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3, 6 substituted-1, 2, 4-triazole [3, 4-alpha] phthalazine compound as well as preparation method and application of 3, 6 substituted-1, 2, 4-triazole [3, 4-alpha] phthalazine compound

A kind of technology of 4-a, triazolo, applied in the field of medicinal chemistry

Inactive Publication Date: 2014-04-02
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, based on the principle of drug molecular synthesis design and assembly, a series of 3, 6-modified 1, 2, 4-triazolo[3, 4-a] phthalazine compounds were synthesized, and their activity tests were screened, which is conducive to the development of There are no relevant reports on the application of anti-tumor active compounds and clinical drug resources

Method used

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  • 3, 6 substituted-1, 2, 4-triazole [3, 4-alpha] phthalazine compound as well as preparation method and application of 3, 6 substituted-1, 2, 4-triazole [3, 4-alpha] phthalazine compound
  • 3, 6 substituted-1, 2, 4-triazole [3, 4-alpha] phthalazine compound as well as preparation method and application of 3, 6 substituted-1, 2, 4-triazole [3, 4-alpha] phthalazine compound
  • 3, 6 substituted-1, 2, 4-triazole [3, 4-alpha] phthalazine compound as well as preparation method and application of 3, 6 substituted-1, 2, 4-triazole [3, 4-alpha] phthalazine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of N-(4-fluorophenyl)-1, 2, 4-triazolo[3, 4-a]phthalazin-6-amine

[0044] Take 6.00 g (40 mmol) of phthalic anhydride in a 100 mL single-necked bottle, add 22 mL of glacial acetic acid and stir, and the dissolution rate will gradually increase as the temperature rises until all the raw materials are dissolved at 120 °C. Slowly add 2.81 mL of hydrazine hydrate dropwise (44 mmol), the reaction solution turned into light yellow milky, and then turned into white milky, and continued to reflux for about 4 h. The reaction solution was cooled to room temperature, filtered with suction, washed twice with petroleum ether, and dried in vacuo to obtain the white product 2, 3-dihydrophthalazine-1, 4-dione.

[0045] Take 1.68 g (10 mmol) of the above-mentioned 2, 3-dihydrophthalazine-1, 4-dione in a 50 mL three-necked flask, add 15 mL of phosphorus oxychloride and stir. When the temperature reaches 80 °C, the raw materials are completely dissolved, and then slowly Warm...

Embodiment 2

[0052] Preparation of N-(4-chlorophenyl)-1, 2, 4-triazolo[3, 4-a]phthalazin-6-amine

[0053] Replace 4-fluoroaniline with 4-chloroaniline, and the preparation method is the same as in Example 1.

[0054] The product is light yellow solid powder. 1 H NMR (400 MHz, DMSO) δ 9.40 (s, 1H, CH), 9.2 (s, 1H, NH), 8.61 (d, J = 8.2 Hz, 1H, ArH), 8.51 (dd, J = 7.8, 0.9 Hz, 1H, ArH), 8.04 (t, J = 7.2 Hz,1H, ArH), 7.95 (m, 1H, ArH), 7.84 (m, 2H, ArH), 7.45 (m, 2H, ArH). 13 C NMR (101 MHz, DMSO) δ 150.09, 141.55, 139.91, 139.17, 133.94, 131.05, 128.97, 127.24, 125.31, 123.86, 123.55, 123.34, 119.39. HR-cdI 15 h 10 ClN 5 , [M+H] + m / z:296.0703, found:296.0708.

[0055]

Embodiment 3

[0057] Preparation of N-(4-methoxyphenyl)-1, 2, 4-triazolo[3, 4-a]phthalazin-6-amine

[0058] Using 4-methoxyaniline instead of 4-fluoroaniline, the preparation method is the same as in Example 1.

[0059] The product is a brown solid powder. 1 H NMR (400 MHz, DMSO) δ 9.17 (s, 1H, CH), 9.14 (s, 1H, NH), 8.59 (d, J = 8.2 Hz, 1H, ArH), 8.49 (m, 1H, ArH), 8.01 (t, J = 7.2 Hz, 1H, ArH), 7.93 (m, 1H, ArH), 7.65 (m, 2H, ArH), 7.00 (m, 2H, ArH), 3.78 (s, 3H, OCH 3 ). 13 C NMR (101 MHz, DMSO) δ 156.18, 150.75, 133.70, 132.75, 131.05, 125.09, 124.62, 123.69, 123.31, 119.43, 114.34, 55.71. HR-MS(ESI): Calcd. C 16 h 13 N 5 O, [M+Na] + m / z:314.1018, found:314.1012.

[0060]

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Abstract

The invention belongs to the field of medicinal chemistry, and discloses a 3, 6 modified-[1, 2, 4] triazole [3, 4-alpha] phthalazine compound having antitumor activity as well as a synthesizing method and application of the 3, 6 modified-[1, 2, 4] triazole [3, 4-alpha] phthalazine compound. The 3, 6 modified-[1, 2, 4] triazole [3, 4-alpha] phthalazine compound has a structure as shown in a general formula I, wherein R1 refers to H, methyl or phenyl; R2 refers to 4-fluorophenyl, 4-chloroanilino, 4-bromophenyl, 4-methoxyphenyl, 4-hydroxydiphenyl, 2-fluorophenyl, 3-trifluoromethyl)phenyl]amino, naphthylamine-1-yl, pyrrolidone-1-yl, piperidine-1-yl, 3,5-dimethyl piperidine-1-yl, morpholine-4-yl, or piperazidine-1-yl. The preliminary in-vitro antitumor activity finds that the serial compounds have obvious inhibit and killing effects on multiple tumor cells, and the 3, 6 modified-[1, 2, 4] triazole [3, 4-alpha] phthalazine compound can act as an active ingredient to be applied to clinical prevention and cancer treatment after being developed into a novel medicament.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to 1, 2, 4-triazolo[3, 4-a] phthalazine derivatives, in particular to 1, 2, 4-triazine modified at positions 3 and 6 with antitumor activity Azolo[3,4-a]phthalazine compounds and their preparation and use. Background technique [0002] A large number of literatures have reported the biological activity and pharmacological activity of phthalazine derivatives. Phthalox compounds show a series of biological activities: such as antimicrobial, antifungal, antibacterial, antitumor and antiepileptic activity, etc., so they have been widely used in the design of drug molecules, and they are excellent representatives of antitumor activity For: vatalanib succinate (vatalanib / PTK787), currently in Phase III clinical trials, and a series of Phase II and Phase I studies are underway. Triazole compounds have attracted much attention due to their diverse biological activities. Triazole compounds ...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/5025A61K31/5377A61P35/00
Inventor 刘宏民张秋荣薛登启陈秀英章旭耀顾一飞邵坤鹏贺鹏陈鹏举吴朝阳
Owner ZHENGZHOU UNIV
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