Compound containing azobenzene base element and preparation method and application of compound

A compound, the technology of azophenyl base, which is applied in the field of compounds containing azophenyl base elements and its preparation, can solve the problems of disturbance superposition stability, poor effect, limited effect, etc.

Pending Publication Date: 2018-12-28
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are obvious defects in this method: azobenzene is used as an additional device in the nucleic acid, and does not participate in the self-assembly process, and its introduction destroys the regularity of the nucleic acid structure (see the general structure of this type of nucleic acid molecule. figure 1 A)
Secondly, the effect of this switch to control self-assembly is not good. The azobenzene group undergoes cis-trans isomerization under light, and the stable trans-azobenzene is a coplanar conjugated п electron planar structure, which can stabilize DNA doublets. chain, while cis-azobenzene is a folded non-planar structure (see figure 1 B); through this azobenzene cis-trans isomerization change to disturb the superposition stability of the base п electron plane of the DNA double strand, the effect of controlling the opening and closing of the DNA double strand is limited

Method used

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  • Compound containing azobenzene base element and preparation method and application of compound
  • Compound containing azobenzene base element and preparation method and application of compound
  • Compound containing azobenzene base element and preparation method and application of compound

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preparation example Construction

[0071] The present invention also provides a preparation method of the compound, comprising the steps of:

[0072] 1) Will and Reaction, obtain described compound;

[0073] And after step 1) also optionally include steps:

[0074] 2) reacting the product obtained in step 1) with 4,4'-bismethoxytrityl chloride to obtain the compound;

[0075] And after step 2) also optionally include steps:

[0076] 3) reacting the product obtained in step 2) with phosphoramidite chloride to obtain the compound,

[0077] in, and R c as defined above.

[0078] application

[0079] The present invention also provides an application of the compound for preparing a composition containing the compound's DNA double-strand or RNA double-strand.

[0080] The present invention also provides a non-diagnostic and non-therapeutic method for regulating the DNA double-strand switch, the DNA double-strand contains the compound, and realizes the control of the reversible switch of the DNA double-stra...

Embodiment 1

[0088] The synthesis of embodiment 1 compound 7

[0089] Synthesis of compound 1:

[0090]

[0091] Synthesis of compound S2 (1,3-bis(4-methylbenzoyl)-7-nitroquinazoline-2,4(1H,3H)-dione):

[0092] In compound S1 (2.07g, 10.0mmol) and triethylamine (Et 3 N, 5ml) was added dropwise to a solution of anhydrous DMF (80mL) at 0 °C (3.56g, 23.0mmol). After the addition, the reaction solution returned to room temperature and continued to stir for 30 minutes. Then the reaction solution was stirred at 50°C for 8 hours, the organic solvent was removed and the residue was dissolved in dichloromethane, washed with brine and dried. The organic phase was removed and the residue was purified by silica gel column chromatography to obtain white solid compound S2 (5.50 g, yield 63%)

[0093] 1 H NMR (300MHz, CDCl 3 )δ8.45(d, J=8.4Hz, 1H), 8.13(dd, J=8.4Hz, J=2.1Hz, 1H), 7.84-7.95(m, 4H), 7.29-7.36(m, 4H), 2.45(s,3H), 2.43(s,3H); 13 C NMR (100MHz, CDCl 3 )δ168.18,166.70,159.68,152.30...

Embodiment 2

[0117] The synthesis of embodiment 2 compound 10

[0118]

[0119] Synthesis of Compound 8:

[0120] Compound 5 (210mg, 1.0mmol) and compound S6 (442mg, 1mmol) were dissolved in anhydrous dry acetic acid (10mL), then the organic solvent was removed, and the residue was purified by column chromatography to obtain red solid compound 8 (473mg , yield 78%).

[0121] 1 H NMR (300MHz, CD 3 OD)δ8.46(d,J=8.6Hz,1H),7.91-7.99(m,6H)7.41-7.75(m,7H),5.14(dd,J=10.5Hz,5.1Hz,1H),4.27( dt, J=5.7,1.5Hz,1H),3.91-3.95(m,1H),3.63-3.65(m,2H),2.48(s,3H), 2.39(s,3H),2.37(s,3H) ,2.17-2.23(m,1H),1.87-1.94(m,1H); 13 C NMR (101MHz, CDCl 3 )δ168.81,167.75,160.98,156.77,152.47,148.47,147.81,147.15,143.96,139.72,130.95,130.67,130.21,130.15,129.93, 129.91,129.23,129.20,129.08,122.25,120.89,118.24,116.44,109.21, 88.18 ,79.71,73.14,62.80,43.70,20.76,20.70; MS(ESI) m / z 633.23 [M+H] + .

[0122] Synthesis of Compound 9:

[0123] DMTrCl (186 mg, 0.55 mmol) was added to a solution of compound 8 (315 m...

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Abstract

The invention relates to a compound containing an azobenzene base element and a preparation method and application of the compound. Specifically, the compound has a structure shown in formula I, wherein the definition of all groups and substituent groups is shown as the description. The invention further discloses the preparation method of the compound and the application of the compound in the field of reversible opening and closing adjustment of DNA double chains. The formula I is shown in the description.

Description

technical field [0001] The invention relates to the field of biomedicine, in particular to a compound containing an azophenyl base element and a preparation method and application thereof. Background technique [0002] Nucleic acid molecules are carriers of genetic information, and nucleic acids with specific recognition and self-assembly functions are also smart materials. Solid-phase synthesis technology enables short-chain nucleic acids to be synthesized automatically and efficiently through solid-phase synthesizers. This technology has greatly promoted the application of nucleic acid in the fields of biology, medicine and nanotechnology. [0003] As a biological macromolecule, the structure of nucleic acid cannot be expressed by the chemical element symbols in the periodic table of elements, but its exact structure can be accurately expressed by the base symbols A, T, C, G and U in nucleic acid. With the deepening of artificial nucleic acid research, more and more arti...

Claims

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Application Information

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IPC IPC(8): C07D405/12C07F9/6558
CPCC07D405/12C07F9/65586
Inventor 谭蔚泓王若文金程
Owner HUNAN UNIV
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