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2,4,6-tri-substituted-1,3,5-triazine derivates library and preparation method

A technology of trisubstitution and triazines, applied in 2 fields, to achieve the effects of high purity and yield, mild synthesis conditions, and easy availability of raw materials

Inactive Publication Date: 2008-11-19
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Hexamethylmelamine is an effective drug against breast cancer, lung cancer and ovarian cancer, but its severe side effects such as nausea, vomiting, abdominal cramps and anorexia limit its clinical application [Cancer Treat.Rev., 1986, 13, 197-217]

Method used

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  • 2,4,6-tri-substituted-1,3,5-triazine derivates library and preparation method
  • 2,4,6-tri-substituted-1,3,5-triazine derivates library and preparation method
  • 2,4,6-tri-substituted-1,3,5-triazine derivates library and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of 2,4-dichloro-6-phenyl-1,3,5-triazine III

[0026] Add 0.78g (33mmol) magnesium bars and 20mL anhydrous tetrahydrofuran (THF) into a 50mL three-necked flask, add a few grains of iodine to activate, slowly add 4.7g (30mmol) bromobenzene to the system, and keep the system in a slightly boiling state. After the dropwise addition was completed, keep the temperature at 65°C for 2 hours. After cooling the room temperature, slowly add the Grignard reagent dropwise to the THF (30mL) solution of cyanuric chloride (2.8g, 15mmol) cooled to 0°C in advance, and keep the internal temperature 0~10°C, react at 20°C for 3 hours after the dropwise addition, dilute the mixture with toluene, wash with 10% hydrochloric acid, wash with water, distill off the solvent under reduced pressure to obtain a yellow solid 2,4-dichloro-6-phenyl-1 , crude product of 3,5-triazine III. Yield 66%, m.p. 110°C.

Embodiment 2

[0027] Example 2: Preparation of 2,4-dichloro-6-(4-methoxyphenyl)-1,3,5-triazine III

[0028]Add 4.2g (176mmol) magnesium bars and 60mL anhydrous THF into a 100mL three-necked flask, add a few grains of iodine to activate, slowly add 24.3g (130mmol) p-bromoanisole into the system, and keep the system in a slightly boiling state. After the dropwise addition was completed, it was kept at 65°C for 0.5 hours. After cooling to room temperature, the Grignard reagent was slowly added dropwise to a THF (60mL) solution of cyanuric chloride (12g, 65mmol) cooled to 0°C in advance, and the internal temperature was kept at 0°C. ~10°C, react at 20°C for 3 hours after the dropwise addition, dilute the mixture with toluene, wash with 10% hydrochloric acid, wash with water, distill off the solvent under reduced pressure to obtain yellow-white solid 2,4-dichloro-6-(4-methyl Crude product of (oxyphenyl)-1,3,5-triazine III. Yield 61%, m.p. 122-124°C.

Embodiment 3

[0029] Example 3: Preparation of 2,4-dichloro-6-(3-chlorophenyl)-1,3,5-triazine III

[0030] Add 3.0g (125mmol) magnesium bars and 50mL anhydrous THF into a 100mL three-necked flask, add a few grains of iodine to activate, slowly add 22.8g (119mmol) m-chlorobromobenzene to the system, and keep the system in a slightly boiling state. After the dropwise addition was completed, keep the temperature at 65°C for 2 hours. After cooling the room temperature, slowly add the Grignard reagent dropwise to the THF (60mL) solution of cyanuric chloride (11.1g, 60mmol) cooled to 0°C in advance, and keep the internal temperature 0~10°C, react at 20°C for 3 hours after the dropwise addition, dilute the mixture with toluene, wash with 10% hydrochloric acid, wash with water, distill off the solvent under reduced pressure to obtain yellow solid 2,4-dichloro-6-(3-chloro Crude phenyl)-1,3,5-triazine III. Yield 58%, m.p. 92-95°C.

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Abstract

The invention provides a solid phase synthesis method for a 2, 4, 6-trisubstituted-1, 3, 5-triazine derivative library. The method comprises the following steps that: aldehyde group resin reacts with primary amine in organic solvent; resin containing a secondary amine structure is obtained through reductive amination; the resin reacts with 2, 4, 6-trisubstituted-1, 3, 5-triazine so as to obtain resin connected with a triazine mother ring, and then the resin reacts with primary amine or secondary amine so as to have 6-chlorine replaced; finally a formed product is cut from the resin through a cutting agent, so as to obtain a 2, 4, 6-trisubstituted-1, 3, 5-triazine derivative with molecular diversity. The 2, 4, 6-trisubstituted-1, 3, 5-triazine derivative provided by the invention is moderate in synthesis condition, easy to get raw materials, high in yield and beneficial to high-throughput screening and the discovery of anti-cancer anticancer drug lead compounds.

Description

technical field [0001] The invention belongs to compound synthesis, and mainly relates to a library of 2,4,6-trisubstituted-1,3,5-triazine derivatives and a solid-phase synthesis method thereof. Background technique [0002] Apoptosis is an important life phenomenon, and the abnormality of apoptosis is an important link in the occurrence and development of tumors. The PKB signaling pathway transmits extracellular stimulation signals such as growth factors, and plays an important role in regulating tumor cell proliferation, apoptosis, metabolism, and tumor angiogenesis. The activation process of PKB is the central part of the signal transduction pathway, and inhibiting the activity of PKB in various ways will promote the process of apoptosis. PKB will be a new and good antitumor drug target. [0003] In the current research on protein kinase inhibitors, Novartis's Gleevec and Astrazenca's Iressa have entered clinical application as drugs for the treatment of chronic leukemi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/48C40B50/14C40B40/04
Inventor 胡章叶苇吴旭伶章国林俞永平
Owner ZHEJIANG UNIV
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