CN101302172A - 3,5-diiodosalicylaldehyde Schiff alkali, preparation and use thereof - Google Patents

3,5-diiodosalicylaldehyde Schiff alkali, preparation and use thereof Download PDF

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CN101302172A
CN101302172A CNA2008101235687A CN200810123568A CN101302172A CN 101302172 A CN101302172 A CN 101302172A CN A2008101235687 A CNA2008101235687 A CN A2008101235687A CN 200810123568 A CN200810123568 A CN 200810123568A CN 101302172 A CN101302172 A CN 101302172A
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徐锁平
宫海滨
朱海亮
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Abstract

The invention provides 3,5-diiodo salicylal Schiff base compounds having a structural formula in a right figure. An experiment shows that 3,5-diiodo salicylal Schiff base compounds play a role in inhibiting Bacillus subtilis (B.subtilis), Staphylococcus aureus (S. aureus), enterococcus faecalis (S.faecalis), pseudomonas aeruginosa (P.aeruginosa), escherichia coli (E.coli) and enterobacter cloacae (E. cloacae) to a different extent, thereby possibly being used for making antibacterial medicines. And the invention discloses a method for making 3,5-diiodo salicylal Schiff base compounds.

Description

3,5-diiodo-salicylic aldehyde Schiff alkali and method for making and purposes
Technical field
The present invention relates to 3,5-diiodo-salicylic aldehyde Schiff alkali and method for making thereof and their application in the preparation antibacterial medicines.
Technical background
Iodo salicylaldehyde is with a wide range of applications as a kind of medicine intermediate.Be that raw material and all kinds of amine effect can generate and contain iodine Schiff alkali with the iodo salicylaldehyde.These Schiff alkali can be reduced into Bian amine (ammonia Bian compounds has the excellent antibiotic activity), also can further synthesize a series of coordination compoundes with metal ion generation coordination.Because its wide biological activity, iodo salicylaldehyde Schiff alkali more and more is used for the industrial or agricultural all respects.
The inventor on the preparation method's of iodo salicylaldehyde invention basis (referring to CN200710190267.1), synthesized again a series of 3,5-diiodo-salicylic aldehyde Schiff alkali cpd, and they have been carried out the inhibiting test of several frequently seen mushroom.
Summary of the invention
The objective of the invention is to 3,5-diiodo-salicylic aldehyde is guide's thing, some ultimate principles synthetic a series of 3 by medicinal design, 5-diiodo-salicylic aldehyde Schiff alkali, on the basis of further investigation structure activity relationship, find to have 3 of higher antimicrobial acivity, 5-diiodo-salicylic aldehyde Schiff alkali, and provide 3, the method for making of 5-diiodo-salicylic aldehyde Schiff alkali.
Technical scheme of the present invention is as follows:
A series of 3,5-diiodo-salicylic aldehyde Schiff alkali cpd, it has following general structure:
Wherein:
R 1For:
Figure A20081012356800042
Figure A20081012356800043
R 2For:
Figure A20081012356800052
Figure A20081012356800053
A kind of 3, the preparation method of 5-diiodo-salicylic aldehyde Schiff alkali cpd, with 3,5-diiodo-salicylic aldehyde with have above-mentioned R 1Or R 2The organic amine of group is in methyl alcohol or ethanol, and reaction is 10-30 minute under the room temperature, obtains 3,5-diiodo-salicylic aldehyde Schiff alkali cpd.
Figure A20081012356800054
Experimental results show that, 3,5-diiodo-salicylic aldehyde Schiff alkali cpd is to Bacillus subtillis (B.subtilis), staphylococcus aureus (S.aureus) Dung faecalis (S.faecalis), Pseudomonas aeruginosa (P.aeruginosa), intestinal bacteria (E.coli) and enterobacter cloacae (E.cloacae) all have restraining effect in various degree.Therefore, 3,5-diiodo-salicylic aldehyde Schiff alkali cpd can be used in the preparation antibacterials.
Embodiment
Further describe the present invention by following examples, but should notice that scope of the present invention is not subjected to any restriction of these embodiment.
Embodiment 1:3,5-diiodo-salicylidene n-Butyl Amine 99 (1) (1 is the compound sequence number, down together)
With 3,5-diiodo-salicylic aldehyde (0.15g) is dissolved in 20mL methyl alcohol with n-Butyl Amine 99 (0.4mL) in the beaker of 100mL, and at room temperature magnetic agitation is 15 minutes, at room temperature leaves standstill then 3 days, a large amount of yellow crystals occur.Filter yellow crystals, and, place in the Calcium Chloride Powder Anhydrous moisture eliminator with methanol wash three times, yellow crystals 0.155g, productive rate: 90%.Mp：84-86℃， 1H?NMR[300MHz，CDCl 3]δppm：15.074(s，1H)；8.052(s，1H)；8.038(d，J＝2.1Hz，1H)；7.466(d，J＝2.1Hz，1H)；3.619(d，J＝12.9Hz，2H)；1.692(d，J＝14.7Hz，2H)；1.427(d，J＝30.0Hz，2H)；0.949(d，J＝14.7Hz，3H)。IR(cm -1，KBr)：2953.5(s)；1645.1(s)；1463.9(s)；1214.6(s)；863.1(s)；654.0(s)；544.2(m)。ESI-MS：429.9(C 11H 14I 2NO+，[M+H]+)。
Embodiment 2:3,5-diiodo-salicylidene-4-fluorobenzene methylamine (4)
With 3,5-diiodo-salicylic aldehyde (0.15g) is dissolved in 20mL ethanol with 4-fluorobenzene methylamine (0.48mL) in the beaker of 100mL, and at room temperature magnetic agitation is 20 minutes, at room temperature leaves standstill then 4 days, a large amount of yellow crystals occur.Filter yellow crystals, and, place in the Calcium Chloride Powder Anhydrous moisture eliminator with washing with alcohol three times, yellow crystals 0.164g, productive rate: 85%.Mp：107-108℃， 1H?NMR[300MHz，CDCl 3]δppm：14.674(s，1H)；8.194(s，1H)；8.050(d，J＝2.1Hz，1H)；7.525(d，J＝2.1Hz，1H)；7.247(d，J＝8.7Hz，2H)；7.064(d，J＝8.7Hz，2H)；4.874(s，2H)。IR(cm -1，KBr)：1624.3(s)；1509.0(s)；1438.8(s)；1271.4(m)；1226.3(s)；1158.2(s)；1038.4(m)；867.5(s)；821.1(s)；657.7(s)；566.7(m)。ESI-MS：481.9(C 14H 11FI 2NO +，[M+H] +)。
Embodiment 3:3,5-diiodo-salicylidene-2-chloroaniline (8)
With 3,5-diiodo-salicylic aldehyde (0.15g) is dissolved in 15mL methyl alcohol with 2-chloroaniline (0.4mL) in the beaker of 50mL, and at room temperature magnetic agitation is 10 minutes, at room temperature leaves standstill then 5 days, a large amount of orange crystal occur.Filter the orange crystal, and, place in the Calcium Chloride Powder Anhydrous moisture eliminator with methanol wash three times, orange crystal 0.174g, productive rate 90%.Mp：150-152℃， 1H?NMR[300MHz，CDCl 3]δppm：14.231(s，1H)；8.460(s，1H)；8.134(d，J＝2.1Hz，1H)；7.690(d，J＝2.1Hz，1H)；7.505(d，J＝7.8Hz，1H)；7.573(d，J＝19.8Hz，2H)；7.232(d，J＝7.8Hz，1H)。IR(cm -1，KBr)：1608.1(s)；1576.4(m)；1433.1(s)；1272.6(m)；1152.6(s)；1048.6(m)；859.8(s)；756.5(s)；738.6(s)；654.0(m)；537.5(m)。ESI-MS：483.8(C 13H 9ClI 2NO +，[M+H] +)。
By above embodiment similar methods, with 3,5-diiodo-salicylic aldehyde and monoamine are raw material, and we have synthesized listed 27 kind 3 of table 1,5-diiodo-salicylic aldehyde monoamine Schiff alkali cpd (1～27).
Table 13,5-diiodo-salicylidene monoamine Schiff alkali cpd
Figure A20081012356800071
Figure A20081012356800081
Embodiment 4:3,5-diiodo-salicylidene diethylenetriamine (33)
With 3,5-diiodo-salicylic aldehyde (0.374g) is dissolved in 30mL ethanol with diethylenetriamine (0.45mL) in the beaker of 100mL, and at room temperature magnetic agitation is 20 minutes, leaves standstill 5 days, a large amount of yellow crystals occur.Filter yellow crystals, and, place in the Calcium Chloride Powder Anhydrous moisture eliminator with washing with alcohol three times, yellow crystals 0.76g, productive rate: 93%.Mp：108-112℃， 1H?NMR[CDCl 3]δppm：14.620(s，2H)；8.072(s，2H)；7.996(d，J＝2.1Hz，2H)；7.937(d，J＝2.1Hz，2H)；3.720(s，4H)；3.042(s，4H)；1.563(s，1H)。IR(cm-1，KBr)：3295.1(m)；3052.8(m)；2888.8(m)；2829.8(m)；1633.5(s)；1276.4(m)；1156.7(s)；656.9(s)；540.6(m)。ESI-MS：815.8(C 18H 18I 4N 3O 2 +，[M+H] +)。
By above embodiment similar methods, with 3,5-diiodo-salicylic aldehyde and polyamines are raw material, and we have synthesized listed 8 kind 3 of table 2,5-diiodo-salicylidene diamines Schiff alkali cpd 28～35.
Table 23,5-diiodo-salicylidene diamines Schiff alkali cpd
Figure A20081012356800092
Embodiment 5:3,5-diiodo-salicylic aldehyde Schiff alkali cpd is to Bacillus subtillis (B.subtilis), staphylococcus aureus (S.aureus) Dung faecalis (S.faecalis), Pseudomonas aeruginosa (P.aeruginosa), the effect of intestinal bacteria (E.coli) and enterobacter cloacae (E.cloacae)
Method: mtt assay.Get the Bacillus subtillis (B.subtilis) of cultivation, staphylococcus aureus (S.aureus), Ji faecalis (S.faecalis), Pseudomonas aeruginosa (P.aeruginosa), the bacterial strain of intestinal bacteria (E.coli) and enterobacter cloacae (E.cloacae) is diluted to 2 * 10 respectively 4Individual/ml, be sub-packed in 96 orifice plates (0.2ml/ hole).If penicillin and kantlex are the reference control group, DMSO is the tested compounds of blank group and 16 different concns, every hole 10 μ l.Each group is established 3 parallel holes, puts in 37 ℃ of constant incubators and cultivates 24h, squeezes into MTT liquid (2mg/ml) 5 μ l/ holes, cultivates 4h again.Take out culture plate, add SDS 100 μ l/ holes, cultivate 12h again, under the 570nm wavelength, measure the OD value, calculate bacterial growth inhibiting rate (minimum half-inhibition concentration, MIC by following formula with BioRad produced in USA 550 type microplate reader s).
Growth inhibition ratio=(the average OD value of the average OD value/control group of 1-medication group) * 100%
MIC sMore little, the germ resistance of this compound is good more, the results are shown in Table 3.
The result shows: 3,5-diiodo-salicylic aldehyde Schiff alkali cpd is to Bacillus subtillis (B.subtilis), staphylococcus aureus (S.aureus), Ji faecalis (S.faecalis), Pseudomonas aeruginosa (P.aeruginosa), intestinal bacteria (E.coli) and enterobacter cloacae (E.cloacae) all have restraining effect in various degree.
35 kind 3 in table 3, the bacteriostatic activity test result of 5-diiodo-salicylic aldehyde Schiff alkali cpd
Figure A20081012356800101
Figure A20081012356800111
The fusing point of compound 1～35, mass spectrum, proton magneto-optic spectrum, infrared spectra and ultimate analysis data
1.2-Butyliminomethyl-4，6-diiodo-phenol
Yellow?crystals，yield?90％，mp：84-86℃， 1H?NMR[300MHz，CDCl 3]δppm：15.074(s，1H)；8.052(s，1H)；8.038(d，J＝2.1Hz，1H)；7.466(d，J＝2.1Hz，1H)；3.619(d，J＝12.9Hz，2H)；1.692(d，J＝14.7Hz，2H)；1.427(d，J＝30.0Hz，2H)；0.949(d，J＝14.7Hz，3H).Selected?IR?data(cm -1，KBr)：2953.5(s)；1645.1(s)；1463.9(s)；1214.6(s)；863.1(s)；654.0(s)；544.2(m).ESI-MS：429.9(C 11H 14I 2NO +，[M+H] +).Anal.Calcd?for?C 11H 13I 2NO：C，30.79％；H，3.05％；N，3.26％；Found：C，30.84％；H，3.08％；N，3.28％.
2.2-(tert-Butylimino-methyl)-4，6-diiodo-phenol
Yellow?crystals，yield?92％，mp：115-117℃， 1H?NMR[300MHz，CDCl 3]δppm：15.714(s，1H)；8.043(d，J＝2.1Hz，1H)；8.014(s，1H)；7.469(d，J＝2.1Hz，1H)；1.404(s，9H).Selected?IR?data(cm -1，KBr)：2967.7(s)；1631.8(s)；1474.8(s)；1214.9(s)；863.2(s)；657.4(s)；539.8(m).ESI-MS：429.9(C 11H 14I 2NO +，[M+H] +).Anal.Calcd?for?C 11H 13I 2NO：C，30.79％；H，3.05％；N，3.26％；Found：C，30.82％；H，3.07％；N，3.29％.
3.2-(Benzylimino-methyl)-4，6-diiodo-phenol
Brown?dope，yield?87％， 1H?NMR[300MHz，CDCl 3]δppm：15.714(s，1H)；8.220(s，1H)；8.075(d，J＝2.1Hz，1H)；7.551(d，J＝2.1Hz，1H)；7.390(d，J＝7.5Hz，2H)；7.352(d，J＝6.3Hz，2H)；7.310(d，J＝12.3Hz，1H)；4.851(s，2H).Selected?IR?data(cm -1，KBr)：1625.0(s)；1435.6(s)；1277.5(m)；1158.0(s)；1028.8(m)；865.8(s)；759.1(s)；702.7(s)；657.8(s)；598.7(m).ESI-MS：463.9(C 14H 12I 2NO +，[M+H] +).Anal.Calcd?for?C 14H 11I 2NO：C，36.31％；H，2.39％；N，3.02％；Found：C，36.28％；H，2.43％；N，3.05％.
4.2-(4-Fluoro-benzylimino-methyl)-4，6-diiodo-phenol
Yellow?crystals，yield?85％，mp：107-108℃， 1H?NMR[300MHz，CDCl 3]δppm：14.674(s，1H)；8.194(s，1H)；8.050(d，J＝2.1Hz，1H)；7.525(d，J＝2.1Hz，1H)；7.247(d，J＝8.7Hz，2H)；7.064(d，J＝8.7Hz，2H)；4.874(s，2H).Selected?IR?data(cm -1，KBr)：1624.3(s)；1509.0(s)；1438.8(s)；1271.4(m)；1226.3(s)；1158.2(s)；1038.4(m)；867.5(s)；821.1(s)；657.7(s)；566.7(m).ESI-MS：481.9(C 14H 11FI 2NO +，[M+H] +).Anal.Calcd?for?C 14H 10FI 2NO：C，34.96％；H，2.10％；N，2.91％；Found：C，34.98％；H，2.13％；N，3.02％.
5.2-[(4-Fluoro-phenylimino)-methyl]-4，6-diiodo-phenol
Nacarat?crystals，yield?90％，mp：145-147℃， 1H?NMR[300MHz，CDCl 3]δppm：14.467(s，1H)；8.426(s，1H)；8.113(d，J＝2.1Hz，1H)；7.764(d，J＝2.1Hz，1H)；7.274(d，J＝8.1Hz，2H)；7.152(d，J＝8.1Hz，2H).Selected?IR?data(cm -1，KBr)：1614.6(s)；1501.8(s)；1435.4(s)；1280.0(m)；1226.3(s)；1150.0(s)；863.9(s)；835.5(s)；790.7(s)；663.3(m)；532.9(m).ESI-MS：467.9(C 13H 9FI 2NO +，[M+H] +).Anal.Calcd?for?C 13H 8FI 2NO：C，33.43％；H，1.73％；N，3.00％；Found：C，34.48％；H，1.76％；N，3.03％.
6.(E)-2，4-diiodo-6-((propylimino)methyl)phenol
Kelly?crystals，yield?81％，mp：72-73℃， 1H?NMR[300MHz，CDCl 3]δppm：15.065(s，1H)；8.057(s，1H)，8.041(d，J＝2.1Hz，1H)；7.471(d，J＝2.1Hz，1H)；3.586(d，J＝13.5Hz，2H)；1.753(d，J＝28.8Hz，2H)；0.990(d，J＝13.5Hz，3H).Selected?IR?data(cm -1，KBr)：2957.2(s)；1631.1(s)；1465.7(s)；1162.6(s)；866.4(s)；655.9(s)；548.8(m).ESI-MS：415.9(C 10H 12I 2NO +，[M+H] +).Anal.Calcd?for?C 10H 11I 2NO：C，28.94％；H，2.67％；N，3.38％；Found：C，28.88％；H，2.62％；N，3.33％.
7.2，4-Diiodo-6-phenyliminomethyl-phenol
Saffron?crystals，yield?91％，mp：145-147℃， 1H?NMR[300MHz，CDCl 3]δppm：14.688(s，1H)；8.456(s，1H)；8.107(d，J＝2.1Hz，1H)；7.671(d，J＝2.1Hz，1H)；7.433(d，J＝7.8Hz，2H)；7.303(d，J＝1.8Hz，1H)；7.267(d，J＝7.8Hz，2H).Selected?IR?data(cm -1，KBr)：1611.2(s)；1581.0(s)；1439.1(s)；1279.4(m)；1198.0(s)；1149.9(s)；845.2(s)；764.1(s)；738.0(s)；658.4(m)；534.8(m).ESI-MS：449.9(C 13H 10I 2NO +，[M+H] +).Anal.Calcd?for?C 13H 9I 2NO：C，34.77％；H，2.02％；N，3.12％；Found：C，34.70％；H，1.96％；N，3.08％.
8.2-[(2-Chloro-phenylimino-methyl)-4，6-diiodo-phenol
Nacarat?crystal，yield?90％，mp：150-152℃， 1H?NMR[300MHz，CDCl 3]δppm：14.231(s，1H)；8.460(s，1H)；8.134(d，J＝2.1Hz，1H)；7.690(d，J＝2.1Hz，1H)；7.505(d，J＝7.8Hz，1H)；7.573(d，J＝19.8Hz，2H)；7.232(d，J＝7.8Hz，1H).Selected?IR?data(cm -1，KBr)：1608.1(s)；1576.4(m)；1433.1(s)；1272.6(m)；1152.6(s)；1048.6(m)；859.8(s)；756.5(s)；738.6(s)；654.0(m)；537.5(m).ESI-MS：483.8(C 13H 9ClI 2NO +，[M+H] +).Anal.Calcd?forC 13H 8ClI 2NO：C，32.30％；H，1.67％；N，2.90％；Found：C，32.24％；H，1.63％；N，2.85％.
9.2-[(2-Bromo-phenylimino-methyl)-4，6-diiodo-phenol
Bisque?crystal，yield?90％，mp：175-178℃， 1H?NMR[300MHz，CDCl 3]δppm：14.325(s，1H)；8.433(s，1H)；8.118(d，J＝2.1Hz，1H)；7.689(d，J＝2.1Hz，1H)；7.565(d，J＝9.0Hz，2H)；7.161(d，J＝9.0Hz，2H).Selected?IR?data(cm -1，KBr)：1607.5(s)；1572.3(m)；1430.4(s)；1197.2(m)；1154.7(s)；1066.3(m)；828.6(s)；800.6(s)；740.0(s)；658.8(m)；527.9(m).ESI-MS：527.8(C 13H 9BrI 2NO +，[M+H] +).Anal.Calcd?for?C 13H 8BrI 2NO：C，29.58％；H，1.53％；N，2.65％；Found：C，29.53％；H，1.50％；N，2.61％.
10.2，4-Diiodo-6-[(4-iodo-phenylimino)-methyl]-phenol
Brown?crystal，yield?85％，mp：180-183℃， 1H?NMR[CDCl 3]δppm：14.352(s，1H)；8.431(s，1H)；8.117(d，J＝2.1Hz，1H)；7.764(d，J＝8.7Hz，2H)；7.671(d，J＝2.1Hz，1H)；7.031(d，J＝8.7Hz，2H).Selected?IR?data(cm -1，KBr)：1606.0(s)；1478.0(m)；1428.8(s)；1197.1(m)；1155.3(s)；1053.2(m)；827.8(s)；800.9(s)；739.7(s)；691.9(m)；658.4(m)；528.4(m).ESI-MS：575.8(C 13H 9I 3NO +，[M+H] +).Anal.Calcd?for?C 13H 8I 3NO：C，27.16％；H，1.40％；N，2.44％；Found：C，27.23％；H，1.32％；N，2.51％.
11.2-[(4-Chloro-phenylimino)-methyl]-4，6-diiodo-phenol
Saffron?crystal，yield?82％，mp：143-145℃， 1H?NMR[DMSO-D6]δppm：14.408(s，1H)；8.931(s，1H)；8.180(d，J＝2.1Hz，1H)；8.018(d，J＝2.1Hz，1H)；7.571(d，J＝2.7Hz，2H)；7.556(d，J＝2.7Hz，2H).Selected?IR?data(cm -1，KBr)：1611.3(s)；1576.0(m)；1485.9(s)；1435.9(s)；1195.6(m)；1151.8(s)；1087.8(m)；1007.9(m)；829.5(s)；740.3(m)；713.5(m)；659.0(m)；531.4(m).ESI-MS：483.8(C 13H 9ClI 2NO +，[M+H] +).Anal.Calcd?for?C 13H 8ClI 2NO：C，32.30％；H，1.67％；N，2.90％；Found：C，32.23％；H，1.62％；N，2.81％.
12.2-[(4-Hydroxy-phenylimino)-methyl]-4，6-diiodo-phenol
Nacarat?crystal，yield?92％，mp：227-230℃， 1H?NMR[DMSO-D6]δppm：15.120(s，1H)；9.814(s，1H)；8.862(s，1H)；8.105(d，J＝2.1Hz，1H)；7.946(d，J＝2.1Hz，1H)；7.410(d，J＝1.8Hz，2H)；6.893(d，J＝1.8Hz，2H).Selected?IR?data(cm -1，KBr)：3046.2(m)；1619.7(s)；1595.7(s)；1462.1(s)；1277.2(s)；1137.2(m)；1016.3(m)；873.8(m)；833.1(m)；737.6(m)；658.0(m)；524.0(m).ESI-MS：465.9(C 13H 10I 2NO +，[M+H] +).Anal.Calcd?for?C 13H 9I 2NO：C，33.58％；H，1.95％；N，3.01％；Found：C，33.53％；H，1.92％；N，2.94％.
13.2-[(2-Fluoro-phenylimino)-methyl]-4，6-diiodo-phenol
Nacarat?crystal，yield?95％，mp：121-122℃， 1H?NMR[DMSO-D6]δppm：14.579(s，1H)；9.006(s，1H)；8.175(d，J＝2.1Hz，1H)；8.023(d，J＝2.1Hz，1H)；7.643(d，J＝15.6Hz，1H)；7.412(d，J＝4.5Hz，1H)；7.369(d，J＝4.5Hz，1H)；7.356(d，J＝12.6Hz，1H).Selected?IRdata(cm -1，KBr)：1614.3(s)；1577.2(m)；1492.0(s)；1437.8(s)；1190.7(m)；1150.0(s)；1106.1(m)；862.9(s)；795.8(s)；758.5(s)；742.7(s)；657.1(m)；522.7(m).ESI-MS：467.9(C 13H 9FI 2NO +，[M+H] +).Anal.Calcd?for?C 13H 8FI 2NO：C，33.43％；H，1.73％；N，3.00％；Found：C，33.36％；H，1.66％；N，2.93％.
14.2-[(2，4-Dichloro-phenylimino)-methyl]-4，6-diiodo-phenol
Bisque?crystal，yield?91％，mp：173-174℃， 1H?NMR[DMSO-D6]δppm：14.298(s，1H)；8.980(s，1H)；8.198(d，J＝2.1Hz，1H)；8.022(d，J＝2.1Hz，1H)；7.814(d，J＝2.4Hz，1H)；7.685(d，J＝8.4Hz，1H)；7.596(d，J＝8.4Hz，1H).Selected?IR?data(cm -1，KBr)：1606.6(s)；1471.1(m)；1428.1(s)；1200.0(m)；1150.9(s)；1103.5(s)；865.4(m)；853.8(m)；805.8(m)；772.6(m)；742.5(s)；659.2(m)；544.3(m).ESI-MS：517.8(C 13H 8Cl 2I 2NO +，[M+H] +).Anal.Calcd?for?C 13H 7Cl 2I 2NO：C，30.15％；H，1.36％；N，2.70％；Found：C，30.09％；H，1.32％；N，2.65％.
15.2-[(2，4-Difluoro-phenylimino)-methyl]-4，6-diiodo-phenol
Bisque?crystal，yield?86％，mp：154-155℃， 1H?NMR[DMSO-D6]δppm：14.383(s，1H)；8.982(s，1H)；8.175(d，J＝2.1Hz，1H)；8.007(d，J＝2.1Hz，1H)；7.715(d，J＝6.0Hz，1H)；7.455(d，J＝11.1Hz，1H)；7.256(d，J＝13.2Hz，1H).Selected?IR?data(cm -1，KBr)：1615.4(s)；1495.7(s)；1433.7(s)；1266.4(s)；1190.1(m)；1150.4(s)；1100.8(m)；965.5(m)；852.7(m)；805.3(s)；741.5(s)；663.1(m)；478.9(m).ESI-MS：485.9(C 13H 8F 2I 2NO +，[M+H] +).Anal.Calcd?for?C 13H 7F 2I 2NO：C，32.19％；H，1.45％；N，2.89％；Found：C，32.15％；H，1.42％；N，2.85％.
16.2-[(2，4-Dibromo-phenylimino)-methyl]-4，6-diiodo-phenol
Bisque?crystal，yield?93％，mp：208-210℃， 1H?NMR[DMSO-D6]δppm：14.152(s，1H)；8.941(s，1H)；8.200(d，J＝2.4Hz，1H)；8.047(d，J＝2.4Hz，1H)；8.027(d，J＝2.1Hz，1H)；7.600(d，J＝8.7Hz，1H)；7.596(d，J＝8.7Hz，1H).Selected?IR?data(cm -1，KBr)：1604.5(s)；1465.4(m)；1426.7(s)；1345.2(s)；1197.0(m)；1149.9(s)；1082.7(m)；1035.1(m)；865.7(s)；854.2(s)；804.3(s)；741.8(m)；653.2(m)；544.3(m).ESI-MS：605.7(C 13H 8Br 2I 2NO +，[M+H] +).Anal.Calcd?for?C 13H 7Br 2I 2NO：C，25.73％；H，1.16％；N，2.31％；Found：C，25.70％；H，1.14％；N，2.36％.
17.2-[(3，5-Dichloro-phenylimino)-methyl]-4，6-diiodo-phenol
Nacarat?crystal，yield?92％，mp：253-255℃， 1H?NMR[DMSO-D6]δppm：13.775(s，1H)；8.933(s，1H)；8.190(d，J＝2.1Hz，1H)；7.991(d，J＝2.1Hz，1H)；7.622(d，J＝1.8Hz，2H)；7.580(d，J＝1.8Hz，1H).Selected?IR?data(cm -1，KBr)：1608.2(s)；1567.3(s)；1426.2(s)；1341.8(m)；1277.2(m)；1158.0(s)；1106.9(m)；1097.3(m)；947.2(s)；873.4(s)；843.4(s)；804.6(s)；740.6(m)；661.4(s)；546.0(m)；532.5(m).ESI-MS：517.8(C 13H 8Cl 2I 2NO +，[M+H] +).Anal.Calcd?for?C 13H 7Cl 2I 2NO：C，30.15％；H，1.36％；N，2.70％；Found：C，30.12％；H，1.31％；N，2.64％.
18.2，4-Diiodo-6-(p-tolylimino-methyl)-phenol
Nacarat?crystal，yield?87％，mp：145-146℃， 1H?NMR[DMSO-D6]δppm：14.886(s，1H)；8.910(s，1H)；8.123(d，J＝2.1Hz，1H)；7.971(d，J＝2.1Hz，1H)；7.398(d，J＝8.7Hz，2H)；7.299(d，J＝8.7Hz，2H)；2.348(s，3H).Selected?IR?data(cm -1，KBr)：2911.8(m)；1616.3(s)；1586.1(m)；1507.8(s)；1436.8(s)；1354.9(m)；1199.2(m)；1154.2(s)；860.0(s)；828.8(m)；811.5(s)；740.7(m)；661.5(m)；652.1(m)；534.1(m).ESI-MS：463.9(C 14H 12I 2NO +，[M+H] +).Anal.Calcd?for?C 14H 11I 2NO：C，36.31％；H，2.39％；N，3.02％；Found：C，36.27％；H，2.36％；N，2.97％.
19.2，4-Diiodo-6-[(2-morpholin-4-yl-ethylimino)-methyl]-phenol
Yellow?crystal，yield?82％，mp：86-88℃， 1H?NMR[CDCl 3]δppm：14.810(s，1H)；8.119(d，J＝2.1Hz，1H)；8.050(s，1H)；7.496(d，J＝2.1Hz，1H)；3.722(s，6H)；2.709(s，2H)；2.530(s，4H).Selected?IR?data(cm -1，KBr)：3423.2(m)；2951.1(m)；2920.4(m)；2816.7(m)；1640.6(s)；1580.4(m)；1445.8(s)；1354.8(m)；1296.1(m)；1278.6(m)；1265.7(m)；1218.3(m)；1113.9(s)；1008.3(m)；866.2(s)；848.1(m)；763.5(s)；654.2(m)；539.8(m).ESI-MS：486.9(C 13H 17I 2N 2O 2 +，[M+H] +).Anal.Calcd?for?C 13H 16I 2N 2O 2：C，32.12％；H，3.32％；N，5.76％；Found：C，32.06％；H，3.28％；N，5.81％.
20.2，4-Diiodo-6-[(3-morpholin-4-yl-prorylimino)-methyl]-phenol
Yellow?dope，yield?80％， 1H?NMR[CDCl 3]δppm：14.935(s，1H)；8.102(d，J＝2.1Hz，1H)；8.045(s，1H)；7.474(d，J＝2.1Hz，1H)；3.715(d，J＝12.6Hz，6H)；2.429(d，J＝12.6Hz，6H)；1.898(d，J＝27.3Hz，2H).Selected?IR?data(cm -1，KBr)：3445.6(m)；2923.1(s)；2852.0(s)；2804.8(s)；1629.4(s)；1583.4(m)；1436.9(s)；1360.4(m)；1343.5(m)；1275.4(s)；1215.9(m)；1114.7(s)；1064.7(m)；1009.4(m)；856.3(s)；794.1(m)；742.6(m)；657.6(s)；545.6(m).ESI-MS：501.0(C 14H 19I 2N 2O 2 +，[M+H] +).Anal.Calcd?for?C 14H 18I 2N 2O 2：C，33.62％；H，3.63％；N，5.60％；Found：C，33.56％；H，3.58％；N，5.63％.
21.2，4-Diiodo-6-(pyridine-2-yliminomethyl)-phenol
Nacarat?crystal，yield?96％，mp：203-205℃， 1H?NMR[DMSO-D6]δppm：14.761(s，1H)；9.411(s，1H)；8.578(d，J＝2.1Hz，1H)；8.185(d，J＝2.1Hz，1H)；8.154(d，J＝2.1Hz，1H)；7.972(d，J＝7.5Hz，1H)；7.432(d，J＝4.8Hz，1H)；7.048(d，J＝4.8Hz，1H).Selected?IRdata(cm -1，KBr)：3055.0(m)；2989.1(m)；1606.5(s)；1587.5(s)；1560.8(s)；1546.2(m)；1460.6(s)；1428.7(s)；1203.5(m)；1158.5(s)；933.0(m)；865.9(s)；838.3(m)；786.3(s)；741.8(s)；660.9(m)；527.8(m).ESI-MS：466.9(C 13H 13I 2N 2O +，[M+H] +).Anal.Calcd?for?C 13H 12I 2N 2O：C，33.50％；H，2.60％；N，6.01％；Found：C，33.54％；H，2.56％；N，5.93％.
22.2，4-Diiodo-6-(isopropylimino-methyl)-phenol
Nacarat?crystal，yield?90％，mp：75-78℃， 1H?NMR[CDCl 3]δppm：14.893(s，1H)；8.458(s，1H)；8.090(d＝2.1，1H)；7.662(d＝2.1，1H)；7.302(d＝8.4，2H)；7.253(d＝8.4，2H)；2.959(d＝27.61H)；1.294(s，3H)；1.270(s，3H).Selected?IR?data(cm -1，KBr)：3348.6(m)；3216.8(m)；3010.3(m)；2956.2(m)；1612.3(s)；1578.5(m)；1510.4(m)；1432.5(s)；1206.1(m)；1174.7(s)；1070.3(m)；820.2(s)；798.5(s)；743.1(s)；530.2(m).ESI-MS：491.9(C 16H 16I 2NO +，[M+H] +).Anal.Calcd?for?C 16H 15I 2NO：C，39.13％；H，3.08％；N，2.85％；Found：C，39.24％；H，3.04％；N，2.91％.
23.2，4-Diiodo-6-[(pyridin-3-ylmethylimino)-methyl]-phenol
Yellow?dope，yield?85％， 1H?NMR[CDCl 3]δppm：14.376(s，1H)；8.582(s，2H)；8.292(s，1H)；8.068(d，J＝2.1Hz，1H)；7.650(d，J＝7.8Hz，1H)；7.563(d，J＝2.1Hz，1H)；7.317(d，J＝12.6Hz，1H)；4.847(s，2H).Selected?IR?data(cm -1，KBr)：3440.1(m)；3312.5(m)；3123.7(m)；1617.5(s)；1578.2(m)；1480.2(s)；1194.6(m)；1134.7(s)；1064.1(m)；822.9(s)；742.3(s)；667.6(m)；524.5(m).ESI-MS：465.9(C 13H 11I 2N 2O +，[M+H] +).Anal.Calcd?forC 13H 10I 2N 2O：C，33.65％；H，2.17％；N，6.04％；Found：C，33.55％；H，2.12％；N，6.11％.
24.2-(Cyclohexylmethylimino-methyl)-4，6-diiodo-phenol
Yellow?crystal，yield?87％，mp：62-65℃， 1H?NMR[CDCl 3]δppm：11.751(s，1H)；9.712(s，1H)；8.260(d，J＝2.1Hz，1H)；7.847(d，J＝2.1Hz，1H)；3.494(s，2H)；1.756(s，2H)；1.550(s，8H)；1.252(s，2H).Selected?IR?data(cm -1，KBr)：3310.4(m)；2920.3(s)；2849.0(s)；1635.6(s)；1578.4(m)；1444.9(s)；1275.3(m)；1141.9(m)；1024.3(m)；891.4(m)；867.3(s)；743.3(m)；654.8(s)；544.6(m).ESI-MS：469.9(C 14H 18I 2NO +，[M+H] +).Anal.Calcd?forC 14H 17I 2NO：C，35.85％；H，3.65％；N，2.99％；Found：C，35.76％；H，3.61％；N，3.12％.
25.2，4-Diiodo-6-[2，2，6，6-tetramethyl-piperidin-4-ylimino]-methyl]-phenol
Yellow?crystal，yield?83％，mp：80-83℃， 1H?NMR[CDCl 3]δppm：15.079(s，1H)；9.738(s，1H)；8.070(d，J＝2.1Hz，1H)；7.520(d，J＝2.1Hz，1H)；3.845(d，J＝7.8Hz，2H)；3.519(s，4H)；3.413(s，1H)；1.309(s，6H)；1.236(s，6H).Selected?IR?data(cm -1，KBr)：3375.8(m)；3055.0(m)；2954.0(m)；2924.4(m)；1626.9(s)；1583.9(m)；1560.1(m)；1438.0(s)；1370.2(m)；1214.8(m)；1153.5(m)；1089.8(m)；865.5(m)；739.6(s)；696.5(m)；657.8(m)；553.5(m).ESI-MS：513.0(C 16H 23I 2N 2O +，[M+H] +).Anal.Calcd?for?C 16H 22I 2N 2O：C，37.52％；H，4.33％；N，5.47％；Found：C，37.44％；H，4.31％；N，5.52％.
26.2-[(1-Bunzyl-piperidin-4-ylimino)-methyl]-4，6-diiodo-phenol
Yellow?crystal，yield?80％，mp：68-72℃， 1H?NMR[CDCl 3]δppm：14.674(s，1H)；8.125(s，1H)；8.041(d，J＝2.1Hz，1H)；7.479(d，J＝2.1Hz，1H)；7.326(d，J＝8.1Hz，4H)；7.262(s，1H)；3.533(d，J＝6.6Hz，2H)；2.857(d，J＝12Hz，2H)；2.062(d，J＝21Hz，2H)；1.839(d，J＝21Hz，4H)；1.461(d，J＝21Hz，2H).Selected?IR?data(cm -1，KBr)：3060.5(m)；3023.9(m)；2938.8(s)；2919.4(s)；2804.5(s)；2761.8(s)；1624.6(s)；1583.9(m)；1492.6(m)；1439.6(s)；1364.2(s)；1342.1(s)；1283.0(m)；1218.6(m)；1154.3(s)；1142.4(s)；1062.8(m)；868.1(s)；743.5(s)；736.2(s)；697.9(s)；657.6(s)；549.2(m).ESI-MS：547.0(C 19H 21I 2N 2O +，[M+H] +).Anal.Calcd?for?C 19H 20I 2N 2O：C，41.78％；H，3.69％；N，5.13％；Found：C，40.84％；H，3.71％；N，5.20％.
27.2，4-Diiodo-6-[(2-piperazin-1-yl-ethylimino)-methyl]-phenol
Red?brown?dope，yield?82％， 1H?NMR[CDCl 3]δppm：15.075(s，1H)；8.094(s，1H)；8.044(d，J＝2.1Hz，1H)；7.483(d，J＝2.1Hz，1H)；3.726(d，J＝10.8Hz，2H)；2.905(s，6H)；2.672(d，J＝10.8Hz，4H)；2.504(s，1H).Selected?IR?data(cm -1，KBr)：2946.5(m)；2822.3(m)；1625.5(s)；1582.8(m)；1450.1(s)；1355.8(m)；1330.6(m)；1320.2(m)；1187.2(m)；1144.9(s)；1056.7(m)；818.5(s)；743.2(s)；661.6(m)；543.5(m).ESI-MS：486.0(C 13H 18I 2N 3O +，[M+H] +).Anal.Calcd?for?C 13H 17I 2N 3O：C，32.19％；H，3.53％；N，8.66％；Found：C，32.02％；H，3.47％；N，8.73％.
28.6，6′-(1E，1′E)-(cyclohexane-1，2-diylbis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(2，4-diiodophenol)
Brilliant?yellow?crystal，yield?92％，mp：124-127℃， 1H?NMR[CDCl 3]δppm：14.566(s，2H)；8.124(d，J＝2.1Hz，1H)；8.040(s，2H)；8.004(d，J＝2.1Hz，1H)；7.514(d，J＝2.1Hz，1H)；7.423(d，J＝2.1Hz，1H)；3.352(d，J＝9.3Hz，2H)；1.920(d，J＝10.2Hz，2H)；1.823(d，J＝10.2Hz，2H)；1.671(d，J＝10.2Hz，2H)；1.470(d，J＝10.2Hz，2H).Selected?IRdata(cm -1，KBr)：3055.1(m)；2927.9(m)；2854.0(m)；1624.2(s)；1584.3(m)；1435.6(s)；1219.9(m)；1155.8(s)；864.4(s)；658.4(m)；551.6(m).ESI-MS：825.8(C 20H 19I 4N 2O 2 +，[M+H] +).Anal.Calcd?for?C 20H 18I 4N 2O 2：C，29.08％；H，2.20％；N，3.39％；Found：C，30.03％；H，2.17％；N，3.32％.
29.6，6′-(1E，1′E)-(3，3′-azanediylbis(propane-3，1-diyl)bis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(2，4-diiodophenol)
Yellow?crystal，yield?90％，mp：55-58℃， 1H?NMR[CDCl 3]δppm：14.890(s，2H)；8.079(s，2H)；8.031(d，J＝2.1Hz，2H)；7.453(d，J＝2.1Hz，2H)；3.680(d，J＝13.5Hz，4H)；2.470(s，4H)；2.237(s，1H)；1.887(d，J＝13.5Hz，4H).Selected?IR?data(cm -1，KBr)：3420.7(m)；3053.9(m)；2940.5(m)；2844.2(m)；2796.5(m)；1631.2(s)；1580.7(m)；1435.7(s)；1214.3(m)；1154.6(s)；864.2(s)；655.7(m)；540.8(m).ESI-MS：843.8(C 20H 22I 4N 3O 2 +，[M+H] +).Anal.Calcd?for?C 20H 21I 4N 3O 2：C，28.49％；H，2.51％；N，4.98％；Found：C，28.31％；H，2.45％；N，5.02％.
30.6，6′-(1E，1′E)-(cyclohexane-1，3-diylbis(methylene))bis(azan-1-yl-1-ylidene)bis(methan-1-yl-l-ylidene)bis(2，4-diiodophenol)
Brilliant?yellow?crystal，yield?86％，mp：105-108℃， 1H?NMR[CDCl 3]δppm：15.001(s，2H)；8.065(s，2H)；8.049(d，J＝2.1Hz，2H)；7.496(d，J＝2.1Hz，2H)；3.559(d，J＝6.9Hz，2H)；3.499(d，J＝6.9Hz，2H)；1.832(s，4H)；1.548(s，4H)；1.482(d，J＝21.3Hz，2H).Selected?IR?data(cm -1，KBr)：3054.1(m)；2916.6(s)；2843.3(m)；1630.0(s)；1581.4(m)；1436.6(s)；1219.9(m)；1156.2(s)；865.8(s)；657.2(m)；549.2(m).ESI-MS：854.8(C 22H 23I 4N 2O 2 +，[M+H] +).Anal.Calcd?for?C 22H 22I 4N 2O 2：C，30.94％；H，2.60％；N，3.28％；Found：C，30.83％；H，2.51％；N，3.22％.
31.2-((E)-2-(((E)-2-hydroxy-3，5-diiodobenzylideneamino)methyl)benzylideneamino)-4，6-diiodophenol
Nacarat?crystal，yield?80％，mp：237-240℃， 1H?NMR[CDCl 3]δppm：14.131(s，1H)；11.745(s，1H)；9.708(s，1H)；8.339(s，1H)；8.256(d，J＝2.1Hz，1H)；8.125(d，J＝2.1Hz，1H)；7.842(d，J＝2.1Hz，1H)；7.455(d，J＝2.1Hz，1H)；4.945(s，2H)；1.560(s，4H).Selected?IR?data(cm -1，KBr)：3055.8(m)；1625.6(s)；1591.9(m)；1437.9(s)；1272.9(m)；1206.2(m)；1154.2(s)；868.4(s)；765.2(s)；740.8(s)；658.6(m)；544.6(m).ESI-MS：834.7(C 21H 15I 4N 2O 2 +，[M+H] +).Anal.Calcd?for?C 21H 14I 4N 2O 2：C，30.24％；H，1.69％；N，3.36％；Found：C，30.18％；H，1.73％；N，3.29％.
32.2-((5-(((E)-2-hydroxy-3，5-diiodobenzylideneamino)methyl)-1，3，3-trimethylcyclohexyl)methyleneamino)-4，6-diiodophenol
Brilliant?yellow?crystal，yield?85％，mp：137-140℃， 1H?NMR[CDCl 3]δppm：15.053(s，1H)；9.804(s，1H)；8.192(s，1H)；8.105(s，1H)；8.083(d，J＝2.1Hz，1H)；8.062(d，J＝2.1Hz，1H)；7.557(d，J＝2.1Hz，1H)；7.521(d，J＝2.1Hz，1H)；3.397(d，J＝11.7Hz，2H)；1.664(s，4H)；1.437(d，J＝12.3Hz，2H)；1.363(s，1H)；1.238(s，3H)；1.143(s，3H)；1.031(s，3H).Selected?IR?data(cm -1，KBr)：3055.1(m)；2949.5(m)；2912.0(m)；2841.8(m)；1627.1(s)；1582.5(m)；1436.1(s)；1199.0(m)；1153.6(s)；865.6(s)；740.3(s)；657.3(m)；549.0(m).ESI-MS：882.8(C 24H 27I 4N 2O 2 +，[M+H] +).Anal.Calcd?for?C 24H 26I 4N 2O 2：C，32.68％；H，2.97％；N，3.18％；Found：C，32.75％；H，2.93％；N，3.24％.
33.6，6′-(1E，1′E)-(2，2′-anaediybis(ethane-2，1-diyl)bis(azan-1-yl-1-ylidene))bis(methan-1-ylidene)bis(2，4-diiodophenol)
Yellow?crystal，yield?93％，mp：108-112℃， 1H?NMR[CDCl 3]δppm：14.620(s，2H)；8.072(s，2H)；7.996(d，J＝2.1Hz，2H)；7.937(d，J＝2.1Hz，2H)；3.720(s，4H)；3.042(s，4H)；1.563(s，1H).Selected?IR?data(cm -1，KBr)：3295.1(m)；3052.8(m)；2888.8(m)；2829.8(m)；1633.5(s)；1580.9(m)；1435.9(s)；1217.6(m)；1156.7(s)；863.6(s)；738.5(m)；656.9(s)；540.6(m).ESI-MS：815.8(C 18H 18I 4N 3O 2 +，[M+H] +).Anal.Calcd?for?C 18H 17I 4N 3O 2：C，26.53％；H，2.10％；N，5.16％；Found：C，26.65％；H，2.03％；N，5.20％.
34.6，6′-(1E，1′E)-(propane-1，3-diylbis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(2，4-diiodophenol)
Yellow?crystal，yield?90％，mp：108-110℃， 1H?NMR[DMSO-D6]δppm：14.610(s，2H)；9.899(s，2H)；8.072(d，J＝2.4Hz，2H)；7.671(d，J＝2.4Hz，2H)；3.707(d，J＝12.6Hz，4H)；2.090(d，J＝13.5Hz，2H).Selected?IR?data(cm -1，KBr)：3051.6(m)；2948.4(m)；2876.9(m)；2830.4(m)；1623.9(s)；1585.0(m)；1434.1(s)；1205.4(m)；1157.6(s)；1062.1(m)；873.7(s)；739.1(m)；658.1(s)；549.0(m).ESI-MS：786.7(C 17H 15I 4N 2O 2 +，[M+H] +).Anal.Calcd?forC 17H 14I 4N 2O 2：C，25.98％；H，1.80％；N，3.56％；Found：C，26.05％；H，1.72％；N，3.60％.
35.6，6′-(1E，1′E)-(propane-1，2-diylbis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(2，4-diiodophenol)
Yellow?crystal，yield?92％，mp：166-168℃， 1H?NMR[DMSO-D6]δppm：14.634(s，1H)；14.550(s，1H)；8.500(s，1H)；8.445(s，1H)；8.041(d，J＝2.1Hz，1H)；8.028(d，J＝2.1Hz，1H)；7.743(d，J＝2.1Hz，1H)；7.712(d，J＝2.1Hz，1H)；3.936(d，J＝3.0Hz，2H)；3.887(d，J＝6.9Hz，1H)；1.346(d，J＝6.0Hz，3H).Selected?IR?data(cm -1，KBr)：3052.8(m)；2964.2(m)；2925.3(m)；2880.8(m)；1627.2(s)；1581.1(m)；1436.0(s)；1219.5(m)；1153.1(s)；1034.7(m)；867.4(s)；739.7(s)；656.9(m)；551.7(m).ESI-MS：786.7(C 17H 15I 4N 2O 2 +，[M+H] +).Anal.Calcd?for?C 17H 14I 4N 2O 2：C，25.98％；H，1.80％；N，3.56％；Found：C，26.08％；H，1.86％；N，3.52％.

Claims (3)

1. a series of 3,5-diiodo-salicylic aldehyde Schiff alkali cpd, it has following general structure:
Figure A2008101235680002C1
Wherein:
R 1For:
Figure A2008101235680002C2
R 2For:
Figure A2008101235680002C4
Figure A2008101235680002C5
One kind to prepare claim 1 described 3, the method for 5-diiodo-salicylic aldehyde Schiff alkali cpd is characterized in that: with 3,5-diiodo-salicylic aldehyde with have the described R of claim 1 1Or R 2The organic amine of group is in methyl alcohol or ethanolic soln, and reaction is 10-30 minute under the room temperature, obtains 3,5-diiodo-salicylic aldehyde Schiff alkali cpd.
3. claim 1 is described 3, the application of 5-diiodo-salicylic aldehyde Schiff alkali cpd in the preparation antibacterials.
CNA2008101235687A 2008-07-08 2008-07-08 3,5-diiodosalicylaldehyde Schiff alkali, preparation and use thereof Pending CN101302172A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110194944A (en) * 2019-06-20 2019-09-03 佛山南宝高盛高新材料有限公司 A kind of structural type antibacterial moisture-curable polyurethane hot melt adhesive and preparation method thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3652770A (en) * 1966-10-28 1972-03-28 Ciba Ltd Combatting phytopathogenic fungi on plants with sub-phytotoxic fungicidally effective amounts of herbicidal oximes of 3 5-dihalosalicylaldehyde

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3652770A (en) * 1966-10-28 1972-03-28 Ciba Ltd Combatting phytopathogenic fungi on plants with sub-phytotoxic fungicidally effective amounts of herbicidal oximes of 3 5-dihalosalicylaldehyde

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
ACS: "RN143159-49-3", 《STN-REGISTRY》 *
ACS: "RN20099-25-6", 《STN-REGISTRY》 *
ACS: "RN278609-89-5", 《STN-REGISTRY》 *
ACS: "RN310458-76-5", 《STN-REGISTRY》 *
ACS: "RN383371-32-2", 《STN-REGISTRY》 *
ACS: "RN415687-57-9", 《STN-REGISTRY》 *
ACS: "RN883030-17-9", 《STN-REGISTRY》 *
H. VOSS ET AL.: "Kinetic Studies on Four-Coordinate Chelate Complexes of Copper(II): Isotopic Ligand Exchange of Bis(salicylaldiminato) copper(II) in Toluene", 《INORGANIC CHEMISTRY》 *
YAYA LIU ET AL.: "Identification of halosalicylamide derivatives as a novel class of allosteric inhibitors of HCV NS5B polymerase", 《BIOORGANIC & MEDICINAL CHEMISTRY LETTERS》 *
张蕊等: "3,5-二碘水杨醛-芳胺Schiff碱的合成与生物活性测试", 《内蒙古大学学报(自然科学版)》 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110194944A (en) * 2019-06-20 2019-09-03 佛山南宝高盛高新材料有限公司 A kind of structural type antibacterial moisture-curable polyurethane hot melt adhesive and preparation method thereof

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