3-acetamidophenyl butyrate | 215949-61-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-acetamidophenyl butyrate
• 英文别名: 1-acetylamino-3-butyryloxy-benzene；1-Acetylamino-3-butyryloxy-benzol；(3-acetamidophenyl) butanoate
• CAS: 215949-61-4
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD27947448
• 分子量: 221.256
• InChiKey: SVENCILGYWBCKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetamidophenyl butyrate 在 2-双环己基膦-2',6'-二甲氧基联苯 、 aluminum (III) chloride 、 sodium tetrahydroborate 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium 10% on activated carbon 、 氢气 、 碘 、 sodium hydride 、 溶剂黄146 、 potassium iodide 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 175.0 ℃ 、413.7 kPa 条件下， 反应 2.75h， 生成 6-butyl-2-methyl-7-(2-phenoxyethoxy)-3-(4-(trifluoromethyl)phenyl)quinolin-4(1H)-one
  参考文献：
  名称：

  7-(2-苯氧基乙氧基)-4(1H)-喹诺酮类的合成、抗疟活性及构效关系

  摘要：

  ICI 56,780 ( 5 ) 在啮齿动物疟疾模型中显示出因果预防和血液分裂活性（ED 50 = 0.05 mg/kg），但在感染伯氏疟原虫的小鼠中迅速获得了寄生虫学抗性。在此，我们描述了针对多药耐药恶性疟原虫的 EC 50低至 0.15 nM的5类似物的合成。通过在 7-(2-phenoxyethoxy)-4(1 H )-quinolone 核心的 3 位引入邻位取代的芳基部分，实现了对 atovaquone 的低交叉阻力指数 (RI) 的最佳活性。

  DOI：

  10.1021/jm200718m
• 作为产物：
  描述：

  丁酰氯 、 N-(3-羟基苯基)乙酰胺 在 吡啶 作用下， 反应 0.5h， 以75%的产率得到3-acetamidophenyl butyrate
  参考文献：
  名称：

  7-(2-苯氧基乙氧基)-4(1H)-喹诺酮类的合成、抗疟活性及构效关系

  摘要：

  ICI 56,780 ( 5 ) 在啮齿动物疟疾模型中显示出因果预防和血液分裂活性（ED 50 = 0.05 mg/kg），但在感染伯氏疟原虫的小鼠中迅速获得了寄生虫学抗性。在此，我们描述了针对多药耐药恶性疟原虫的 EC 50低至 0.15 nM的5类似物的合成。通过在 7-(2-phenoxyethoxy)-4(1 H )-quinolone 核心的 3 位引入邻位取代的芳基部分，实现了对 atovaquone 的低交叉阻力指数 (RI) 的最佳活性。

  DOI：

  10.1021/jm200718m

文献信息

• 4(1H)-Quinolones Having Antimalarial Activity With Reduced Chemical Resistance
  申请人：Manetsch Roman

  公开号：US20130123258A1

  公开（公告）日：2013-05-16

  Provided are 4(1H)-quinolone derivatives effective in inhibiting or eliminating the viability of at least one of the stages in the life-cycle of the malarial parasite, and to show a reduced propensity to induce resistance to the compound by the target parasite. In particular, the compounds can be derivatives of phenoxyethoxy-quinolones, and including, but not only, 7-(2-phenoxyethoxy)quinolin derivatives. These compounds may be administered by themselves, with at least one other derivative compound, or with other antimalarial compounds, to an animal or human subject. The therapeutic compositions can be and formulated to reduce the extent of a Plasmodium infection in the recipient subject, or to reduce the likelihood of the onset or establishment of a Plasmodium infection if administered prior to the parasite contacting the subject. The therapeutic compositions can be formulated to provide an effective single dose amount of an antimalarial compound or multiple doses for administering over a period of time.

  提供了4(1H)-喹啉酮衍生物，能有效抑制或消除疟原虫生命周期中至少一个阶段的生存能力，并且显示出减少目标寄生虫对化合物产生抗药性的倾向。具体来说，这些化合物可以是苯氧乙氧基喹啉酮的衍生物，包括但不限于7-(2-苯氧乙氧基)喹啉衍生物。这些化合物可以单独或与至少另一种衍生物化合物或其他抗疟疾化合物一起，向动物或人类受试者施用。治疗组合物可以配制成减少受试者体内疟原虫感染程度的程度，或者在寄生虫接触受试者之前施用，以减少疟原虫感染的可能性。治疗组合物可以配制成提供有效的单剂量抗疟疾化合物或多剂量，以在一段时间内施用。
• 4(1H)-quinolones having antimalarial activity with reduced chemical resistance
  申请人：Manetsch Roman

  公开号：US08877752B2

  公开（公告）日：2014-11-04

  Provided are 4(1H)-quinolone derivatives effective in inhibiting or eliminating the viability of at least one of the stages in the life-cycle of the malarial parasite, and to show a reduced propensity to induce resistance to the compound by the target parasite. In particular, the compounds can be derivatives of phenoxyethoxy-quinolones, and including, but not only, 7-(2-phenoxyethoxy)quinolin derivatives. These compounds may be administered by themselves, with at least one other derivative compound, or with other antimalarial compounds, to an animal or human subject. The therapeutic compositions can be and formulated to reduce the extent of a Plasmodium infection in the recipient subject, or to reduce the likelihood of the onset or establishment of a Plasmodium infection if administered prior to the parasite contacting the subject. The therapeutic compositions can be formulated to provide an effective single dose amount of an antimalarial compound or multiple doses for administering over a period of time.

  提供了4(1H)-喹啉衍生物，它们有效地抑制或消除疟原虫生命周期中至少一个阶段的活力，并显示出减少诱导目标疟原虫对化合物的抗性的倾向。特别地，这些化合物可以是苯氧乙氧基喹啉衍生物，包括但不限于7-(2-苯氧乙氧基)喹啉衍生物。这些化合物可以单独或与至少一种其他衍生物化合物或其他抗疟疾化合物一起，用于动物或人类受试者。治疗组合物可以被配制成减少受试者中恶性疟原虫感染程度或在疟原虫接触受试者之前使用以减少恶性疟原虫感染的发生或建立可能性的有效单剂量抗疟疾化合物或多剂量抗疟疾化合物。
• Structure and anticoccidial activity among some 4-hydroxyquinolinecarboxylates
  作者：Renat H. Mizzoni

  DOI：10.1021/jm00299a019

  日期：1970.9
• Julia; Baillarge, Bulletin de la Societe Chimique de France, 1952, p. 639
  作者：Julia、Baillarge

  DOI：——

  日期：——
• Antitumor effects of guanosine-analog phosphonates identified by molecular modelling
  作者：Anja Schwanke、Caterina Murruzzu、Barbara Zdrazil、Ralf Zuhse、Maja Natek、Monika Höltje、Hans Christian Korting、Hans-Ulrich Reissig、Hans-Dieter Höltje、Monika Schäfer-Korting

  DOI：10.1016/j.ijpharm.2010.06.036

  日期：2010.9

  Aiming to address new drug targets, molecular modelling is gaining increasing importance although the prediction capability of the in silico method is still under debate. For an improved treatment of actinic keratosis and squamous cell carcinoma, inhibitors of human DNA polymerase alpha (pol alpha) are developed by docking nucleoside phosphonate diphosphates into the active site of pol alpha. The most promising prodrugs OxBu and OxHex were then prepared by total synthesis and tested in the squamous cancer cell line SCC25. OxBu and OxHex proved cytotoxic and antiproliferative in the nanomolar concentration range and thus exceeded activity of aphidicolin, the relevant model compound, and 5-fluorouracil, the current standard for the therapy of actinic keratosis. Interestingly, the cytotoxicity in normal human keratinocytes with OxHex was clearly less pronounced and even not detectable with OxBu. Moreover, cytotoxicity of OxBu in particular with the colorectal carcinoma cell line HT29 even surmounted cytotoxicity in SCC25, and other tumor cell lines were influenced, too, by both agents. Taken together, OxBu and OxHex may offer a new approach to cancer therapy, given the agents are sufficiently well tolerated in vivo which is to be suspected beside their chemical structure. (C) 2010 Elsevier B.V. All rights reserved.