CN107501307A - 4 (double (4 carboxybenzyl) amino of N, N ') benzene sulfonic acid eutectic Zn complexes and preparation method thereof - Google Patents
4 (double (4 carboxybenzyl) amino of N, N ') benzene sulfonic acid eutectic Zn complexes and preparation method thereof Download PDFInfo
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- CN107501307A CN107501307A CN201710873197.3A CN201710873197A CN107501307A CN 107501307 A CN107501307 A CN 107501307A CN 201710873197 A CN201710873197 A CN 201710873197A CN 107501307 A CN107501307 A CN 107501307A
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- C07—ORGANIC CHEMISTRY
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- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/06—Zinc compounds
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Abstract
The present invention relates to a kind of 4 (double (4 carboxybenzyl) amino of N, N ') benzene sulfonic acid eutectic Zn complexes, expression formula is { [Zn (phen)2(H2O)2]·(HL)·(H2O)6, wherein, H3L is 4 (double (4 carboxybenzyl) amino of N, N ') benzene sulfonic acids, and phen is Phen；Described 4 (double (4 carboxybenzyl) amino of N, N ') benzene sulfonic acid eutectic Zn complex monomer molecule formula is：C46H49N5O15SZn, molecular weight are：1009.33g/mol.The complex can be used as anticarcinogen, and medicine stability is good, rate of dissolution, dissolution rate, and bioavilability etc. has very big change, and have the advantages that technique is simple, cost is cheap, chemical constituent is easily controllable, reproducible and yield is high.
Description
Technical field
The present invention relates to a kind of 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid eutectic Zn complex, belong to medicine
Eutectic technical field.
Background technology
In recent years, the research on aromatic carboxylic acids class organic ligand is more and more.Aromatic carboxylic acids class is removed as organic ligand
Carboxyl has outside complicated coordination mode in itself, also has conjugated pi body with special aromatic ring frame, this kind of organic ligand
System, the pi accumulation that easily forms π ... and C-H ... π interactions, and then have one to forming corresponding aromatic metal carboxyl complex
Fixed influence.Aromatic carboxylic acids is widely used in the synthesis of novel complex because it contains multiple dentates.Secondly, one
Aromatic carboxylic acids class organic compound containing polysubstituted group a bit, the substituent therein either hetero-aromatic ring such as nitrogenous, oxygen, sulphur, can
Complex is formed with metallic ion coordination, largely enriches the research of Coordinative Chemistry space structure.Rigid ligand is general
Refer to skeleton structure to fix, easily controlled in complexation process by people, it is not easy to a kind of part of geometric distortion occurs.Rigidity is matched somebody with somebody
Body matches somebody with somebody space width, links the configuration with tooth group and all compares fixation with bottom angle, is advantageous to people and predicts its structure.Institute
So that rigid ligand is one of current most widely used a kind of part.Conventional rigid ligand includes aromatic polycarboxylic acids part, contained
Nitrogen heterocycles part (Phen, 2,2- bipyridyls etc.), chemical research persons are using the autotelic structure of rigid ligand
Build out the complex with unique texture.
Eutectic has very big application value in pharmacy, and it can be introduced while medicine covalent structure is constantly changed
New component, the physicochemical property of medicine is substantially improved, can not only ensure the stability of medicine, and in other respects as molten
Point, rate of dissolution, dissolution rate, bioavilability etc. have very big change.
The content of the invention
It is an object of the invention to provide a kind of cooperation of 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid eutectic zinc
Thing, for use as anticarcinogen.
Another object of the present invention also resides in offer 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid eutectic zinc and matched somebody with somebody
The preparation method of compound.
Technical scheme
A kind of 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid eutectic Zn complex, expression formula is { [Zn (phen)2
(H2O)2]·(HL)·(H2O)6, wherein, H3L is 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid, and phen is adjacent Féraud
Quinoline；4- (N, N '-bis- (4- carboxybenzyls) amino) the benzene sulfonic acid eutectic Zn complex monomer molecule formula is：
C46H49N5O15SZn, molecular weight are：1009.33g/mol.
4- (N, N '-bis- (4- carboxybenzyls) amino) the benzene sulfonic acid eutectic Zn complex category monoclinic system, space group are
P21/ c, cell parameter：α=90.00 °, β=
92.832 (5) °, γ=90.00 °.
The preparation method of above-mentioned 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid eutectic Zn complex：Take 0.110-
0.220 part of 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid and 0.050-0.100 part Phens are dissolved in redistilled water
In, acetic acid is added dropwise, after stirring, adds 0.055-0.111 part zinc acetates, is placed in autoclave and is reacted, instead
Answer product to be placed in oven for drying, produce, above-mentioned number is parts by weight.
4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid eutectic Zn complex of the present invention can be used as anticarcinogen, medicine
Thing stability is good, rate of dissolution, dissolution rate, and bioavilability etc. has a very big change, and with technique is simple, cost
Cheap, the advantages that chemical constituent is easily controllable, reproducible and yield is high.
Brief description of the drawings
Fig. 1 is { [Zn (phen) made from embodiment 12(H2O)2]·(HL)·(H2O)6Monomer structure schematic diagram；
Fig. 2 is { [Zn (phen) made from embodiment 12(H2O)2]·(HL)·(H2O)6Three-dimensional packed structures signal
Figure.
Embodiment
The invention will be further described with reference to the accompanying drawings and examples.
Embodiment 1
By 0.110g H3L and 0.050g Phens are dissolved in 10mL redistilled waters, and 5 drop acetic acid are added dropwise, stir
Afterwards, add 0.055g and analyze pure zinc acetate, be placed in polytetrafluoroethylene (PTFE) autoclave and reacted, reaction product is placed in baking
180 DEG C of drying of case, produce 0.121g { [Zn (phen)2(H2O)2]·(HL)·(H2O)6, yield 48%.
Fig. 1 is the monomer structure schematic diagram of product, and Fig. 2 is the three-dimensional packed structures schematic diagram of product.
The structure of product is determined by single crystal diffractometer, crystal structural data is shown in Table 1, and bond distance's bond angle data are shown in Table 2.
{ [the Zn (phen) of table 12(H2O)2]·(HL)·(H2O)6Crystal structural data
aR1=Σ | | Fo|–|Fc||/Σ|Fo|.b wR2=[Σ w (| Fo 2|–|Fc 2|)2/Σw(|Fo 2|)2]1/2
{ [the Zn (phen) of table 22(H2O)2]·(HL)·(H2O)6Bond distance's bond angle data
Embodiment 2
By 0.220g H3L and 0.100g Phens are dissolved in 20mL redistilled waters, and 10 drop acetic acid are added dropwise, and stirring is equal
After even, add 0.111g and analyze pure zinc acetate, be placed in polytetrafluoroethylene (PTFE) autoclave and reacted, reaction product is placed in
180 DEG C of drying of baking oven, produce 0.252g { [Zn (phen)2(H2O)2]·(HL)·(H2O)6, yield 50%.
The structure of product is determined by single crystal diffractometer, crystal structural data is with table 1, and bond distance's bond angle data are the same as table 2.
Complex made from embodiment 2 is subjected to inhibition of cancer cell experiment, the results are shown in Table 3：
{ [the Zn (phen) of table 32(H2O)2]·(HL)·(H2O)6To the IC50 values of different cell lines
In table：MGC803 is gastric carcinoma cells, and HepG2 is human liver cancer cell, and NCI-H460 is human breast cancer cell, BEL-
7404 be Proliferation of Human Ovarian Cell, and HL-7702 is human normal hepatic cell strain.
Claims (3)
1. a kind of 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid eutectic Zn complex, it is characterised in that expression formula is
{[Zn(phen)2(H2O)2]·(HL)·(H2O)6, wherein, H3L is 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid,
Phen is Phen；4- (N, N '-bis- (4- carboxybenzyls) amino) the benzene sulfonic acid eutectic Zn complex monomer molecule formula is：
C46H49N5O15SZn, molecular weight are：1009.33g/mol.
2. 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid eutectic Zn complex as claimed in claim 1, its feature exist
In, 4- (N, N '-bis- (4- carboxybenzyls) amino) the benzene sulfonic acid eutectic Zn complex category monoclinic system, space group P21/ c,
Cell parameter：α=90.00 °, β=92.832
(5) °, γ=90.00 °.
The preparation side of the 4- of claim 1 or 2 3. (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acid eutectic Zn complex
Method, it is characterised in that take 0.110-0.220 parts 4- (N, N '-bis- (4- carboxybenzyls) amino) benzene sulfonic acids and 0.050-0.100 parts
Phen is dissolved in redistilled water, and acetic acid is added dropwise, after stirring, adds 0.055-0.111 part zinc acetates, is placed in height
Reacted in pressure reactor, reaction product is placed in oven for drying, produces, and above-mentioned number is parts by weight.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112851535A (en) * | 2021-01-22 | 2021-05-28 | 广东石油化工学院 | Synthesis and application of novel 4, 4' - ((polyhalogenated phenyl) azadiyl) bis (methylene) dibenzoic acid |
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2017
- 2017-09-25 CN CN201710873197.3A patent/CN107501307A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112851535A (en) * | 2021-01-22 | 2021-05-28 | 广东石油化工学院 | Synthesis and application of novel 4, 4' - ((polyhalogenated phenyl) azadiyl) bis (methylene) dibenzoic acid |
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Application publication date: 20171222 |