2-phenyl-4H-benzo [1, 3] oxazine derivative containing 3-phenylfuran as well as preparation and application thereof

Abstract

The invention belongs to the technical field of pharmaceutical chemicals, and particularly relates to a 2-phenyl-4H-benzo [1, 3] oxazine derivative containing 3-phenylfuran as well as preparation and application thereof. The 2-phenyl-4H-benzo [1, 3] oxazine derivative containing 3-phenylfuran provided by the invention can be prepared only through one-step reaction. According to the invention, compounds which can be purchased in the market or are easy to synthesize are used as raw materials, and the reaction has the characteristics of simple operation, mild conditions, few steps, fast reaction speed, low cost, few generated wastes, high atom economy and the like. Meanwhile, the derivative shows a certain inhibitory activity on four tumor cells (human osteosarcoma cells, human colon cancer cells, human non-small cell lung cancer cells and human breast cancer cells), and is expected to be prepared into drugs for inhibiting tumor cells, especially drugs for inhibiting non-small cell lung cancer cells.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and specifically relates to a 2-phenyl-4H-benzo[1,3]oxazine derivative containing 3-phenylfuran and its preparation and application. Background technique [0002] 4H-[1,3]-Benzoxazine has excellent pharmaceutical activity and has the potential to be transformed into more complex compounds. The biological activities of 4H-[1,3]benzoxazines and their derivatives are usually antitumor, postoperative analgesia, anti-inflammatory and antibacterial. 4H-[1,3]benzoxazine is an important class of core skeletons, which not only widely exist in drugs and natural products (such as: anti-anxiety drug etifocine and fungicides), but also have important biological Active heterocyclic compounds are often used as an important class of intermediates in the synthesis (such as herbicides and progesterone receptor agonists). At the same time, the application of benzoxazines in materials can mak...

AI Technical Summary

Problems solved by technology

At present, the synthesis of 4H-benzo[1,3]oxazines mainly adopts traditional synthesis methods and Lewis acid-mediated olefin synthesis methods, and the traditional synthesis methods of benzoxazines use metal-catalyzed or metal-free reactions. Under the system, the ring closure of aldehyde and o-ethanol aniline produces benzoxazine, which cannot produce optically pure benzoxazine

The method of Lewis acid-mediated synthesis of benzoxazine from alkenes is to make styrene and its ortho amide undergo a ring-closing reaction under the mediation of Lewis acid to generate benzoxazine. The reaction time of this method is long, usually one to three days reaction time and cannot achieve stereoselective synthesis

It can be seen that the current synthesis method of 4H-benzo[1,3]oxazine compounds has disadvantages such as difficulty in achieving stereoselective control, long reaction time, need for additives, harsh and complex reaction conditions, etc.

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