1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one | 351339-23-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
• 英文别名: 3'-bromo-3,4-dimethoxy-chalcone
• CAS: 351339-23-6
• 化学式: C₁₇H₁₅BrO₃
• 分子量: 347.208
• InChiKey: CIADKJFJYZARIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one 在 氯磺酸 、 溴 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 (8,9-dimethoxy-3-methyl-6,6-dioxido-2,3,4,10b-tetrahydro-1H-benzo[4,5]isothiazolo[2,3-a]pyrazin-1-yl)(3-bromophenyl)methanone
  参考文献：
  名称：

  苯并[4,5]异噻唑并[2,3-a]吡嗪-6,6-二氧化物衍生物的合成及抗菌活性

  摘要：

  使用常规程序，苯并[4,5]异噻唑并[2,3-a]吡嗪-6,6-二氧化物环系统的许多衍生物已经从容易获得的起始材料合成。合成了一系列查耳酮，随后与氯磺酸反应生成查耳酮磺酰氯。然后用溴处理查耳酮磺酰氯以生成二溴查耳酮磺酰氯。这些随后在沸腾的乙醇中与 1,2-二氨基丙烷和 2-甲基-1,2-二氨基丙烷反应，分别生成化合物 2-10 和 11-19，产率为 12-80%。产物通过光谱分析表征，化合物 11 的最终结构通过 X 射线晶体学确定。筛选合成的化合物对枯草芽孢杆菌的潜在抗菌特性，

  DOI：

  10.3390/molecules22111889
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 3'-溴苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Zhao, Fei; Zhao, Qing-Jie; Zhang, Da-Zhi, Asian Journal of Chemistry, 2011, vol. 23, # 12, p. 5339 - 5342

  摘要：

  DOI：

文献信息

• Synthesis and Antimicrobial Activity of 1,2-Benzothiazine Derivatives
  作者：Chandani Patel、Jatinder Bassin、Mark Scott、Jenna Flye、Ann Hunter、Lee Martin、Madhu Goyal

  DOI：10.3390/molecules21070861

  日期：——

  2-benzothiazines 28–72. Compounds 28–72 were evaluated for their antimicrobial activity using broth microdilution techniques against two Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and two Gram-negative bacteria (Proteus vulgaris and Salmonella typhimurium). The results demonstrated that none of the compounds showed any activity against Gram-negative bacteria P. vulgaris and S. typhimurium;

  许多 1,2-苯并噻嗪已在三步法中合成。九个带有甲基、氟、氯和溴取代基的查耳酮 1-9 用氯磺酸进行氯磺化，生成查耳酮磺酰氯 10-18。这些通过与冰醋酸中的溴反应转化为二溴化合物 19-27。化合物 19-27 与氨、甲胺、乙胺、苯胺和苄胺反应生成 45 个 1,2-苯并噻嗪 28-72 库。使用肉汤微量稀释技术对两种革兰氏阳性菌（枯草芽孢杆菌和金黄色葡萄球菌）和两种革兰氏阴性菌（变形杆菌和鼠伤寒沙门氏菌）评估化合物 28-72 的抗菌活性。结果表明，没有一种化合物对革兰氏阴性细菌 P. vulgaris 和 S. typhimurium 显示出任何活性；然而，化合物 31、33、38、43、45、50、53、55、58、60、63 和 68 显示出对革兰氏阳性细菌枯草芽孢杆菌和金黄色葡萄球菌的活性。最低抑菌浓度 (MIC) 和最低杀菌浓度 (MBC) 的范围为 25–600 µg/mL，但部分
• Synthesis and antifungal activity of chalcone derivatives
  作者：Yuanyuan Zheng、Xuesong Wang、Sumei Gao、Min Ma、Guiming Ren、Huabing Liu、Xiaohong Chen

  DOI：10.1080/14786419.2015.1007973

  日期：2015.10.2

  In the present study, using chalcone as a lead compound, a series of its derivatives (compounds 1-30) were designed and synthesised. Their activity of anti-pathogenic fungi of plants has been evaluated. It is found that these compounds have good antifungal activity against Sclerotinia sclerotiorum, Helminthosprium maydis, Botrytis cinerea, Rhizoctonia solani and Gibberella zeae. Among them, the inhibition of growth for compound 30 against S. sclerotiorum showed 89.9%, with the median effective concentrations (EC50) of 15.4gmL(-1). The inhibition of growth for compounds 28, 29 and 30 at a concentration of 100gmL(-1) against H. maydis is 90.3%, 90.7% and 91.1%, with EC50 of 15.1, 18.3 and 18.1gmL(-1), respectively.
• Rational design, synthesis and in vitro evaluation of allylidene hydrazinecarboximidamide derivatives as BACE-1 inhibitors
  作者：Priti Jain、Pankaj K. Wadhwa、Shilpa Rohilla、Hemant R. Jadhav

  DOI：10.1016/j.bmcl.2015.11.044

  日期：2016.1

  BACE-1 (beta-secretase) is considered to be one of the promising targets for treatment of Alzheimer's disease as it catalyzes the rate limiting step of A beta-42 production. Herein, we report a novel class of allylidene hydrazinecarboximidamide derivatives as moderately potent BACE-1 inhibitors, having aminoguanidine substitution on allyl linker with two aromatic groups on either side. A library of derivatives was designed based on the docking studies, synthesized and evaluated for BACE-1 inhibition in vitro. The designed ligands displayed interactions with the catalytic aspartate dyad through guanidinium functionality. Further, the aromatic rings placed on either side of the linker occupied S1 and S3 active site regions contributing to the activity. These ligands were also predicted to follow Lipinski rule and cross blood brain barrier. Compound 2.21, having high docking score, was found to be most active with IC50 of 6.423 mu M indicating good correlation with docking prediction. (C) 2015 Elsevier Ltd. All rights reserved.