含苯并三嗪酮的1,4-戊二烯-3-酮衍生物的合成及抑菌活性

Synthesis and Antibacterial Activities of Penta-1,4-dien-3-one Derivatives Containing a Benzotriazin-4(3H)-one Moiety

为了得到生物活性较好的姜黄素衍生物,通过1-苯基-5-取代基-1,4-戊二烯-3-酮和3-氯甲基苯并三嗪酮反应,合成了14个含苯并三嗪酮的1,4-戊二烯-3-酮衍生物;采用核磁共振波谱(NMR)和高分辨质谱(HRMS)对化合物的结构进行了表征.初步的生物活性测试结果表明,部分化合物显示出较好的抑菌活性,在100μg/mL剂量下,化合物6b,6j和6l对柑橘溃疡病菌(Xac)的抑制率分别为68.8%,71.0%和100%;化合物6a,6d,6h和6i对烟草青枯病菌(R.solanacearum)的抑制率分别为51.8%,53.0%,50.7%和76.9%.此外,化合物6l和6i对柑橘溃疡病菌和烟草青枯病菌的半最大效应浓度(EC50)值分别为27.44和48.77μg/mL,优于对照药剂噻菌铜(51.35和87.26μg/mL),有望成为柑橘溃疡病菌和烟草青枯病菌的抑制剂.

To find novel curcumin derivatives with potent biological activities,fourteen new penta-1,4-dien-3-one derivatives containing benzotriazin-4（ 3 H）-one moiety were synthesized by multistep synthetic procedures with two key intermediates penta-1,4-dien-3-one and 3-（ chloromethyl） benzo[1,2,3]triazin-4（ 3 H）-one. The structures of target compounds 6 were confirmed by means of nuclear magnetic resonance（ NMR）,and high resolution mass spectrometer（ HRMS）. The bioassay data showed that some compounds exhibited good antibacterial activities at the dosage of 100 μg/mL and 50 μg/mL against Xanthomonas axonopodis pv. Citri（ Xac） and Ralstonia solanacearum（ R. solanacearum）. Moreover,compounds 6 b,6 j and 6 l had 68. 8%,71. 0% and 100% antibacterial activity against Xac at 100 μg/mL. Compounds 6 a,6 d,6 h and 6 i showed51. 8%,53. 0%,50. 7 and 76. 9% antibacterial activity against R. solanacearum at 100 μg/mL. Meanwhile,all target compounds displayed excellent antibacterial activity against R. solanacearum at 50 μg/mL,which were superior to that of thiodiazole copper. In addition,compounds 6 l and 6 i showed wonderful inhibitory activities against Xac and R. solanacearum with the EC（50） values of 27. 44 and 48. 77 μg/mL,respectively. which were better than those of thiodiazole copper（ 51. 35 μg/mL and 87. 26 μg/mL,respectively）. Those two penta-1,4-dien-3-one derivatives could be considered as useful templates for future development to obtain more potent antibacterial agents.