trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane | 227951-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane
• 英文别名: trimethyl(6-nitrobenzo[1,3]-dioxol-5-yl)stannane；trimethyl(6-nitro-1,3-benzodioxol-5-yl)stannane；trimethyl-(2-nitro-4,5-methylenedioxy)stannane；trimethyl(2-nitro-4,5-methylenedioxy)stannane；trimethyl(3,4-methylenedioxy-6-nitro)stannane；trimethyl-(6-nitro-1,3-benzodioxol-5-yl)stannane
• CAS: 227951-11-3
• 化学式: C₁₀H₁₃NO₄Sn
• 分子量: 329.928
• InChiKey: DJLDZTLFZFWEPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.87
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane 在 palladium on activated charcoal 、 四(三苯基膦)钯 氢气 、 copper(I) bromide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 16.0h， 生成 6-(2-amino-4,5-methylenedioxyphenyl)-2-methoxynaphthalene
  参考文献：
  名称：

  取代的二苯并[c，h] cinnolines：拓扑异构酶I靶向抗癌药。

  摘要：

  合成了几种取代的二苯并[c，h]肉桂啉，并评估了其靶向拓扑异构酶I的潜力以及相对的细胞毒性活性。选择的苯并[i]菲啶能够稳定由拓扑异构酶I和DNA形成的可裂解复合物。开始这项研究以检查本质上是苯并[i]菲啶的氮杂类似物的二苯并[c，h] cinnolines是否具有相似的药理特性。就靶向拓扑异构酶I的活性和细胞毒性而言，2，3-二甲氧基-8，9-亚甲基二氧基苯并[i]菲啶是更有效的苯并[i]菲啶衍生物之一。用这些取代的二苯并[c，h] cinnolines观察到的结构活性关系与苯并[i]菲啶衍生物观察到的相似。与类似取代的苯并[i]菲啶相比，二苯并[c，h] cinnoline类似物表现出更强的拓扑异构酶I靶向活性和细胞毒性。在评估2,3-二甲氧基-8,9-亚甲基二氧基二苯并[c，h] cinnoline和2,3-二甲氧基-8,9-亚甲基二氧基苯并[i]菲啶在人淋巴母细胞瘤中的细胞毒性时获

  DOI：

  10.1016/s0968-0896(02)00604-1
• 作为产物：
  描述：

  六甲基二锡 、 trimethyl(2-nitro-4,5-dimethoxyphenyl)stannane 在 四(三苯基膦)钯 氮气 、 四氢呋喃 、 二氯甲烷 、 氟化钾，无水 、 Brine 、 Sodium sulfate-III 、 乙酸乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以ethyl acetate to give 62 (0.5 g) in 54% yield的产率得到trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane
  参考文献：
  名称：

  Heterocyclic cytotoxic agents

  摘要：

  本发明提供了式I的化合物：其中R1-R8和A-G具有规范中定义的任何含义及其药学上可接受的盐。本发明还提供了包括式I化合物的制药组合物，制备式I化合物的方法，用于制备式I化合物的中间体，以及使用式I化合物治疗癌症的治疗方法。

  公开号：

  US06740650B2

文献信息

• Substituted benzo[i]phenanthridines as mammalian topoisomerase-Targeting agents
  作者：Darshan Makhey、Dajie Li、Baoping Zhao、Sai-Peng Sim、Tsai-Kun Li、Angela Liu、Leroy F Liu、Edmond J LaVoie

  DOI：10.1016/s0968-0896(03)00053-1

  日期：2003.4

  benzo[i]phenanthridines were synthesized as potential bioisosteres of nitidine and its analogues. In the present study, 2,3-methylenedioxy-8,9-dimethoxybenzo[i]phenanthridine, 2,3-methylenedioxy-8,9-dimethoxy-5-methylbenzo[i]phenanthridine, 2,3,8,9-tetramethoxybenzo[i]phenanthridine and 5-methyl-2,3,8,9-tetramethoxybenzo[i]phenanthridine were synthesized. These benzo[i]phenanthridine derivatives were

  已知在拓扑异构酶I或II的存在下，几种苯并[c]菲啶和原小ber碱生物碱，如亚尼替丁和小ber红素，可诱导DNA裂解。对与苯并[c]菲啶和原小ber碱生物碱相关的各种类似物进行的结构活性研究，为了解影响这种拓扑异构酶靶向活性的结构特征提供了见识。苯并[c]菲啶和原小ber碱生物碱的A环内的修饰可显着改变其增强DNA和拓扑异构酶之间可裂解复合物形成的能力。合成了选定的苯并[i]菲啶作为亚硝胺及其类似物的潜在生物等排体。在本研究中，2,3-亚甲基二氧基-8,9-二甲氧基苯并[i]菲啶，2,3-亚甲基二氧基-8,9-二甲氧基-5-甲基苯并[i]菲啶 合成了2,3,8,9-四甲氧基苯并[i]菲啶和5-甲基-2,3,8,9-四甲氧基苯并[i]菲啶。评价这些苯并[i]菲啶衍生物在拓扑异构酶和DNA存在下增强可裂解复合物形成的能力，以及它们对人淋巴母细胞瘤细胞系RPMI8402的细胞毒性。2,3-亚甲基二氧基-8
• 8,9-Methylenedioxybenzo[i]phenanthridines
  作者：Dajie Li、Baoping Zhao、Sai-Peng Sim、Tsai-Kun Li、Angela Liu、Leroy F Liu、Edmond J LaVoie

  DOI：10.1016/s0968-0896(03)00394-8

  日期：2003.8

  Substituted benzo[i]phenanthridines that have incorporated within their structure an 8,9-methylenedioxy group can exhibit topoisornerase I-targeting activity. Structure-activity studies were performed to examine the influence of saturation at the 11,12-positions of several substituted 8,9-methylenedioxybenzo[i]phenanthridines. The activities of these dihydro analogues were compared to those of their unsaturated analogues. In addition, the influence of varying substituents at the 2- and 3-positions within the A-ring of these 8,9-methylenedioxybenzo[i]phenanthridines on their relative potency as topoisomerase I-targeting agents and cell proliferation as determined using the MTT assay was investigated. 2,3-Dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine and its 11,12-dihydro derivative were among the more potent analogues evaluated with regard to topoisomerase I-targeting activity and cytotoxicity. (C) 2003 Elsevier Ltd. All rights reserved.
• Nitroarylstannanes as Synthons for the Preparation of Phenanthridine and Benzo[<i>i</i>]phenanthridine Derivatives
  作者：Dajie Li、Baoping Zhao、Edmond J. LaVoie

  DOI：10.1021/jo991318g

  日期：2000.5.1
• 2,3-Dimethoxybenzo[i]phenanthridines: topoisomerase I-targeting anticancer agents
  作者：Dajie Li、Baoping Zhao、Sai-Peng Sim、Tsai-Kun Li、Angela Liu、Leroy F Liu、Edmond J LaVoie

  DOI：10.1016/s0968-0896(02)00530-8

  日期：2003.2

  Appropriately substituted benzo[i]phenanthridines structurally related to nitidine, a benzo[c]phenanthridine alkaloid with antitumor activity, are active as topoisomerase 1-targeting agents. Studies on benzo[i]phenanthridines have indicated analogues that possess a 2,3-methylenedioxy moiety and at least one and preferably two methoxyl groups at the 8- and 9-positions, such as 8,9-dimethoxy-2,3-methylenedioxybenzo[i]phenanthridine, 2, are active as topoisomerase 1-targeting agents. Tetramethoxylated benzo[i]phenanthridines, wherein the 2,3-methylenedioxy moiety is replaced with methoxyl groups at the 2- and 3-position, are inactive as a topoisomerase 1-targeting agent. These results initially suggested that the 2,3-methylenedioxy moiety was critical to the retention of potent activity. Further studies revealed that 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine, 7a, is more potent than 2 as a topoisomerase 1-targeting agent. The observation that 2,3-dimethoxylated benzo[i]phenanthridines can actually exhibit enhanced activity prompted the present study in which several 8-substituted 2,3-dimethoxybenzo[i]phenanthridines were prepared and their pharmacological activities evaluated. The influence of NH2, CN, CH2OH, OBn, OCH3, OH, and NHCOCH3 substituents at the 8-position on the relative activity of these 2,3 -dimethoxybenzo[i]phenanthridines was examined. Relative to these derivatives, 7a was the most potent topoisomerase I-targeting agent, possessing similar cytotoxicity to that of nitidine in the human lymphoblast tumor cell line, RPMI8402. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Palladium-catalyzed syntheses of tetrahydrocarbazolones as advanced intermediates to carbazole alkaloids
  作者：Tricia L. Scott、Xiaomei Yu、Sobha P. Gorugantula、Grissell Carrero-Martínez、Björn C.G. Söderberg

  DOI：10.1016/j.tet.2006.08.100

  日期：2006.11

  Two sequential palladium-catalyzed reactions, an intermolecular Stille cross-coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation, have been employed as the key synthetic steps toward six tetrahydrocarbazolones. The products are advanced intermediates toward a number of naturally occurring carbazole alkaloids. (c) 2006 Elsevier Ltd. All rights reserved.