Background: Quinoline derivatives have been attracted much attention in drug discovery, and synthetic derivatives of these scaffolds present a range of pharmacological activities. Therefore, organoselenium compounds are valuable scaffolds in organic synthesis because of their pharmacological activities and their use as versatile building blocks for regio-, chemo-and stereoselective reactions. Thus, the synthesis of selenium-containing quinolines has great significance, and their applicability range from simple antioxidant agents, to selective DNA-binding and photocleaving agents.

Objective: In the present study, we describe the synthesis and antioxidant activity in vitro of new 7- chloro-N(arylselanyl)quinolin-4-amines 5 by the reaction of 4,7-dichloroquinoline 4 with (arylselanyl)- amines 3.

Methods: For the synthesis of 7-chloro-N(arylselanyl)quinolin-4-amines 5, we performed the reaction of (arylselanyl)-amines 3 with 4,7-dichloroquinoline 4 in the presence of Et₃N at 120 °C in a sealed tube. The antioxidant activities of the compounds 5 were evaluated by the following in vitro assays: 2,2- diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, 2,2-azinobis-3- ethylbenzothiazoline-6-sulfonic acid (ABTS), ferric ion reducing antioxidant power (FRAP), nitric oxide (NO) scavenging and superoxide dismutase-like activity (SOD-Like).

Results: 7-Chloro-N(arylselanyl)quinolin-4-amines 5a-d have been synthesized in yields ranging from 68% to 82% by the reaction of 4,7-dichloroquinoline 4 with arylselanyl-amines 3a-d using Et3N as a base, at 120 °C, in a sealed tube for 24 hours and tolerates different substituents, such as -OMe and -Cl, in the arylselanyl moiety. The obtained compounds 5a-d presented significant results concerning the antioxidant potential, which had an effect in the tests of inhibition of radical’s DPPH, ABTS+ and NO, as well as in the analysis that evaluates the capacity (FRAP) and in the superoxide dismutase-like activity assay (SOD-Like). It is worth mentioning that 7-chloro- N(arylselanyl)quinolin-4-amine 5b presented excellent results, demonstrating a better antioxidant capacity when compared to the others.

Conclusion: According to the obtained results, 7-chloro-N(arylselanyl)quinolin-4-amines 5 were synthesized in good yields by the reaction of 4,7-dichloroquinoline with arylselanyl-amines and tolerated different substituents in the arylselanyl moiety. The tested compounds presented significant antioxidant potential in the tests of inhibition of DPPH, ABTS+, and NO radicals, as well as in the FRAP and superoxide dismutase-like activity assays (SOD-Like).

背景：喹啉衍生物在药物发现中备受关注，这些支架的合成衍生物具有一系列药理活性。因此，有机硒化合物是有机合成中有价值的支架，因为它们具有药理活性，并且可以用作区域、化学和立体选择性反应的通用构件。因此，含硒喹啉的合成具有重要意义，其适用范围从简单的抗氧化剂到选择性DNA结合剂和光裂解剂。

目的：在本研究中，我们通过 4,7-二氯喹啉 4 与（芳基硒基）-胺 3 的反应，描述了新的 7-氯-N（芳基硒基）喹啉-4-胺 5 的合成和体外抗氧化活性。

方法：为了合成 7-氯-N（芳基硒基）喹啉-4-胺 5，我们在 Et ₃ N存在下，在 120 °C下进行（芳基硒基）-胺 3 与 4,7-二氯喹啉 4 的反应在密封管中。化合物5的抗氧化活性通过以下体外试验评价：2,2-二苯基-1-苦基肼(DPPH)自由基清除活性、2,2-氮杂双-3-乙基苯并噻唑啉-6-磺酸(ABTS)、铁离子还原抗氧化能力 (FRAP)、一氧化氮 (NO) 清除和超氧化物歧化酶样活性 (SOD-Like)。

结果：通过使用 Et3N 作为 4,7-二氯喹啉 4 与芳基硒基胺 3a-d 的反应，以 68% 至 82% 的产率合成了 7-氯-N（芳基硒基）喹啉-4-胺 5a-d一种碱，在 120 °C 下，在密封管中放置 24 小时，并且可以耐受芳基硒基部分中的不同取代基，例如 -OMe 和 -Cl。获得的化合物5a-d在抗氧化能力方面表现出显着的结果，这在抑制自由基DPPH、ABTS+和NO的测试以及评估能力（FRAP）和超氧化物歧化酶-的分析中具有作用。样活性测定（SOD-Like）。值得一提的是，7-氯-N（芳基硒基）喹啉-4-胺 5b 表现出优异的结果，与其他产品相比，表现出更好的抗氧化能力。

结论：根据所得结果，4,7-二氯喹啉与芳基硒基胺反应并能耐受芳基硒基部分的不同取代基，以良好的收率合成了7-氯-N(芳基硒基)喹啉-4-胺5。测试的化合物在抑制 DPPH、ABTS+ 和 NO 自由基的测试中以及在 FRAP 和超氧化物歧化酶样活性测定 (SOD-Like) 中表现出显着的抗氧化潜力。