ω-anilino-3-acetylbenzopyran-2-one | 88735-81-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: ω-anilino-3-acetylbenzopyran-2-one
• 英文别名: 3-(2-anilinoacetyl)-2H-1-benzopyran-2-one；3-[2-(phenylamino)acetyl]-2H-chromen-2-one；3-(N-phenyl-glycyl)-coumarin；3-(N-Phenyl-glycyl)-cumarin；3-(Anilinoacetyl)-2H-1-benzopyran-2-one；3-(2-anilinoacetyl)chromen-2-one
• CAS: 88735-81-3
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: YKXZYCLGHUGSAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ω-anilino-3-acetylbenzopyran-2-one 在 苯胺氢溴酸盐 、 三氯氧磷 作用下， 反应 1.25h， 生成 2-(2-oxo-2H-chromen-3-yl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  Sinnur, K. H.; Siddappa, S.; Hiremath, Shivayogi P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 894 - 896

  摘要：

  DOI：
• 作为产物：
  描述：

  3-乙酰基香豆素 在 乙醇 、 氯仿 、 溴 、 苯胺 作用下， 生成 ω-anilino-3-acetylbenzopyran-2-one
  参考文献：
  名称：

  Bromination of 3-Acetocoumarin

  摘要：

  DOI：

  10.1021/ja01163a053

文献信息

• Efficient, Stereoselective Approach to the Synthesis of 3-(1-Phenyl-2-(<i>Z</i>-styrylsulfonyl)-1<i>H</i>-imidazol-4-yl)-2<i>H</i>-chromen-2-ones
  作者：Nalajam Guravaiah、Vedula Rajeswar Rao

  DOI：10.1080/00397911003797874

  日期：2011.3.28

  Abstract Reaction of phenyl acetylene with 3-(1-aryl-2-mercapto-4-imidazolyl)-2H-1-benzopyran-2-ones (4) in the presence of sodium hydroxide in absolute ethanol led to the formation of 3-(1-phenyl-2-(Z-styrylthio)-1H-imidazol-4-yl)-2H-chromen-2-ones (6) in excellent yields. These, on further oxidation with H2O2/AcOH, gave the corresponding sulfones (7) with retention of stereochemistry.

  摘要 苯乙炔与 3-(1-芳基-2-巯基-4-咪唑基)-2H-1-苯并吡喃-2-酮 (4) 在氢氧化钠存在下在无水乙醇中反应生成 3- (1-苯基-2-(Z-苯乙烯硫基)-1H-咪唑-4-基)-2H-色烯-2-酮 (6) 以极好的收率。这些，用 H2O2/AcOH 进一步氧化，得到相应的砜 (7)，保留立体化学。
• Facile synthesis of 1,4-oxazines by ruthenium-catalyzed tandem N–H insertion/cyclization of α-arylamino ketones and diazo pyruvates
  作者：Farrukh Sajjad、Yanmei Chen、Xue Tian、Suzhen Dong、Alavala Gopi Krishna Reddy、Wenhao Hu、Dong Xing

  DOI：10.1039/d0ob01913e

  日期：——

  Herein, we report an efficient strategy for the rapid construction of 1,4-oxazines starting from simple α-amino ketones and diazo pyruvates under mild reaction conditions. This transformation is efficiently catalyzed by RuCl3 through a tandem N–H insertion/cyclization sequence via an enol formation. This reaction shows broad functional group tolerance, and the resulting 1,4-oxazine products show promising

  本文中，我们报告了在温和的反应条件下，从简单的α-氨基酮和重氮丙酮酸开始快速构建1,4-恶嗪的有效策略。RuCl 3通过一串N–H插入/环化序列（通过烯醇形成）有效地催化了这种转变。该反应显示出广泛的官能团耐受性，并且所得的1，4-恶嗪产物显示出对HCT116的有希望的抗癌活性。
• Czerney, P.; Hartmann, H., Journal fur praktische Chemie (Leipzig 1954), 1983, vol. 325, # 4, p. 551 - 560
  作者：Czerney, P.、Hartmann, H.

  DOI：——

  日期：——
• Skripskaya, O. V.; Yagodinets, P. I.; Chernyuk, I. N., Russian Journal of General Chemistry, 1994, vol. 64, # 11.1, p. 1625 - 1627
  作者：Skripskaya, O. V.、Yagodinets, P. I.、Chernyuk, I. N.

  DOI：——

  日期：——
• Identification of novel molecular scaffolds for the design of MMP-13 inhibitors: A first round of lead optimization
  作者：Valeria La Pietra、Luciana Marinelli、Sandro Cosconati、Francesco Saverio Di Leva、Elisa Nuti、Salvatore Santamaria、Isabella Pugliesi、Matteo Morelli、Francesca Casalini、Armando Rossello、Concettina La Motta、Sabrina Taliani、Robert Visse、Hideaki Nagase、Federico da Settimo、Ettore Novellino

  DOI：10.1016/j.ejmech.2011.10.035

  日期：2012.1

  Osteoarthritis (OA) is the leading cause of joint pain and disability in middle-aged and elderly patients, and is characterized by progressive loss of articular cartilage. Among the various matrix metalloproteinases (MMPs), MMP-13 is specifically expressed in the cartilage of human OA patients and is not present in normal adult cartilage. Thus. MMP-13-selective inhibitors are promising candidates in ostearthritis therapy. Recently, we designed an N-isopropoxy-arylsulfonamide-based hydroxamate inhibitor, which showed low nanomolar activity and high selectivity for MMP-13. In parallel to further studies aiming to assess the in vivo activity of our compound, we screened the Life Chemicals database through computational docking to seek for novel scaffolds as zinc-chelating non-hydroxamate inhibitors. Experimental evaluation of 20 selected candidate compounds verified five novel leads with IC50 in the low mu M range. These newly discovered inhibitors are structurally unrelated to the ones known so far and provide useful scaffolds to develop compounds with more desirable properties. Finally, a first round of structure-based optimization on lead 1 was accomplished and led to an increase in potency of more than 5 fold. (C) 2011 Elsevier Masson SAS. All rights reserved.