(E)-3-(3-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one | 108979-34-6

• 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: (E)-3-(3-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
• CAS: 108979-34-6
• 化学式: C₁₇H₁₅ClO₄
• 分子量: 318.757
• InChiKey: PZXYOXQIPYPMEE-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 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：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  哌啶 、 聚合甲醛 、 (E)-3-(3-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 在 盐酸 作用下， 以 异丙醇 为溶剂， 生成 (E)-3-(3-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxy-3-(piperidin-1-ylmethyl)phenyl)-2-propylen-1-one
  参考文献：
  名称：

  Synthesis and biological evaluation of nitrogen-containing chalcones as possible anti-inflammatory and antioxidant agents

  摘要：

  A novel series of nitrogen-containing chalcones were synthesized by Mannich reaction and were screened for anti-inflammatory related activities such as inhibition of cyclooxygenase-2 (COX-2), trypsin and beta-glucuronidase. The antioxidant potential was demonstrated using 1,1-diphenyl-2-picryl hydrazine (DPPH) radical scavenging activity. The results of the above studies shows that the compounds synthesized were found to be effective inhibitors of above pro-inflammatory enzymes, and were found to be possess moderate radical scavenging potential. Overall, the results of the studies reveal that the chalcones with N-methyl piperazine methyl and piperidine methyl substitution (4c, 3b, 4d, 6b) seems to be important for inhibition of beta-glucuronidase. Whereas the chalcones with piperidine methyl substitution (8b, 7b, 7c, 6c, 4b, 3c, 3b) were observed as effective inhibitors of COX-2, while the same compounds were found to be less reactive against COX-1 as compared to COX-2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.068
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 (E)-3-(3-chlorophenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  设计，合成和生物评价二甲基小豆蔻（DMC）衍生物作为P糖蛋白介导的多药耐药逆转剂。

  摘要：

  背景：过去十年来，P-糖蛋白（P-gp）被认为是肿瘤细胞多药耐药性（MDR）的重要因素，可以通过抑制Pgp逆转MDR来解决。因此，开发P-gp抑制剂是一种有效的策略。 目的：本研究在二甲基小豆蔻苷（DMC）的基础上，通过生物等位线设计进行了一系列衍生物的合成。随后，我们评估了它们作为潜在的P-糖蛋白（P-gp）介导的多药耐药性（MDR）药物的逆转活性。 方法：在40％KOH存在下，通过Claisen-Schmidt反应，由苯乙酮和相应的苯甲醛合成二甲基豆蔻苷衍生物。用MTT评估它们的体外细胞毒性和逆转活性。此外，通过阿霉素（DOX）积累，蛋白质印迹和伤口愈合分析对化合物B4进行了深入评估。 结果与讨论：结果表明，化合物B2，B4和B6具有MDR反向剂的效力，而固有的细胞毒性很小。同时，这些化合物还显示出抑制MCF-7和MCF-7 / DOX细胞迁移的能力。此外，选择了最多的化合物B4进行进一步的研究，它促进了DOX在MCF-7

  DOI：

  10.2174/1570180817999200531162015

文献信息

• Trimethoxy-chalcone derivatives inhibit growth of Leishmania braziliensis: Synthesis, biological evaluation, molecular modeling and structure–activity relationship (SAR)
  作者：Murilo Lamim Bello、Louise Domeneghini Chiaradia、Luiza Rosaria Sousa Dias、Letícia Kramer Pacheco、Taisa Regina Stumpf、Alessandra Mascarello、Mário Steindel、Rosendo Augusto Yunes、Helena Carla Castro、Ricardo José Nunes、Carlos Rangel Rodrigues

  DOI：10.1016/j.bmc.2011.06.023

  日期：2011.8

  we described the synthesis, the antileishmanial activity and the molecular modeling and structure–activity relationship (SAR) evaluations of a series of chalcone derivatives. Among these compounds, the methoxychalcones 2h, 2i, 2j, 2k and 2l showed significant antileishmanial activity (IC50 <10 μM). Interestingly 2i (IC50 = 2.7 μM), 2j (IC50 = 3.9 μM) and 2k (IC50 = 4.6 μM) derivatives presented better

  在这项工作中，我们描述了一系列查尔酮衍生物的合成，抗菌活性以及分子建模和结构-活性关系（SAR）评估。在这些化合物中，甲氧基查耳酮2h，2i，2j，2k和2l表现出显着的抗菌活性（IC 50  <10μM）。有趣的是2i（IC 50  = 2.7μM），2j（IC 50  =  3.9μM ）和2k（IC 50 = 4.6μM）衍生物表现出比对照药物喷他idine（IC 50 = 6.0μM）。我们的SAR研究表明，在苯环A上进行甲氧基二邻取代的重要性以及这些分子的前沿轨道HOMO系数分布与其活性之间的关系。活性最高的化合物2h，2i，2j，2k和2l符合Lipinski的5法则，这在理论上对于良好的药物吸收和通过生物膜的渗透非常重要。2j的电位分布（IC 50  = 3.9μM，CC 50  = 216μM）表明，这种查耳酮衍生物是一种命中化合物，需要在抗衰老药物设计中进一步探索。
• Design, Synthesis and Docking Studies of Flavokawain B Type Chalcones and Their Cytotoxic Effects on MCF-7 and MDA-MB-231 Cell Lines
  作者：Addila Abu Bakar、Muhammad Akhtar、Norlaily Mohd Ali、Swee Yeap、Ching Quah、Wan-Sin Loh、Noorjahan Alitheen、Seema Zareen、Zaheer Ul-Haq、Syed Shah

  DOI：10.3390/molecules23030616

  日期：——

  Flavokawain B (1) is a natural chalcone extracted from the roots of Piper methysticum, and has been proven to be a potential cytotoxic compound. Using the partial structure of flavokawain B (FKB), about 23 analogs have been synthesized. Among them, compounds 8, 13 and 23 were found in new FKB derivatives. All compounds were evaluated for their cytotoxic properties against two breast cancer cell lines

  Flavokawain B（1）是从Piper methysticum的根中提取的天然查尔酮，已被证明是潜在的细胞毒性化合物。使用黄酮类固醇B的部分结构（FKB），已经合成了约23个类似物。其中，在新的FKB衍生物中发现了化合物8、13和23。评估了所有化合物对两种乳腺癌细胞MCF-7和MDA-MB-231的细胞毒性，从而建立了结构-活性关系。FKB衍生物16（IC50 = 6.50±0.40和4.12±0.20μg/ mL），15（IC50 = 5.50±0.35和6.50±1.40μg/ mL）和13（IC50 = 7.12±0.80和4.04±0.30μg/ mL）对MCF-7和MDA-MB-231细胞系具有潜在的细胞毒性作用。但是，甲氧基在化合物2的第3位和第4位取代（IC50 = 8.90±0.60和6.80±0。35μg/ mL）和22（IC50 = 8.80±0.35和14.16±1
• Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
  作者：Louise Domeneghini Chiaradia、Alessandra Mascarello、Marcela Purificação、Javier Vernal、Marlon Norberto Sechini Cordeiro、María Emilia Zenteno、Andréa Villarino、Ricardo José Nunes、Rosendo Augusto Yunes、Hernán Terenzi

  DOI：10.1016/j.bmcl.2008.09.105

  日期：2008.12

  In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were obtained by aldolic condensation between aldehydes and acetophenones, under basic conditions. Five compounds presented moderate or good activity. The structure - activity analysis reveals that the predominant factor for the activity is the molecule planarity/hydrophobicity and the nature of the substituents. (C) 2008 Elsevier Ltd. All rights reserved.
• Hydroxychalcones induce apoptosis in B16-F10 melanoma cells via GSH and ATP depletion
  作者：Andréia Lilian Formento Navarini、Louise Domeneghini Chiaradia、Alessandra Mascarello、Márcio Fritzen、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.ejmech.2008.09.009

  日期：2009.4

  Searching for leading compounds of new drugs for cancer therapy, we studied the toxicity of 13 hydroxychalcones never tested before toward melanoma cell line (B16-F10). The compounds were obtained by aldolic condensation between aldehydes and hydroxylated acetophenones, in alkaline conditions. Three of them showed cytotoxicity to the cell line. Two of them induced mitochondrial GSH and ATP depletion and promoted cell death through apoptosis in melanoma cells. One of the compounds induced cell death through necrosis but did not significantly decrease the intracellular mitochondrial GSH and ATP levels in melanoma cells. The results suggest that the predominant factor for the activity is the molecule shape, and secondarily the number of hydroxyl groups. (c) 2008 Published by Elsevier Masson SAS.
• Hsue et al., Taiwan Kexue, 1959, vol. 13, p. 91,92
  作者：Hsue et al.

  DOI：——

  日期：——