3-amino-3-(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione | 368427-26-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-amino-3-(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione
• 英文别名: ethyl 3-amino-4,9-dioxo-2H-benzo[f][1]benzothiole-3-carboxylate
• CAS: 368427-26-3
• 化学式: C₁₅H₁₃NO₄S
• 分子量: 303.339
• InChiKey: SYTKECPNIDQWSC-UHFFFAOYSA-N

物化性质

• 沸点：
  479.7±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-3-(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 为溶剂， 以15%的产率得到3-aminonaphtho[2,3-b]thiophene-4,9-dione
  参考文献：
  名称：

  Unprecedented synthesis of a novel amino quinone ring system via oxidative decarboxylation of quinone-based α,α-amino esters

  摘要：

  描述了一种从相应的α,α-氨基酸酯合成新型醌基胺及其衍生物的非同寻常且高效的合成方法。该过程涉及在碱性水解过程中通过氢转移实现醌基体系的氧化脱羧。这种合成方法以良好的产率，快速地合成出可能具有细胞毒性的新型醌类化合物。

  DOI：

  10.1039/b918898c
• 作为产物：
  描述：

  (4R)-ethyl-2-(4-chlorophenyl) thiazolidine-4-carboxylate 在 盐酸 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 silver carbonate 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.0h， 生成 3-amino-3-(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione
  参考文献：
  名称：

  噻唑烷衍生物的环加成反应。一种合成新的功能化杂环系统的方法

  摘要：

  描述了一种一锅法，用于合成具有苯并[ g ]异喹啉-5,10-二酮和二氢噻吩并[2,3 - b ]萘-4,9-二酮（DTNQ）结构的两个官能化三环系统。这些新系列是由萘醌和芳基噻唑烷衍生物之间的环加成反应合成的，后者分别作为高反应性N-芳基二氢丙氨酸乙酯（2-AD）或作为氨基酯亲核物质。

  DOI：

  10.1016/s0040-4039(01)01035-8

文献信息

• Design, Synthesis, and Cytotoxic Evaluation of a New Series of 3-Substituted Spiro[(dihydropyrazine-2,5-dione)-6,3‘-(2‘,3‘-dihydrothieno[2,3-<i>b</i>]naphtho-4‘,9‘-dione)] Derivatives
  作者：Isabel Gomez-Monterrey、Pietro Campiglia、Alfonso Carotenuto、Daniela Califano、Claudio Pisano、Loredana Vesci、Teresa Lama、Alessia Bertamino、Marina Sala、Antonio Mazzella di Bosco、Paolo Grieco、Ettore Novellino

  DOI：10.1021/jm0612158

  日期：2007.4.1

  A series of 3-substituted spiro[(dihydropyrazine-2,5-dione)-6,3'-(2',3'-dihydrothieno[2,3-b]naphtho-4',9'-d ione)] derivatives were prepared using an easy synthetic route via condensation of the 3-amino-3-(ethoxycarbonyl)-2,3-dihydrothieno[2,3-b]naphtho-4,9-dione system and amino acids followed by intramolecular lactamization. Amino acids containing alkyl and aryl, linear and cyclic, polar and apolar

  一系列3-取代的螺[（二氢吡嗪-2,5-二酮）-6,3'-（2'，3'-二氢噻吩并[2,3-b]萘-4'，9'-d离子）]使用3-氨基-3-（乙氧基羰基）-2,3-二氢噻吩并[2,3-b]萘-4,9-二酮系统与氨基酸的缩合反应，然后通过分子内酰胺化，通过简单的合成途径制备衍生物。掺入了含有烷基和芳基，线性和环状，极性和非极性以及碱性和酸性残基的氨基酸。对MCF-7人乳腺癌和SW 620人结肠癌细胞系的这些类似物进行评估后发现，它们源自Pro（7a），Cys（11a）和Met（12a）和3R的3S，3'R异构体D-Pro（7c）衍生的，3'S异构体，其细胞毒性效力与阿霉素相当或更高。这些选择的类似物中的一些在其他几种敏感和耐药的人类实体瘤细胞系中是有效的细胞毒性剂，并且可能能够规避多重耐药机制。特别是，在已知对阿霉素（MCF-7 / Dx和A2780 / Dx）有抗性的所选肿瘤细胞亚系中，仅
• A practical, green, and selective approach toward the synthesis of pharmacologically important quinone-containing heterocyclic systems using alumina-catalyzed Michael addition reaction
  作者：Sabrina Castellano、Alessia Bertamino、Isabel Gomez-Monterrey、Marisabella Santoriello、Paolo Grieco、Pietro Campiglia、Gianluca Sbardella、Ettore Novellino

  DOI：10.1016/j.tetlet.2007.11.148

  日期：2008.1

  A convenient method for double Michael additions to quinone systems catalyzed by Al2O3, is reported. The advantages of this method include the use of a cheap and environment-friendly catalyst, a straightforward isolation of the pure product by filtration, high yields, and excellent selectivity, thus providing rapid access to useful building blocks for the preparation of biologically active quinones

  报道了一种方便的方法，用于通过Al 2 O 3催化将迈克尔双加成到醌体系中。该方法的优点包括使用便宜且环境友好的催化剂，通过过滤直接分离纯产物，高收率和优异的选择性，从而为制备生物活性醌提供了快速获得有用的结构单元的途径。
• Design, Synthesis, and Cytotoxic Evaluation of Acyl Derivatives of 3-Aminonaphtho[2,3-<i>b</i>]thiophene-4,9-dione, a Quinone-Based System
  作者：Isabel Gomez-Monterrey、Pietro Campiglia、Claudio Aquino、Alessia Bertamino、Ilaria Granata、Alfonso Carotenuto、Diego Brancaccio、Paola Stiuso、Ilaria Scognamiglio、M. Rosaria Rusciano、Angela Serena Maione、Maddalena Illario、Paolo Grieco、Bruno Maresca、Ettore Novellino

  DOI：10.1021/jm200094h

  日期：2011.6.23

  A series of 3-acyl derivatives of the dihydronaphtho[2,3-b]thiophen-4,9-dione system were studied with respect to cytotoxicity and topoisomerase II inhibitory activity. These analogues were designed as electron-deficient anthraquinone analogues with potential intercalation ability. Derivatives 3-(diethylamino)-N-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)propanamide (11m) and 3-(2-(dimethyl-amino)ethylamino)-N-(4,9-dioxo-4,9-dihydronaphtho[2,3-b]thiophen-3-yl)propanamide (11p) showed a high efficacy in cell lines that were highly resistant to treatment with doxorubicin, such as MDA-MB435 (melanoma), IGROV (ovarian), and SF-295 (glioblastoma) human cell lines. Both compounds inhibit topoisomerase II mediated relaxation of DNA, while only 11p incites arrest at the S phase in Caco-2 cells, inducing a delay of cell cycle progression and an increase of cell differentiation. The ability of these derivatives to modulate small heat shock proteins and cardiotoxicy effects was also explored. In addition, the DNA-binding properties of these compounds were investigated and discussed.
• New benzo[g]isoquinoline-5,10-diones and dihydrothieno [2,3-b]naphtho-4,9-dione derivatives
  作者：Isabel Gomez-Monterrey、Pietro Campiglia、Paolo Grieco、Maria Vittoria Diurno、Adele Bolognese、Paolo La Colla、Ettore Novellino

  DOI：10.1016/s0968-0896(03)00310-9

  日期：2003.8

  Novel antitumoral agents with quinonic structure were synthesized and evaluated for their in vitro cytotoxic activities. This study examines the cytotoxic activities of several aryl benzo[g]isoquinoline-5,10-dione derivatives and a number of aminoacyl dihydrothieno[2,3-b]naphtho-4.9-dione (DTNQ) derivatives containing amino acids in position 3 of the ring system. Compound 6 showed remarkable cytotoxic activity at submicromolar concentration not only against several human leukaemia and solid tumour cell lines, but also toward sensitive and resistant human cell lines. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and Cytotoxic Evaluation of Novel Spirohydantoin Derivatives of the Dihydrothieno[2,3-<i>b</i>]naphtho-4,9-dione System
  作者：Isabel Gomez-Monterrey、Giovanni Santelli、Pietro Campiglia、Daniela Califano、Fabiano Falasconi、Claudio Pisano、Loredana Vesci、Teresa Lama、Paolo Grieco、Ettore Novellino

  DOI：10.1021/jm0408565

  日期：2005.2.1

  The synthesis and cytotoxic evaluation of 3-(alkyl)(alkyl-substituted)spiro[(dihydroimidazo-2,4-dione)-5,3'-(2',3'-dihydrothieno[2,3-b]naphtho-4',9'-dione)] derivatives are described. Evaluation of these analogues against the MCF-7 human breast carcinoma and SW 620 human colon carcinoma cell lines uncovered for most of the compounds a cytotoxic potency comparable to or greater than that of doxorubicin. Compound 15 exhibited remarkable cytotoxic activity against several other human solid tumor cell lines. Interestingly, only a partial, cross-resistance to compound 15 in selected tumor cell sublines known to be resistant to doxorubicin (MCF-7/Dx and A2780/Dx) was observed, whereas a total absence of cross-resistance in a tumor cell subline selected for resistance to cisplatin was found (A2780/DDP).