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Phentriazine derivative preparation and uses

A technology of benzotriazine and derivatives, which is applied in the field of compound preparation methods and can solve problems such as toxic and side effects

Inactive Publication Date: 2006-02-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although tirapazamine has higher activity, there are also some toxic and side effects such as causing muscle spasms in patients (Senan S. et al, Int.J.Radiat.Oncol.Biol.Phys., 1994, 29 (2), 379-82.; Luo, Chuanhuan et al, Faming Zhuanli Shenqing Gongkai Shuomingshu, 2003, 6pp), so it is very important to seek low-toxic and efficient N-oxygen bioreduction reagents on this basis

Method used

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  • Phentriazine derivative preparation and uses
  • Phentriazine derivative preparation and uses
  • Phentriazine derivative preparation and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Detailed steps of the target compound: 39.6g (0.13mol) of triphosgene was dissolved in 30ml of toluene, and 27.6g (0.2mol) of o-nitroaniline (I) and 27.6ml (0.2mol) of triethylamine were added dropwise under the protection of nitrogen at room temperature. The toluene solution in 30min was added dropwise, and the temperature was raised to the reflux temperature of toluene. After 3h, o-nitroisocyanate (II) was obtained. After cooling, anhydrous ammonia gas was passed directly into it for 30min without separation, filtered, and washed with petroleum ether and hot water in turn. 30.4 g of o-nitrourea (III) was obtained, and 3-hydroxyl-1,2,4-benzotriazine-1-oxide (IV) 17.3 g was obtained by ring closure with 30% sodium hydroxide, 3-hydroxyl- 1,2,4-Benzotriazine-1-oxide (IV) with POCl 3 Substitution gives 3-Cl-1,2,4-benzotriazine-1-oxide (V) 16.6g, V and C 4 -C 10 fatty amine, C 3 -C 6 Condensation of cycloalkylamines, substituted arylamines and substituted benzylamines t...

Embodiment 2

[0027] 3-Hydroxy-1,2,4-benzotriazine-1-oxide (IV): prepared by referring to the literature method (F. J. Wolf et al, J. Amer. Chem. Soc., 1954, 4611-4613).

[0028] 1 H NMR (DMSO, AM=400): δ8.07(d, 1H), 7.76~7.80(t, 1H), 7.28~7.34(q, 2H), 3.34(s, 1H)

Embodiment 3

[0030] 3-Cl-1,2,4-Benzotriazine-1-oxide (V): Prepared by reference method (R.F. Robbins et al, J. Chem. Soc., 1957, 3186-3194).

[0031] 1 H NMR (CDCl 3 , AM=400): δ8.44~8.46(d, 1H), 8.02~8.03(d, 2H), 7.78~7.81(q, 1H)

[0032] MS(EI): MW=181, 183(34.85), 181(100), 137(10.53), 116(13.60), 102(6.91), 90(83.15), 76(29.81), 63(51.70), 50 (26.52), 43 (2.70)

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Abstract

The invention discloses a hentriazine derivative, i.e. N-substituted-3-amino-1,2,4-phentriazine-1,4-dioxide, which is prepared through the following steps: (1) reacting o-nitroaniline and bis(trichloromethyl)carbonate to obtain 2-nitrophenyl isocyanate, then reacting with anhydrous ammonia to obtain o-nitrobenzol urea, subjecting the compound III to cyclization under alkaline condition, acidifying to obtain 3-hydroxyl-1,2,4-phentriazine-1-oxide, acting with POC13 to obtain 3-chloro-1,2,4-phentriazine-1-oxide, then reacting various primary amines to obtain N-substituted-3-amino-1,2,4-phentriazine-1-oxide, finally reacting with glacial acetic acid / hydrogen peroxide to obtain the destination compound.

Description

technical field [0001] The invention belongs to a compound preparation method and relates to benzotriazine derivatives, mainly to the preparation and application of N-substituted-3-amino-1,2,4-benzotriazine-1,4-dioxide. Background technique [0002] Tumor is a common and frequently occurring disease that threatens human health. Among them, solid tumors account for more than 90% of all human tumors. Studies have shown that hypoxia is one of the necessary environmental conditions during the development of solid tumors, and it is also one of the important reasons why solid tumors are resistant to radiotherapy and chemotherapy, and is closely related to tumor metastasis (Shannon A.M., et al, Cancer Treat. Rev., 2003, 29(4), 297-307). Therefore, it is very important to seek low-toxicity and high-efficiency anti-tumor drugs based on tumor hypoxia as the target. [0003] Bioreductants are a class of effective hypoxic anti-tumor prodrugs that have been studied for many years. They...

Claims

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Application Information

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IPC IPC(8): C07D253/08A61K31/53A61P35/00
Inventor 胡永洲姜发琴杨波何俏军
Owner ZHEJIANG UNIV
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