12b-hydroxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinolin-8-one | 28455-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 12b-hydroxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinolin-8-one
• 英文别名: 12b-Hydroxy-5,6,8,12b-tetrahydro-8-isoindolo-<1,2-a>isochinolon；12b-hydroxy-5,12b-dihydro-6H-isoindolo[1,2-a]isoquinolin-8-one；12b-Hydroxy-5,6-dihydroisoindolo[1,2-a]isoquinolin-8-one
• CAS: 28455-53-0
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: KLABROOVNYKWIZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12b-hydroxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinolin-8-one 在 盐酸 、 硫酸 、 palladium on activated charcoal 、 三氧化硫 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 55.0h， 生成 7H-二苯并[de,H]喹啉-7-酮
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of some 1-azabenzanthrone derivatives

  摘要：

  Some synthetic 1-azabenzanthrones (7H-dibenzo[de,h]quinolin-7-ones) are weakly to moderately cytotoxic, suggesting that they might also show antiparasitic activity. We have now tested a small collection of these compounds in vitro against a chloroquine-resistant Plasmodium falciparum strain, comparing their cytotoxicity against normal human fibroblasts. Our results indicate that 5-methoxy-1-azabenzanthrone and its 2,3-dihydro analogue have low micromolar antiplasmodial activities and showed more than 10-fold selectivity against the parasite, indicating that the dihydro compound, in particular, might serve as a lead compound for further development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.092
• 作为产物：
  描述：

  2,3-dihydro-3-hydroxy-2-(2-phenylethyl)-1H-isoindol-1-one 在 盐酸 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 25.0h， 生成 12b-hydroxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinolin-8-one
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of some 1-azabenzanthrone derivatives

  摘要：

  Some synthetic 1-azabenzanthrones (7H-dibenzo[de,h]quinolin-7-ones) are weakly to moderately cytotoxic, suggesting that they might also show antiparasitic activity. We have now tested a small collection of these compounds in vitro against a chloroquine-resistant Plasmodium falciparum strain, comparing their cytotoxicity against normal human fibroblasts. Our results indicate that 5-methoxy-1-azabenzanthrone and its 2,3-dihydro analogue have low micromolar antiplasmodial activities and showed more than 10-fold selectivity against the parasite, indicating that the dihydro compound, in particular, might serve as a lead compound for further development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.092

文献信息

• Brønsted acid assisted activation of imide carbonyl group: regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine
  作者：Jayaraman Selvakumar、Chinnasamy Ramaraj Ramanathan

  DOI：10.1039/c1ob06349a

  日期：——

  Activation of imide carbonyl group with trifluoromethanesulfonic acid facilitates the intramolecular cyclization of phenethylphthalimides to give a fused isoindoloisoquinolinone skeleton. The first one pot regioselective synthesis of isoindoloisoquinolinone alkaloid (±)-nuevamine has been successfully executed using this methodology.

  用三氟甲磺酸活化酰亚胺羰基有助于苯乙基邻苯二甲酰亚胺的分子内环化，从而得到融合的异吲哚异喹啉酮骨架。利用这种方法，首次成功地进行了异吲哚异喹啉酮生物碱 (±)-nuevamine 的一锅区域选择性合成。
• Metal free synthesis of functionalized 1-aryl isoquinolines via iodine mediated oxidative dehydrogenation and ring opening of lactam in isoindoloisoquinolinones
  作者：Kamsali Murali Mohan Achari、Muthupandi Karthick、Chinnasamy Ramaraj Ramanathan

  DOI：10.1007/s12039-017-1301-7

  日期：2017.6

  facile and convenient method for the synthesis of substituted 2-(isoquinolin-1-yl)benzoic acids from isoindoloisoquinolinones in the presence of molecular iodine under sealed tube condition at 100\(^\circ }\hbox C}\) has been developed. This methodology involves the oxidative dehydrogenation and ring opening of hydroxy lactam/methoxy lactam to furnish the 2-(isoquinolin-1-yl)benzoic acids. Some of

  摘要一种用于合成容易且方便的方法，取代的2-（异喹啉-1-基）从在100中密封管条件下，分子碘的存在isoindoloisoquinolinones苯甲酸\（^ \ CIRC} \ hbox中C} \）具有已开发。该方法涉及羟基内酰胺/甲氧基内酰胺的氧化脱氢和开环以提供2-（异喹啉-1-基）苯甲酸。这些酸中的一些已成功环化，以提供氮杂苯并蒽醌衍生物，这是合成半月板碱生物碱和柔红霉素异四氢萘的潜在前体。 图形概要 提要报道了在密封管条件下，使用碘从异吲哚异喹啉酮类化合物无金属合成1-芳基异喹啉或氮杂苯甲酮类化合物的合成前体。该方法被成功地用于合成1-氮杂苯并蒽醌和半月板碱的类似物，即5-甲氧基-6-羟基-1-氮杂苯并蒽醌。
• P₄O₁₀/TfOH mediated domino condensation–cyclization of amines with diacids: a route to indolizidine alkaloids under catalyst- and solvent-free conditions
  作者：Ketan S. Mandrekar、Santosh G. Tilve

  DOI：10.1039/d2ra02534e

  日期：——

  employment of either a catalyst or solvent. The use of a few aliphatic and aromatic dicarboxylic acids is shown along with various primary amines. This method is suitable for synthesizing pyrrolo[2,1-a]isoquinolines, pyrido[2,1-a]isoquinolines, and isoindolo[1,2-a]isoquinolinones in excellent yields. When phthalic acid is used, a workup with either NaBH4 or a saturated NaHCO3 solution provided 12b-H or 12b-OH

  开发了一种多米诺缩合环化方法，使用 P 4 O 10 /TfOH 试剂系统合成吲哚里西啶生物碱，无需使用催化剂或溶剂。显示了一些脂肪族和芳香族二羧酸以及各种伯胺的使用。该方法适用于合成吡咯并[2,1- a ]异喹啉、吡啶并[2,1- a ]异喹啉和异吲哚[1,2- a ]异喹啉酮，收率良好。当使用邻苯二甲酸时，使用 NaBH 4或饱和 NaHCO 3溶液进行后处理得到 12 b -H 或 12 b -OH 异吲哚[1,2- a]异喹啉酮，分别。
• ¹H AND 13C NMR SPECTRAL ASSIGNMENTS AND X-RAY CRYSTALLOGRAPHY OF 4,5,8,12b-TETRAHYDRO-ISOINDOLO[1,2 -α ]ISOQUINOLINE AND DERIVATIVES
  作者：VICENTE CASTRO-CASTILLO、ANTONIO GALDÁMEZ、MARCO REBOLLEDO-FUENTES、BRUCE K CASSELS

  DOI：10.4067/s0717-97072012000100004

  日期：——

  12b-Hydroxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinolin-8-one (4), 5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinoline (5) and 12b-hydroxy-5,6,8,12b-tetrahydroisoindolo[1,2-a]isoquinoline (6) were obtained by reduction of 4,5,8,12b-tetrahydroisoindolo[1,2-a]isoquinolin-8-one (3) with LiAlH4/THF/N-2. The precursor and products were characterized by NMR spectroscopy and the X-ray crystal structure of 5 hydrochloride monohydrate (5a) was determined. H-1 and C-13 NMR spectra were completely assigned for compounds 3, 4, and 5a, using two-dimensional experiments (H-H COSY, HMQC, HMBC and H-H NOESY).
• Synthesis and antiplasmodial activity of some 1-azabenzanthrone derivatives
  作者：Vicente Castro-Castillo、Cristian Suárez-Rozas、Adriana Pabón、Edwin G. Pérez、Bruce K. Cassels、Silvia Blair

  DOI：10.1016/j.bmcl.2012.10.092

  日期：2013.1

  Some synthetic 1-azabenzanthrones (7H-dibenzo[de,h]quinolin-7-ones) are weakly to moderately cytotoxic, suggesting that they might also show antiparasitic activity. We have now tested a small collection of these compounds in vitro against a chloroquine-resistant Plasmodium falciparum strain, comparing their cytotoxicity against normal human fibroblasts. Our results indicate that 5-methoxy-1-azabenzanthrone and its 2,3-dihydro analogue have low micromolar antiplasmodial activities and showed more than 10-fold selectivity against the parasite, indicating that the dihydro compound, in particular, might serve as a lead compound for further development. (C) 2012 Elsevier Ltd. All rights reserved.