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Module compound with hydrogen bond sequence specificity combination and preparation method thereof

A technology of modular compounds and compounds, applied in the preparation of sulfides, organic chemistry, etc., can solve the problems of long synthetic routes, difficult large-scale preparations, complex reaction processes, etc.

Active Publication Date: 2013-03-20
SHANGHAI JIAO TONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

A good preparation method has been provided in the published patent (inventors: Shen Yumei, Gong Bing, Cui Wei, Zhu Hua) 201110023046.1 "Modular compound for the synthesis of amphiphilic block copolymer and its preparation method" , the synthesis reaction conditions are relatively mild. However, the synthesis route is relatively long, the reaction process is complicated, and it is difficult to prepare on a large scale

Method used

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  • Module compound with hydrogen bond sequence specificity combination and preparation method thereof
  • Module compound with hydrogen bond sequence specificity combination and preparation method thereof
  • Module compound with hydrogen bond sequence specificity combination and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] Embodiment 1, the synthesis of hydrophilic module P2

[0088] The hydrophilic module P2 is synthesized from compounds A4 and P1. The specific synthesis process is as follows:

[0089]

[0090] 1.1 Synthesis of intermediate compound A4

[0091] 1.1.1 Synthesis of reaction intermediate A2

[0092] Add 3,5-diaminobenzoic acid (1.52 g, 10 mmol), 5 mL of concentrated sulfuric acid, and 50 mL of methanol into a 100 mL single-necked round bottom flask, and reflux at 100° C. for 6-8 hours. Rotate the reaction solution under reduced pressure to remove methanol to a viscous liquid, pour it into a separatory funnel and add 300mL ethyl acetate to dilute, wash 3 times with 200mL tap water, wash 2 times with 150mL saturated sodium chloride solution, dichloromethane organic phase Dry with anhydrous sodium sulfate for 6h. Filtration and rotary evaporation under reduced pressure to remove ethyl acetate gave 1.21 g of reddish-brown solid, Yield: 72.89%.

[0093] 1 H NMR (400MHz...

Embodiment 2

[0132] Embodiment 2, the synthesis of hydrophobic module BLOCK-1

[0133] The hydrophobic module compound BLOCK-1 is synthesized from compounds B5 and Y3.

[0134] 2.1 Synthesis of intermediate compound Y3

[0135] The specific synthesis process is as follows:

[0136]

[0137] 2.1.1 Synthesis of intermediate compound Y1

[0138] Add 5-aminoisophthalic acid (5.02g, 28mmol) and 25mL of 4M aqueous sodium hydroxide solution into a 50mL single-necked round-bottomed flask, stir in an ice bath, add chloroacetyl chloride (8mL, 101mmol) dropwise, and a solid precipitates out. After 40 minutes, the dropwise addition was completed, and the reaction was continued for 30 minutes. Add dropwise 6M hydrochloric acid aqueous solution to acidify to pH ≈ 1.5, terminate the reaction, filter with suction, rinse with ice water for 300-400 mL, collect the filter cake and dry it in a vacuum oven to obtain 6.34 g of white solid, Yield 85.34%. Mp>250°C.

[0139] 1 H NMR(DMSO-d6,400MHz)δ13.3...

Embodiment 3

[0155] Embodiment 3, the synthesis of hydrophobic module BLOCK-2

[0156] The hydrophobic module compound BLOCK-2 is synthesized from compound B4 and Y4 or Y2. Wherein, compound Y4 is synthesized as follows:

[0157] Add Y2 (2.15g, 2.5mmol), potassium formate (0.84g, 10mmol), tetra-n-butylamine (0.80g, 2.5mmol) 1mL tap water, DMF 20mL, and oil bath at 100°C for 12h in a 50mL single-necked round bottom flask. The reaction was also diluted with 100 mL of ethyl acetate, washed 4 times with 100 mL of tap water, washed 3 times with saturated brine, dried over anhydrous sodium sulfate, filtered, and the ethyl acetate was removed under reduced pressure to obtain a white powder Y41.78g, Yield: 84.76% . The infrared spectrum of Y4 is as follows Figure 5 shown.

[0158] 1 H NMR (CDCl 3,400MHz)δ8.94(b,1H,NH),7.93(s,2H,ArH),7.75(s,1H,ArH),7.09~7.42(m,30H,ArH),7.06(b,2H,NH ),4.06(s,2H,CH 2 ),3.23(m,4H,CH 2 ),2.48(m,4H,CH 2 ).IR(KBr,cm -1 ):3329,3287,3082,3055,3030,2980,2934,28...

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PUM

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Abstract

The present invention discloses a module compound with hydrogen bond sequence specificity combination and a preparation method thereof. The structure formula of the compound module is as follows: wherein, when R is (m is any integer of 1-200), the module compound is a hydrophilic module compound P2; when R is (n is any integer of 2-140), the module compound corresponds to the hydrophobic module compound of BLOCK-1, BLOCK-2 or BLOCK-3. As the module compound has hydrogen-sequence specificity and the two complementary single-stranded can mutually recognize and match with specificity, the block copolymer which is not easy to synthesize by other methods can be easily prepared by using a molecular glue group.

Description

technical field [0001] The invention relates to a modular compound with a specific combination of hydrogen bond sequences and a preparation method thereof in the fields of chemistry and biomedicine, in particular to a modular compound with a specific combination of hydrogen bond sequences and a preparation method thereof. Background technique [0002] At present, the improvement of the solubility of insoluble antineoplastic drugs, antihypertensive drugs, antibacterial drugs, and gene therapy drugs at home and abroad is mainly carried out by using amphiphilic block copolymer self-assembled micelles or polymer network hydrogels. Encapsulation, a self-assembled structure spontaneously formed in aqueous solution - nanomicelle, with small particle size, narrow particle size distribution, stable structure, wide drug loading range, long residence time in vivo, high drug loading capacity and unique in vivo distribution And other characteristics, to achieve the purpose of solubilizin...

Claims

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Application Information

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IPC IPC(8): C08G65/48C08G63/78C08G63/688C08G63/08C08G81/00C07D249/04C07C323/52C07C319/20
Inventor 沈玉梅龚兵赵读恩伍新燕刘亚智
Owner SHANGHAI JIAO TONG UNIV
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