3-(2-oxo-2-phenylethyl)isobenzofuran-1(3H)-one | 72897-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(2-oxo-2-phenylethyl)isobenzofuran-1(3H)-one
• 英文别名: 5,5-dimethyl-2-(3-oxo-1H-2-benzofuran-1-yl)cyclohexane-1,3-dione
• CAS: 72897-60-0
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: PJZPFOMWBRSXLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(2-oxo-2-phenylethyl)isobenzofuran-1(3H)-one 、 邻苯二胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以93%的产率得到7,7-dimethyl-7,8-dihydro-4bH-dibenzo[2,3:5,6][1,4]diazepino[7,1-a]isoindole-5,15(6H,9H)-dione
  参考文献：
  名称：

  An approach to dihydroisoindolobenzodiazepinones—three-dimensional molecular frameworks

  摘要：

  A concise two-step procedure is developed for the preparation of dihydroisoindolobenzodiazepinones, which represent derivatives of three-dimensional molecular frameworks derived from classical privileged structures of medicinal chemistry. The method commences from the readily available starting materials (i.e., 2-formylbenzoic acid, o-phenylenediamine, and various ketones) and enables the synthesis of the title compounds in 58-82% overall yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.065
• 作为产物：
  描述：

  5,5-二甲基-1,3-环己二酮 、 邻羧基苯甲醛 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以81%的产率得到3-(2-oxo-2-phenylethyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  An approach to dihydroisoindolobenzodiazepinones—three-dimensional molecular frameworks

  摘要：

  A concise two-step procedure is developed for the preparation of dihydroisoindolobenzodiazepinones, which represent derivatives of three-dimensional molecular frameworks derived from classical privileged structures of medicinal chemistry. The method commences from the readily available starting materials (i.e., 2-formylbenzoic acid, o-phenylenediamine, and various ketones) and enables the synthesis of the title compounds in 58-82% overall yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.12.065

文献信息

• The Antileishmanial Potential of C-3 Functionalized Isobenzofuranones against Leishmania (Leishmania) Infantum Chagasi
  作者：Wagner Pereira、Raphael de Souza Vasconcellos、Christiane Mariotini-Moura、Rodrigo Saar Gomes、Rafaela Firmino、Adalberto da Silva、Abelardo Silva Júnior、Gustavo Bressan、Márcia Almeida、Luís Crocco Afonso、Róbson Teixeira、Juliana Lopes Rangel Fietto

  DOI：10.3390/molecules201219857

  日期：——

  Leishmaniases are diseases caused by protozoan parasites of the genus Leishmania. Clinically, leishmaniases range from cutaneous to visceral forms, with estimated global incidences of 1.2 and 0.4 million cases per year, respectively. The treatment of these diseases relies on multiple parenteral injections with pentavalent antimonials or amphotericin B. However, these pharmaceuticals are either too toxic or expensive for routine use in developing countries. These facts call for safer, cheaper, and more effective new antileishmanial drugs. In this investigation, we describe the results of the assessment of the activities of a series of isobenzofuran-1(3H)-ones (phtalides) against Leishmania (Leishmania) infantum chagasi, which is the main causative agent of visceral leishmaniasis in the New World. The compounds were tested at concentrations of 100, 75, 50, 25 and 6.25 µM over 24, 48, and 72 h. After 48 h of treatment at the 100 µM concentration, compounds 7 and 8 decreased parasite viability to 4% and 6%, respectively. The concentration that gives half-maximal responses (LC50) for the antileishmanial activities of compounds 7 and 8 against promastigotes after 24 h were 60.48 and 65.93 µM, respectively. Additionally, compounds 7 and 8 significantly reduced parasite infection in macrophages.

  利什曼病是由利什曼属的原生动物寄生虫引起的疾病。临床上，利什曼病从皮肤型到内脏型不等，全球估计每年分别有120万和40万例病例。这些疾病的治疗依赖于多次静脉注射五价锑或两性霉素B。然而，这些药物要么毒性过大，要么价格昂贵，不适宜在发展中国家常规使用。这些事实呼吁更安全、更廉价、更有效的新型抗利什曼药物。在本研究中，我们描述了评估一系列异苯并呋喃-1(3H)-酮（酞类）对利什曼原虫（Leishmania）婴儿型查加斯菌活性结果，该菌是新大陆内脏利什曼病的主要致病因子。这些化合物在100、75、50、25和6.25微摩尔浓度下分别测试了24、48和72小时。经过100微摩尔浓度下48小时的治疗后，化合物7和8分别将寄生虫存活率降低到4%和6%。在24小时后，化合物7和8对前鞭毛体的半最大效应浓度（LC50）分别是60.48和65.93微摩尔。此外，化合物7和8显著减少了巨噬细胞中的寄生虫感染。