(E)-N-(4-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide | 52923-38-3

• 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)-N-(4-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide
• 英文别名: N-[4-[(E)-3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]phenyl]acetamide
• CAS: 52923-38-3
• 化学式: C₁₇H₁₅NO₃
• 分子量: 281.311
• InChiKey: TYZLHSJJXYRANH-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  (E)-N-(4-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 4-amino-2'-hydroxychalcone
  参考文献：
  名称：

  Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships

  摘要：

  A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2007.03.031
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 对乙酰氨基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E)-N-(4-(3-(2-hydroxyphenyl)-3-oxoprop-1-en-1-yl)phenyl)acetamide
  参考文献：
  名称：

  Evaluation and Optimization of the Anti-Melanogenic Activity of 1-(2-Cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone Derivatives

  摘要：

  生物活性化合物的化学修饰和优化是药物开发中寻找有前途的先导化合物的关键步骤。我们先前报告了1-(2-环己基甲氧基-6-羟基苯基)-3-(4-羟甲基苯基)-丙酮（查尔酮21）的抗黑色素生成活性。在本研究中，我们合成了21个查尔酮21衍生物，并在-MSH诱导的B16F10细胞中评估了它们的抗黑色素生成活性。N-(4-(3-(2-（环己基甲氧基）苯基）-3-氧代丙-1-烯-1-基）苯乙酰胺（查尔酮21-21）表现出最强的细胞黑色素生成抑制作用，其IC50值为0.54 M。它比查尔酮21和已知的抗黑色素生成剂曲酸和熊果苷更具潜力，它们的IC50值分别为4.9、38.5和148.4 M。查尔酮21-21降低了酪氨酸酶的表达和活性。它还降低了TRP1、TRP2和MITF的表达，CREB和ERK1/2的磷酸化，以及MITF和CRE的转录活性。我们的结果表明，查尔酮21-21是一种具有抗黑色素生成活性的有效先导化合物。

  DOI：

  10.3390/molecules24071372

文献信息

• Amino-substituted flavans useful as anti-viral agents
  申请人：——

  公开号：US04461907A1

  公开（公告）日：1984-07-24

  Novel compounds of formula (IID) ##STR1## wherein either both X and Y represent groups independently selected from amino and lower alkylamino, or one of X and Y represents a group selected from amino and lower alkylamino and the other of X and Y represents a hydrogen atom have been found to be active against rhinoviruses and other viruses. Processes for producing these compounds include reduction of flavanone derivatives or of flavenes. Alternatively, reductive cyclization of chalcones affords the compounds. These may also be prepared by condensation of o-(substituted methyl)phenols with styrene derivatives. Pharmaceutical formulations and methods for the administration of the compounds are described.

  已经发现了具有公式(IID)的新化合物##STR1##，其中X和Y中的一个或两个分别选自氨基和较低的烷基氨基，或者X和Y中的一个代表氨基或较低的烷基氨基，另一个代表氢原子，这些化合物已被发现对鼻病毒和其他病毒具有活性。制备这些化合物的方法包括还原黄酮酮衍生物或黄酮类化合物。另外，还可以通过还原环化的方式合成这些化合物。这些化合物也可以通过对邻位取代的甲基苯酚与苯乙烯衍生物的缩合来制备。还描述了这些化合物的制药配方和给药方法。
• 찰콘 유도체를 포함하는 피부 미백용 조성물
  申请人：DAEJEON UNIVERSITY Industry-University Cooperation Foundation 대전대학교 산학협력단(120080024434) Corp. No ▼ 160171-0004131BRN ▼305-82-13385

  公开号：KR20200010955A

  公开（公告）日：2020-01-31

  본 발명은 찰콘 유도체를 포함하는 피부 미백용 조성물에 관한 것으로, 멜라닌 생성을 효과적으로 억제할 수 있어, 멜라닌이 과다 침착된 피부의 미백에 유용하게 활용할 수 있다.

  这是关于包含鹰嘴豆指导剂的皮肤美白配方的发明，它可以有效地抑制黑色素的生成，因此可以有用地用于美白过度沉淀黑色素的皮肤。
• Novel intermediates and process for their preparation
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0051061A2

  公开（公告）日：1982-05-05

  Known and novel compounds of formula (I), wherein R, and R2 represent substituents selected from halogen atoms and nitro, cyano, trifluoromethyl, lower alkyl, lower alkoxyl, amino and hydroxyl groups are active against viruses, especially rhinoviruses. Methods for producing the compounds are described, as are pharmaceutical formulations and methods for administering the compounds to cure or prevent rhinoviral infections.

  已知的和新型的式 (I) 化合物，其中 R 和 R2 代表选自卤素原子和硝基、氰基、三氟甲基、低级烷基、低级烷氧基、氨基和羟基的取代基，对病毒，特别是鼻病毒具有活性。 描述了生产这些化合物的方法，以及使用这些化合物治疗或预防鼻病毒感染的药物制剂和方法。
• Reichel; Hempel, Justus Liebigs Annalen der Chemie, 1959, vol. 625, p. 184,193
  作者：Reichel、Hempel

  DOI：——

  日期：——
• Kasahara, Nippon Kagaku Zasshi, 1955, vol. 76, p. 535,536
  作者：Kasahara

  DOI：——

  日期：——