7-(4-(fluorobenzyl)amino)-3,4,5,5a-tetrahydropyrrolo[4,3,2-de]quinolin-8(1H)-one | 1020003-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 7-(4-(fluorobenzyl)amino)-3,4,5,5a-tetrahydropyrrolo[4,3,2-de]quinolin-8(1H)-one
• 英文别名: FBA-TBQ；7-(4-fluorobenzylamino)-1,3,4,8-tetrahydropyrrolo[4,3,2-de]quinolin-8(1H)-one
• CAS: 1020003-33-1
• 化学式: C₁₇H₁₄FN₃O
• 分子量: 295.316
• InChiKey: ZNPUQIXPWYXYQT-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  10-[(4-Fluorophenyl)methylamino]-2-(4-methylphenyl)sulfonyl-2,7-diazatricyclo[6.3.1.04,12]dodeca-1(12),3,7,9-tetraen-11-one 在 sodium azide 、 N,N-二甲基甲酰胺 作用下， 反应 4.0h， 以98%的产率得到7-(4-(fluorobenzyl)amino)-3,4,5,5a-tetrahydropyrrolo[4,3,2-de]quinolin-8(1H)-one
  参考文献：
  名称：

  Azide-Mediated Detosylation of N-Tosylpyrroloiminoquinones and N-Tosylindole-4,7-quinones

  摘要：

  NaN3作为N-甲苯磺酰吡咯并咪诺喹啉和N-甲苯磺酰吲哚-4,7-喹啉脱甲苯磺酰化反应试剂的实用性已经得到了描述。在极性质子惰性溶剂如DMF和DMSO中进行NaN3介导的脱甲苯磺酰化反应。该反应在温和中性条件下进行，并能获得较好的至优异的脱甲苯磺酰化喹啉产率。

  DOI：

  10.1055/s-0028-1083570

文献信息

• Synthesis and antiproliferative activity of benzyl and phenethyl analogs of makaluvamines
  作者：Bidhan A. Shinkre、Kevin P. Raisch、Liming Fan、Sadanandan E. Velu

  DOI：10.1016/j.bmc.2007.11.051

  日期：2008.3

  inhibition against several tested cancer cell lines. Benzyl and 4-fluorobenzyl analogs were relatively more active than 3,4-dimethoxy phenethyl and 3,4-methylenedioxy phenethyl analogs. In NCI assays, the best LogGI(50) values were shown by the fluorobenzyl analog against the renal cancer cell line RXF-393 (<-8.0M) and dimethoxy phenethyl analog against the CNS cancer cell line, SF-268 (<-8.0M). The

  合成了带有取代的苄基和取代的苯乙基侧链的海洋生物碱，makaluvamine的类似物，并评估了它们的抗增殖活性。4-甲基，4-氯和4-氟取代的苄基类似物在乳腺癌细胞系MCF-7的IC（50）值分别为2.3 microM，1.8 microM和2.8 microM时具有明显的抗增殖作用。4-甲基，4-氯和3,4-亚甲二氧基衍生物在苯乙基类似物中表现出对MCF-7的最佳活性，其IC（50）值分别为2.3 microM，2.8 microM和2.4muM。通常，在苄基和苯乙基系列中，甲氧基取代都会导致活性的轻微损失。苄基，4-氟苄基，3,4-二甲氧基苯乙基和3，通过NCI在其60个细胞系的体外人类癌细胞筛选中测试了4-亚甲基二氧基苯乙基类似物。所有四种化合物对几种测试的癌细胞系均表现出优异的抑制作用。苄基和4-氟苄基类似物比3,4-二甲氧基苯乙基和3,4-亚甲二氧基苯乙基类似物具有更高的活性。在
• Pyrroloquinolin compounds and methods of using same
  申请人：The Regents of the University of California

  公开号：US11020488B2

  公开（公告）日：2021-06-01

  Provided are pyrroloquinolin compounds of formula (1) or (II). In certain aspects, the pyrroloquinolin compounds are therapeutic, e.g., for treating a cell proliferative disorder. Also provided are conjugates that include the pyrroloquinolin compounds of the present disclosure. Compositions, e.g., pharmaceutical compositions, that include the pyrroloquinolin compounds and conjugates of the present disclosure are also provided. Further provided are therapeutic methods involving the administration of the pyrroloquinolin compounds, conjugates or compositions of the present disclosure. Kits that include the pyrroloquinolin compounds, conjugates or compositions are also provided.

  所提供的是式(1)或(II)的吡咯喹啉化合物。在某些方面，这些吡咯喹啉化合物具有治疗作用，例如用于治疗细胞增殖性疾病。还提供了包括本公开的吡咯喹啉化合物的共轭物。还提供了包括本公开的吡咯喹啉化合物和共轭物的组合物，例如药物组合物。此外，还提供了涉及施用本公开的吡咯喹啉化合物、共轭物或组合物的治疗方法。还提供了包括吡咯喹啉化合物、共轭物或组合物的试剂盒。
• Marine Alkalod Makaluvamines and Derivatives Thereof
  申请人：Velu Sadanandan E.

  公开号：US20100144779A1

  公开（公告）日：2010-06-10

  The present disclosure provides compounds based on the marine alkaloid makaluvamine. Described are compounds of the general formula (I) and (II). Also described are pharmaceutical compositions comprising one or more of the compounds of the general formula (I) and (II). The compounds and pharmaceutical compositions described inhibit the growth of several cancer lines, induce apoptosis and cell cycle arrest, display topoisomerase II inhibitory activity and modulate the activity and/or expression of key proteins involved in the regulation of cell growth. Methods of treatment and prevention using the compounds and pharmaceutical compositions described are also provided.
• PYRROLOQUINOLIN COMPOUNDS AND METHODS OF USING SAME
  申请人：The Regents of the University of California

  公开号：US20200129631A1

  公开（公告）日：2020-04-30

  Provided are pyrroloquinolin compounds of formula (1) or (II). In certain aspects, the pyrroloquinolin compounds are therapeutic, e.g., for treating a cell proliferative disorder. Also provided are conjugates that include the pyrroloquinolin compounds of the present disclosure. Compositions, e.g., pharmaceutical compositions, that include the pyrroloquinolin compounds and conjugates of the present disclosure are also provided. Further provided are therapeutic methods involving the administration of the pyrroloquinolin compounds, conjugates or compositions of the present disclosure. Kits that include the pyrroloquinolin compounds, conjugates or compositions are also provided.
• [EN] MARINE ALKALOID MAKALUVAMINES AND DERIVATIVES THEREOF<br/>[FR] ALCALOÏDES MAKALUVAMINES MARINS ET LEURS DÉRIVÉS
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2008103483A2

  公开（公告）日：2008-08-28

  [EN] The present disclosure provides compounds based on the marine alkaloid makaluvamine. Described are compounds of the general formula (I) and (II). Also described are pharmaceutical compositions comprising one or more of the compounds of the general formula (I) and (II). The compounds and pharmaceutical compositions described inhibit the growth of several cancer lines, induce apoptosis and cell cycle arrest, display topoisomerase II inhibitory activity and modulate the activity and/or expression of key proteins involved in the regulation of cell growth. Methods of treatment and prevention using the compounds and pharmaceutical compositions described are also provided.
  [FR] La présente invention concerne des composés fondés sur l'alcaloïde makaluvamine marin. Les composés de formule générale (I) et (II) sont décrits. L'invention concerne également des compositions pharmaceutiques comprenant un ou plusieurs des composés de formule générale (I) et (II). Les composés et les compositions pharmaceutiques décrits inhibent la croissance de plusieurs lignées cancéreuses, induisent l'apoptose et stoppent le cycle cellulaire, affichent une activité d'inhibition de la topoisomérase II et modulent l'activité et/ou l'expression de protéines clés impliquées dans la régulation de la croissance cellulaire. L'invention concerne également des procédés de traitement et de prévention qui utilisent les composés et les compositions pharmaceutiques décrits.