(2E)-1-(2-naphthyl)-3-(1-naphthyl)-2-propen-1-one | 38767-64-5

• 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: (2E)-1-(2-naphthyl)-3-(1-naphthyl)-2-propen-1-one
• 英文别名: 1-(2-naphthyl)-3-(1-naphthyl)-2-propen-1-one；3t-[1]naphthyl-1-[2]naphthyl-propenone；3t-[1]Naphthyl-1-[2]naphthyl-propenon；(E)-3-(1-naphthyl)-1-(2-naphthyl)prop-2-en-1-one；(E)-3-naphthalen-1-yl-1-naphthalen-2-ylprop-2-en-1-one
• CAS: 38767-64-5
• 化学式: C₂₃H₁₆O
• 分子量: 308.379
• InChiKey: HTFOFUHKAZYGLA-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E)-1-(2-naphthyl)-3-(1-naphthyl)-2-propen-1-one 以72%的产率得到
  参考文献：
  名称：

  EL-BAYOUKI, KHAIRY A. M.;IBRAHIM, I. H.;LATIF, N., EGYPT. J. CHEM., 29,(1986) N 1, 107-116

  摘要：

  DOI：
• 作为产物：
  描述：

  1-萘甲醛 、 2-萘乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 25.0h， 以70%的产率得到(2E)-1-(2-naphthyl)-3-(1-naphthyl)-2-propen-1-one
  参考文献：
  名称：

  查尔酮衍生物作为卵巢癌细胞生长抑制剂的合成及其构效关系

  摘要：

  背景：卵巢癌仍然是一种五年生存率很低的疾病。因此，需要新颖的疗法。天然查耳酮及其合成衍生物已在包括抑制癌细胞生长在内的许多领域显示出生物活性。 目的：建立查尔酮衍生物文库，包括新颖的结构，并确定其对卵巢癌细胞生长的抑制作用及其与结构-活性的关系。 方法：用取代的苯乙酮与芳族醛之间的Claisen-Schmidt缩合反应，以中等至极好的收率和良好的纯度生产了一系列新型查耳酮。用MTS测定法测量CA-OV3细胞的细胞增殖。 结果：在34种合成化合物中，有8种是新衍生物。合成的化合物通过1 H NMR，13 C NMR和HRMS进行表征。在CA-OV3细胞中对这些β-苯基丙烯酮衍生物进行的生物学评估显示出有趣的抗增殖活性，提供了初始结构-活性信息。 结论：在34种测试的化合物中，有14种显示出显着的活性，其中一些显示在100 µM时几乎完全抑制了生长。结构-活性关系表明，对A环的修饰是宽容的，对

  DOI：

  10.2174/1570180814666170505120258

文献信息

• Synthesis and biological evaluation of aromatic enones related to curcumin
  作者：Thomas Philip Robinson、Richard B. Hubbard、Tedman J. Ehlers、Jack L. Arbiser、David J. Goldsmith、J. Phillip Bowen

  DOI：10.1016/j.bmc.2005.03.054

  日期：2005.6

  It has been specifically shown to be an effective inhibitor of angiogenesis both in vitro and in vivo. Using curcumin as a lead compound for anti-angiogenic analog design, a series of structurally related compounds utilizing a substituted chalcone backbone have been synthesized and tested via an established SVR cell proliferation assay. The results have yielded a wide range of compounds that equal or

  姜黄素是从香料姜黄中分离得到的天然产物，已显示出广泛的药理活性，包括某些抗癌特性。它已被明确地证明是在体外和体内血管生成的有效抑制剂。使用姜黄素作为抗血管生成类似物设计的先导化合物，已经合成了一系列利用取代的查尔酮骨架的结构相关化合物，并通过已建立的SVR细胞增殖测定法进行了测试。结果产生了范围广泛的化合物，这些化合物等于或超过姜黄素体外抑制内皮细胞生长的能力。由于它们的商业可获得性和相当简单的合成制备方法，这些低分子量化合物是开发未来血管生成抑制剂的诱人线索。
• Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states
  申请人：Bowen J. Phillip

  公开号：US20090018167A1

  公开（公告）日：2009-01-15

  The present invention relates to chalcone and chalcone derivatives and analogs which are useful as angiogenesis inhibitors. The present compounds, which are inexpensive to synthesize, exhibit unexpectedly good activity as angiogenesis inhibitors. The present invention also relates to the use of chalcone and its analogs as antitumor/anticancer agents and to treat a number of conditions or disease states in which angiogenesis is a factor, including angiogenic skin diseases such as psoriasis, acne, rosacea, warts, eczema, hemangiomas, lymphangiogenesis, among numerous others, as well as chronic inflammatory disease such as arthritis.

  本发明涉及用作血管生成抑制剂的查尔酮和查尔酮衍生物和类似物。这些廉价合成的化合物表现出意外的良好的血管生成抑制活性。本发明还涉及将查尔酮及其类似物用作抗肿瘤/抗癌剂，并用于治疗许多与血管生成有关的疾病或病态，包括血管生成性皮肤疾病，如银屑病、痤疮、酒渣鼻、疣、湿疹、血管瘤、淋巴管生成等，以及慢性炎症性疾病，如关节炎。
• 1,3,5-Triaryl-2-pyrazolines for Use as Scintillation Solutes
  作者：RICHARD H. WILEY、C. H. JARBOE、F. N. HAYES、E. HANSBURY、J. T. NIELSEN、P. X. CALLAHAN、M. C. SELLARS

  DOI：10.1021/jo01099a025

  日期：1958.5
• Naphthylchalcones induce apoptosis and caspase activation in a leukemia cell line: The relationship between mitochondrial damage, oxidative stress, and cell death
  作者：Evelyn Winter、Louise Domeneghini Chiaradia、Clarissa A.S. de Cordova、Ricardo José Nunes、Rosendo Augusto Yunes、Tânia Beatriz Creczynski-Pasa

  DOI：10.1016/j.bmc.2010.09.025

  日期：2010.11

  In this study, we investigated the effects of 24 chalcone derivatives from 2-naphthylacetophenone toward a lymphoblastic leukemia cell line (L1210). Three compounds, called R7, R13, and R15, presented concentration- and time-dependent cytotoxicity and induced cellular death by apoptosis via mitochondrial injury and oxidative stress. The effects of these compounds appear to occur through different mechanisms because R13 and R7 induced a greater disturbance of mitochondrial potential, and all compounds induced disturbances of cellular ATP content and increased caspase-3 activity before cellular death. These compounds also interfered with antioxidant enzymes activities and GSH content through different mechanisms. (C) 2010 Elsevier Ltd. All rights reserved.
• Chiral recognition and molecular interaction in cellulose derivatives
  作者：Kenji Itoh、Tomiki Ikeda、Shigeo Tazuke、Tohru Shibata

  DOI：10.1021/j100193a020

  日期：1992.7

  Nineteen 1,3-bis(aryl)propane derivatives and six model compounds with a single chromophore were used to explore the chiral discrimination ability of cellulose derivatives, in particular cellulose triphenylcarbamate (CTC), in connection with the mode of interaction of these probe molecules with adsorbents. The interaction was evaluated by conformational analysis of the probe molecules and circular dichroism. Thc 1,3-bis(aryl)propanes with 9-anthryl moieties possessed a highly limited conformation owing to thc bulky substituent and hardly changed their shape on CTC as evidenced by CD spectra; thus, they may be regarded as ''rigid'' substrates. However, these ''rigid'' substrates were resolved quite effectively. On the other hand, those with 2-naphthyl moieties possessed a number of stable conformations and could change their shape in diastereomeric complexes on CTC; thus, they may be assumed as ''soft'' substrates, against which the chiral discrimination was inefficient. The present study revealed that the optical resolution may be interpreted at least partly in terms of the ''rigid'' and ''soft'' concept.