoretical
Yield 3.12g), yield 60%.
(5) synthesis of 3- (hydroxymethyl) quinazoline -4 (3H) ketone：
Quinazoline -4 (3H) ketone (3.00g, 20.53mmol), formalin are sequentially added in the there-necked flask of 100mL
(30mL) and Isosorbide-5-Nitrae-dioxane (40mL), it is to be mixed it is uniform after, be heated to reflux reacting after 3~4h terminating.Then rapidly by body
System is transferred in the beaker of 500mL, produces a large amount of white solids, suction filtration to obtain white solid 2.94g after adding suitable quantity of water dispersion
(theoretical yield 3.63g), yield 81%.
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Sequentially added in the there-necked flask of 100mL 3- (hydroxymethyl) quinazoline -4 (3H) ketone (3.00g, 17.03mmol),
Thionyl chloride (30mL) and Isosorbide-5-Nitrae-dioxane (40mL), it is to be mixed it is uniform after, be heated to reflux reacting after 3~4h terminating.Then
It is rapid by system be transferred in the beaker of 500mL and with concentrated sodium hydroxide regulation system to strong basicity after, then extracted with dichloromethane
Take 3 times, merge organic phase, go molten, obtain final product white solid 2.00g (theoretical yield 3.33g), yield 60%.
(7) (3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4-
The synthesis of pentadiene -3- ketoxime ethers：
1- (4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- penta 2 is sequentially added in the there-necked flask of 50mL
Alkene -3- ketoximes (0.50g, 1.28mmol), 3- (chloromethyl) quinazoline -4 (3H) ketone (0.30g, 1.54mmol), potassium carbonate
(0.35g, 2.56mmol) and acetonitrile (35mL), it is to be mixed it is uniform after, be heated to reflux reacting after 3~4h terminating.System mistake while hot
Filter, filtrate go it is molten, then with acetonitrile (35mL × 3) recrystallize, obtain final product white needle-like crystals 0.25g (theoretical yield 0.69g), produce
Rate 36%.
Embodiment 2
(3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals) -1,4- penta 2
(compound number is I for the synthesis of alkene -3- ketoxime ethers2), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (3- pyridine radicals) -5- (4- hydroxy phenyls) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd), difference is with pyridine -3- formaldehyde as raw material.
(3) synthesis of 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference is with 1- (3- pyridine radicals) -5- (4- hydroxy phenyls)-Isosorbide-5-Nitrae-pentadiene -3-
Ketone and o-chloro benzyl chloride are raw material.
(4) synthesis of 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference is with 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) quinazoline -4 (3H) ketone：
Such as the step of embodiment 1 (5th).
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Such as the step of embodiment 1 (6th).
(7) (3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals) -1,4-
The synthesis of pentadiene -3- ketoxime ethers：
Such as the step of embodiment 1 (7th), difference is with 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketoximes are raw material.
Embodiment 3
(3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals) -1,4- penta
(compound number is I for the synthesis of diene -3- ketoxime ethers3), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (2- pyridine radicals) -5- (4- hydroxy phenyls) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd).
(3) synthesis of 1- (4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), it with a methyl benzyl chloride is raw material that difference is.
(4) synthesis of 1- (4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference be with 1- (4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae -
Pentadiene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) quinazoline -4 (3H) ketone：
Such as the step of embodiment 1 (5th).
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Such as the step of embodiment 1 (6th).
(7) (3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals) -1,
The synthesis of 4- pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference be with 1- (4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae -
Pentadiene -3- ketoximes are raw material.
Embodiment 4
(3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- penta 2
(compound number is I for the synthesis of alkene -3- ketoxime ethers4), comprise the following steps：
(1) synthesis of 2- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st), difference is with salicylide as raw material.
(2) synthesis of 1- (2- pyridine radicals) -5- (2- hydroxy phenyls) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd), difference is with 2- (hydroxy phenyl)-3- butene-2 -one as raw material.
(3) synthesis of 1- (2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference be with o-chloro benzyl chloride and 1- (2- pyridine radicals) -5- (2- hydroxy phenyls)-Isosorbide-5-Nitrae -
Pentadiene -3- ketone is raw material.
(4) synthesis of 1- (2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference is with 1- (2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) quinazoline -4 (3H) ketone：
Such as the step of embodiment 1 (5th).
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Such as the step of embodiment 1 (6th).
(7) (3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4-
The synthesis of pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference is with 1- (2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketoximes are raw material.
Embodiment 5
(3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- penta 2
(compound number is I for the synthesis of alkene -3- ketoxime ethers5), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (4- hydroxy phenyls) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd).
(3) synthesis of 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference is with o-chloro benzyl chloride as raw material.
(4) synthesis of 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference is with 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) quinazoline -4 (3H) ketone：
Such as the step of embodiment 1 (5th).
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Such as the step of embodiment 1 (6th).
(7) (3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4-
The synthesis of pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference is with 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketoximes are raw material.
Embodiment 6
(3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(2- (2,4- dichloro-benzyloxies) phenyl) -5- (2- pyridine radicals) -1,4-
(compound number is I for the synthesis of pentadiene -3- ketoxime ethers6), comprise the following steps：
(1) synthesis of 2- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st), difference is with salicylide as raw material.
(2) synthesis of 1- (2- hydroxy phenyls) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd), difference is with 2- (hydroxy phenyl)-3- butene-2 -one as raw material.
(3) synthesis of 1- (2- (2,4- dichloro-benzyloxies) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference is with 1- (2- hydroxy phenyls) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae-pentadiene -3-
Ketone and 2,4- dichloros benzyl chloride are raw material.
(4) synthesis of 1- (2- (2,4- dichloro-benzyloxies) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference be with 1- (2- (2,4- dichloro-benzyloxy) phenyl) -5- (2- pyridine radicals) -1,
4- pentadiene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) quinazoline -4 (3H) ketone：
Such as the step of embodiment 1 (5th).
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Such as the step of embodiment 1 (6th).
(7) (3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(2- (2,4- dichloro-benzyloxies) phenyl) -5- (2- pyridine radicals) -
The synthesis of 1,4- pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference be with 1- (2- (2,4- dichloro-benzyloxy) phenyl) -5- (2- pyridine radicals) -1,
4- pentadiene -3- ketoximes are raw material.
Embodiment 7
(3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- penta 2
(compound number is I for the synthesis of alkene -3- ketoxime ethers7), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (4- hydroxy phenyls) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd).
(3) synthesis of 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference is to be raw material to benzyl chloride chlorine.
(4) synthesis of 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference is with 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) quinazoline -4 (3H) ketone：
Such as the step of embodiment 1 (5th).
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Such as the step of embodiment 1 (6th).
(7) (3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4-
The synthesis of pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference is with 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketoximes are raw material.
Embodiment 8
(3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (4- benzyl chlorides epoxide) phenyl) -5- (2- thienyls) -1,4- penta 2
(compound number is I for the synthesis of alkene -3- ketoxime ethers8), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (4- hydroxy phenyls) -5- (2- thienyls) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd), difference is with 2 thiophene carboxaldehyde as raw material.
(3) synthesis of 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- thienyls) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference be with to benzyl chloride chlorine and 1- (4- hydroxy phenyls) -5- (2- thienyls)-Isosorbide-5-Nitrae -
Pentadiene -3- ketone is raw material.
(4) synthesis of 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- thienyls) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference is with 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- thienyls)-Isosorbide-5-Nitrae-penta
Diene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) quinazoline -4 (3H) ketone：
Such as the step of embodiment 1 (5th).
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Such as the step of embodiment 1 (6th).
(7) (3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (4- benzyl chlorides epoxide) phenyl) -5- (2- thienyls) -1,4-
The synthesis of pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference is with 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- thienyls)-Isosorbide-5-Nitrae-penta
Diene -3- ketoximes are raw material.
Embodiment 9
(3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (2,4- dichloro-benzyloxies) phenyl) -5- (2- thienyls) -1,4-
(compound number is I for the synthesis of pentadiene -3- ketoxime ethers9), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (4- hydroxy phenyls) -5- (2- thienyls) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd), difference is with 2 thiophene carboxaldehyde as raw material.
(3) synthesis of 1- (4- (2,4- dichloro-benzyloxies) phenyl) -5- (2- thienyls) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference is with to 2,4- dichloros benzyl chloride and 1- (4- hydroxy phenyls) -5- (2- thiophene
Base) -1,4- pentadiene -3- ketone be raw material.
(4) synthesis of 1- (4- (2,4- dichloro-benzyloxies) phenyl) -5- (2- thienyls) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference be with 1- (4- (2,4- dichloro-benzyloxy) phenyl) -5- (2- thienyls) -1,
4- pentadiene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) quinazoline -4 (3H) ketone：
Such as the step of embodiment 1 (5th).
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Such as the step of embodiment 1 (6th).
(7) (3- (4 (3H)-quinazolinone)) methyl isophthalic acid-(4- (2,4- dichloro-benzyloxies) phenyl) -5- (2- thienyls) -
The synthesis of 1,4- pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference be with 1- (4- (2,4- dichloro-benzyloxy) phenyl) -5- (2- thienyls) -1,
4- pentadiene -3- ketoximes are raw material.
Embodiment 10
(3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals) -
(compound number is I for the synthesis of 1,4- pentadiene -3- ketoxime ethers10), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (4- hydroxy phenyls) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd).
(3) synthesis of 1- (4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), it with a methyl benzyl chloride is raw material that difference is.
(4) synthesis of 1- (4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference be with 1- (4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae -
Pentadiene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) -6- chloro-quinazolines -4 (3H) ketone：
Such as the step of embodiment 1 (5th), difference is with 6- chloro-quinazolines -4 (3H) ketone as raw material.
(6) synthesis of 3- (chloromethyl) quinazoline -4 (3H) ketone:
Such as the step of embodiment 1 (6th), difference is with (3H) ketone of 3- (hydroxymethyl) -6- chloro-quinazolines -4 as raw material.
(7) (3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(4- (3- methylbenzyloxies) phenyl) -5- (2- pyridines
Base) -1,4- pentadiene -3- ketoxime ethers synthesis:
Such as the step of embodiment 1 (7th), difference be with 1- (4- (3- methylbenzyloxies) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae -
Pentadiene -3- ketoximes are raw material.
Embodiment 11
(3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,
(compound number is I for the synthesis of 4- pentadiene -3- ketoxime ethers11), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (4- hydroxy phenyls) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd).
(3) synthesis of 1- (4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd).
(4) synthesis of 1- (4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th).
(5) synthesis of 3- (hydroxymethyl) -6- chloro-quinazolines -4 (3H) ketone：
Such as the step of embodiment 1 (5th), difference is with 6- chloro-quinazolines -4 (3H) ketone as raw material.
(6) synthesis of 3- (chloromethyl) -6- chloro-quinazolines -4 (3H) ketone:
Such as the step of embodiment 1 (6th), difference is with (3H) ketone of 3- (hydroxymethyl) -6- chloro-quinazolines -4 as raw material.
(7) (3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(4- (3- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -
The synthesis of 1,4- pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference is with (3H) ketone of 3- (chloromethyl) -6- chloro-quinazolines -4 as raw material.
Embodiment 12
(3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,
(compound number is I for the synthesis of 4- pentadiene -3- ketoxime ethers12), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (4- hydroxy phenyls) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd).
(3) synthesis of 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference is to be raw material to benzyl chloride chlorine.
(4) synthesis of 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference is with 1- (4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) -6- chloro-quinazolines -4 (3H) ketone：
Such as the step of embodiment 1 (5th), difference is with 6- chloro-quinazolines -4 (3H) ketone as raw material.
(6) synthesis of 3- (chloromethyl) -6- chloro-quinazolines -4 (3H) ketone:
Such as the step of embodiment 1 (6th), difference is with (3H) ketone of 3- (hydroxymethyl) -6- chloro-quinazolines -4 as raw material.
(7) (3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(4- (4- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -
The synthesis of 1,4- pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference is with (3H) ketone of 3- (chloromethyl) -6- chloro-quinazolines -4 and 1- (4- (4- chlorine
Benzyloxy) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes be raw material.
Embodiment 13
(3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,
(compound number is I for the synthesis of 4- pentadiene -3- ketoxime ethers13), comprise the following steps：
(1) synthesis of 2- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st), difference is with salicylide as raw material.
(2) synthesis of 1- (2- hydroxy phenyls) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd), difference is with 2- (hydroxy phenyl)-3- butene-2 -one as raw material.
(3) synthesis of 1- (2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference be with o-chloro benzyl chloride and 1- (2- hydroxy phenyls) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae -
Pentadiene -3- ketone is raw material.
(4) synthesis of 1- (2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference is with 1- (2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) -6- chloro-quinazolines -4 (3H) ketone：
Such as the step of embodiment 1 (5th), difference is with 6- chloro-quinazolines -4 (3H) ketone as raw material.
(6) synthesis of 3- (chloromethyl) -6- chloro-quinazolines -4 (3H) ketone:
Such as the step of embodiment 1 (6th), difference is with (3H) ketone of 3- (hydroxymethyl) -6- chloro-quinazolines -4 as raw material.
(7) (3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(2- (2- benzyl chlorides epoxide) phenyl) -5- (2- pyridine radicals) -
The synthesis of 1,4- pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference is with (3H) ketone of 3- (chloromethyl) -6- chloro-quinazolines -4 and 1- (2- (2- chlorine
Benzyloxy) phenyl) -5- (2- pyridine radicals) -1,4- pentadiene -3- ketoximes be raw material.
Embodiment 14
(3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals) -1,
(compound number is I for the synthesis of 4- pentadiene -3- ketoxime ethers14), comprise the following steps：
(1) synthesis of 4- (hydroxy phenyl)-3- butene-2 -one：
Such as the step of embodiment 1 (1st).
(2) synthesis of 1- (4- hydroxy phenyls) -5- (3- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (2nd), difference is with 3- pyridine carboxaldehydes as raw material.
(3) synthesis of 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals) -1,4- pentadiene -3- ketone：
Such as the step of embodiment 1 (3rd), difference be with o-chloro benzyl chloride and 1- (4- hydroxy phenyls) -5- (3- pyridine radicals)-Isosorbide-5-Nitrae -
Pentadiene -3- ketone is raw material.
(4) synthesis of 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals) -1,4- pentadiene -3- ketoximes：
Such as the step of embodiment 1 (4th), difference is with 1- (4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals)-Isosorbide-5-Nitrae-penta
Diene -3- ketone is raw material.
(5) synthesis of 3- (hydroxymethyl) -6- chloro-quinazolines -4 (3H) ketone：
Such as the step of embodiment 1 (5th), difference is with 6- chloro-quinazolines -4 (3H) ketone as raw material.
(6) synthesis of 3- (chloromethyl) -6- chloro-quinazolines -4 (3H) ketone:
Such as the step of embodiment 1 (6th), difference is with (3H) ketone of 3- (hydroxymethyl) -6- chloro-quinazolines -4 as raw material.
(7) (3- ((the 3H)-quinazolinones of 6- chloro- 4)) methyl isophthalic acid-(4- (2- benzyl chlorides epoxide) phenyl) -5- (3- pyridine radicals) -
The synthesis of 1,4- pentadiene -3- ketoxime ethers:
Such as the step of embodiment 1 (7th), difference is with (3H) ketone of 3- (chloromethyl) -6- chloro-quinazolines -4 and 1- (4- (2- chlorine
Benzyloxy) phenyl) -5- (3- pyridine radicals) -1,4- pentadiene -3- ketoximes be raw material.
The physicochemical property and spectra count of the 1,4- pentadiene -3- ketoxime ether derivatives containing 4 (3H)-quinazolinones of synthesis
According to being shown in Table 1, proton nmr spectra (1H NMR) and carbon spectrum (13C NMR) data are shown in Table 2 and table 3.
The target compound physicochemical property of table 1 and its analytical data of mass spectrum
The target compound hydrogen nuclear magnetic resonance modal data of table 2
The target compound carbon-13 nmr spectra data of table 3
The activity of resisting tobacco mosaic virus of above-mentioned target compound：
(1) method of testing
A. Virus purification
Using week snow quadratic method (Zhou, X.P.；Xu,Z.X.；Xu,J.；Li,D.B.J.South
Chin.Agric.Univ.1995,16,74-79.), choose inoculation more than 3 weeks, TMV systemic infection hosts Nicotiana
Tabacum.L plant upper blades, are homogenized in phosphate buffer, double gauze filtering, 8000g centrifugations, through 2 polyethylene glycol
Treatment, then be centrifuged, precipitation is suspended with phosphate buffer, that is, obtain the refining liquid body of TMV.Whole experiment is carried out at 4 DEG C.With purple
The absorbance of outer spectrophotometric determination 260nm wavelength, virus concentration is calculated according to formula.
Virus concentration (mg/mL)=(A260× extension rate)/E0.1% 1cm 260nm
When wherein E represents extinction coefficient, i.e. wavelength 260nm, concentration is the suspension of 0.1% (1mg/mL), is in light path
Absorbance value during 1cm.The E of TMV0.1% 1cm 260nmIt is 5.0.
B. the live body therapeutic action that medicament infects to TMV
Live body therapeutic action of the medicament to infecting：Select the Nicotiana glutinosa of growing way consistent 5-6 leaf phases to pinch, gold is sprinkled evenly to full leaf
Emery, viral juice (6 × 10 is dipped with spread pen-3Mg/mL) full leaf virus inoculation, is rinsed after drying naturally with clear water.Treat blade
After dry, medicament is gently spread in left half leaf with writing brush, the solvent that right half leaf spreads the concentration of correspondence solvent is compared, 6-7d postscripts
Record withered spot number, inhibiting rate is calculated by following equation.
C. the live body protective effect that medicament infects to TMV
The live body protective effect that medicament infects to TMV：Select the Nicotiana glutinosa of growing way consistent 5-6 leaf phases to pinch, existed with writing brush
Zuo Banye gently spreads medicament, and the solvent that right half leaf spreads the concentration of correspondence solvent is compared.After 24h, Buddha's warrior attendant is sprinkled evenly to full leaf
Sand, viral juice (6 × 10 is dipped with spread pen-3Mg/mL) full leaf virus inoculation, is rinsed with clear water, and withered spot number is recorded after 6-7d, is pressed
Following equation calculates inhibiting rate.
Wherein, the average withered spot number for being not coated with the leaf of dispenser agent half and the half leaf withered spot number for spreading medicament all use three weights of each group
Multiple average.
(2) biological activity test result
Protection and therapeutic activity of the target compound of table 4 to tobacco mosaic virus (TMV)
It is control with commodity medicament Ningnanmycin using half leaf withered spot method, when test concentrations are 500 μ g/mL, tests
Treatments and protection activity (be shown in Table 4) of the target compound I1~I14 to tobacco mosaic virus (TMV) (TMV).The test result shows：Greatly
Partial target compound has preferably treatment and protection activity to TMV.Wherein, target compound I2, I4, I5, I6 and I7 couple
TMV possesses preferable therapeutic action, and its inhibiting rate is respectively 53.5%, 55.4%, 55.9%, 59.1% and 53.4%, slightly excellent
In Ningnanmycin (51.8%).Target compound I4、I5And I6Possess TMV preferable protective effect, its inhibiting rate is respectively
67.7%th, 69.8% and 72.0%, slightly better than Ningnanmycin (65.7%).
To further appreciate that the anti-TMV activity of the Isosorbide-5-Nitrae containing 4 (3H)-quinazolinones-pentadiene -3- ketoxime ether derivatives,
We determine the compound I with excellent activity in terms of therapeutic activity4And I6EC50Value, measurement result is shown in Table 5.
The compound I of table 54、I6With Ningnanmycin to the EC of TMV therapeutic activities50Value
The result display compound I of table 54And I6To the EC of the therapeutic action of TMV50Value is respectively 132.9 μ g/mL and 125 μ
G/mL, is superior to its comparison medicament Ningnanmycin 207.3 μ g/mL.This also indicates that such compound possesses TMV preferably suppression
Effect, Isosorbide-5-Nitrae-pentadiene -3- ketoxime ether derivative of the which part containing 4 (3H)-quinazolinones is presented with excellent to plant virus
Good inhibitory activity, can be used as potential Antiphytoviral medicine, the prospect with preferable application.
Claims (5)
1. one kind contains the Isosorbide-5-Nitrae-pentadiene -3- ketoxime ether derivatives of 4 (3H)-quinazolinones, it is characterised in that：Its formula is as follows
It is shown：
Wherein, R1It is phenyl, substituted-phenyl or substitution aromatic heterocyclic；R2It is phenyl, substituted-phenyl or substitution aromatic heterocyclic；R3For
More than one hydrogen atom, methoxyl group, nitro, methyl, the fluoroform contained on 5,6,7 or 8 of 4 (3H)-quinazolinones
Base or halogen atom.
2. one kind according to claim 1 contains the Isosorbide-5-Nitrae-pentadiene -3- ketoxime ether derivatives of 4 (3H)-quinazolinones, its
It is characterised by：Described substituted-phenyl be it is o-, m- on phenyl ring, pair or foregoing two upper contain more than one methoxyl group, nitro, first
Base, trifluoromethyl or halogen atom；Described substitution aromatic heterocyclic is furyl, pyridine radicals, thienyl, pyrrole radicals, thiazolyl, 2-
Chloropyridine base or 2- diuril oxazolyls.
3. one kind as claimed in claim 1 contains the system of the 1,4- pentadiene -3- ketoxime ether derivatives of 4 (3H)-quinazolinones
Preparation Method, it is characterised in that：With 3- (chloromethyl) quinazoline -4 (3H) ketone and 1- (4- (substituted benzyloxy) benzene containing substitution base
Base) -5- substituted aryl -1,4- pentadiene -3- ketoximes or 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryls -1,4- penta 2
Alkene -3- ketoximes are that raw material prepares the 1,4- pentadiene -3- ketoxime ether derivatives containing 4 (3H)-quinazolinones:
4. one kind according to claim 3 contains the 1,4- pentadiene -3- ketoxime ether derivatives of 4 (3H)-quinazolinones
Preparation method, it is characterised in that：Described 1- (4- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketoximes
Or the preparation method of 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketoximes is：(1) with acetone,
Salicylide or 4- hydroxy benzaldehydes are raw material, and 2- (hydroxy phenyl) -3- butene-2s -one or 4- (hydroxyls are prepared in the basic conditions
Phenyl)-3- butene-2 -one:
(2) with substituted aroma aldehyde, 2- (hydroxy phenyl)-3- butene-2s -one or 4- (hydroxy phenyl)-3- butene-2 -one as raw material,
1- substituted aryls -5- (4- hydroxy phenyls) -1,4- pentadiene -3- ketone or 1- substituted aryls -5- (2- hydroxyls are prepared in the basic conditions
Base phenyl) -1,4- pentadiene -3- ketone：
(3) replacing benzyl chloride, 1- substituted aryls -5- (4- hydroxy phenyls) -1,4- pentadiene -3- ketone or 1- substituted aryl -5- (2-
Hydroxy phenyl) -1,4- pentadiene -3- ketone be raw material prepare 1- (4- (substituted benzyloxy) phenyl) -5- substituted aryls -1,4- penta 2
Alkene -3- ketone or 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone：
(4) with hydroxylamine hydrochloride, 1- (4- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone or 1-, (2- (takes
For benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone be raw material prepare 1- (4- (substituted benzyloxy) phenyl) -5-
Substituted aryl -1,4- pentadiene -3- ketoximes or 1- (2- (substituted benzyloxy) phenyl) -5- substituted aryl -1,4- pentadiene -3- ketone
Oxime：
5. one kind according to claim 3 contains the 1,4- pentadiene -3- ketoxime ether derivatives of 4 (3H)-quinazolinones
Preparation method, it is characterised in that：The preparation method of described 3- (chloromethyl) quinazoline -4 (3H) ketone containing substitution base is：(1)
3- (hydroxymethyl) quinazoline -4 (3H) containing substitution base is prepared as raw material with (3H) ketone of quinazoline -4 and formaldehyde containing substitution base
Ketone：
(2) 3- containing substitution base is prepared as raw material with (3H) ketone of 3- hydroxymethyls quinazoline -4 and thionyl chloride containing substitution base
(chloromethyl) quinazoline -4 (3H) ketone：
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| CN108606967A (en) * | 2018-04-19 | 2018-10-02 | 泮宝峰 | A kind of Ketoconazol/Clobetasol Propionate topical composition |
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