(E)-4-(3-(4-fluorophenyl)-3-oxoprop-1-en-1-yl)benzaldehyde | 1261352-76-4

• 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-fluorophenyl)-3-oxoprop-1-en-1-yl)benzaldehyde
• 英文别名: 4-[(E)-3-(4-fluorophenyl)-3-oxoprop-1-enyl]benzaldehyde
• CAS: 1261352-76-4
• 化学式: C₁₆H₁₁FO₂
• 分子量: 254.261
• InChiKey: CZXZCFBHBUYECV-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-(3-(4-fluorophenyl)-3-oxoprop-1-en-1-yl)benzaldehyde 在 三乙酰氧基硼氢化钠 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 顺-1,2-二氯乙烯 、 甲醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.08h， 生成 (E)-2,6-bis(chloroamino)-N-(4-(3-(4-fluorophenyl)-3-oxoprop-1-en-1-yl)benzyl)-N-nonylhexanamide
  参考文献：
  名称：

  Antibacterial efficacy evaluation and mechanism probe of small lysine chalcone peptide mimics

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114885
• 作为产物：
  描述：

  对苯二甲醛缩二乙醛 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 (E)-4-(3-(4-fluorophenyl)-3-oxoprop-1-en-1-yl)benzaldehyde
  参考文献：
  名称：

  Synthesis and Characterization of Novel Mono- and Bis-Guanyl Hydrazones as Potent and Selective ASIC1 Inhibitors Able to Reduce Brain Ischemic Insult

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00305

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 biological evaluation of chalcone derivatives containing aminoguanidine or acylhydrazone moieties
  作者：Zhi-Yu Wei、Ke-Qiang Chi、Zhan-Kui Yu、Hong-Yan Liu、Liang-Peng Sun、Chang-Ji Zheng、Hu-Ri Piao

  DOI：10.1016/j.bmcl.2016.11.001

  日期：2016.12

  Three novel series of chalcone derivatives containing an aminoguanidine or acylhydrazone moiety were designed, synthesized and evaluated in terms of their antibacterial, antifungal and anti-inflammatory activities. Most of the synthesized compounds showed potent inhibitory activity towards various bacteria and one fungus with minimum inhibitory concentrations (MICs) ranging from 1 to 8mug/mL. Compared

  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。
• Discovery of Isaindigotone Derivatives as Novel Bloom’s Syndrome Protein (BLM) Helicase Inhibitors That Disrupt the BLM/DNA Interactions and Regulate the Homologous Recombination Repair
  作者：Qi-Kun Yin、Chen-Xi Wang、Yu-Qing Wang、Qian-Liang Guo、Zi-Lin Zhang、Tian-Miao Ou、Shi-Liang Huang、Ding Li、Hong-Gen Wang、Jia-Heng Tan、Shuo-Bin Chen、Zhi-Shu Huang

  DOI：10.1021/acs.jmedchem.9b00083

  日期：2019.3.28

  approach in DNA damage repair, is an attractive target in cancer therapy and drug design. The Bloom syndrome protein (BLM) is a 3'-5' DNA helicase that performs an important role in HRR regulation. However, limited studies about BLM inhibitors and their biological effects have been reported. Here, we identified a class of isaindigotone derivatives as novel BLM inhibitors by synthesis, screening, and evaluating

  同源重组修复（HRR）是DNA损伤修复的关键方法，在癌症治疗和药物设计中是一个有吸引力的目标。Bloom综合征蛋白（BLM）是3'-5'DNA解旋酶，在HRR调节中起重要作用。然而，已经报道了关于BLM抑制剂及其生物学作用的有限研究。在这里，我们通过合成，筛选和评估，将一类异靛酮衍生物鉴定为新型BLM抑制剂。其中，发现化合物29是有效的BLM抑制剂，其具有高结合亲和力和对BLM的良好抑制作用。细胞评估表明，有29种细胞有效地破坏了BLM在DNA双链断裂位点的募集，促进了RAD51的积累，并调节了HRR过程。同时，有29种显着诱导DNA损伤反应，以及癌细胞的凋亡和增殖停滞。我们的发现基于通过小分子干扰BLM提供了一种潜在的抗癌策略。
• Synthesis of flavonoids based novel tetrahydropyran conjugates (Prins products) and their antiproliferative activity against human cancer cell lines
  作者：Naseem Ahmed、Naveen Kumar Konduru、Sarfaraz Ahmad、Mohammad Owais

  DOI：10.1016/j.ejmech.2014.01.033

  日期：2014.3

  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.