CN115057873A - 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound and preparation method thereof - Google Patents
5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound and preparation method thereof Download PDFInfo
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- 229930002875 chlorophyll Natural products 0.000 title claims abstract description 23
- 235000019804 chlorophyll Nutrition 0.000 title claims abstract description 23
- -1 chlorophyll compound Chemical class 0.000 title claims abstract description 20
- XNMZJOTVPWFLCX-UHFFFAOYSA-N FC(C(C1=C(C=CC=C2)C2=NS1)=C(C(F)=C1F)F)=C1F Chemical compound FC(C(C1=C(C=CC=C2)C2=NS1)=C(C(F)=C1F)F)=C1F XNMZJOTVPWFLCX-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title abstract description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003480 eluent Substances 0.000 claims abstract description 7
- ULOCHOLAPFZTGB-UHFFFAOYSA-N 1,3-benzothiazol-3-ium;bromide Chemical compound [Br-].C1=CC=C2SC=[NH+]C2=C1 ULOCHOLAPFZTGB-UHFFFAOYSA-N 0.000 claims abstract description 6
- OGZSUORSSIIDJK-UHFFFAOYSA-N FC1=C(F)C(F)=C(F)C(F)=C1C1=CC2=CC([N]3)=CC=C3C=C(C=C3)NC3=CC([N]3)=CC=C3C=C1N2 Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C1=CC2=CC([N]3)=CC=C3C=C(C=C3)NC3=CC([N]3)=CC=C3C=C1N2 OGZSUORSSIIDJK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012043 crude product Substances 0.000 claims abstract description 6
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000003756 stirring Methods 0.000 claims abstract description 4
- 238000005303 weighing Methods 0.000 claims abstract description 4
- 238000001816 cooling Methods 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 14
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical class C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 9
- 238000004809 thin layer chromatography Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 238000004817 gas chromatography Methods 0.000 claims description 2
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 12
- 230000003595 spectral effect Effects 0.000 description 10
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 9
- 238000012512 characterization method Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000002428 photodynamic therapy Methods 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
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Abstract
The invention discloses a 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound and a preparation method thereof. The compound 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound has a structural formula shown in a formula (1). The preparation method mainly comprises the steps of weighing a certain amount of 2-nitro-5, 10,15, 20-tetra (pentafluorophenyl) porphyrin, 2-arylformyl benzothiazole bromide and triethylamine to be placed in a reactor; adding a dichloromethane solvent into the reactor, stirring for 1-3 hours at room temperature, and tracking the reaction by a chromatographic method; and after the reaction is completed, cooling to room temperature, directly separating by using a chromatographic column, collecting a first red band which is a crude product by using dichloromethane and n-hexane as eluent, and concentrating and drying the crude product to obtain the target compound. The invention has simple synthetic route and provides a brand new synthetic approach for synthesizing 5,10,15, 20-tetraarylchlorophyll.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole condensed chlorophyll compound and a preparation method thereof.
Background
The 5,10,15, 20-tetraarylporphyrin has very wide application prospect in the fields of chemical catalysis, molecular switches, anion sensors, biologically-related metal chemistry, photodynamic therapy, supramolecular self-assembly chemistry and coordination chemistry. And derivatization research is carried out on 5,10,15, 20-tetraarylporphyrin, so that the 5,10,15, 20-tetraarylchlorophyll is converted into a functionalized molecule for scientific research, and the method becomes one of the research hotspots of domestic and foreign research.
At present, no literature report exists on a synthetic method of a 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound. Through research and multiple attempts of the applicant, a novel method is developed, a simple synthetic route is obtained through a large amount of experimental exploration, the 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole condensed chlorophyll compound is obtained through one-step synthesis, and a brand-new synthetic approach is provided for the synthesis of 5,10,15, 20-tetraarylchlorophyll.
Disclosure of Invention
One of the purposes of the invention is to provide a novel compound 5,10,15, 20-tetrakis (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound synthesized by the one-step method, which has a structural formula shown in a formula (1):
in the formula (1), Ar is one of structural formulas shown in formulas (2) to (8):
it is another object of the present invention to provide a method for preparing the above 5,10,15, 20-tetrakis (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound, which comprises the following sequential steps:
(1) weighing a certain amount of 2-nitro-5, 10,15, 20-tetra (pentafluorophenyl) porphyrin, 2-arylformyl benzothiazole bromide and triethylamine, and placing the weighed substances in a reactor; wherein the structural formula of the 2-arylformyl benzothiazole bromide is shown as the formula (9):
in formula (9), Ar is one of the structural formulas shown in formula (2) to formula (8):
(2) adding a dichloromethane solvent into the reactor in the step (1), stirring for 1-3 hours at room temperature, and tracking the reaction by a chromatographic method;
(3) and after the reaction is completed, cooling to room temperature, directly separating by using a chromatographic column, collecting a first red band which is a crude product by using dichloromethane and n-hexane as eluent, and concentrating and drying the crude product to obtain the target compound.
Preferably, in the step (1), the mass ratio of the three reactants of the 2-nitro-5, 10,15, 20-tetra (pentafluorophenyl) porphyrin, the 2-arylformylbenzothiazole bromide and the triethylamine is 1: 2: 3.
specifically, in the step (2), the chromatographic method for tracking the reaction is any one of thin layer chromatography, gas chromatography and high performance liquid chromatography.
Preferably, in the step (3), the eluent is a mixture of eluent and water in a volume ratio of 1: 3, a mixed solvent of dichloromethane and n-hexane.
Compared with the prior art, the invention has the following characteristics and beneficial effects:
(1) the synthesis method of the 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound is not reported in the literature at present, has the characteristics of mild reaction conditions, simple and safe operation and the like, and is a brand new technology.
(2) The method can prepare 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compounds with different substituents by changing different substituents on a benzene ring.
(3) The 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound prepared by the method has potential significance in research and application of photodynamic cancer treatment.
Drawings
FIG. 1 and FIG. 2 are respectively a calculated high-resolution mass spectrum and a high-resolution mass spectrum of 5,10,15, 20-tetrakis (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll as a target product in example 1 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to the accompanying drawings and specific experimental examples, which are not intended to limit the present invention in any way.
Example 1:
weighing 2-nitro-5, 10,15, 20-tetra (pentafluorophenyl) porphyrin (0.05mmol), 2-benzoylbenzothiazole bromide (0.10mmol) and triethylamine (0.15mmol) in a 25mL round-bottom flask, adding dichloromethane (4mL) into the reactor, stirring at room temperature for 1 hour, tracking the reaction by Thin Layer Chromatography (TLC), and after the reaction is completed, performing column chromatography by using 200-mesh 300-mesh silica gel, and performing column chromatography by using a volume ratio of 1: 3, collecting the solution of the first elution zone, concentrating and drying the collected solution to obtain a dark brown product, namely the product 5,10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole thick chlorophyll compound, wherein the yield is 57%.
Product spectral characterization data are as follows: 1 H NMR(400MHz,CDCl 3 ,298K)δ:-2.19(br,1H),-2.17(br,1H),5.12-5.14(m,1H),6.27-6.31(m,1H),6.53-6.55(m,1H),6.68-6.70(m,1H),6.77-6.82(m,1H),6.98-7.00(m,1H),7.04(s,1H),7.37-7.40(m,2H),7.48-7.52(m,2H),7.62-7.66(m,1H),8.34-8.41(m,2H),8.54-8.59(m,2H),8.73-8.80(m,2H).UV-vis(CH 2 Cl 2 )λ max /nm(logε):407(4.96),503(3.91),531(3.52),594(3.38),647(4.26).API-HRMS calc.for C 59 H 21 F 20 N 6 O 3 S + [M+H] + :1273.1071,Found:1273.1071。
the spectral data show that the preparation method obtains 5,10,15, 20-tetra (pentafluorophenyl) -2,3- (benzoyl) benzothiazole fused chlorophyll.
Example 2:
the same synthetic procedure as in example 1 was used in this example, except that the starting material was changed to 2- (4-bromo) benzoyl benzothiazole bromide, to give a dark brown product, i.e., 5,10,15, 20-tetrakis (pentafluorophenyl) -2,3- (4-bromobenzoyl) benzothiazole fused chlorophyll, in a yield of 61%.
Product spectral characterization data are as follows: 1 H NMR(400MHz,CDCl 3 ,298K)δ:-2.18(br,1H),-2.16(br,1H),5.06-5.07(m,1H),6.31-6.33(m,1H),6.58-6.62(m,1H),6.70-6.72(m,1H),6.82-6.85(m,1H),6.95-6.96(m,1H),7.04(s,1H),7.34-7.36(m,2H),7.53-7.55(m,2H),8.37-8.42(m,2H),8.56-8.60(m,2H),8.76-8.82(m,2H).UV-vis(CH 2 Cl 2 )λ max /nm(logε):UV-vis(CH 2 Cl 2 )λ max /nm(logε):407(5.07),503(4.04),531(3.65),594(3.52),647(4.39).API-HRMS calc.for C 59 H 20 BrF 20 N 6 O 3 S + [M+H] + :1351.0176,Found:1351.0176。
the spectral data show that the preparation method obtains the 5,10,15, 20-tetra (pentafluorophenyl) -2,3- (4-bromobenzoyl) benzothiazole fused chlorophyll compound.
Example 3:
the present example employed substantially the same synthetic procedure as in example 1, except that the starting material was changed to 2- (4-chloro) benzoylbenzothiazole bromide to give a dark brown product, i.e., 5,10,15, 20-tetrakis (pentafluorophenyl) -2,3- (4-chlorobenzoyl) benzothiazole fused chlorophyll, in a yield of 63%.
Product spectral characterization data are as follows: 1 H NMR(400MHz,CDCl 3 ,298K)δ:-2.18(br,1H),-2.15(br,1H),5.06-5.08(m,1H),6.31-6.33(m,1H),6.57-6.61(m,1H),6.70-6.72(m,1H),6.81-6.85(m,1H),6.95-6.97(m,1H),7.05(s,1H),7.35-7.38(m,2H),7.42-7.44(m,2H),8.37-8.42(m,2H),8.57-8.59(m,2H),8.76-8.82(m,2H).UV-vis(CH 2 Cl 2 )λ max /nm(logε):407(5.01),503(3.98),531(3.58),594(3.44),647(4.32).API-HRMS calc.for C 59 H 20 ClF 20 N 6 O 3 S + [M+H] + :1307.0681,Found:1307.0688。
the spectral data show that the 5,10,15, 20-tetra (pentafluorophenyl) -2,3- (4-chlorobenzoyl) benzothiazole fused chlorophyll compound is obtained by the preparation method.
Example 4:
the present example employed substantially the same synthetic procedure as in example 1, except that the starting material was changed to 2- (4-fluoro) benzoyl benzothiazole bromide, to give a dark brown product, i.e., 5,10,15, 20-tetrakis (pentafluorophenyl) -2,3- (4-fluorobenzoyl) benzothiazole fused chlorophyll compound, in a yield of 79%.
Product spectral characterization data are as follows: 1 H NMR(400MHz,CDCl 3 ,298K)δ:-2.19(br,1H),-2.17(br,1H),5.07-5.08(m,1H),6.29-6.31(m,1H),6.56-6.59(m,1H),6.70-6.71(m,1H),6.80-6.84(m,1H),6.96-6.97(m,1H),7.04(s,1H),7.06-7.08(m,2H),7.51-7.53(m,2H),8.36-8.41(m,2H),8.56-8.59(m,2H),8.75-8.81(m,2H).UV-vis(CH 2 Cl 2 )λ max /nm(logε):407(5.02),503(3.97),531(3.56),594(3.41),647(4.33).API-HRMS calc.for C 59 H 20 F 21 N 6 O 3 S + [M+H] + :1291.0977,Found:1291.0974。
the spectral data show that the preparation method obtains the 5,10,15, 20-tetra (pentafluorophenyl) -2,3- (4-fluorobenzoyl) benzothiazole fused chlorophyll compound.
Example 5:
the present example employed substantially the same synthetic procedure as in example 1, except that the starting material was changed to 2- (3-chloro) benzoyl benzothiazole bromide to give a dark brown product, i.e., 5,10,15, 20-tetrakis (pentafluorophenyl) -2,3- (3-chlorobenzoyl) benzothiazole fused chlorophyll compound in a yield of 66%.
Product spectral characterization data are as follows: 1 H NMR(400MHz,CDCl 3 ,298K)δ:-2.18(br,1H),-2.16(br,1H),5.07-5.08(m,1H),6.32-6.33(m,1H),6.58-6.59(m,1H),6.72-6.74(m,1H),6.84-6.85(m,1H),6.95-6.96(m,1H),7.05-7.06(m,1H),7.33-7.63(m,4H),8.38-8.43(m,2H),8.58-8.60(m,2H),8.78-8.83(m,2H).UV-vis(CH 2 Cl 2 )λ max /nm(logε):407(5.08),503(4.02),531(3.59),594(3.42),647(4.36).API-HRMS calc.for C 59 H 20 ClF 20 N 6 O 3 S + [M+H] + :1307.0681,Found:1307.0684。
the spectral data show that the 5,10,15, 20-tetra (pentafluorophenyl) -2,3- (3-chlorobenzoyl) benzothiazole fused chlorophyll compound is obtained by the preparation method.
Claims (5)
1. A5, 10,15, 20-tetra (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compound has a structural formula shown in a formula (1):
in the formula (1), Ar is one of structural formulas shown in formulas (2) to (8):
2. a method for preparing 5,10,15, 20-tetrakis (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compounds of claim 1, comprising the sequential steps of:
(1) weighing a certain amount of 2-nitro-5, 10,15, 20-tetra (pentafluorophenyl) porphyrin, 2-arylformyl benzothiazole bromide and triethylamine, and placing the weighed substances in a reactor; wherein the structural formula of the 2-arylformyl benzothiazole bromide is shown as the formula (9):
in formula (9), Ar is one of the structural formulas shown in formula (2) to formula (8):
(2) adding a dichloromethane solvent into the reactor in the step (1), stirring for 1-3 hours at room temperature, and tracking the reaction by a chromatographic method;
(3) and after the reaction is completed, cooling to room temperature, directly separating by using a chromatographic column, collecting a first red band which is a crude product by using dichloromethane and n-hexane as eluent, and concentrating and drying the crude product to obtain the target compound.
3. A method for preparing 5,10,15, 20-tetrakis (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compounds of claim 2, wherein: in the step (1), the mass ratio of the three reactants of the 2-nitro-5, 10,15, 20-tetra (pentafluorophenyl) porphyrin, the 2-arylformyl benzothiazole bromide and the triethylamine is 1: 2: 3.
4. a method for preparing 5,10,15, 20-tetrakis (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compounds of claim 2, wherein: in the step (2), the chromatographic method for tracking the reaction is any one of thin layer chromatography, gas chromatography and high performance liquid chromatography.
5. A method for preparing 5,10,15, 20-tetrakis (pentafluorophenyl) -2, 3-benzothiazole fused chlorophyll compounds of claim 2, wherein: in the step (3), the eluent is a mixture of eluent with the volume ratio of 1: 3, a mixed solvent of dichloromethane and n-hexane.
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Non-Patent Citations (3)
| Title |
|---|
| LACERDA, PAULA S. S.: "[2,3,3]Triazolo[4,5-b]porphyrins: new building blocks for porphyrinic materials", ANGEWANDTE CHEMIE, vol. 45, no. 33, pages 5487 * |
| SNIECHOWSKA, JUSTYNA: "New synthetic pathway leading to oxospirochlorins", RSC ADVANCES, vol. 8, no. 38, pages 2046 - 2069 * |
| 李莎;荆芬;付小云;赵继军;王雪峰;李宝林;刘玉明;陈宝泉;: "含1,3,4-噻二唑的二硫醚衍生物的合成及抗肿瘤活性研究", 有机化学, vol. 35, no. 12, pages 2624 - 2628 * |
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Application publication date: 20220916 |