(E)-4-(3-(4-chlorophenyl)-3-oxo-propenyl)benzaldehyde | 1261352-79-7

• 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-chlorophenyl)-3-oxo-propenyl)benzaldehyde
• 英文别名: (E)-4-(3-(4-chlorophenyl)-3-oxoprop-1-en-1-yl)benzaldehyde；4-[(E)-3-(4-chlorophenyl)-3-oxoprop-1-enyl]benzaldehyde
• CAS: 1261352-79-7
• 化学式: C₁₆H₁₁ClO₂
• 分子量: 270.715
• InChiKey: JNPDERHZWDONGF-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-chlorophenyl)-3-oxo-propenyl)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-chlorophenyl)-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 、 对氯苯乙酮 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-4-(3-(4-chlorophenyl)-3-oxo-propenyl)benzaldehyde
  参考文献：
  名称：

  具有潜在的抗菌活性的含有若丹宁-3-乙酸部分的新查尔酮衍生物的合成

  摘要：

  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。

  DOI：

  10.1016/j.ejmech.2010.09.031

文献信息

• 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。
• 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.
• 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