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Method for modifying nucleoside by spiro pyran and spiro oxazine photo chromic compound

A photochromic, spiropyran light technology, applied in the field of biochemistry

Inactive Publication Date: 2008-08-06
SHANGHAI DESANO PHARMA SCI & TECH DEV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are many reports on nucleoside modification (Chemistry of Nucleosides and Nucleotides, L.B. Townsend, Ed., Plenum Press, New York, 1988.), and the modification method has alkylation (M.Gniazdowsk and C.Cera, Chem.Res., 1996, 96, 619.), halogenation (E.A.Veliz and P.A.Beal, J.Org.Chem., 2001, 66, 8592.), morphology modification (K.L.Seley, L.Zhang, A.Hogos, et al., J.Org.Chem., 2002, 67, 3365.) and the introduction of functional groups such as biotin, fluorescein (S.L.Beaucage and R.P.Iyer, Tetrahedron, 1993, 49, 1925.) etc., but so far no light A report on the introduction of nucleosides into chromogenic materials

Method used

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  • Method for modifying nucleoside by spiro pyran and spiro oxazine photo chromic compound
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  • Method for modifying nucleoside by spiro pyran and spiro oxazine photo chromic compound

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Experimental program
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Embodiment 1

[0017] Embodiment 1: (synthesis of compound 1-A)

[0018] 190 mg (0.5 mmol) of compound 1 and 153 mg (0.5 mmol) of compound A were uniformly mixed in 5.5 mL of ethylene glycol dimethyl ether (EGD), and a catalytic amount (12.2 mg, 0.1 mmol) of 4-N, N'-di Methylaminopyridine (DMAP), finally added 188mg (0.9mmol) N, N'-dicyclohexylcarbodiimide (DCC), stirred for 24 hours, and the solvent was removed by rotary evaporation, and the residue was separated and purified by silica gel thin layer chromatography (dichloromethane:methanol=13:1), recrystallized from ethyl acetate-petroleum ether to obtain 182 mg of khaki solid powder 1-A, yield 53%.

Embodiment 2

[0019] Embodiment 2: (synthesis of compound 1'-U)

[0020] Prepared by the reaction of compound 1' and compound U, the method is the same as in Example 1, and the yield is 72%.

Embodiment 3

[0021] Embodiment 3: (synthesis of compound 3)

[0022] 1.52g (4.0mmol) of compound 1, 480mg (4.2mmol) of N-hydroxysuccinimide (NHS) was dissolved in 40mL of ethylene glycol dimethyl ether (EGD), and then 1170mg (5.6mmol) of N,N'- Dicyclohexylcarbodiimide (DCC), stirred for 24 hours, a precipitate formed. The resulting dicyclohexyl urea precipitate was removed by suction filtration, the solvent was removed by rotary evaporation, separated by silica gel column chromatography (chloroform: petroleum ether = 1:5), and recrystallized with ethyl acetate-petroleum ether to obtain 21.6 g of yellow crystals. Yield 84%.

[0023] 477mg (1.0mmol) of compound 2 was dissolved in 10mL of EGD, and a solution of 82mg (1.1mmol) of glucosine and 170mg (2.0mmol) of sodium bicarbonate in 7.5mL of water prepared in advance was added dropwise. Turbidity appeared during the dropping process, and the color deepened. After the dropping was completed, it was stirred for 5-7 hours to obtain a dark purp...

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Abstract

The invention belongs to the technological field of biochemistry. The invention provides a method to modify the nucleoside with spiral pyran and spiral oxaxine photochromic compound. The method of the invention realizes the graft between the photochromic optical information material and nucleoside for the first time, and introduces the amino acid as the connecting arm into the nucleoside modified by the photochromic compound for the first time. It has important use value in the fields of the development of new drugs, designs and calculation of pharmic molecular, biological information technology and so on.

Description

Technical field: [0001] The invention belongs to the technical field of biochemistry. It specifically relates to a method for modifying nucleosides with spiropyran and spirooxazine photochromic compounds. Background technique: [0002] As an important optical information material, photochromic materials have been widely used in high-tech fields such as two-dimensional and three-dimensional optical information storage, special optical devices and anti-counterfeiting identification, and breakthroughs have been made in the application of life sciences in recent years Sexual progress has received great attention. Spiropyran and spirooxazine photochromic compounds are the photochromic systems with the longest research history and the widest research scope. They have rapid photochromic reaction, excellent photochromic performance, thermal stability and fatigue resistance. Well, so it's always been valued. In addition, nucleoside is a very important kind of living substance, and...

Claims

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Application Information

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IPC IPC(8): C07H19/00C07H19/06C07H19/16
Inventor 孟继本李金亮高宇秦璇季齐邹武新
Owner SHANGHAI DESANO PHARMA SCI & TECH DEV