2-(but-2-ynyloxy)naphthalene-1-carbaldehyde | 1026773-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(but-2-ynyloxy)naphthalene-1-carbaldehyde
• 英文别名: 2-But-2-ynoxynaphthalene-1-carbaldehyde
• CAS: 1026773-09-0
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: CVBRXLSCFHUETD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(but-2-ynyloxy)naphthalene-1-carbaldehyde 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以76%的产率得到(E)-2-(but-2-ynyloxy)naphthalene-1-carbaldehyde oxime
  参考文献：
  名称：

  Novel Synthesis of Naphthopyranoisoxazoles and Versatile Access to ­Naphthopyranoisoxazolines

  摘要：

  2-(烯酰氧基)萘-1-甲醛肟经碘化钾、碘和碳酸氢钠氧化后直接生成新型萘并吡喃异恶唑。用次氯酸钠和三乙胺氧化 2-(3-氯烯氧基)萘-1-甲醛肟或 2-(炔氧基)萘-1-甲醛肟，也能制备出萘并吡喃异恶唑。用次氯酸钠和三乙胺氧化 2-(烯酰氧基)萘-1-甲醛肟可得到新型萘并异噁唑类化合物。据初步推测，前一种反应是通过碘中间体活化烯侧链，然后与氧化腈侧基发生 1,3 双极作用，或与羟肟酸碘化侧基发生环化作用而发生的。

  DOI：

  10.1055/s-2008-1032178
• 作为产物：
  描述：

  1-溴-2-丁炔 、 2-羟基-1-萘甲醛 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 2-(but-2-ynyloxy)naphthalene-1-carbaldehyde
  参考文献：
  名称：

  Development of 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and their salts as potent cytotoxic agents and topoisomerase I/IIα inhibitors

  摘要：

  A novel series of 35 angularly fused pentacyclic 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridin-5-ium chlorides were designed and synthesized. Their cytotoxic activities were investigated against six human cancer cell lines (NCIH23, HCT15, NUGC-3, ACHN, PC-3, and MDA-MB-231). Among all screened compounds; 28, 30, 34, 35, 46, 48, 52, and 53 compounds exhibited potent cytotoxic activities against all tested human cancer cell lines. Further, these potent lead cytotoxic agents were evaluated against human Topoisomerase I and II alpha inhibition. Among them, the compound 48 exhibited dual Topoisomerase I and II alpha inhibition especially at 20 mu M concentrations the compound 48 exhibited 1.25 times more potent Topoisomerase II alpha inhibitory activity (38.3%) than the reference drug etoposide (30.6%). The compound 52 also exhibited excellent (88.4%) topoisomerase I inhibition than the reference drug camptothecin (66.7%) at 100 mu M concentrations. Molecular docking studies of the compounds 48 and 52 with topo I discovered that they both intercalated into the DNA single-strand cleavage site where the compound 48 have van der Waals interactions with residues Arg364, Pro431, and Asn722 whilst the compound 52 have with Arg364, Thr718, and Asn722 residues. Both the compounds 48 and 52 have pi-pi stacking interactions with the stacked DNA bases. The docking studies of the compound 48 with topo IIa explored that it was bound to the topo II alpha DNA cleavage site where etoposide was situated. The benzo[f]chromeno[4,3-b][1,7]naphthyridine ring of the compound 48 was stacked between the DNA bases of the cleavage site with pi-pi stacking interactions and there were no hydrogen bond interactions with topo II alpha.

  DOI：

  10.1016/j.bmc.2018.09.019

文献信息

• Design, Synthesis, and Cytotoxicity and Topoisomerase I/IIα Inhibition Activity of Pyrazolo[4,3-f]quinoline Derivatives
  作者：Chhabi Lal Chaudhary、Seungyun Ko、Chaerim Lee、Yerin Kim、Chanhyun Jung、Soonsil Hyun、Youngjoo Kwon、Jong-Soon Kang、Jae-Kyung Jung、Heesoon Lee

  DOI：10.3390/ph15040399

  日期：——

  topoisomerase activity is one of the well-known focuses in cancer chemotherapy. Here, we describe the design and synthesis of a novel series of pyrazolo[4,3-f]quinolines with potential anticancer/topoisomerase inhibition activity. Forty newly designed pyrazolo[4,3-f]quinoline derivatives were synthesized via inverse imino Diels–Alder reaction. The antiproliferative activity of the synthesized derivatives was

  随着癌症治疗的几个目标，DNA拓扑异构酶活性的抑制是癌症化疗中众所周知的焦点之一。在这里，我们描述了具有潜在抗癌/拓扑异构酶抑制活性的新型吡唑并[4,3- f ]喹啉系列的设计和合成。通过反亚氨基Diels-Alder反应合成了40种新设计的吡唑并[4,3 - f ]喹啉衍生物。最初在人 NUGC-3 癌细胞系中测量了合成衍生物的抗增殖活性。然后，选择的化合物1B、1C、1M、2A、2D、2E、2F和2R在被测化合物中具有较高活性的化合物针对 ACHN、HCT-15、MM231、NCI-H23、NUGC-3 和 PC-3 等六种癌细胞系进行了筛选。结果表明，化合物1M、2E和2P在所有 GI 50低于 8 µM的癌细胞系中最有效。其中，2E在 100 µM 剂量下显示出与依托泊苷（阳性对照）等效的拓扑异构酶 IIα 活性抑制模式。
• Development of 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and their salts as potent cytotoxic agents and topoisomerase I/IIα inhibitors
  作者：Sateesh Kumar Arepalli、Chaerim Lee、Seongrak Sim、Kiho Lee、Hyunji Jo、Kyu-Yeon Jun、Youngjoo Kwon、Jong-Soon Kang、Jae-Kyung Jung、Heesoon Lee

  DOI：10.1016/j.bmc.2018.09.019

  日期：2018.10

  A novel series of 35 angularly fused pentacyclic 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridines and 13H-benzo[f]chromeno[4,3-b][1,7]naphthyridin-5-ium chlorides were designed and synthesized. Their cytotoxic activities were investigated against six human cancer cell lines (NCIH23, HCT15, NUGC-3, ACHN, PC-3, and MDA-MB-231). Among all screened compounds; 28, 30, 34, 35, 46, 48, 52, and 53 compounds exhibited potent cytotoxic activities against all tested human cancer cell lines. Further, these potent lead cytotoxic agents were evaluated against human Topoisomerase I and II alpha inhibition. Among them, the compound 48 exhibited dual Topoisomerase I and II alpha inhibition especially at 20 mu M concentrations the compound 48 exhibited 1.25 times more potent Topoisomerase II alpha inhibitory activity (38.3%) than the reference drug etoposide (30.6%). The compound 52 also exhibited excellent (88.4%) topoisomerase I inhibition than the reference drug camptothecin (66.7%) at 100 mu M concentrations. Molecular docking studies of the compounds 48 and 52 with topo I discovered that they both intercalated into the DNA single-strand cleavage site where the compound 48 have van der Waals interactions with residues Arg364, Pro431, and Asn722 whilst the compound 52 have with Arg364, Thr718, and Asn722 residues. Both the compounds 48 and 52 have pi-pi stacking interactions with the stacked DNA bases. The docking studies of the compound 48 with topo IIa explored that it was bound to the topo II alpha DNA cleavage site where etoposide was situated. The benzo[f]chromeno[4,3-b][1,7]naphthyridine ring of the compound 48 was stacked between the DNA bases of the cleavage site with pi-pi stacking interactions and there were no hydrogen bond interactions with topo II alpha.
• Novel Synthesis of Naphthopyranoisoxazoles and Versatile Access to ­Naphthopyranoisoxazolines
  作者：George Varvounis、Theodoros Liaskopoulos、Stavroula Skoulika、Petros Tsoungas

  DOI：10.1055/s-2008-1032178

  日期：2008.3

  2-(Alkenyloxy)naphthalene-1-carbaldehyde oximes are oxidized with potassium iodide, iodine and sodium bicarbonate directly to novel naphthopyranoisoxazoles. Naphthopyranoisoxazoles are also prepared from 2-(3-chloroallyloxy)naphthalene-1-carbaldehyde oxime or 2-(alkynyloxy)naphthalene-1-carbaldehyde oximes by oxidation with sodium hypochlorite and triethylamine. The oxidation of 2-(alkenyloxy)naphthalene-1-carbaldehyde oximes with sodium hypochlorite and triethylamine afforded novel naphthopyranoisoxazolines. The former reaction is tentatively proposed to occur via activation of the alkene side chain by means of an iodonium intermediate and either 1,3-dipolar interaction with a nitrile oxide side-group or cyclization with a hydroximic acid iodide side-group.

  2-(烯酰氧基)萘-1-甲醛肟经碘化钾、碘和碳酸氢钠氧化后直接生成新型萘并吡喃异恶唑。用次氯酸钠和三乙胺氧化 2-(3-氯烯氧基)萘-1-甲醛肟或 2-(炔氧基)萘-1-甲醛肟，也能制备出萘并吡喃异恶唑。用次氯酸钠和三乙胺氧化 2-(烯酰氧基)萘-1-甲醛肟可得到新型萘并异噁唑类化合物。据初步推测，前一种反应是通过碘中间体活化烯侧链，然后与氧化腈侧基发生 1,3 双极作用，或与羟肟酸碘化侧基发生环化作用而发生的。