Dichloracetyl-L-phenylalanin | 38969-81-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Dichloracetyl-L-phenylalanin
• 英文别名: N-dichloroacetyl-L-phenylalanine；N-Dichloracetyl-L-phenylalanin；Dichloroacetyl-phenylalanine；(2S)-2-[(2,2-dichloroacetyl)amino]-3-phenylpropanoic acid
• CAS: 38969-81-2
• 化学式: C₁₁H₁₁Cl₂NO₃
• 分子量: 276.119
• InChiKey: DQUUPSCLZCPYKD-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  姜黄素 、 Dichloracetyl-L-phenylalanin 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到((1E,3Z,6E)-3-hydroxy-5-oxohepta-1,3,6-triene-1,7-diyl)bis(2-methoxy-4,1-phenylene)(2S,2'S)-bis(2-(2,2-dichloroacetamido)-3-phenylpropanoate)
  参考文献：
  名称：

  姜黄素杂交偶联物作为乳腺癌潜在治疗药物的设计、合成和分子对接研究

  摘要：

  姜黄素 (CUR) 由于其抗癌、抗炎和抗氧化的特性，在过去的二十年中受到了极大的关注。同样，丙酮酸脱氢酶激酶 1 (PKD1) 抑制剂二氯乙酸 (DCA) 作为一种潜在的抗癌药物受到了广泛关注。然而，这两种药物的临床应用非常有限，因为它们分别具有较差的生物利用度和不请自来的副作用。我们已经合成了 CUR 和 DCA 与氨基酸接头的融合缀合物，以通过利用分子杂交方法克服这些限制。分子对接研究显示了姜黄素修饰偶联物 (CMC) 在乳腺癌细胞中的潜在靶点。我们合成了六种名为CMC1-6 的杂化偶联物. 这六种 CMC 偶联物在体外人类正常永生化乳腺上皮细胞系 (MCF10A) 和体内 C57BL/6 小鼠中未显示任何显着毒性。然而，用CMC1和CMC2治疗显着降低了几个人类乳腺癌细胞 (BC) 中的集落形成试验的生长和克隆形成存活率。用CMC2对转基因小鼠 BC 和转移性 BC 荷瘤小鼠进行口服

  DOI：

  10.3390/ph15040451
• 作为产物：
  描述：

  2-benzoylaminocinnamic acid 在 palladium on activated charcoal 、 乙醇 、 soil bacteria 作用下， 生成 Dichloracetyl-L-phenylalanin
  参考文献：
  名称：

  Kameda et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 767

  摘要：

  DOI：

文献信息

• Design, synthesis, antimicrobial, and DNA gyrase inhibitory properties of fluoroquinolone–dichloroacetic acid hybrids
  作者：Israa A. Seliem、Siva S. Panda、Adel S. Girgis、Yosra I. Nagy、Riham F. George、Walid Fayad、Nehmedo G. Fawzy、Tarek S. Ibrahim、Amany M. M. Al‐Mahmoudy、Rajeev Sakhuja、Zakaria K. M. Abdel‐samii

  DOI：10.1111/cbdd.13638

  日期：2020.2

  AbstractA series of new fluoroquinolone conjugates 8a–g and 9a–f were synthesized via benzotriazole‐mediated synthetic approach with good yield and purity. Some of the synthesized analogs exhibited significant antibacterial properties against Escherichia coli and Staphylococcus aureus with potency higher than that of the parent drugs through in vitro standard bioassay procedure (conjugates 8c and 8d reveal antimicrobial properties with potency 1.9, 61.9, 20.7 and 2.4, 37.1, 8.3 folds relative to the parent antibiotic 6 against E. coli, S. aureus, and Enterococcus faecalis, respectively). The observed experimental data were supported by enzymatic DNA gyrase inhibitory property. Developed BMLR‐QSAR model validates the observed experimental data and recognizes the parameters responsible for the enhanced antibacterial properties.
• METHODS FOR MAKING EMBRYONIC CELLS, EMBRYOS, AND ANIMALS SENSITIZED TO STRESS
  申请人：Wangh Lawrence J.

  公开号：US20120198576A1

  公开（公告）日：2012-08-02

  Embodiments of the invention are based upon the discovery that exposure of cleavage-stage embryos to a stress inducer, e.g. heat shock or chemical, renders the exposed embryos more sensitive to a secondary treatment with a stress inducer, e.g. heat shock or chemical inducer. Accordingly, the present invention is directed to methods for making embryos, embryonic cells arising from them, and animals and plants that are sensitized to stress, e.g. physiologic or chemical stressors. Methods of screening for inducers and inhibitors of stress using, as test model systems, embryonic cells, embryos, animals, and plants that are sensitized to stress are also disclosed.
• [EN] METHODS FOR MAKING EMBRYONIC CELLS, EMBRYOS, AND ANIMALS SENSITIZED TO STRESS<br/>[FR] PROCÉDÉS DE FABRICATION DE CELLULES EMBRYONNAIRES, EMBRYONS, ET ANIMAUX SENSIBILISÉS AU STRESS
  申请人：UNIV BRANDEIS

  公开号：WO2011002955A2

  公开（公告）日：2011-01-06

  Embodiments of the invention are based upon the discovery that exposure of cleavage-stage embryos to a stress inducer, e.g. heat shock or chemical, renders the exposed embryos more sensitive to a secondary treatment with a stress inducer, e.g. heat shock or chemical inducer. Accordingly, the present invention is directed to methods for making embryos, embryonic cells arising from them, and animals and plants that are sensitized to stress, e.g. physiologic or chemical stressors. Methods of screening for inducers and inhibitors of stress using, as test model systems, embryonic cells, embryos, animals, and plants that are sensitized to stress are also disclosed.
• Kameda et al., Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 767
  作者：Kameda et al.

  DOI：——

  日期：——
• Design, Synthesis, and Molecular Docking Studies of Curcumin Hybrid Conjugates as Potential Therapeutics for Breast Cancer
  作者：Siva S. Panda、Queen L. Tran、Pragya Rajpurohit、Girinath G. Pillai、Sean J. Thomas、Allison E. Bridges、Jason E. Capito、Muthusamy Thangaraju、Bal L. Lokeshwar

  DOI：10.3390/ph15040451

  日期：——

  with CMC1 and CMC2 significantly reduced the growth and clonogenic survival by colony-formation assays in several human breast cancer cells (BC). Treatment by oral gavage of a transgenic mouse BC and metastatic BC tumor-bearing mice with CMC2 significantly reduced tumor growth and metastasis. Overall, our study provides strong evidence that CUR and DCA conjugates have a significant anticancer properties

  姜黄素 (CUR) 由于其抗癌、抗炎和抗氧化的特性，在过去的二十年中受到了极大的关注。同样，丙酮酸脱氢酶激酶 1 (PKD1) 抑制剂二氯乙酸 (DCA) 作为一种潜在的抗癌药物受到了广泛关注。然而，这两种药物的临床应用非常有限，因为它们分别具有较差的生物利用度和不请自来的副作用。我们已经合成了 CUR 和 DCA 与氨基酸接头的融合缀合物，以通过利用分子杂交方法克服这些限制。分子对接研究显示了姜黄素修饰偶联物 (CMC) 在乳腺癌细胞中的潜在靶点。我们合成了六种名为CMC1-6 的杂化偶联物. 这六种 CMC 偶联物在体外人类正常永生化乳腺上皮细胞系 (MCF10A) 和体内 C57BL/6 小鼠中未显示任何显着毒性。然而，用CMC1和CMC2治疗显着降低了几个人类乳腺癌细胞 (BC) 中的集落形成试验的生长和克隆形成存活率。用CMC2对转基因小鼠 BC 和转移性 BC 荷瘤小鼠进行口服