2,3-dihydro[1H]-pyrrolo[3,4-b]quinolin-3-one | 34535-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,3-dihydro[1H]-pyrrolo[3,4-b]quinolin-3-one
• 英文别名: 1,2-dihydro-pyrrolo[3,4-b]quinolin-3-one；1,2-dihydropyrrolo[3,4-b]quinoline-3-one；1H-pyrrolo[3,4-b]quinolin-3(2H)-one；3-oxo-1H-pyrrolo[3,4-b]quinoline；1,2-dihydro-pyrrolo[3,4-b]quinolin-3-one；1H,2H,3H-pyrrolo[3,4-b]quinolin-3-one；1,2-dihydropyrrolo[3,4-b]quinolin-3-one
• CAS: 34535-42-7
• 化学式: C₁₁H₈N₂O
• 分子量: 184.197
• InChiKey: IPXZMXGCEORBNJ-UHFFFAOYSA-N

物化性质

• 沸点：
  504.7±39.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro[1H]-pyrrolo[3,4-b]quinolin-3-one 在 palladium on activated charcoal K-10 clay 、 氢气 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 6.12h， 生成 7-Amino-3,11,21-triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2,4(9),5,7,15,17,19-heptaen-10-one
  参考文献：
  名称：

  Synthesis and cytotoxic activity of substituted Luotonin A derivatives

  摘要：

  Luotonin A is a cytotoxic alkaloid that has been shown to inhibit topoisomerase I via stabilization of the binary complex topoisomerase-DNA in the same fashion as camptothecin. The synthesis and the cytotoxic activity on the lung carcinoma cell line H460 of a series of derivatives of Luotonin A is reported. The compounds inhibit topoisomerase I but show weak cytotoxic activity, thus confirming the peculiarity of ring E of camptothecin for antitumor activity. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.09.039
• 作为产物：
  描述：

  1-(二甲氧基甲基)-2-氨基苯 在 盐酸 、 对甲苯磺酸 、 三苯基膦 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.0h， 生成 2,3-dihydro[1H]-pyrrolo[3,4-b]quinolin-3-one
  参考文献：
  名称：

  Synthesis of novel building blocks of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one and evaluation of their antitumor activity

  摘要：

  A series of new building blocks consisting of 1H-pyrrolo[3,4-b]quinolin-3(2H)-one with potential as selective antitumor agents is described. Compounds were synthesized by using Heck reaction of N-allyl-1H-pyrrolo[3,4-b]quinolin-3(2H)-one with p-bromophenyl acetic acid followed by formation of amide (1a-h, 2a-d) by reaction with several secondary amines in good yields. The cytotoxicity of these compounds was evaluated against human cancer cell lines in vitro (SK-N-NH, A549). Studies suggest that most of these compounds were effective in inhibiting neuroblastoma cell growth, compound 1d was the most potent one (% IC50 = 8.62 mu M).

  DOI：

  10.1007/s00044-012-0018-x

文献信息

• New Route to Natural Camptothecin through Isomünchnone Cycloaddition
  作者：Alice Kanazawa、Mauro Muniz、Barbora Baumlová、Natalie Ljungdahl、Andrew Greene

  DOI：10.1055/s-2008-1078205

  日期：——

  A novel approach to camptothecin by [3+2] cycloaddition of an isomünchnone intermediate is described.

  一种新颖的喜树碱合成方法被报道，该方法通过异穆钦内酯中间体的[3+2]环加成反应实现。
• A Domino N-Amidoacylation/Aldol-Type Condensation Approach to the Synthesis of the Topo-I Inhibitor Rosettacin and Derivatives
  作者：Frédéric Pin、Sébastien Comesse、Morgane Sanselme、Adam Daïch

  DOI：10.1021/jo702387q

  日期：2008.3.1

  The pot, atom, and step-economic synthesis of Rosettacin topo-I poison and its derivatives has been achieved using a novel domino N-amidoacylation/aldol-type condensation, followed by decarboxylation of the ester function. The key domino procedure simply involves mixing HOBt ester as new reagent with lactam and NaH together in THF or THF/ DMF. The reaction seems to be general and led to suitable N-heterocyclic

  Rosettacin topo-I毒物及其衍生物的锅，原子和逐步经济合成已使用新型的多米诺骨牌N-酰胺酰化/醛醇缩合，然后酯功能脱羧而实现。关键的多米诺骨牌程序仅涉及将作为新试剂的HOBt酯与内酰胺和NaH一起混合在THF或THF / DMF中。该反应似乎是普遍的，并导致中等至良好产率的合适的N-杂环产物。
• One-Pot Synthesis of Simple Alkaloids: 2,3-Polymethylene-4(3<i>H</i>)-quinazolinones, Luotonin A, Tryptanthrin, and Rutaecarpine
  作者：Katherine Chae Jahng、Seung Ill Kim、Dong Hyeon Kim、Chang Seob Seo、Jong-Keun Son、Seung Ho Lee、Eung Seok Lee、Yurngdong Jahng

  DOI：10.1248/cpb.56.607

  日期：——

  One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl2 is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.

  本文描述了从邻氨基苯甲酸、相应的内酰胺和SOCl2中一锅合成多种2,3-聚甲基-4(3H)-喹唑啉酮的方法，该方法可用于合成简单的4(3H)-喹唑啉酮衍生物生物碱，如鲁托霉素A、曲普坦和鲁托卡品。
• Synthesis and topoisomerase I inhibitory properties of luotonin A analogues
  作者：Ali Cagir、Brian M. Eisenhauer、Rong Gao、Shannon J. Thomas、Sidney M. Hecht

  DOI：10.1016/j.bmc.2004.08.052

  日期：2004.12

  reaction proceeded to a single product. In contrast when the reaction was carried out in tetrahydrofuran or in phosphorus oxychloride, an additional isomeric product was obtained. The luotonin A analogues were evaluated for their ability to effect stabilization of the covalent binary complex formed between human topoisomerase I and DNA, and for cytotoxicity toward a yeast strain expressing the human

  萤光素A是一种天然存在的吡咯并喹唑啉喹啉生物碱，先前已证明是拓扑异构酶I毒物。现在，在氧氯化磷存在下，通过邻氨基苯甲酸衍生物与1,2-二氢吡咯并[3,4-b]喹啉-3-one的缩合反应，制得了许多褪黑素A衍生物。当使用二氯甲烷作为溶剂时，反应进行为单一产物。相反，当反应在四氢呋喃或三氯氧磷中进行时，获得了另外的异构体产物。评价了褪黑素A类似物对人拓扑异构酶I和DNA之间形成的共价二元复合物的稳定作用的能力，以及对表达人拓扑异构酶I的酵母菌株的细胞毒性。
• A facile synthesis of simple alkaloids—synthesis of 2,3-polymethylene-4(3H)-quinazolinones and related alkaloids
  作者：Eung Seok Lee、Jae-Gyu Park、Yurngdong Jahng

  DOI：10.1016/s0040-4039(03)00080-7

  日期：2003.2

  An efficient procedure for preparation of the simple alkaloids, 2,3-polymethylene-4(3H)-quinazolinones, luotonin A, tryptanthrin, and rutaecarpine has been established by the reaction of lactam-HCI salts with POCl3 followed by cyclization with methyl anthranilate. (C) 2003 Published by Elsevier Science Ltd.