(E)-4-(3-(4-bromophenyl)-3-oxo-propenyl)benzaldehyde | 1261352-83-3

• 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: (E)-4-(3-(4-bromophenyl)-3-oxo-propenyl)benzaldehyde
• 英文别名: (E)-4-(3-(4-bromophenyl)-3-oxoprop-1-en-1-yl)benzaldehyde；4-[3-(4-Bromophenyl)-3-oxo-1-propenyl]benzenecarbaldehyde；4-[(E)-3-(4-bromophenyl)-3-oxoprop-1-enyl]benzaldehyde
• CAS: 1261352-83-3
• 化学式: C₁₆H₁₁BrO₂
• 分子量: 315.166
• InChiKey: CXWUVXDIHQERNK-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-4-(3-(4-bromophenyl)-3-oxo-propenyl)benzaldehyde 在 三氟乙酸 作用下， 以 氯仿 、 水 为溶剂， 反应 0.5h， 生成 (2R,4S,6S)-2-(4-bromophenyl)-6-(4-((E)-3-(4-bromophenyl)-3-oxo-propenyl) phenyl)-4-hydroxy tetrahydropyran
  参考文献：
  名称：

  Synthesis of flavonoids based novel tetrahydropyran conjugates (Prins products) and their antiproliferative activity against human cancer cell lines

  摘要：

  Following our previously reported Prins cyclization strategy, a series of novel and highly functionalized flavonoid based THPs (Prins products) were designed, synthesized and evaluated for their anti-proliferative activity. Novel products were afforded in excellent yields (72-96%) within 20-90 min at 62 degrees C using flavonoid aldehydes, homoallylic alcohols, p-TSA center dot H2O (catalyst and reagent) and MS 4 angstrom in CHCl3. Deprotection of tosyl group was achieved with TFA (catalyst and solvent) at 140 degrees C to obtain 4-hydroxytetrahydropyrans and further reaction of 4-hydroxytetrahydropyrans with cinnamoyl chloride afforded 4-cinnamate tetrahydropyrans under neat condition. Synthesized compounds evaluated against human cancer cell lines (Hep3 beta, MCF-7 and Hela), have shown moderate to good antiproliferative activity in vivo. Compounds 3q and 3zb exhibited similar cytotoxicity (IC50 6.6 +/- 1.4, 6.9 +/- 1.0 mu M, respectively) to the reference drug doxorubicin (IC50 7.6 +/- 0.9 mu M) against the MCF-7 cancer cell line. Compound 3zb was found equally active as the standard drug (IC50 4.48 +/- 2.1 mu M) against the Hep3 beta cell line and compounds 3c and 3q showed moderate cytotoxicity (IC50 10.40 +/- 1.1, 12.9 +/- 1.7 mu M, respectively) against the HeLa cell line. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.033
• 作为产物：
  描述：

  对苯二甲醛 、 4-溴苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-4-(3-(4-bromophenyl)-3-oxo-propenyl)benzaldehyde
  参考文献：
  名称：

  含有氨基胍或酰基hydr部分的查耳酮衍生物的合成和生物学评估。

  摘要：

  根据其抗菌，抗真菌和抗炎活性，设计，合成和评估了三个新颖的包含氨基胍或酰基hydr部分的查耳酮衍生物。大多数合成的化合物显示出对各种细菌和一种真菌的有效抑制活性，最低抑制浓度（MIC）为1至8ug / mL。与我们先前报道的查耳酮衍生物（MICs> 64mug / mL）相比，这些化合物对革兰氏阴性细菌菌株（大肠杆菌1924和1356）显示出更高的抗菌活性（MICs = 2mug / mL）。发现化合物4f和4h对革兰氏阴性细菌鼠伤寒沙门氏菌1926和白色念珠菌7535的MIC最有效，MIC值为1mug / mL。化合物4f在本研究中制备的所有化合物中显示出最有效的抗炎活性，腹膜内给药后抑制率为92.45％，使其比参考药物吲哚美辛和布洛芬更有效。在HeLa，Hep3B和L02细胞中评估了化合物4f的细胞毒活性。

  DOI：

  10.1016/j.bmcl.2016.11.001

文献信息

• Synthesis and evaluation of the antibacterial activities of aryl substituted dihydrotriazine derivatives
  作者：Tian-Yi Zhang、Zhan-Kui Yu、Xue-Jun Jin、Ming-Yue Li、Liang-Peng Sun、Chang-Ji Zheng、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2018.03.037

  日期：2018.5

  containing chalcone (13a–i), phenoxy acetophenone (14a–b), benzyl benzene (15a–c), naphthoxyl acetophenone (16a–b) and benzyl naphthalene (17a–h) moieties were designed and synthesized. The antibacterial and antifungal activities of these compounds were evaluated against several strains of Gram-positive and Gram-negative bacteria, as well as a single fungus. Compound 17h was found to be the most potent of all

  设计并合成了包含查尔酮（13a–i），苯氧基苯乙酮（14a–b），苄苯（15a–c），萘氧基苯乙酮（16a–b）和苄基萘（17a–h）部分的五个系列的二氢三嗪衍生物。评估了这些化合物对几种革兰氏阳性和革兰氏阴性细菌菌株以及单一真菌的抗菌和抗真菌活性。发现化合物17h是所有测试化合物中最有效的，对几种革兰氏阳性菌（金黄色葡萄球菌4220和QRSA CCARM 3505）和革兰氏阴性菌（大肠杆菌）的MIC值为0.5μg/ mL1924）菌株。但是，该化合物对铜绿假单胞菌2742和鼠伤寒沙门氏菌2421无活性，表明其抗菌谱与阳性对照加替沙星和莫西沙星相似。在人正常肝细胞中评估了化合物13i，16b和17h的细胞毒活性。
• Synthesis of new chalcone derivatives containing a rhodanine-3-acetic acid moiety with potential anti-bacterial activity
  作者：Zhen-Hua Chen、Chang-Ji Zheng、Liang-Peng Sun、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2010.09.031

  日期：2010.12

  With an intention to synergize the anti-bacterial activity of chalcones and rhodanine-3-acetic acid, several hybrid compounds possessing chalcone and rhodanine-3-acetic acid moieties were synthesized and tested for their anti-bacterial activity. Some compounds presented great anti-microbial activities against Gram-positive bacteria (including the multidrug-resistant clinical isolates). This class of

  为了协同查尔酮和罗丹宁-3-乙酸的抗菌活性，合成了几种具有查尔酮和罗丹宁-3-乙酸部分的杂合化合物，并测试了它们的抗菌活性。一些化合物对革兰氏阳性细菌（包括耐多药临床分离株）表现出极大的抗菌活性。这类化合物对金黄色葡萄球菌具有很高的效力，其中衍生物5k的MIC为2μg/ mL，与标准药物（诺氟沙星）一样有效，而活性却不如奥沙西林。化合物5a–s不会抑制革兰氏阴性细菌大肠杆菌CCARM 1924或大肠杆菌的生长 CCARM 1356的浓度为64μg/ mL。
• Synthesis and antimicrobial evaluation of l-phenylalanine-derived C5-substituted rhodanine and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone
  作者：Xin Jin、Chang-Ji Zheng、Ming-Xia Song、Yan Wu、Liang-Peng Sun、Yin-Jing Li、Li-Jun Yu、Hu-Ri Piao

  DOI：10.1016/j.ejmech.2012.08.026

  日期：2012.10

  Four novel series of compounds, including the L-phenylalanine-derived C5-substituted rhodanine (6a-q, 7a-j) and chalcone derivatives containing thiobarbituric acid or 2-thioxo-4-thiazolidinone (9a-e, 11a-e) have been designed, synthesized, characterized, and evaluated for their antibacterial activity. Some of these compounds showed significant antibacterial activity against Gram-positive bacterias, especially against the strains of multidrug-resistant clinical isolates, among which compounds 6c-e, 6g, 6i, 6j and 6q exhibiting high levels of antimicrobial activity against Staphylococcus aureus RN4220 with minimum inhibitory concentration (MIC) values of 2 mu g/mL. Compound 6q showed the most potent activity of all of the compounds against all of the test multidrug-resistant clinical isolates tested. Unfortunately, however, none of the compounds were active against Gram-negative bacteria at 64 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Antibacterial efficacy evaluation and mechanism probe of small lysine chalcone peptide mimics
  作者：Bo-Yuan Shen、Ming-Ming Wang、Shuai-Min Xu、Chen Gao、Meng Wang、Sen Li、Maxwell Ampomah-Wireko、Sheng-Cong Chen、Da-Chao Yan、Shangshang Qin、En Zhang

  DOI：10.1016/j.ejmech.2022.114885

  日期：2022.12
• Synthesis and Evaluation of Chalcone Derivatives as Prospective Anti-Inflammatory Compounds
  作者：Xueqian Bai、Zhe Liu、Yue Sheng、Fuyun Liu、Tianyi Zhang

  DOI：10.1007/s10600-024-04341-3

  日期：2024.5